Co-reporter:Tao Feng, Xue-Mei Li, Jun He, Hong-Lian Ai, He-Ping Chen, Xiao-Nian Li, Zheng-Hui Li, and Ji-Kai Liu
Organic Letters October 6, 2017 Volume 19(Issue 19) pp:
Publication Date(Web):September 7, 2017
DOI:10.1021/acs.orglett.7b02559
Nicotabin A (1), a sesquiterpenoid derivative possessing a fused 5/6/5/5/5 ring system, was isolated from leaves of Nicotiana tabacum. The structure was elucidated by extensive spectroscopic methods and confirmed by single crystal X-ray diffraction. The plausible biosynthetic pathway for 1 was proposed. Compound 1 inhibited nitric oxide production in LPS-activated RAW264.7 macrophages with an IC50 of 22.1 μM.
Co-reporter:Ying Huang, Shuai-Bing Zhang, He-Ping Chen, Zhen-Zhu Zhao, Zhong-Yu Zhou, Zheng-Hui Li, Tao Feng, and Ji-Kai Liu
Journal of Agricultural and Food Chemistry May 17, 2017 Volume 65(Issue 19) pp:3835-3835
Publication Date(Web):May 4, 2017
DOI:10.1021/acs.jafc.7b00899
Thirteen new acetylenic acids and their derivatives, craterellynes G–Q (1, 2, 4–10, 12, 13), 9-epi-craterellyne H (3), and 14-O-ethyl-craterellyne O (11), were isolated from the fruiting bodies of edible mushrooms Craterellus lutescens. The structures of these compounds were identified by various spectroscopic and chemical means. The stereoconfigurations of 1–13 were elucidated by the combination of acetonide formation, J-based configuration analysis, and modified Mosher’s method. Craterellyne I exhibited cytotoxicities against human cancer strains and inhibition of nitric oxide (NO) production, as well as weak antimicrobial activity against Candida albicans.Keywords: acteylenic acids; Craterellus lutescens; craterellynes; cytotoxicity; mushroom;
Co-reporter:Zhen-Zhu Zhao, He-Ping Chen, Bin Wu, Ling Zhang, Zheng-Hui Li, Tao Feng, and Ji-Kai Liu
The Journal of Organic Chemistry August 4, 2017 Volume 82(Issue 15) pp:7974-7974
Publication Date(Web):July 10, 2017
DOI:10.1021/acs.joc.7b01230
Matsutakone (1), a novel sterol with an unprecedented polycyclic ring system, together with a new norsteroid matsutoic acid (2) were isolated from the fruiting bodies of Tricholoma matsutake. Their structures and absolute configurations were assigned by extensive spectroscopic analyses and computational methods. Bioassay results showed that compounds 1 and 2 exhibited inhibitory activities against acetylcholinesterase (IC50 20.9 μM for 1).
Co-reporter:Lin Chen, Zheng-Hui Li, Jian-Neng Yao, Yue-Ling Peng, Rong Huang, Tao Feng, Ji-Kai Liu
Fitoterapia 2017 Volume 122(Volume 122) pp:
Publication Date(Web):1 October 2017
DOI:10.1016/j.fitote.2017.08.017
Hericium caput-medusae is an edible and medicinal mushroom closely relative to H. erinaceus. According to our detailed chemical investigation, two novel isoindolinone-containing meroterpene dimers, caputmedusins A (1) and B (2), as well as nine analogues, caputmedusins C–K (3–11), were isolated from the fermentation broth of H. caput-medusae. Their structures were elucidated by analyses of 1D and 2D NMR spectroscopic methods. The absolute configurations of 1–4 were speculated based on the specific optical rotation and biogenetic consideration. The absolute configurations of 10 and 11 were rationalized by the calculation of 1H NMR chemical shifts. Caputmedusins A–C (1–3) showed moderate inhibitory activity against α-glucosidase with the IC50 values of 39.2, 36.2 and 40.8 μM, respectively.Download high-res image (192KB)Download full-size image
Co-reporter:Chun-Nan Wen, He-Ping Chen, Zhen-Zhu Zhao, Dong-Bao Hu, ... Ji-Kai Liu
Phytochemistry Letters 2017 Volume 20(Volume 20) pp:
Publication Date(Web):1 June 2017
DOI:10.1016/j.phytol.2017.03.004
•Betulactone A (1) possessed a novel rigid spiro-γ-lactone backbone with a 5/5/6 ring system.•Betulactone B (2) was a highly degraded sterol.•Computational ECD analysis was used for absolute configuration elucidation.Betulactones A (1) and B (2) were isolated from the cultures of basidiomycete Lenzites betulinus. Betulactone A (1) was a novel highly oxygenated rigid spiro-γ-lactone with the 5/5/6 ring system rarely found in fungal sources while betulactone B (2) was a highly degraded sterol. These structures were elucidated by extensive spectroscopic methods and computational ECD analysis. Compounds 1 and 2 were evaluated for their inhibitory activity of protein tyrosine phosphatase (PTP) 1B in vitro.Download high-res image (156KB)Download full-size image
Co-reporter:Hua Guo, Quan-Ping Diao, Dong-Yan Hou, Zheng-Hui Li, ... Ji-Kai Liu
Phytochemistry Letters 2017 Volume 21(Volume 21) pp:
Publication Date(Web):1 September 2017
DOI:10.1016/j.phytol.2017.06.007
•Four new sesquiterpenoids were isolated from Craterellus cornucopioides..•New compounds were named craterellins A-C and gymnomitr-3-en-10β,15-diol.•Craterellin C exhibited moderate cytotoxicity against A-549.Three illudin sesquiterpenoids, craterellins A–C, and one gymnomitrane sesquiterpenoids, gymnomitr-3-en-10β,15-diol, were isolated from cultures of the basidiomycete Craterellus cornucopioides, along with four previously reported compounds: illudin F, illudin M, illudin T and illudalenol. Structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and their cytotoxic activities on five tumor cell lines were evaluated.Download high-res image (163KB)Download full-size image
Co-reporter:Xiao-Jing Zhao, Jie Zhao, Xin Sun, Ji-Kai Liu, Bin Wu
Tetrahedron 2017 Volume 73, Issue 25(Issue 25) pp:
Publication Date(Web):22 June 2017
DOI:10.1016/j.tet.2017.05.017
•An efficient Lewis acid-promoted cascade reaction with dimethyl sulfoxide as a methylene source for the synthesis of Michael acceptors is reported.•The selection of a mild base is the key for this reaction.•Extensive studies were performed to gain insight into a possible reaction mechanism.An efficient Lewis acid-promoted cascade reaction with dimethyl sulfoxide as a methylene source for the synthesis of Michael acceptors is reported. The key to developing this procedure is the selection of a mild base to modulate the equilibrium of various intermediates in order to drive the reaction forward to the formation of Michael acceptor and dimeric compound products. Extensive studies were performed to gain insight into a possible reaction mechanism.Download high-res image (153KB)Download full-size image
Co-reporter:He-Ping Chen, Zhen-Zhu Zhao, Yu Zhang, Xue Bai, Ling Zhang and Ji-Kai Liu
RSC Advances 2016 vol. 6(Issue 69) pp:64469-64473
Publication Date(Web):20 Jun 2016
DOI:10.1039/C6RA10638B
(+)- and (−)-Ganodilactone (1), a pair of novel meroterpenoid dimers possessing a unique 5′H-spiro[chroman-4,2′-furan]-2,5′-dione ring system, along with their biogeneticly-related compound, ganomycin I (2), were discovered from the fruiting bodies of Ganoderma leucocontextum. The structures and absolute configurations were assigned with the aid of 1D and 2D NMR spectra, HRESIMS analysis and ECD calculations. (±)-, (+)-, and (−)-ganodilactone (1) showed pancreatic lipase inhibitory activities and exhibited the IC50 values as 27.3, 4.0, and 2.5 μM, respectively.
Co-reporter:Tao Feng, Jin-Long Cai, Xue-Mei Li, Zhong-Yu Zhou, Zheng-Hui Li, and Ji-Kai Liu
Journal of Agricultural and Food Chemistry 2016 Volume 64(Issue 9) pp:1945-1949
Publication Date(Web):February 23, 2016
DOI:10.1021/acs.jafc.6b00176
Phellinus rhabarbarinus soaked in wine has folk usages by local residents of Ailao mountain of Yunnan province, China, which were to daub the wound to prevent infection and to drink to enhance immunity and treat other diseases such as cough, gastritis, and cancer. Systemic investigation on the chemical constituents of fruiting bodies of P. rhabarbarinus resulted in the isolation of 11 lanostane triterpenoids (1–10) including three new ones, namely, phellibarins A–C (1–3), together with five ergosterols (11–15). This is the first time reporting secondary metabolites of P. rhabarbarinus. Compounds 2, 3, 7, and 8 showed inhibitory activities against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages, whereas compounds 2–4, 6, 7, and 10 exhibited cytotoxicities against human cancer cell lines. The results of this assessment suggested that the lanostane triterpenoids in fruiting bodies of P. rhabarbarinus played key roles in its folk usages.
Co-reporter:Dr. Xia Yin;Dr. Tao Feng;Zheng-Hui Li;Dr. Ji-Kai Liu
Chemistry - A European Journal 2016 Volume 22( Issue 16) pp:5789-5792
Publication Date(Web):
DOI:10.1002/chem.201504410
Abstract
Recently, Dr. Paolo Davoli and his colleagues stated that the conclusions drawn by us were misleading from a mycotoxicological perspective, as they cast doubts on the edibility of a mushroom species (Tricholoma terreum) that has been always recognized as safe. Unfortunately, they made a mistake, and seriously misinterpreted our data, which resulted in scepticism of our research. Saponaceolides B and M were tested for their stabilities heating directly on and boiling in water. It is undoubted that both saponaceolides B and M are capable of withstanding prolonged heating during cooking.
Co-reporter:Dongdong Xu, Wen-Wu Sun, Yanli Xie, Ji-Kai Liu, Bin Liu, Yingbi Zhou, and Bin Wu
The Journal of Organic Chemistry 2016 Volume 81(Issue 22) pp:11081-11094
Publication Date(Web):October 28, 2016
DOI:10.1021/acs.joc.6b02078
Mild, metal-free, highly regioselective hypervalent-iodine mediated C-2 acetoxylation and C-3 oxidations of N-substituted indoles with (diacetoxyiodo)benzene [PhI(OAc)2] have been reported. The reaction involves three cascade steps. The quantity of PhI(OAc)2 employed in this reaction plays a key role in the outcome of three types of products (2a–4a). Furthermore, the mild and highly regioselective C-2 oxidation and C-3 dichlorination of N-substituted indoles with PhICl2 have been developed. Extensive studies including in situ IR techniques and H2O18-labeling experiment were performed to gain insight into the possible reaction mechanism.
Co-reporter:Yan-Long Yang;Hui Zhou;Gang Du;Ke-Na Feng;Dr. Tao Feng;Xiao-Li Fu;Dr. Ji-Kai Liu; Ying Zeng
Angewandte Chemie International Edition 2016 Volume 55( Issue 18) pp:5463-5466
Publication Date(Web):
DOI:10.1002/anie.201510928
Abstract
The oxidative decarboxylation of prenyl 4-hydroxybenzoate to prenylhydroquinone has been frequently proposed for the biosynthesis of prenylated (hydro)quinone derivates (sometimes meroterpenoids), yet no corresponding genes or enzymes have so far been reported. A FAD-binding monooxygenase (VibMO1) was identified that converts prenyl 4-hydroxybenzoate into prenylhydroquinone and is likely involved in the biosynthesis of vibralactones and other meroterpenoids in the basidiomycete Boreostereum vibrans. Feeding of 3-allyl-4-hydroxybenzylalcohol, an analogue of the vibralactone pathway intermediate 3-prenyl-4-hydroxybenzylalcohol, generated 20 analogues with different scaffolds. This demonstrated divergent pathways to skeletally distinct compounds initiating from a single precursor, thus providing the first insight into a novel biosynthetic pathway for 3-substituted γ-butyrolactones from a shikimate origin.
Co-reporter:Yan-Long Yang;Hui Zhou;Gang Du;Ke-Na Feng;Dr. Tao Feng;Xiao-Li Fu;Dr. Ji-Kai Liu; Ying Zeng
Angewandte Chemie 2016 Volume 128( Issue 18) pp:5553-5556
Publication Date(Web):
DOI:10.1002/ange.201510928
Abstract
The oxidative decarboxylation of prenyl 4-hydroxybenzoate to prenylhydroquinone has been frequently proposed for the biosynthesis of prenylated (hydro)quinone derivates (sometimes meroterpenoids), yet no corresponding genes or enzymes have so far been reported. A FAD-binding monooxygenase (VibMO1) was identified that converts prenyl 4-hydroxybenzoate into prenylhydroquinone and is likely involved in the biosynthesis of vibralactones and other meroterpenoids in the basidiomycete Boreostereum vibrans. Feeding of 3-allyl-4-hydroxybenzylalcohol, an analogue of the vibralactone pathway intermediate 3-prenyl-4-hydroxybenzylalcohol, generated 20 analogues with different scaffolds. This demonstrated divergent pathways to skeletally distinct compounds initiating from a single precursor, thus providing the first insight into a novel biosynthetic pathway for 3-substituted γ-butyrolactones from a shikimate origin.
Co-reporter:He-Ping Chen;Zhen-Zhu Zhao;Zheng-Hui Li;Ze-Jun Dong;Dr. Kun Wei;Xue Bai;Dr. Ling Zhang;Chun-Nan Wen;Dr. Tao Feng;Dr. Ji-Kai Liu
ChemistryOpen 2016 Volume 5( Issue 2) pp:142-149
Publication Date(Web):
DOI:10.1002/open.201500198
Abstract
A variety of novel natural products with significant bioactivities are produced by the basidiomycete Boreostereum vibrans. In the present study, we describe 16 novel natural oximes and oxime esters with a vibralactone backbone, vibralactoximes, which were isolated from the scale-up fermentation broth of B. vibrans. Their structures were determined through extensive spectroscopic analyses. These compounds represent the first oxime esters from nature. The hypothetical biosynthetic pathway of these compounds was also proposed. Seven compounds exhibited significant pancreatic lipase inhibitory activity, while ten compounds exhibited cytotoxicities against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480), with IC50 values comparable with those of cisplatin.
Co-reporter:Liang-Yan Liu;Han Sun;Christian Griesinger
Natural Products and Bioprospecting 2016 Volume 6( Issue 1) pp:41-48
Publication Date(Web):2016 February
DOI:10.1007/s13659-015-0084-0
A new alkylpyrrole derivative, fusariumin A (1), was isolated from the culture broth of the fungus Fusarium sp. The absolute configuration of fuasiumin A has been established as (2′R,3′R) using a combination of RDC (residual dipolar coupling)-based NMR and DFT-supported chiroptical spectroscopy. It is worth to note that in this study without the aid of the RDC analysis, an unambiguous determination of configuration and conformation was not feasible due to the excessive conformational possibilities of this open-chain compound.
Co-reporter:Zhen-Zhu Zhao;He-Ping Chen;Ying Huang
Natural Products and Bioprospecting 2016 Volume 6( Issue 2) pp:103-109
Publication Date(Web):2016 April
DOI:10.1007/s13659-016-0089-3
Six new lanostane-type triterpenoids, namely leucocontextins S–X (1–6), together with twelve known compounds, were isolated from the fruiting bodies of Ganoderma leucocontextum. Their structures were established by MS and NMR data.
Co-reporter:Yuan Gao;Yan-Fen Niu;Fei Wang;Ping Hai;Fang Wang
Natural Products and Bioprospecting 2016 Volume 6( Issue 5) pp:247-255
Publication Date(Web):2016 October
DOI:10.1007/s13659-016-0109-3
Four new clerodane diterpenoids, tinosporols A–C (2–4) and tinosporoside A (5), together with six known analogues were isolated from the vines of Tinospora crispa. Their structures were established by extensive spectroscopic analysis. The relative configuration at C-12 in the known diterpenoid borapetoside E (1), the major component of the plant, was firstly established with the aid of molecular model. Compound 1 significantly reduced serum glucose levels at dose-dependent manners in alloxan-induced hyperglycemic mice and db/db type 2 diabetic mice.
Co-reporter:Ling Zhang;Zheng-Hui Li;Ze-Jun Dong;Yan Li
Natural Products and Bioprospecting 2015 Volume 5( Issue 2) pp:99-103
Publication Date(Web):2015 April
DOI:10.1007/s13659-015-0058-2
Investigation on the cultures of Hypsizygus marmoreus resulted in the isolation of a new viscidane diterpene, 8-oxoviscida-3,11(18)-diene-13,14,15,19-tetraol (1) and two new polyacetylenes, (E)-10-(1,1-dimethyl-2-propenyloxy)-2-decene-4,6,8-triyn-1-ol (2) and 10-(1,1-dimethyl-2-propenyloxy)deca-4,6,8-triyn-1-ol (3), together with two known polyacetylenes, (E)-2-decen-4,6,8-triyn-1-ol (4) and 4,6,8-decatriyn-1-ol (5). Their structures were elucidated on the basis of extensive spectroscopic studies. Compound 1 is the first finding of viscidane diterpene in mushrooms. Compounds 1, 3 and 5 were tested for cytotoxicity against human tumor cell lines HL-60, SMMC-7721, A-549, MCF-7 and SW-480. None of the compounds showed cytotoxic activity (IC50 > 40 µM).
Co-reporter:Yang Wang;Ling Zhang;Fang Wang;Zheng-Hui Li
Natural Products and Bioprospecting 2015 Volume 5( Issue 2) pp:69-75
Publication Date(Web):2015 April
DOI:10.1007/s13659-015-0055-5
One new cleistanthane-type diterpene named engleromycenolic acid A (1), one new rosane-type diterpene named engleromycenolic acid B (2) and one new natural rosane-type diterpene, engleromycenol (3), along with three known rosane-type diterpenes, rosololactone (4), rosenonolactone (5) and 7-deoxyrosenonolactone (6) were isolated from cultures of the fungus Engleromyces goetzii, where it naturally grows on Alpine bamboo culms. The new compounds were elucidated based on their spectroscopic data. In addition, compounds 1–6 were evaluated for their cholesterol ester transfer protein (CETP) inhibition activity. This paper reports the isolation, structural elucidation, and CETP inhibition activity of these compounds.
Co-reporter:Yang Wang;Ling Zhang;Gen-Tao Li;Zheng-Hui Li
Natural Products and Bioprospecting 2015 Volume 5( Issue 1) pp:47-53
Publication Date(Web):2015 February
DOI:10.1007/s13659-014-0051-1
Engleromyces goetzii is a traditional medicinal mushroom that is widely used to treat infection, inflammation and cancer in Tibet, Sichuan and Yunnan provinces of China. Two new trichothecenes, engleromycones A and B (1 and 2), one new cuparane-type sesquiterpenoid named infuscol F (11), eight known trichothecene analogs, sambucinol (3), 3-deoxysambucinol (4), trichothecolone (5), trichodermol (6), 8-deoxytrichothecin (7), trichothecin (8), trichothecinol B (9) and trichothecinol A (10), and one known cyclopentanoid sesquiterpene cyclonerodiol (12) were isolated from the cultures of E. goetzii. The new compounds were elucidated through spectroscopic analyses. The anticancer effects of trichothecenes 1–10 were examined in the HL-60, SMMC-7721, A549, MCF-7, and SW-480 human cancer cell lines using an MTT assay. Trichothecinol A (10) significantly inhibited the growth of MCF-7 cells, with an IC50 value of 0.006 µM, which was comparable to the cytotoxic activity of the positive control, paclitaxel, indicating that trichothecinol A (10) represents a potential anticancer agent.
Co-reporter:Zhen-Zhu Zhao;He-Ping Chen;Tao Feng;Zheng-Hui Li
Natural Products and Bioprospecting 2015 Volume 5( Issue 1) pp:23-28
Publication Date(Web):2015 February
DOI:10.1007/s13659-014-0047-x
Four new sesquiterpenoids, namely 12-hydroxy-3-oxodrimenol (1), 11-hydroxyacetoxydrim-7-en-3β-ol (2), 2,6-dimethyl-7,10-epoxy-10-hydroxymethyldodeca-2,11-dien-6-ol (3), and 7,10-epoxy-2,6,10-trimethyldodeca-2,11-diene-4,6-diol (4), along with fourteen known compounds, were isolated from the cultures of Phellinidium sulphurascens. The structures of compounds 1–4 were established on the basis of extensive spectroscopic analysis. All of them were evaluated for their cytotoxic activities.
Co-reporter:Rong-Hua Yin;Zhen-Zhu Zhao;Xu Ji;Ze-Jun Dong
Natural Products and Bioprospecting 2015 Volume 5( Issue 1) pp:17-22
Publication Date(Web):2015 February
DOI:10.1007/s13659-014-0045-z
Two new steroids, 3α,17α,19,20-tetrahydroxy-4α-methylpregn-8-ene (1) and 3α,12α,17α,20-tetrahydroxy-4α-methylpregn-8-ene (2) and three new sesquiterpenoids, 12-hydroxy-α-cadinol (3), 3α,12-dihydroxy-δ-cadinol (4), and 3α,6α-dihydroxyspiroax-4-ene (5), have been isolated from cultures of the fungus Phellinus igniarius. Their structures were characterized based on extensive spectroscopic data. In preliminary in vitro assays, compounds 3 and 4 exhibited the vascular-activities against phenylephrine-induced vasoconstriction with the relaxing rates of 11.0 % and 7.0 % at 3 × 10−4 M, respectively.
Co-reporter:Kun Wei;Gang-Qiang Wang;Xue Bai;Yan-Fen Niu
Natural Products and Bioprospecting 2015 Volume 5( Issue 3) pp:129-157
Publication Date(Web):2015 June
DOI:10.1007/s13659-015-0062-6
The unusual fused β-lactone vibralactone was isolated from cultures of the basidiomycete Boreostereum vibrans and has been shown to significantly inhibit pancreatic lipase. In this study, a structure-based lead optimization of vibralactone resulted in three series of 104 analogs, among which compound C1 exhibited the most potent inhibition of pancreatic lipase, with an IC50 value of 14 nM. This activity is more than 3000-fold higher than that of vibralactone. The effect of compound C1 on obesity was investigated using high-fat diet (HFD)-induced C57BL/6 J obese mice. Treatment with compound C1 at a dose of 100 mg/kg significantly decreased HFD-induced obesity, primarily through the improvement of metabolic parameters, such as triglyceride levels.
Co-reporter:Zi-ming Chen, He-Ping Chen, Yan Li, Tao Feng and Ji-Kai Liu
The Journal of Antibiotics 2015 68(1) pp:23-26
Publication Date(Web):June 25, 2014
DOI:10.1038/ja.2014.87
Two new cytochalsians, multirostratin A (1) and 20-oxo-deoxaphomin (2), together with five known analogues (3–7), were obtained from the endophytic fungus Phoma multirostrata EA-12. The structures of 1 and 2 were elucidated by MS and 1D- and 2D-NMR spectroscopic data analyses, as well as by comparison of data with those of analogues reported in the literature. Compounds 1 and 2 showed moderate cytotoxicity against five tumor cell lines (HL-60, A-549, SMMC-7721, MCF-7 and SW-480).
Co-reporter:Longyan Zhao;Mingyi Wu;Chuang Xiao;Lian Yang;Lutan Zhou;Na Gao;Jun Chen;Zi Li;Jinhua Zhao;Jianchao Chen;Jikai Liu;Hongbo Qin
PNAS 2015 Volume 112 (Issue 27 ) pp:8284-8289
Publication Date(Web):2015-07-07
DOI:10.1073/pnas.1504229112
Selective inhibition of the intrinsic coagulation pathway is a promising strategy for developing safer anticoagulants that
do not cause serious bleeding. Intrinsic tenase, the final and rate-limiting enzyme complex in the intrinsic coagulation pathway,
is an attractive but less explored target for anticoagulants due to the lack of a pure selective inhibitor. Fucosylated glycosaminoglycan
(FG), which has a distinct but complicated and ill-defined structure, is a potent natural anticoagulant with nonselective
and adverse activities. Herein we present a range of oligosaccharides prepared via the deacetylation–deaminative cleavage
of FG. Analysis of these purified oligosaccharides reveals the precise structure of FG. Among these fragments, nonasaccharide
is the minimum fragment that retains the potent selective inhibition of the intrinsic tenase while avoiding the adverse effects
of native FG. In vivo, the nonasaccharide shows 97% inhibition of venous thrombus at a dose of 10 mg/kg in rats and has no
obvious bleeding risk. This nonasaccharide may therefore serve as a novel promising anticoagulant.
Co-reporter:Xing-Na Wang, Wu-Yang Huang, Jian-Chang Du, Chun-Yang Li, Ji-Kai Liu
Biochemical Systematics and Ecology 2014 Volume 54() pp:157-159
Publication Date(Web):June 2014
DOI:10.1016/j.bse.2013.12.018
•This is the first report on detailed chemical investigation of Xylaria euglossa.•Three compounds were isolated from the family of Xylariaceae for the first time.•Three compounds were considered chemo taxonomically significant for the species Xylaria euglossa.•The taxonomic position of X. euglossa was supported by this chemical investigation.Three anthracenones (1–3), two lactams (4–5), three sterols (6–8), one ceramides (9), one long-strain fatty acid (10) were isolated from the fruiting bodies of Xylaria euglossa Fr. All the compounds were isolated from this fungus for the first time. Compound 1, 4 and 5 were isolated from the family Xylariaceae for the first time. Compound 1 and 4–5 were considered chemotaxonomically significant for the species Xylaria euglossa.
Co-reporter:Xia Yin;Dr. Tao Feng; Jian-Hua Shang;Yun-Li Zhao;Fang Wang;Zheng-Hui Li;Ze-Jun Dong;Dr. Xiao-Dong Luo;Dr. Ji-Kai Liu
Chemistry - A European Journal 2014 Volume 20( Issue 23) pp:7001-7009
Publication Date(Web):
DOI:10.1002/chem.201400226
Abstract
The established tradition of consuming and marketing wild mushrooms has focused attention on mycotoxicity, which has become a global issue. In the present study, we describe the toxins found in a previously unknown poisonous European mushroom Tricholoma terreum. Fifteen new triterpenoids terreolides A–F (1–6) and saponaceolides H–P (8–16) were isolated from the fruiting bodies of the toxic mushroom T. terreum. Terreolides A–C (1–3) possessed a unique 5/6/7 trioxaspiroketal system, whereas terreolides D–F (4–6) possessed an unprecedented carbon skeleton. Two abundant compounds in the mushroom, saponaceolide B (7) and saponaceolide M (13), displayed acute toxicity, with LD50 values of 88.3 and 63.7 mg kg−1 when administered orally in mice. Both compounds were found to increase serum creatine kinase levels in mice, indicating that T. terreum may be the cause of mushroom poisoning ultimately leading to rhabdomyolysis.
Co-reporter:He-Ping Chen;Zhen-Zhu Zhao;Rong-Hua Yin;Xia Yin
Natural Products and Bioprospecting 2014 Volume 4( Issue 5) pp:271-276
Publication Date(Web):2014 October
DOI:10.1007/s13659-014-0029-z
Phytochemical reinvestigation on the cultural broth of Boreostereum vibrans led to the isolation of six new vibralactone derivatives, vibralactone N (1), vibralactone O (2), vibralactone P (3), 10-lactyl vibralactone G (4), (3S*, 4R*)-6-acetoxymethyl-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol (5), vibralactone Q (6). Their structures were elucidated by extensive spectroscopic methods.
Co-reporter:Xiao-Yan Yang, Tao Feng, Gang-Qiang Wang, Jian-Hai Ding, Zheng-Hui Li, Yan Li, Shuang-Hui He, Ji-Kai Liu
Phytochemistry 2014 Volume 104() pp:89-94
Publication Date(Web):August 2014
DOI:10.1016/j.phytochem.2014.04.015
•Eight compounds were isolated from cultures of the basidiomycete Trichaptum pargamenum.•Their structures were elucidated by extensive spectroscopic analyses and chemical methods.•Absolute configurations of 1 and 3 were confirmed by single crystal X-ray diffractions.Four cadinane-type sesquiterpenes and four 13-carbon γ-lactones, together with three known compounds, were isolated from cultures of the basidiomycete Trichaptum pargamenum. Their structures were elucidated on the basis of extensive spectroscopic methods. The absolute configurations of two of the cadinene type sesquiterpenes 1 and 3 were confirmed by single crystal X-ray diffractions.Four cadinane-type sesquiterpenes (1–4) and four 13-carbon γ-lactones (5–8), together with three known compounds, were isolated from cultures of the basidiomycete Trichaptum pargamenum. Their structures were elucidated on the basis of extensive spectroscopic methods. The absolute configurations of 1 and 3 were confirmed by single crystal X-ray diffractions.
Co-reporter:Rong-Hua Yin, Zhen-Zhu Zhao, He-Ping Chen, Xia Yin, Xu Ji, Ze-Jun Dong, Zheng-Hui Li, Tao Feng, Ji-Kai Liu
Phytochemistry Letters 2014 10() pp: 300-303
Publication Date(Web):
DOI:10.1016/j.phytol.2014.10.019
Co-reporter:Zi-Ming Chen;Qiong-Ying Fan;Xia Yin;Xiao-Yan Yang
Natural Products and Bioprospecting 2014 Volume 4( Issue 4) pp:207-211
Publication Date(Web):2014 August
DOI:10.1007/s13659-014-0032-4
Three new humulane-type sesquiterpenes, antrodols A–C (1–3), were isolated from cultures of the fungus Antrodiella albocinnamomea. Their structures were elucidated on the basis of extensive spectroscopic analysis. Antrodols A–C (1–3) are first examples of humulane-type sesquiterpenes isolated from cultures of higher fungi, and antrodol A (1) was the first report of humulane-type sesquiterpene with a methyl rearranged at C-3. All compounds were evaluated in the enzyme inhibition assay against two protein-tyrosine phosphatases (PTPs): MEG2 and PTP1Bc.
Co-reporter:Jiang-Bo He;Tao Feng;Shen Zhang;Ze-Jun Dong
Natural Products and Bioprospecting 2014 Volume 4( Issue 1) pp:21-25
Publication Date(Web):2014 February
DOI:10.1007/s13659-014-0002-x
Seven new drimane-type sesquiterpennoids, phellinuins A–G (1–7), together with one known compound 3β,11,12-trihydroxydrimene (8) were isolated from the cultures of mushroom Phellinus tuberculosus. Their structures were elucidated on the basis of NMR and MS spectroscopic data and by comparison with data reported in the literature.
Co-reporter:Liang-Yan Liu;Zheng-Hui Li;Gang-Qiang Wang
Natural Products and Bioprospecting 2014 Volume 4( Issue 2) pp:119-128
Publication Date(Web):2014 April
DOI:10.1007/s13659-014-0015-5
Nine previously-unreported farnesylphenols, involving eight neogrifolin derivatives (1–8) and one grifolin analogue (9), together with three known compounds, were isolated from the fruiting bodies of the mushroom Albatrellus caeruleoporus. Their structures were elucidated as (S)-17-hydroxy-18,20-ene-neogrifolin (1), (S)-18,19-dihydroxyneogrifolin (2), (S)-9-hydroxy-10,22-ene-neogrifolin (3), (9S,10R)-6,10-epoxy-9-hydroxyneo grifolin (4), (9S,10R)-6,9-epoxy-10-hydroxyneogrifolin (5), (−)-13,14-dihydroxyneogrifolin (6), albatrelin G (7), albatrelin H (8), and one grifolin analogue, (S)-10-hydroxygrifolin (9), grifolin (10), neogrifolin (11), and albatrellin (12) by extensive spectroscopic analyses and chemical methods. Compounds 7 and 8 showed weak cytotoxic activity to cell lines HL-60, SMMC-7721, A-549, and MCF-7, in vitro.
Co-reporter:Xia Yin;Tao Feng;Zheng-Hui Li;Ying Leng
Natural Products and Bioprospecting 2014 Volume 4( Issue 3) pp:149-155
Publication Date(Web):2014 June
DOI:10.1007/s13659-014-0020-8
Five new guanacastane-type diterpenes, named guanacastepenes P–T (1–5), were isolated from cultures of the fungus Psathyrella candolleana. Their structures were elucidated on the basis of extensive spectroscopic methods. All of the compounds were tested for their 11β-hydroxysteroid dehydrogenase (11β-HSD1) inhibitory activity. Compound 3 exhibited inhibitory activity against both human and mouse isozymes of 11β-HSD1 with IC50 values of 6.2 and 13.9 μM, respectively.
Co-reporter:Q Deng, X Yu, L Xiao, Z Hu, X Luo, Y Tao, L Yang, X Liu, H Chen, Z Ding, T Feng, Y Tang, X Weng, J Gao, W Yi, A M Bode, Z Dong, J Liu and Y Cao
Cell Death & Disease 2013 4(9) pp:e804
Publication Date(Web):2013-09-01
DOI:10.1038/cddis.2013.324
Many natural compounds derived from plants or microbes show promising potential for anticancer treatment, but few have been found to target energy-relevant regulators. In this study, we report that neoalbaconol (NA), a novel small-molecular compound isolated from the fungus, Albatrellus confluens, could target 3-phosphoinositide-dependent protein kinase 1 (PDK1) and inhibit its downstream phosphoinositide-3 kinase (PI3-K)/Akt-hexokinase 2 (HK2) pathway, which eventually resulted in energy depletion. By targeting PDK1, NA reduced the consumption of glucose and ATP generation, activated autophagy and caused apoptotic and necroptotic death of cancer cells through independent pathway. Necroptosis was remarkably induced, which was confirmed by several necroptosis-specific markers: the activation of autophagy, presence of necrotic morphology, increase of receptor-interacting protein 1 (RIP1)/RIP3 colocalization and interaction and rescued by necroptosis inhibitor necrostatin-1. The possibility that Akt overexpression reversed the NA-induced energy crisis confirmed the importance of the PDK1-Akt-energy pathway in NA-mediated cell death. Moreover, NA shows the capability to inhibit PI3-K/Akt signaling and suppress tumor growth in the nasopharyngeal carcinoma (NPC) nude mouse model. These results supported the feasibility of NA in anticancer treatments.
Co-reporter:Xia Yin, Tao Feng, Zheng-Hui Li, Ze-Jun Dong, Yan Li, and Ji Kai Liu
Journal of Natural Products 2013 Volume 76(Issue 7) pp:1365-1368
Publication Date(Web):July 9, 2013
DOI:10.1021/np400359y
Four new meroterpenoids, terreumols A–D (1–4), with a rare 10-membered ring system, were isolated from the fruiting bodies of Tricholoma terreum. Their structures with absolute stereochemistry were determined by comprehensive spectroscopic methods, as well as single-crystal X-ray diffractions. Compounds 1, 3, and 4 were evaluated for their cytotoxicities against five human cancer cell lines; all of them exhibited inhibitory effects, with IC50 values comparable to those of cisplatin.
Co-reporter:Liang-Yan Liu ; Zheng-Hui Li ; Zhi-Hui Ding ; Ze-Jun Dong ; Gen-Tao Li ; Yan Li
Journal of Natural Products 2013 Volume 76(Issue 1) pp:79-84
Publication Date(Web):January 10, 2013
DOI:10.1021/np300751m
Eight grifolin derivatives, involving three new monomers, albatrelins A–C (1–3), three novel dimers (meroterpenoid pigments), albatrelins D–F (4–6), and two known ones, 6a,7,8,9,10,10a-hexahydro-3,6,9-trimethyl-6-(4-methyl-3-penten-1-yl)-1,9-epoxy-6H-dibenzo[b,d]pyran (7) and confluentin (8), were isolated from Albatrellus ovinus. Their structures were established by extensive spectroscopic analysis. The absolute configurations of compounds 2–4 were determined as 9R by comparing their optical rotations with data reported in the literature. Albatrelin F (6) was isolated as a pair of C-2′ tautomers with a ratio of 1.3:1. Confluentin (8) showed weak cytotoxicity against four human tumor cell lines, HL-60, SMMC-7712, A-549, and MCF-7, in vitro.
Co-reporter:Jian-Hai Ding, Tao Feng, Bao-Kai Cui, Kun Wei, Zheng-Hui Li, Ji-Kai Liu
Tetrahedron Letters 2013 Volume 54(Issue 21) pp:2651-2654
Publication Date(Web):22 May 2013
DOI:10.1016/j.tetlet.2013.03.038
Irlactins A–D (1–4), four novel sesquiterpenoids with a rearranged 6/6 bicyclic system, together with their presumed biosynthetic precursor irlactin E (5), were isolated from cultures of the Irpex lacteus. Their structures were elucidated by means of spectroscopic methods, and the absolute configurations of 1–4 were established by single crystal X-ray diffraction analysis. A hypothetical biogenetic pathway for irlactins A–D (1–4) was proposed.
Co-reporter:Yuan Gao;Gen-Tao Li;Yan Li;Ping Hai;Fei Wang
Natural Products and Bioprospecting 2013 Volume 3( Issue 1) pp:14-19
Publication Date(Web):2013 February
DOI:10.1007/s13659-012-0102-4
Guajadials C-F (1–4), four sesquiterpenoid-based meroterpenoids with unprecedented skeletons were isolated from the leaves of Psidium guajava. Their structures and relative configurations were established by extensive spectroscopic analysis. A possible biosynthetic pathway for 1–4 was also proposed.
Co-reporter:Hua Guo;Tao Feng;Zheng-Hui Li
Natural Products and Bioprospecting 2013 Volume 3( Issue 1) pp:8-13
Publication Date(Web):2013 February
DOI:10.1007/s13659-012-0088-y
Aurovertins J-S (1–10), together with four known metabolites, aurovertins B, C, E, and I (11–14), were isolated from cultures of the basidiomycete Albatrellus confluens. The structures of compounds 1–10 were elucidated on the basis of extensive spectroscopic analysis. All compounds were evaluated for their cytotoxic activities on five tumor cell lines.
Co-reporter:Fei Wang, Mei-Fen Mao, Guo-Zhu Wei, Yuan Gao, Fu-Cai Ren, Ji-Kai Liu
Phytochemistry 2013 Volume 95() pp:428-435
Publication Date(Web):November 2013
DOI:10.1016/j.phytochem.2013.07.005
•Three structurally unusual alkaloids were isolated from Daphniphyllum longeracemosum.•Their structures were determined by extensive spectroscopic analysis.•Hybridaphniphyllines A and B represent a hitherto unknown class of natural product hybrids.•Hybridaphniphyllines A and B were possibly generated via Diels–Alder cycloaddition.Two Daphniphyllum alkaloid and iridoid hybrids with the hitherto unknown decacyclic fused skeletons, hybridaphniphyllines A and B, along with one diamino Daphniphyllum alkaloid, daphnicyclidin I, were isolated from dried stems and leaves of Daphniphyllum longeracemosum. Their structures were elucidated on the basis of extensive spectroscopic analysis, and the absolute configuration of daphnicyclidin I was deduced by the CD exciton chirality method. A biogenetic pathway for 1 and 2 involving natural Diels–Alder cycloaddition is proposed.Two Daphniphyllum alkaloid and iridoid hybrids, hybridaphniphyllines A (1) and B (2), along with one diamino Daphniphyllum alkaloid, daphnicyclidin I, were isolated from Daphniphyllum longeracemosum. Natural Diels–Alder cycloaddition is suggested in the biogenetic pathway to 1 and 2.
Co-reporter:Xiao-Yan Yang;Tao Feng;Jian-Hai Ding;Zheng-Hui Li
Natural Products and Bioprospecting 2013 Volume 3( Issue 4) pp:154-157
Publication Date(Web):2013 August
DOI:10.1007/s13659-013-0030-y
Co-reporter:Tao Feng;Zheng-Hui Li;Xia Yin;Ze-Jun Dong
Natural Products and Bioprospecting 2013 Volume 3( Issue 4) pp:150-153
Publication Date(Web):2013 August
DOI:10.1007/s13659-013-0048-1
Co-reporter:Jiang-Yuan Zhao;Tao Feng;Zheng-Hui Li;Ze-Jun Dong
Natural Products and Bioprospecting 2013 Volume 3( Issue 6) pp:271-276
Publication Date(Web):2013 December
DOI:10.1007/s13659-013-0065-0
Co-reporter:Bing-Ji Ma;Chun-Nan Wen;Yuan Gao;Fu-Cai Ren
Natural Products and Bioprospecting 2013 Volume 3( Issue 3) pp:107-111
Publication Date(Web):2013 June
DOI:10.1007/s13659-013-0029-4
Co-reporter:Dong-Ze Liu
Natural Products and Bioprospecting 2013 Volume 3( Issue 5) pp:161-206
Publication Date(Web):2013 October
DOI:10.1007/s13659-013-0042-7
Co-reporter:Yuan Gao;Yin-Dong Fang;Ping Hai;Fei Wang
Natural Products and Bioprospecting 2013 Volume 3( Issue 5) pp:250-255
Publication Date(Web):2013 October
DOI:10.1007/s13659-013-0053-4
Co-reporter:Fei Wang;Xu-Long Li;Guo-Zhu Wei;Fu-Cai Ren
Natural Products and Bioprospecting 2013 Volume 3( Issue 5) pp:238-242
Publication Date(Web):2013 October
DOI:10.1007/s13659-013-0062-3
Co-reporter:Xiao-Yan Yang;Tao Feng;Jian-Hai Ding;Xia Yin
Natural Products and Bioprospecting 2013 Volume 3( Issue 2) pp:48-51
Publication Date(Web):2013 April
DOI:10.1007/s13659-013-0003-1
Co-reporter:Xiao-Yan Yang, Tao Feng, Zheng-Hui Li, Yu Sheng, Xia Yin, Ying Leng, and Ji-Kai Liu
Organic Letters 2012 Volume 14(Issue 20) pp:5382-5384
Publication Date(Web):October 5, 2012
DOI:10.1021/ol302468a
Conosilane A (1), a novel sesquiterpene with an unprecedented carbon skeleton, was isolated from the cultures of the basidiomycete Conocybe siliginea. Its structure was elucidated by extensive spectroscopic methods, and the absolute configuration was determined by single crystal X-ray diffraction analysis. Conosilane A was found to inhibit 11β-hydroxysteroid dehydrogenase significantly.
Co-reporter:Jian-Hai Ding, Tao Feng, Zheng-Hui Li, Xiao-Yan Yang, Hua Guo, Xia Yin, Gang-Qiang Wang, and Ji-Kai Liu
Organic Letters 2012 Volume 14(Issue 18) pp:4976-4978
Publication Date(Web):September 6, 2012
DOI:10.1021/ol302184r
Trefolane A (1), an unprecedented skeleton with a 5/6/4 tricyclic ring system, was isolated from cultures of the basidiomycete Tremella foliacea. The structure was elucidated by means of spectroscopic methods and further confirmed by single crystal X-ray diffraction analysis. A possible biogenesis for trefolane A (1) was also proposed.
Co-reporter:Yuan Gao, Gang-Qiang Wang, Kun Wei, Ping Hai, Fei Wang, and Ji-Kai Liu
Organic Letters 2012 Volume 14(Issue 23) pp:5936-5939
Publication Date(Web):November 19, 2012
DOI:10.1021/ol302849v
(±)-Guajadial B (1), an unusual humulene-based meroterpenoid, was isolated as a racemate from the leaves of Psidium guajava, collected from Vietnam. The structure of this novel secondary metabolite was established on the basis of extensive analysis of NMR spectra and confirmed by biomimetic synthesis in a domino three-component coupling reaction.
Co-reporter:Xiaoyan Yang;Tao Feng;Xia Yin;Zhenghui Li;Lin Zhang;Jikai Liu
Chinese Journal of Chemistry 2012 Volume 30( Issue 6) pp:1231-1235
Publication Date(Web):
DOI:10.1002/cjoc.201200189
Abstract
Seven new tremulane-type sesquiterpenes (1–7) have been isolated from cultures of the basidiomycete Conocybe siliginea. Their structures and relative configurations were elucidated by extensive spectroscopic data (HSQC, HMBC, 1H-1H COSY, ROESY) and MS analysis.
Co-reporter:Liang-Yan Liu;Zheng-Hui Li;Ze-Jun Dong
Natural Products and Bioprospecting 2012 Volume 2( Issue 3) pp:130-132
Publication Date(Web):2012 June
DOI:10.1007/s13659-012-0031-2
Co-reporter:Dr. Zhong-Yu Zhou;Dr. Guo-Qing Shi;Dr. Robert Fontaine;Kun Wei;Tao Feng;Fang Wang;Gang-Qiang Wang;Yan Qu;Zheng-Hui Li;Ze-Jun Dong;Hua-Jie Zhu;Zhu-Liang Yang; Guang Zeng;Dr. Ji-Kai Liu
Angewandte Chemie International Edition 2012 Volume 51( Issue 10) pp:2368-2370
Publication Date(Web):
DOI:10.1002/anie.201106502
Co-reporter:Hua Guo;Tao Feng;Zheng-Hui Li
Natural Products and Bioprospecting 2012 Volume 2( Issue 4) pp:170-173
Publication Date(Web):2012 August
DOI:10.1007/s13659-012-0057-5
Co-reporter:Xia Yin;Tao Feng
Natural Products and Bioprospecting 2012 Volume 2( Issue 6) pp:245-248
Publication Date(Web):2012 December
DOI:10.1007/s13659-012-0077-1
Three new sesquiterpene aryl esters, named 10-dehydroxy-melleoliede B (1), 1-O-formyl-10-dehydroxy-melleoliede B (2) and 10-oxo-melleoliede B (3) together with six known ones (4–9), were isolated from the cultures of Armillaria sp. The structures of the new compounds were elucidated based on the extensive spectroscopic methods. Compounds 1, 2, and 5–9 exhibited moderate cytotoxicities.
Co-reporter:Shuang Wang;Ling Zhang;Liang-Yan Liu;Ze-Jun Dong
Natural Products and Bioprospecting 2012 Volume 2( Issue 6) pp:240-244
Publication Date(Web):2012 December
DOI:10.1007/s13659-012-0058-4
Investigation of the culture of basidiomycete Polyporus ellisii led to the isolation of a novel compound 3β,9α,15α-trihydroxy-(22E,24R)-10(5→4)-abeo-ergosta-6,8(14),22-trien-5-one (1) with a new 5/7/6/5 ring system of ergosterol skeleton. In addition, five new steroids, 5β,6β-epoxy-3β,7α,9α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (2), 5β,6β-epoxy-3β,7α-dihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (3), 5α,6α-epoxy-3β,9α,15α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-7-one (4), 15α-acetoxy-(22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (5), 15β-methoxy-(22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (6), along with four known ergosterols (7–10), were obtained. All structures were elucidated based on 1D and 2D NMR spectral data. New compounds were evaluated for cytotoxicity against five human cancer cell lines, only compound 4 was found to exhibit a favorable cytotoxicity profile toward all tested tumor cell lines.
Co-reporter:Yuan Gao;Dong-Sheng Zhou;Ling-Mei Kong;Ping Hai
Natural Products and Bioprospecting 2012 Volume 2( Issue 2) pp:65-69
Publication Date(Web):2012 April
DOI:10.1007/s13659-012-0012-5
Five new indole alkaloids rauvotetraphyllines A–E (1–5), together with eight known analogues, were isolated from the aerial parts of Rauvolfia tetraphylla. The structures were established by means of spectroscopic methods. Open image in new window
Co-reporter:Jian-Hai Ding;Tao Feng;Zheng-Hui Li;Liang Li
Natural Products and Bioprospecting 2012 Volume 2( Issue 5) pp:200-205
Publication Date(Web):2012 October
DOI:10.1007/s13659-012-0060-x
Seven cadinane sesquiterpenoids, named boreovibrins A–G (1–7), three dihydrobenzofurans (8–10), and two lactones (11 and 12), together with one known compound (13), were isolated from cultures of the basidiomycete Boreostereum vibrans. The new structures were elucidated by means of spectroscopic methods. Compounds 5, 6, and 11 showed weak inhibitory activities against isozymes of 11β-hydroxysteroid dehydrogenases (11β-HSD).
Co-reporter:Fei Wang, Dong-Sheng Zhou, Guo-Zhu Wei, Fu-Cai Ren, Ji-Kai Liu
Phytochemistry 2012 Volume 77() pp:312-317
Publication Date(Web):May 2012
DOI:10.1016/j.phytochem.2012.02.008
Six eudesmane-type sesquiterpene lactones, named chlorantholides A–F, were isolated from the ethanol extract of Chloranthus elatior (Chloranthaceae) together with 12 known compounds. Their structures were elucidated on the basis of extensive spectroscopic analysis, and their absolute configurations were studied by the CD exciton chirality method. The structure of a recently reported eudesmanolide from Chloranthus anhuiensis: 8β-hydroxy-1-oxoeudesma-3,7(11)-dien-12,8-olide, was also revised as 8β-hydroxy-2-oxoeudesma-3,7(11)-dien-12,8-olide (chlorantholide D).Graphical abstractSix eudesmane sesquiterpene lactones, chlorantholides A–F (1–6), were isolated from Chloranthus elatior. The structure of an eudesmanolide from C. anhuiensis: 8β-hydroxy-1-oxoeudesma-3,7(11)-dien-12,8-olide (4a), was revised as 8β-hydroxy-2-oxoeudesma-3,7(11)-dien-12,8-olide (chlorantholide D, 4).Highlights► Six eudesmane sesquiterpene lactones were isolated from Chloranthus elatior. ► The structure of an eudesmanolide was revised. ► The HMBC and ROESY correlations of hydroxy proton signals were applied for structure elucidation. ► The CD exciton chirality method was employed to determine absolute configuration.
Co-reporter:Meng-Yuan Jiang, Tao Feng and Ji-Kai Liu
Natural Product Reports 2011 vol. 28(Issue 4) pp:783-808
Publication Date(Web):08 Feb 2011
DOI:10.1039/C0NP00006J
Covering: January 2004 to December 2009
Co-reporter:Tao Feng, Jia Su, Zhi-Hui Ding, Yong-Tang Zheng, Yan Li, Ying Leng, and Ji-Kai Liu
Journal of Agricultural and Food Chemistry 2011 Volume 59(Issue 21) pp:11690-11695
Publication Date(Web):September 28, 2011
DOI:10.1021/jf202544w
Gingerols and their corresponding dehydration products shogaols were considered as the active principles of ginger, the rhizome of the plant Zingiber officinale, for its antioxidant, anti-inflammatory, and antitumor activities. Ginger (Z. officinale) has been cultivated for thousands of years as a spice and for medicinal purposes in China. Tongling (Anhui province, China) has traditionally been regarded as an ideal cultivation place. “Tongling White Ginger” enjoys a reputation for being one of the top gingers in China for its thin white peel, tender flesh, rich juice, and flavor. In this study, we have isolated and identified two novel gingerdione dimers, bisgingerdiones A (1) and B (2); two new gingerol derivatives, (5R)-5-acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one (3) and methyl (Z)-neral acetal-[6]-gingerdiol (4); and 38 known compounds (5–42) from rhizomes of Zingiber officinale collected from Tongling, China. Their structures were elucidated by means of spectroscopic methods. Compounds 1–4 showed weak cytotoxic and anti-HIV-1 activities. Compounds 6, 8, and 26 showed inhibitory activities against human and mouse 11β-HSD1 (11β-hydroxysteroid dehydrogenases) with IC50 values between 1.09 and 1.30 μM.
Co-reporter:Gang-Qiang Wang, Kun Wei, Lin Zhang, Tao Feng, Fei Wang, Qiu-An Wang, Ji-Kai Liu
Tetrahedron Letters 2011 Volume 52(Issue 21) pp:2719-2721
Publication Date(Web):25 May 2011
DOI:10.1016/j.tetlet.2011.03.081
Co-reporter:Liang-Yan Liu;Ling Zhang;Tao Feng;Zheng-Hui Li
Natural Products and Bioprospecting 2011 Volume 1( Issue 2) pp:87-92
Publication Date(Web):2011 October
DOI:10.1007/s13659-011-0018-4
Co-reporter:Xia Yin;Tao Feng;Zheng-Hui Li;Jia Su;Yan Li
Natural Products and Bioprospecting 2011 Volume 1( Issue 2) pp:75-80
Publication Date(Web):2011 October
DOI:10.1007/s13659-011-0011-y
Co-reporter:Yuan Gao;Fei Wang;Dong-Sheng Zhou;Yan Li
Natural Products and Bioprospecting 2011 Volume 1( Issue 3) pp:104-107
Publication Date(Web):2011 December
DOI:10.1007/s13659-011-0023-7
Co-reporter:Tao Feng;Zheng-Hui Li;Ze-Jun Dong;Jia Su;Yan Li
Natural Products and Bioprospecting 2011 Volume 1( Issue 1) pp:29-32
Publication Date(Web):2011 August
DOI:10.1007/s13659-011-0005-9
Three non-isoprenoid botryane sesquiterpenoids, named boledulins A-C (1–3), have been isolated from the cultures of basidiomycete Boletus edulis Bull. The structures were established by means of spectroscopic methods. Boledulin A (1) exhibited moderate inhibitory activity against five human cancer cell lines. Open image in new window
Co-reporter:Sheng-Tao Fang;Tao Feng;Ling Zhang;Ze-Jun Dong
Natural Products and Bioprospecting 2011 Volume 1( Issue 1) pp:37-40
Publication Date(Web):2011 August
DOI:10.1007/s13659-011-0002-z
Co-reporter:Meng-Yuan Jiang, Yan Li, Fei Wang, Ji-Kai Liu
Phytochemistry 2011 Volume 72(Issue 9) pp:923-928
Publication Date(Web):June 2011
DOI:10.1016/j.phytochem.2011.03.011
Nine oxygenated cyclohexanoids, speciosins L–T (1–9) as well as a 5H-furan-2-one metabolite, 5′-O-acetylaporpinone A (10), together with known analogs, speciosins A, B, D, E, F, I and K (11–17), and aporpinone A (18), were isolated from a scale-up cultures of the basidiomycete Hexagonia speciosa. Their structures were elucidated by analysis of spectroscopic data, including 1D and 2D NMR. Speciosin B (12) showed significant cytotoxicity against several tumor cell lines with IC50 values in the range 0.23–3.30 μM.Graphical abstractNine oxygenated cyclohexanoids, speciosins L–T (1–9), together with nine known analogs, were isolated from the basidiomycete Hexagonia speciosa. Speciosin B (12) showed significant cytotoxicity against several tumor cell lines with IC50 values in the range 0.23–3.30 μM.Highlights► Nine oxygenated cyclohexanoids from the basidiomycete Hexagonia speciosa. ► Significant cytotoxicity against tumor cell lines with IC50 values 0.23–3.30 μM. ► Rare cyclohexanoids in nature.
Co-reporter:Zhong-Yu Zhou and Ji-Kai Liu
Natural Product Reports 2010 vol. 27(Issue 11) pp:1531-1570
Publication Date(Web):09 Aug 2010
DOI:10.1039/C004593D
Covering: June 2003 to December 2009. Previous review: Nat. Prod. Rep., 2003, 20, 615
Co-reporter:Ling Zhang, Rong-Hua Luo, Fei Wang, Meng-Yuan Jiang, Ze-Jun Dong, Liu-Meng Yang, Yong-Tang Zheng and Ji-Kai Liu
Organic Letters 2010 Volume 12(Issue 1) pp:152-155
Publication Date(Web):December 7, 2009
DOI:10.1021/ol9025638
Trigonothyrins A−C (1−3), which are highly functionalized daphnane diterpenoids, were isolated from the stems of Trigonostemon thyrsoideum. Compounds 1−3 represent the first examples of daphnanes with an oxygen-bridged four-membered-ring system, and a linkage mode of 12,13,14-orthoester. Compound 3 was observed to inhibit HIV-1 induced cytopathic effects. The EC50 value was 2.19 μg/mL, and the therapeutic index (TI) was more than 90.
Co-reporter:Fei Wang, Yuan Gao, Ling Zhang and Ji-Kai Liu
Organic Letters 2010 Volume 12(Issue 10) pp:2354-2357
Publication Date(Web):April 26, 2010
DOI:10.1021/ol1007247
Bi-linderone (1) was isolated as racemate from the traditional Chinese medicinal plant Lindera aggregata. The structure elucidation of bi-linderone was reported on the basis of extensive analysis of NMR spectra and crystal X-ray diffraction. Bi-linderone has an unprecedented spirocyclopentenedione-containing carbon skeleton and showed significant activity against glucosamine-induced insulin resistance in HepG2 cells at a concentration of 1 μg/mL.
Co-reporter:Fei Wang, Yuan Gao, Ling Zhang, Bing Bai, Ya Nan Hu, Ze Jun Dong, Qi Wei Zhai, Hua Jie Zhu and Ji Kai Liu
Organic Letters 2010 Volume 12(Issue 14) pp:3196-3199
Publication Date(Web):June 14, 2010
DOI:10.1021/ol1011289
(+)-Linderaspirone A and (−)-linderaspirone A, a pair of natural windmill-shaped enantiomers, were isolated from the traditional Chinese medicine plant Lindera aggregate by HPLC using a chiral column, achieving over 98% ee. Their structures and absolute configurations were determined on the basis of extensive analysis of NMR spectra, crystal X-ray diffraction, and calculation of the optical rotations (OR). They have an unprecedented carbon skeleton and showed significant activity against glucosamine-induced insulin resistance.
Co-reporter:Wanqiu Yang, Jikai Liu, Hongbin Zhang
Tetrahedron Letters 2010 Volume 51(Issue 37) pp:4874-4876
Publication Date(Web):15 September 2010
DOI:10.1016/j.tetlet.2010.07.044
A flexible and practical strategy toward the synthesis of rare 2H-furo[3,2-b]benzopyran-2-one skeleton has been developed. With a microwave-assisted cyclization–dehydration as the key transformation, the first total synthesis of pulverolide has been completed in 10 steps with 9% overall yield, leading to the revision of its proposed structure.
Co-reporter:Ying-Cheng Zhu, Gang Wang, Xiao-Long Yang, Du-Qiang Luo, Qin-Chang Zhu, Tao Peng, Ji-Kai Liu
Tetrahedron Letters 2010 Volume 51(Issue 26) pp:3443-3445
Publication Date(Web):30 June 2010
DOI:10.1016/j.tetlet.2010.04.128
The isolation, structure elucidation, and relative stereochemistry assignment of a novel illudane–illudane bis-sesquiterpene, agrocybone (1), from the basidiomycete Agrocybe salicacola, were reported. Agrocybone represents a structure with eight rings (including two spiro rings) and seven stereogenic carbon atoms. Agrocybone was found to exhibit weak antiviral activity against respiratory syncytial virus (RSV) with IC50 value of 100 μM.
Co-reporter:Dong-Ze Liu, Ze-Jun Dong, Fang Wang, Ji-Kai Liu
Tetrahedron Letters 2010 Volume 51(Issue 23) pp:3152-3153
Publication Date(Web):9 June 2010
DOI:10.1016/j.tetlet.2010.04.048
Two novel 3-nor-methyl-chamigrane sesquiterpene peroxides, named steperoxide A (1) and B (2), have been isolated from basidiomycete Steccherinum ochraceum. This is the first report on the isolation of chamigrane sesquiterpene from higher fungi. The structures of 1 and 2 were established on the basis of spectroscopic data and single-crystal X-ray analysis.
Co-reporter:Ling Zhang, Rong-Hua Luo, Fei Wang, Ze-Jun Dong, Liu-Meng Yang, Yong-Tang Zheng, Ji-Kai Liu
Phytochemistry 2010 Volume 71(Issue 16) pp:1879-1883
Publication Date(Web):November 2010
DOI:10.1016/j.phytochem.2010.08.008
Four highly oxygenated daphnane diterpenoids, trigonothyrins D–G (1–4), were isolated from the stems of Trigonostemon thyrsoideum, and their structures were elucidated on the basis of extensive spectroscopic studies. Inhibitory activity against HIV-1 was assessed for compounds 1, 3 and 4, wherein, 3 showed activity with an EC50 value of 0.13 μg/mL and a therapeutic index (TI) of 75.1.Trigonothyrins D–G (1–4), four highly oxygenated daphnane diterpenoids, were isolated from the stems of Trigonostemon thyrsoideum. Trigonothyrin F (3) showed significant activity against HIV-1.
Co-reporter:Ling Zhang, Yu Shen, Fei Wang, Ying Leng, Ji-Kai Liu
Phytochemistry 2010 Volume 71(Issue 1) pp:100-103
Publication Date(Web):January 2010
DOI:10.1016/j.phytochem.2009.09.020
Rare merosesquiterpenoids, craterellins A–C (1–3), were isolated from cultures of basidiomycete Craterellus odoratus together with the previously known massarinolin C (4). Structures of 1–3 were elucidated on the basis of extensive spectroscopic analysis. Compounds 1–3 possess a rare, epoxymethylenecyclohexanetriol-bicyclofarnesane sesquiterpene hybrid skeleton. Compounds 1–4 were evaluated for their inhibitory activities against two isozymes of 11β-hydroxysteroid dehydrogenases (11β-HSD1 and 11β-HSD2).Merosesquiterpenids, craterellins A–C (1–3), were isolated from cultures of the basidiomycete Craterellus odoratus together with the previously known massarinolin C (4). Compounds 1–3 possess a rare, epoxymethylenecyclohexanetriol-bicyclofarnesane sesquiterpene hybrid skeleton. Compounds 1–4 were evaluated for their inhibitory activities against 11β-hydroxysteroid dehydrogenases.
Co-reporter:Fei Wang, Xue-Lian Cheng, Ya-Ju Li, Song Shi and Ji-Kai Liu
Journal of Natural Products 2009 Volume 72(Issue 11) pp:2005-2008
Publication Date(Web):October 8, 2009
DOI:10.1021/np900449r
Six new ent-pimarane diterpenoids, namely, ent-14β,16-epoxy-8-pimarene-3β,15α-diol (1), 7β-hydroxydarutigenol (2), 9β-hydroxydarutigenol (3), 16-O-acetyldarutigenol (4), 15,16-di-O-acetyldarutoside (5), and 16-O-acetyldarutoside (6), were isolated from the ethanol extract of Siegesbeckia orientalis. Their structures were elucidated on the basis of spectroscopic studies, and the absolute configuration of 1 was established by the modified Mosher’s method. Furthermore, the structure of ent-12β,16-epoxy-8-pimarene-2α,15β,19-triol, recently isolated from the same plant, should be revised as ent-14β,16-epoxy-8-pimarene-2α,15α,19-triol (10).
Co-reporter:Meng-Yuan Jiang, Ling Zhang, Rong Liu, Ze-Jun Dong and Ji-Kai Liu
Journal of Natural Products 2009 Volume 72(Issue 8) pp:1405-1409
Publication Date(Web):July 22, 2009
DOI:10.1021/np900182m
Eleven new oxygenated cyclohexanoids, speciosins A−K (1−11), and aporpinone A (12) were isolated from broth cultures of the basidiomycete Hexagonia speciosa. Their structures were elucidated on the basis of extensive spectroscopic analysis, while the structure of 8 was additionally confirmed by analysis of single-crystal X-ray diffraction data.
Co-reporter:Rong Liu;Zhong-Yu Zhou;Di Xu;Fei Wang
Helvetica Chimica Acta 2009 Volume 92( Issue 2) pp:375-378
Publication Date(Web):
DOI:10.1002/hlca.200800298
Co-reporter:Fei Wang, Fu-Cai Ren, Ji-Kai Liu
Phytochemistry 2009 Volume 70(Issue 5) pp:650-654
Publication Date(Web):March 2009
DOI:10.1016/j.phytochem.2009.03.007
2,3-Secofernane triterpenoids, alstonic acids A (1) and B (2), were isolated from the leaves of Alstonia scholaris together with an indole alkaloid, N1-methoxymethyl picrinine (3). Their structures were established from MS and NMR spectroscopic analyses and confirmed by single crystal X-ray diffraction analysis.2,3-Secofernane triterpenoids, alstonic acids A (1) and B (2), were isolated from leaves of Alstonia scholaris together with an indole alkaloid, N1-methoxymethyl picrinine. Their structures were established from MS and NMR spectroscopic analysis and confirmed by single crystal X-ray diffraction analysis.
Co-reporter:Ling Zhang, Yu Shen, Hua-Jie Zhu, Fei Wang, Ying Leng and Ji-Kai Liu
The Journal of Antibiotics 2009 62(5) pp:239-242
Publication Date(Web):March 27, 2009
DOI:10.1038/ja.2009.17
Five new secondary metabolites derived from pentanol, namely catathelasmols A–E (1–5), were isolated from the fruiting bodies of the basidiomycete Catathelasma imperiale. Their structures were elucidated on the basis of spectroscopic analysis, and the absolute configurations were determined by computational chemistry. Compounds 3, 4 and 5 showed inhibitory activities against two isozymes of 11-hydroxysteroid dehydrogenases (11-HSD1 and 11-HSD2), with IC50 values of 28.7–62.3 g ml−1 (human 11-HSD1), 30.4–149.2 g ml−1 (mouse 11-HSD1), 5.1–177 g ml−1 (human 11-HSD2) and 32.3–129.1 g ml−1 (mouse 11-HSD2), which catalyze the interconversion of cortisol and cortisone.
Co-reporter:Qiuyan Liu, Xiaoli Shu, Li Wang, Anna Sun, Jikai Liu and Xuetao Cao
Cellular & Molecular Immunology 2008 5(4) pp:271-278
Publication Date(Web):2008-08-01
DOI:10.1038/cmi.2008.33
Discovery and functional identification of plant-derived small compounds as the immunosuppressant attract much attention these years. Albaconol is a new kind of small compound, prenylated resorcinol, isolated from the fruiting bodies of the inedible mushroom Albatrellus confluens. Our previous studies showed that albaconol can inhibit tumor cell growth and dendritic cell maturation. However, the immunomodulatory roles and the underlying mechanisms of albaconol have not been fully understood. In this study we investigated the effects of albaconol on the proliferation and LPS-induced proinflammatory cytokine production of macrophages. Albaconol, when used at a dose higher than 1.0 g/ml, inhibited proliferation of RAW264.7 cells in a dose- and time-dependent manner, and could induce cellular apoptosis when used at high dosage ( 7.5 g/ml). Furthermore, we found that albaconol used at a lower dosage without apoptosis induction could significantly inhibit LPS-induced TNF-, IL-6, IL-1 and NO production in RAW264.7 cells. The inhibition of NF-B activation and enhancement of SOCS1 expression in LPS-stimulated macrophages by albaconol may contribute to the above immunosuppressive or anti-inflammatory activities of albaconol. Our results suggest that albaconol may be a potential immunosuppressive and anti-inflammatory drug.
Co-reporter:Zhong-Yu Zhou, Jian-Guo Tang, Fei Wang, Ze-Jun Dong and Ji-Kai Liu
Journal of Natural Products 2008 Volume 71(Issue 8) pp:1423-1426
Publication Date(Web):July 4, 2008
DOI:10.1021/np8002657
Five new tremulane-type sesquiterpenes, 11,12-dihydroxy-1-tremulen-5-one (1), 11,12-epoxy-12β-hydroxy-1-tremulen-5-one (2), 5α,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate (3), 2α,11-dihydroxy-1(10)-tremulen-5,12-olide (4), and 10β,11-dihydroxy-5,6-seco-1,6(13)-tremuladien-5,12-olide (5), as well as three new aliphatic diketones, 2,3-dihydroxydodecane-4,7-dione (9 and 10) and 1-hydroxydecane-2,5-dione (11), together with three known sesquiterpene analogues, tremulenediol A (6), conocenol B (7), and conocenolide A (8), were isolated from cultures of the basidiomycete Conocybe siliginea.
Co-reporter:Zhong-Yu Zhou, Fei Wang, Jian-Guo Tang, Li-Zhen Fang, Ze-Jun Dong and Ji-Kai Liu
Journal of Natural Products 2008 Volume 71(Issue 2) pp:223-226
Publication Date(Web):February 2, 2008
DOI:10.1021/np070638p
Nine new acetylenic acids, gallicynoic acids A−I (1–9), have been isolated from a culture of the basidiomycete Coriolopsis gallica. The structures of 1–9 were elucidated on the basis of spectroscopic and chemical means.
Co-reporter:Xiao-Long Yang;Cheng Qin;Fei Wang;Ze-Jun Dong
Chemistry & Biodiversity 2008 Volume 5( Issue 3) pp:484-489
Publication Date(Web):
DOI:10.1002/cbdv.200890047
Abstract
A new farnesyl phenol named (+)-(R)-grifolinone C (1) has been isolated from the fruiting bodies of the basidiomycete Albatrellus confluens. (+)-(R)-Grifolinone C (1), a dimeric meroterpenoid, is accompanied by albatrellin (2), grifolinone B (3), grifolin (4), and grifolinone A (5). Albatrellin (2) exhibited cytotoxic activity against HepG2 human lung carcinoma cells with IC50 value of 1.55 μg ml−1. The structures were established on the basis of spectral evidence (IR, 1D- and 2D-NMR, and MS analyses).
Co-reporter:Jian-Guo Tang;Yun-Hua Wang;Rui-Rui Wang;Ze-Jun Dong;Liu-Meng Yang;Yong-Tang Zheng
Chemistry & Biodiversity 2008 Volume 5( Issue 3) pp:447-460
Publication Date(Web):
DOI:10.1002/cbdv.200890044
Abstract
Flazin isolated from the fruiting bodies of Suillus granulatus was found to possess weak anti-HIV activity (EC50=2.36 μM, TI=12.1). To establish a SAR study, 46 flazin analogues were synthesized, and their anti-HIV activities were evaluated in vitro. Among them, flazinamide (9a) showed the most potent activity with an EC50 value of 0.38 μM and a TI value of 312.0. The results suggested that appropriate substituents at positions 3, 1′, and 5′ of flazin might play a crucial role in determining their anti-HIV activities, and that flazinamide can be considered as a promising, readily available anti-HIV agent.
Co-reporter:Xiang-Dong Qin, Hong-Jun Shao, Ze-Jun Dong and Ji-Kai Liu
The Journal of Antibiotics 2008 61(9) pp:556-562
Publication Date(Web):2008-09-01
DOI:10.1038/ja.2008.74
Six new sesquiterpenes having the botryane carbon skeleton (1~6), together with known compounds (7~10) were induced and isolated from the ascomycete Daldinia concentrica (strain S 0318). Structures elucidation was accomplished by NMR spectroscopic and X-ray crystallographic studies.
Co-reporter:Hong-Jun Shao, Xiang-Dong Qin, Ze-Jun Dong, Hong-Bin Zhang and Ji-Kai Liu
The Journal of Antibiotics 2008 61(3) pp:115-119
Publication Date(Web):2008-03-01
DOI:10.1038/ja.2008.119
Daldinin A, B, C with a new skeleton, together with four known compounds, were induced and isolated from cultures of the ascomycete Daldinia concentrica. Their structures were elucidated by spectroscopic analysis, and that of daldinin A was confirmed by single-crystal X-ray diffraction.
Co-reporter:Dong-Ze Liu, Fei Wang and Ji-Kai Liu
Journal of Natural Products 2007 Volume 70(Issue 9) pp:1503-1506
Publication Date(Web):September 7, 2007
DOI:10.1021/np070140n
Six new tremulane sesquiterpenes, conocenol A–D (2–5), conocenolide A (6), and conocenolide B (7), have been isolated from cultures of the basidiomycete Conocybe siliginea. The structures of 2–7 were elucidated by the analysis of spectroscopic data, including heteronuclear multiple-bond correlation, heteronuclear single-quantum coherence, and 1H,1H correlation spectroscopy, and a comparison with known analogues.
Co-reporter:Dong-Ze Liu, Fei Wang, Liu-Meng Yang, Yong-Tang Zheng and Ji-Kai Liu
The Journal of Antibiotics 2007 60(5) pp:332-334
Publication Date(Web):2007-05-01
DOI:10.1038/ja.2007.44
A new cadinane sesquiterpene (4,14-dihydroxy-6,7H-1(10)-cadinene, 1) was isolated from the cultures of the basidiomycete, Tyromyces chioneus. Its structure was established on the basis of spectral measurements (MS, IR, 1D and 2D NMR experiments). 1 showed significant anti-HIV-1 activity with EC50=3.0 g/ml (SI=25.4).
Co-reporter:Xiang-Dong Qin;Ze-Jun Dong;Liu-Meng Yang;Rui-Rui Wang;Yong-Tang Zheng;Yang Lu;Yun-Shan Wu;Qi-Tai Zheng
Helvetica Chimica Acta 2006 Volume 89(Issue 1) pp:127-133
Publication Date(Web):19 JAN 2006
DOI:10.1002/hlca.200690004
A novel benzofuran lactone, named concentricolide (= rel-(6R)-6-ethylbenzo[2,1-b:3,4-c′]difuran-8(6H)-one; 1), was isolated along with four known compounds (friedelin, cytochalasin L-696,474, armillaramide, and russulamide) from the fruiting bodies of the xylariaceous ascomycete Daldinia concentrica. The structure of 1 was established by spectroscopic methods and X-ray crystallographic analysis. Its anti-HIV-1 activity was tested. Results showed that 1 inhibited HIV-1 induced cytopathic effects. The EC50 value was 0.31 μg/ml. The therapeutic index (TI) was 247. Concentricolide exhibited the blockage (EC50 0.83 μg/ml) on syncytium formation between HIV-1 infected cells and normal cells.
Co-reporter:Xiao-Long Yang;Du-Qiang Luo;Ze-Jun Dong
Helvetica Chimica Acta 2006 Volume 89(Issue 5) pp:988-990
Publication Date(Web):24 MAY 2006
DOI:10.1002/hlca.200690103
Two new, red-colored azulene pigments, 7-(1,2-dihydroxy-1-methylethyl)-4-methylazulene-1-carbaldehyde (1) and 7-acetyl-4-methylazulene-1-carbaldehyde (2), were isolated from the fruiting bodies of the basidiomycete Lactarius deliciosus, together with a related, known compound (3). Their structures were established on the basis of spectroscopic evidence including 2D-NMR experiments.
Co-reporter:Ji-Kai Liu;Hong-Jun Shao;Wan-Qiu Yang;Li-Zhen Fang
Helvetica Chimica Acta 2006 Volume 89(Issue 7) pp:1463-1466
Publication Date(Web):26 JUL 2006
DOI:10.1002/hlca.200690147
Two new azulene pigments, 7-(1-hydroxy-1-methylethyl)-4-methylazulene-1-carbaldehyde (1) and 4-methyl-7-(1-methylethyl)azulene-1-carboxylic acid (2), were isolated from the fruiting bodies of the basidiomycete Lactarius hatsudake, together with one known azulene pigment (3). Their structures were determined by spectroscopic means (including 2D-NMR) and by HR-TOF-MS experiments.
Co-reporter:Li-Zhen Fang, Chen Qing, Hong-Jun Shao, Yi-Dong Yang, Ze-Jun Dong, Fei Wang, Wei Zhao, Wan-Qiu Yang and Ji-Kai Liu
The Journal of Antibiotics 2006 59(6) pp:351-354
Publication Date(Web):
DOI:10.1038/ja.2006.49
A fungal pigment, hypocrellin D (1), together with three known perylenequinone derivatives hypocrellin A (2), B (3) and C (4), was isolated from the fruiting bodies of Shiraia bambusicola. Its structure was elucidated on the basis of spectral data including 2D NMR experiments. Hypocrellin D (1) significantly inhibited the growth of tumor cell lines Bel-7721, A-549 and Anip-973 with IC50 values of 1.8, 8.8, 38.4 g/ml, respectively.
Co-reporter:Xing-Na Wang, Jian-Hua Shen, Jian-Chang Du and Ji-Kai Liu
The Journal of Antibiotics 2006 59(10) pp:669-672
Publication Date(Web):
DOI:10.1038/ja.2006.90
One lactone marasmane sesquiterpene named 8,13-dihydroxy-marasm-5-oic acid -lactone (1) and one unsaturated marasmane sesquiterpene named 13-hydroxy-marasm-7(8)-en-5-methoxy -acetal (2) together with a known compound: 7,8,13-trihydroxy-marasm-5-oic acid -lactone (3) were isolated from the fruiting bodies of Russula foetens. Their structures were established on the basis of spectral methods (MS, IR, 1D and 2D NMR experiments).
Co-reporter:Hong-Jun Shao, Chen Qing, Fei Wang, Yan-Li Zhang, Du-Qiang Luo and Ji-Kai Liu
The Journal of Antibiotics 2005 58(12) pp:828-831
Publication Date(Web):
DOI:10.1038/ja.2005.111
A new cytotoxic lanostane triterpenoid, 24(E)-3-hydroxylanosta-8,24-dien-26-al-21-oic acid (1), was isolated from the fruiting bodies of the mushroom Hebeloma versipelle. The structure was elucidated on the basis of spectroscopic studies including 2D NMR experiments. Compound 1 moderately inhibited the growth of several tumor cell lines (IC50 1025.0 g/ml).
Co-reporter:Fei Wang, Du-Qiang Luo and Ji-Kai Liu
The Journal of Antibiotics 2005 58(6) pp:412-415
Publication Date(Web):
DOI:10.1038/ja.2005.53
A new polyene pyrone, aurovertin E (2), was isolated along with aurovertin B (1) from the culture mycelia of the basidiomycete Albatrellus confluens. Their structures were elucidated on the basis of spectroscopic studies including 2D NMR experiments. This is the first example of the occurrence of aurovertins in basidiomycetes.
Co-reporter:Xing-Na Wang, Ren-Xiang Tan and Ji-Kai Liu
The Journal of Antibiotics 2005 58(4) pp:268-270
Publication Date(Web):
DOI:10.1038/ja.2005.31
A novel nitrogen-containing compound, named xylactam (1), was isolated from the fruiting bodies of ascomycete Xylaria euglossa together with two known compounds penochalasin B2 and neoechinulin A. Their structures were elucidated on the basis of spectral data.
Co-reporter:Du-Qiang Luo, Fei Wang, Xiao-Ying Bian and Ji-Kai Liu
The Journal of Antibiotics 2005 58(7) pp:456-459
Publication Date(Web):
DOI:10.1038/ja.2005.60
A new lactarane sesquiterpene, rufuslactone (1), was isolated from the fruiting bodies of the basidiomycete Lactarius rufus. Rufuslactone (1) is an isomer of a previously described lactarane 3,8-oxa-13-hydroxylactar-6-en-5-oic acid -lactone (2) from Lactarius necatar. Its structure was elucidated on the basis of spectroscopic data. Rufuslactone (1) showed antifungal properties against plant pathogenic fungi.
Co-reporter:Jian-Wen Tan;Ji-Bin Xu;Ze-Jun Dong;Du-Qiang Luo
Helvetica Chimica Acta 2004 Volume 87(Issue 4) pp:1025-1028
Publication Date(Web):26 APR 2004
DOI:10.1002/hlca.200490074
Nigricanin (1), the first ellagic acid related derivative from higher fungi, has been isolated from the fruiting bodies of the Basidiomycetes Russula nigricans. The structure of the novel compound was established by spectroscopic and chemical methods.
Co-reporter:Jian-Wen Tan;Fei Wang
Helvetica Chimica Acta 2004 Volume 87(Issue 7) pp:1912-1915
Publication Date(Web):27 JUL 2004
DOI:10.1002/hlca.200490170
A novel N-containing compound, vibratilicin (=3-[3-(dimethylamino)-4-(hydroxyamino)-4-oxobutoxy]-2-(palmitoyloxy)propyl (9E,12E)-octadeca-9,12-dienoate; 1), was isolated from the fruiting bodies of the basidiomycete Cortinarius vibratilis Fr. Compound 1 is a representative of the rare natural products containing hydroxamic acid moieties, and can be viewed as a derivative of neoengleromycin (2). Also isolated from the same fungus were five known compounds: ergosta-5,7,22-trien-3β-ol, 5α,8α-epidioxyergosta-6,22-dien-3β-ol, p-anisic acid, N-(2-hydroxyhexadecanoyl)-4-sphingenine, and (4E,8E)-2-N-(2′-hydroxypalmitoyl)-1-O-(β-D-glucopyranosyl)-9-methyl-4,8-sphingadienine. Their structures were determined mainly spectroscopically, including 2D-NMR techniques (HMBC, HMQC, 1H,1H-COSY).
Co-reporter:Xiang-Dong Qin
Helvetica Chimica Acta 2004 Volume 87(Issue 8) pp:2022-2024
Publication Date(Web):27 AUG 2004
DOI:10.1002/hlca.200490181
A new homologous series of 3-alkyl-5-methoxy-2-methyl-1,4-benzoquinones (1–3), with chain lengths of C21 to C23, were isolated from the fruiting bodies of Daldinia concentrica, together with five known compounds. The molecular structures were established by spectroscopic methods.
Co-reporter:Ji-Kai Liu;Fei Wang
Helvetica Chimica Acta 2004 Volume 87(Issue 8) pp:2131-2134
Publication Date(Web):27 AUG 2004
DOI:10.1002/hlca.200490193
A pair of novel heptentriol stereoisomers, hept-6-ene-2,4,5-triols 2 and 3, were isolated from the culture broth of the ascomycete Daldinia concentrica (Bolton : Fries) Cesati & De Notaris, besides three known compounds, i.e., 2,3-dihydro-5-hydroxy-2-methyl-4H-1-benzopyran-4-one (1), 3,5-dihydroxy-2-(1-oxobutyl)-cyclohex-2-en-1-one (4), and pyroglutamic acid (=5-oxo-L-proline; 5). Their structures were determined by spectroscopic means, including 2D-NMR (HMQC, HMBC, 1H,1H-COSY).
Co-reporter:Ji-Kai Liu;Bing-Ji Ma;Hua-Jie Zhu
Helvetica Chimica Acta 2004 Volume 87(Issue 11) pp:2877-2881
Publication Date(Web):24 NOV 2004
DOI:10.1002/hlca.200490259
The novel cyathane-type diterpenoids scabronine G and H (1 and 2, resp.) were isolated from the fruiting bodies of the basidiomycete Sarcodon scabrosus together with four known compounds, allocyathin B2 (3), sarcodonin A (4), sarcodonin G (5), and scabronine F (6). Their structures were determined by spectroscopic means, including 2D-NMR (HMBC, HMQC, ROESY, 1H,1H-COSY).
Co-reporter:Ji-Kai Liu;Lin Hu;Ze-Jun Dong;Qun Hu
Chemistry & Biodiversity 2004 Volume 1(Issue 4) pp:601-605
Publication Date(Web):27 APR 2004
DOI:10.1002/cbdv.200490050
The antioxidant activities of ten natural p-terphenyl derivatives, 1–10, obtained from the fruiting bodies of three edible mushrooms (Thelephora ganbajun, Thelephora aurantiotincta, Boletopsis grisea) indigenous to China were evaluated in comparison with BHA (‘butylated hydroxyanisole’=(1,1-dimethylethyl)-4-methoxyphenol) and α-tocopherol by the DPPH (‘1,1-diphenyl-2-picrylhydrazyl’=2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl) radical-scavenging method. The compounds 1–3 showed significant antioxidant activity. The antioxidant activities of compounds 1–10 and reference compounds followed the order: 2>BHA>1>3>α-tocopherol>10>9>6 > 5>8>7>4. The compound 2 exhibited the strongest radical-scavenging activity with an EC50 value of 0.07 (EC50(BHA) 0.09; EC50(α-tocopherol) 0.25).
Co-reporter:Jianwen Tan;Zejun Dong;Lin Hu;Jikai Liu
Helvetica Chimica Acta 2003 Volume 86(Issue 2) pp:307-309
Publication Date(Web):26 FEB 2003
DOI:10.1002/hlca.200390032
A novel N-containing aristolane sesquiterpenoid compound, lepidamine (1), was isolated from the fruiting bodies of Basidiomycete Russula lepida. Its structure was established by spectroscopic means. It is the first aristolane-type sesquiterpene alkaloid isolated from nature.
Co-reporter:Xing Zhang;Duqiang Luo;Jikai Liu;Xuan Tian
Helvetica Chimica Acta 2003 Volume 86(Issue 8) pp:2784-2786
Publication Date(Web):28 AUG 2003
DOI:10.1002/hlca.200390228
A novel diterpenoid-related compound, triptowilfolide (1), was isolated from the root bark of the Tripterygium wilfordii. Its structure was established by spectroscopic means.
Co-reporter:Ding Zhi-Hui;Li Jing-Ping;Wang Cheng;Zheng Qi-Tai;Liu Ji-Kai;Lu Yang
Helvetica Chimica Acta 2002 Volume 85(Issue 3) pp:882-884
Publication Date(Web):26 APR 2002
DOI:10.1002/1522-2675(200203)85:3<882::AID-HLCA882>3.0.CO;2-A
A novel, highly symmetrical compound, named tremellin (1), was isolated from the fruiting bodies of the basidiomycete Tremella aurantilba. Its structure was established by spectroscopic means and X-ray analysis.
Co-reporter:Tan Jian-Wen;Dong Ze-Jun;Liu Ji-Kai
Helvetica Chimica Acta 2000 Volume 83(Issue 12) pp:3191-3197
Publication Date(Web):21 DEC 2000
DOI:10.1002/1522-2675(20001220)83:12<3191::AID-HLCA3191>3.0.CO;2-V
Three new triterpenoids and two new aristolane sesquiterpenoids, namely (24E)-3β-hydroxycucurbita-5,24-diene-26-oic acid (1), (24E)-3,4-secocucurbita-4,24-diene-3,26-dioic acid (4), (24E)-3,4-secocucurbita-4,24-diene-3,26,29-trioic acid (5), rulepidadiol (6), and rulepidatriol (7), were isolated from the fruiting bodies of Basidiomycetes Russula lepida. Their structures were established by spectral methods. Acids 4, and 5 are the first examples of naturally occurring seco-ring-A cucurbitane triterpenoids. Alcohols 6 and 7, belonging to the aristolane-type sesquiterpenoids, are of a type rather rare in nature, especially among fungal species.
Co-reporter:Fei Wang, Ku Yang, Fu-Cai Ren, Ji-Kai Liu
Fitoterapia (January 2009) Volume 80(Issue 1) pp:21-24
Publication Date(Web):1 January 2009
DOI:10.1016/j.fitote.2008.09.009
Phytochemical study on the ethanol extract of the aerial parts of Carpesium abrotanoides led to the isolation of two new sesquiterpene lactones, carabrolactone A (1) and carabrolactone B (2). Their structures were elucidated on the basis of extensive spectroscopic analysis.
Co-reporter:Ying Huang, Shuai-Bing Zhang, He-Ping Chen, Zhen-Zhu Zhao, Zheng-Hui Li, Tao Feng, Ji-Kai Liu
Fitoterapia (December 2016) Volume 115() pp:177-181
Publication Date(Web):1 December 2016
DOI:10.1016/j.fitote.2016.10.006
Five new acetylenic acid analogues, craterellynes A–E (1–5), together with three known compounds (6–8), were isolated from the fruiting bodies of Craterellus lutescens. Their structures were elucidated on the basis of spectroscopic and chemical means. The absolute configurations of 1–6 were determined by the modified Mosher method.Graphical abstractDownload high-res image (108KB)Download full-size image
Co-reporter:Long-Fei Li, Ben Chung-Lap Chan, Grace Gar-Lee Yue, Clara Bik-San Lau, Quan-Bin Han, Ping-Chung Leung, Ji-Kai Liu, Kwok-Pui Fung
Phytomedicine (15 October 2013) Volume 20(Issue 13) pp:1196-1202
Publication Date(Web):15 October 2013
DOI:10.1016/j.phymed.2013.06.005
Rubinoboletus ballouii is an edible mushroom wildly grown in Yunnan province, China. Up till now, little was known about the chemical and biological properties of this mushroom. The aim of this study was to investigate the immunomodulatory effects of the ethanolic extract of Rubinoboletus ballouii and its fractions on human peripheral blood mononuclear cells (PBMCs) using bioactivity-guided fractionation. The crude extract of the fruiting bodies of RB was fractionated by high-speed counter current chromatography (HSCCC). Twelve fractions were obtained and the third fraction (Fraction C) exerted the most potent anti-inflammatory activities in mitogen-activated PBMCs. Further fractionation of fraction C led to the isolation of two single compounds which were elucidated as 1-ribofuranosyl-s-triazin-2(1H)-one and pistillarin, respectively. The results showed that both 1-ribofuranosyl-s-triazin-2(1H)-one and pistillarin exhibited significant immunosuppressive effects on phytohemagglutinin (PHA)-stimulated human PBMCs by inhibiting [methyl-3H]-thymidine uptake and inflammatory cytokines productions such as tumor necrosis factor (TNF)-α, interleukin (IL)-10, interferon (IFN)-γ and IL-1β. Besides, 1-ribofuranosyl-s-triazin-2(1H)-one was firstly found in natural resources, and pistillarin was also isolated from the family Boletaceae for the first time. They exhibited great potential in developing as anti-inflammatory reagents.Download high-res image (196KB)Download full-size image
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