Co-reporter:Junjie Han, Congcong Liu, Li Li, Hui Zhou, Li Liu, Li Bao, Qian Chen, Fuhang Song, Lixin Zhang, Erwei Li, Ling Liu, Yunfei Pei, Cheng Jin, Yanfen Xue, Wenbing Yin, Yanhe Ma, and Hongwei Liu
The Journal of Organic Chemistry November 3, 2017 Volume 82(Issue 21) pp:11474-11474
Publication Date(Web):October 11, 2017
DOI:10.1021/acs.joc.7b02010
New tetramic acid derivatives, (±)-conipyridoins A–D (1–4), conipyridoins E (5) and F (6), and new 4-hydroxy-2-pyridone alkaloids (±)-didymellamide E (7), (+)-didymellamide B (8), (+)-N-hydroxyapiosporamide (9), and didymellamides F–H (10–12) were isolated and identified from the solid culture of the fungus Coniochaeta cephalothecoides. Chiral resolution of 1, 2, 3, 4, and 7 gave five pairs of enantiomers: 1a/1b, 2a/2b, 3a/3b, 4a/4b, and 7a/7b, respectively. Stereochemistry of 1a and 1b, and 2a and 2b was established and confirmed by the single-crystal X-ray diffraction and electronic circular dichroism (ECD) methods. Absolute configuration in 3a, 3b, 4a, 4b, 7a, and 7b was assigned by ECD calculations. Compounds 1–6 possess an unprecedented chemical skeleton featuring a decalin ring and a tetramic acid moiety. Compound 11 significantly inhibited the growth of Candida albicans and Aspergillus fumigatus with minimum inhibitory concentration (MIC) of 3.13 and 1.56 μM, respectively, and was further confirmed to be a new chitin synthesis inhibitor. Compound 5 exhibited the strongest activity against the growth of both Staphylococcus aureus and MRSA with MIC value of 0.97 μM. In the light of a co-occurrence of 3-acyl tetramic acids and biogenetically related pyridine alkaloids, the biosynthetic pathway for 1–12 was postulated.
Co-reporter:Li Liu, Long Wang, Li Bao, Jinwei Ren, Buddha Bahadur Basnet, Ruixing Liu, Luwei He, Junjie Han, Wen-Bing Yin, and Hongwei Liu
Organic Letters February 17, 2017 Volume 19(Issue 4) pp:
Publication Date(Web):February 9, 2017
DOI:10.1021/acs.orglett.7b00145
Three highly modified indole alkaloids, versicoamides F–H (1–3), together with seven known alkaloids (4–10) were isolated from the fungus Aspergillus tennesseensis. The structures of new compounds were determined by analysis of the NMR and MS spectroscopic data. The absolute configurations of 1 and 2 were assigned by single-crystal X-ray diffraction experiments. Compounds 1 and 2 showed weak antiproliferative activity against the H460 cell line. Compounds 1–3 represent a new class of natural product hybrids with new chemical skeletons.
Co-reporter:Kai Wang, Li Bao, Ke Ma, Jinjin Zhang, Baosong Chen, Junjie Han, Jinwei Ren, Huajun Luo, Hongwei Liu
European Journal of Medicinal Chemistry 2017 Volume 127(Volume 127) pp:
Publication Date(Web):15 February 2017
DOI:10.1016/j.ejmech.2016.11.015
•Three new meroterpenoids were isolated from the fruiting bodies of Ganoderma leucocontextum.•The inhibitory effects of 1–8 on HMG-CoA reductase and α-glucosidase were tested in vitro.•Ganomycin I (4) exerted hypoglycemic, hypolipidemic and insulin-sensitizing effects in KK-Ay mice.Three new meroterpenoids, ganoleucin A-C (1–3), together with five known meroterpenoids (4–8), were isolated from the fruiting bodies of Ganoderma leucocontextum. The structures of the new compounds were elucidated by extensive spectroscopic analysis, circular dichroism (CD) spectroscopy, and chemical transformation. The inhibitory effects of 1–8 on HMG-CoA reductase and α-glucosidase were tested in vitro. Ganomycin I (4), 5, and 8 showed stronger inhibitory activity against HMG-CoA reductase than the positive control atorvastatin. Compounds 1, and 3–8 presented potent noncompetitive inhibitory activity against α-glucosidase from both yeast and rat small intestinal mucosa. Ganomycin I (4), the most potent inhibitor against both α-glucosidase and HMG-CoA reductase, was synthesized and evaluated for its in vivo bioactivity. Pharmacological results showed that ganomycin I (4) exerted potent and efficacious hypoglycemic, hypolipidemic, and insulin-sensitizing effects in KK-Ay mice.Download high-res image (225KB)Download full-size image
Co-reporter:Baosong Chen, Jin Tian, Jinjin Zhang, Kai Wang, Li Liu, Bo Yang, Li Bao, Hongwei Liu
Fitoterapia 2017 Volume 120(Volume 120) pp:
Publication Date(Web):1 July 2017
DOI:10.1016/j.fitote.2017.05.005
Seven new compounds including four lanostane triterpenoids, lucidenic acids Q-S (1–3) and methyl ganoderate P (4), and three triterpene-farnesyl hydroquinone conjugates, ganolucinins A-C (5–7), one new natural product ganomycin J (8), and 73 known compounds (9–81) were isolated from fruiting bodies of Ganoderma lucidum. The structures of the compounds 1–8 were determined by spectroscopic methods. Bioactivities of compounds isolated were assayed against HMG-CoA reductase, aldose reductase, α-glucosidase, and PTP1B. Ganolucidic acid η (39), ganoderenic acid K (44), ganomycin J (8), and ganomycin B (61) showed strong inhibitory activity against HMG-CoA reductase with IC50 of 29.8, 16.5, 30.3 and 14.3 μM, respectively. Lucidumol A (67) had relatively good effect against aldose reductase with IC50 of 19.1 μM. Farnesyl hydroquinones ganomycin J (8), ganomycin B (61), ganomycin I (62), and triterpene-farnesyl hydroquinone conjugates ganoleuconin M (76) and ganoleuconin O (79) possessed good inhibitory activity against α-glucosidase with IC50 in the range of 7.8 to 21.5 μM. This work provides chemical and biological evidence for the usage of extracts of G. lucidum as herbal medicine and food supplements for the control of hyperglycemic and hyperlipidemic symptoms.Download high-res image (141KB)Download full-size image
Co-reporter:Li Liu;Ruixing Liu;Buddha Bahadur Basnet;Li Bao;Junjie Han;Jinwei Ren;Zhaoqing Zeng;Wenying Zhuang
RSC Advances (2011-Present) 2017 vol. 7(Issue 82) pp:51986-51992
Publication Date(Web):2017/11/07
DOI:10.1039/C7RA11365J
One new pimarane diterpene (1) and four new β-resorcylic acid lactones (2–5), together with eight known compounds (6–13) were isolated from the solid culture of the fungicolous Hypomyces subiculosus. The structures of the new compounds were elucidated using extensive spectroscopic methods, including 1D and 2D NMR, HRESIMS, CD experiments, and chemical means. Compound 1 is a ring cleavage pimarane diterpene possessing a bicyclic ring system. All compounds were evaluated for cytotoxic activities. Only compound 7 showed moderate cytotoxicity against the A549 cell line with an IC50 of 44.5 μM.
Co-reporter:Luwei He, Junjie Han, Baowei Li, Li Huang, Ke Ma, Quan Chen, Xinzhong Liu, Li Bao, Hongwei Liu
European Journal of Medicinal Chemistry 2016 Volume 111() pp:183-192
Publication Date(Web):23 March 2016
DOI:10.1016/j.ejmech.2016.01.056
•We revealed a new fungal diterpene named as cyathin Q.•Cyathin Q suppressed the growth of HCT 116 and bax-deficiency HCT116 cells in vivo and in vitro.•Apoptosis induction of cyathin Q is ROS-mediated.•The anticancer activity of cyathin Q is dependent on mitochondria and autophagy-related apoptosis.Diterpenes has been reported to possess multiple bioactivities consisting of anti-microbial and anti-inflammatory properties. This study reveals a new cyathane-type diterpene (cyathin Q) from the culture of the fungus Cyathus africanus by bioactivity-guided separation. The structure of cyathin Q was determined based on spectroscopic measurements (NMR and MS). The bioactivity evaluation shows that cyathin Q has a strong anticancer activity against HCT116 cells and Bax-deficient HCT116 in vitro and in vivo. This compound induced hallmarks of apoptotic events in HCT116 cells, including caspase activation, cytochrome c release, poly (ADP-ribose) polymerase (PARP) cleavage, and depolarization of the mitochondrial inner transmembrane potential. This process is accompanied with the increased mitochondrial ROS, down-regulation of Bcl-2 protein, and up-regulation of Bim protein. We also observed the cleavage of autophagy-related protein ATG5 in cyathin Q-induced apoptosis. Taken together, our study identified a new fungal diterpene that exhibited anticancer activity via induction of mitochondria and autophagy-dependent apoptosis in HCT116 cells.
Co-reporter:Song Wang;Xiaoqin Luo;Ruoxiang Yan;Quanxin Wang;Qiuyue Qi
Protein & Cell 2016 Volume 7( Issue 11) pp:839-843
Publication Date(Web):2016 November
DOI:10.1007/s13238-016-0325-y
Co-reporter:Qiaoqiao Tao, Ke Ma, Yanlong Yang, Kai Wang, Baosong Chen, Ying Huang, Junjie Han, Li Bao, Xiao-Bin Liu, Zhuliang Yang, Wen-Bing Yin, and Hongwei Liu
The Journal of Organic Chemistry 2016 Volume 81(Issue 20) pp:9867-9877
Publication Date(Web):September 29, 2016
DOI:10.1021/acs.joc.6b01971
Twelve putative sesquiterpene synthases genes were found in clades along with enzymes with 1,6-, 1,10-, and 1,11-cyclase activities in the genome of Flammulina velutipes. Chemistry investigation of F. velutipes led to the identification of two seco-cuparane sesquiterpenes, flammufuranone A (1) and B (2); 13 new sesquiterpenes with nor-eudesmane, spiroaxane, cadinane, and cuparane skeletons (3-14, 16); as well as two new ergosterol derivatives (17 and 18). Sesquiterpenes (3–14) derived from 1,10-cyclizing enzyme were first reported from this mushroom. The absolute configurations in 1 (3R,7S) and 2 (3R,7R) were assigned by electronic circular dichroism (ECD) calculation. The absolute configuration in 3 was confirmed by X-ray diffraction analysis. The absolute configurations in the 1,2-diol moiety of 13, and in the 1,3-diol moiety of 17 and 18 were determined using Snatzke’s method. Among these compounds, 3, 5, 13, and 14 were found to inhibit the HMG-CoA reductase with IC50 of 114.7, 77.6, 55.5, and 87.1 μM, respectively. Compounds 5, 6, 7, 10, 13, and 14 showed DPP-4 inhibitory activity with IC50 of 75.9, 83.7, 70.9, 79.7, 80.5, and 74.8 μM, respectively. The biosynthesis for sesquiterpenes in F. velutipes was also discussed.
Co-reporter:Jun-Jie Han, Li Bao, Qiao-Qiao Tao, Yi-Jian Yao, Xing-Zhong Liu, Wen-Bing Yin, and Hong-Wei Liu
Organic Letters 2015 Volume 17(Issue 10) pp:2538-2541
Publication Date(Web):April 27, 2015
DOI:10.1021/acs.orglett.5b01080
Ten new ergosteroids, gloeophyllins A–J (1–10), have been isolated from the solid cultures of Gloeophyllum abietinum. The absolute configurations of 1, 2, and 9 were determined by X-ray crystallographic analysis. Compound 1 has a rare C-nor-D-homosteroid skeleton. Compound 9 possesses an unusual ergostane skeleton having a 10-oxabicyclo [4.3.1] decane moiety replacing 6/5 fused C/D rings. Compound 10 represents the first ergosteroid featuring the cleavage of a C8–C14 bond. The cytotoxicity of 1–10 was tested against the human cancer cell lines K562 and HCT116. The biosynthetic pathway for 1–10 is postulated.
Co-reporter:Qiu-Yue Qi, Jin-Wei Ren, Li-Wei Sun, Lu-Wei He, Li Bao, Wei Yue, Qin-Miao Sun, Yi-Jian Yao, Wen-Bing Yin, and Hong-Wei Liu
Organic Letters 2015 Volume 17(Issue 12) pp:3098-3101
Publication Date(Web):June 11, 2015
DOI:10.1021/acs.orglett.5b01356
Two new heterodimeric sesquiterpenes, sterhirsutins C (1) and D (2), along with eight new sesquiterpenoid derivatives, sterhirsutins E–-L (3–10), were isolated from the culture of Stereum hirsutum. The absolute configuration of 1 was assigned by a single-crystal X-ray diffraction experiment. Compounds 1 and 2 possessed an unprecedented chemical skeleton with a 5/5/5/6/9/4 fused ring system. Compound 10 is the first sesquiterpene coupled with a xanthine moiety. Compounds 1–10 showed cytotoxicity against K562 and HCT116 cell lines. Compound 9 induced autophagy in HeLa cells. Compound 5 inhibited the activation of IFNβ promoter in Sendai virus infected cells.
Co-reporter:Kai Wang; Li Bao; Qiuyue Qi; Feng Zhao; Ke Ma; Yunfei Pei
Journal of Natural Products 2015 Volume 78(Issue 1) pp:146-154
Publication Date(Web):January 7, 2015
DOI:10.1021/np5004388
The well-known edible and medicinal mushroom Hericium erinaceus produces various bioactive secondary metabolites. Ten new isoindolin-1-ones, named erinacerins C–L (1–10), together with (E)-5-(3,7-dimethylocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one (11) were isolated from the solid culture of H. erinaceus. The structures of new metabolites were established by spectroscopic methods. The absolute configurations of 3, 4, 9, and 10 were assigned by comparing their specific rotations with those of related phthalimidines (13–20). Compounds 5 and 6, 7 and 8, and 9 and 10 are double-bond positional isomers. In a α-glucosidase inhibition assay, compounds 2–11 showed inhibitory activity with IC50 values ranging from 5.3 to 145.1 μM. Preliminary structure–activity analysis indicated that the terpenoid side chain and the phenolic hydroxy groups contributed greatly to the α-glucosidase inhibitory activity of 1–11. In a cytotoxicity assay, compound 11 also presented weak cytotoxicity against two cell lines, A549 and HeLa, with IC50 values of 49.0 and 40.5 μM.
Co-reporter:Kai Wang, Li Bao, Weiping Xiong, Ke Ma, Junjie Han, Wenzhao Wang, Wenbing Yin, and Hongwei Liu
Journal of Natural Products 2015 Volume 78(Issue 8) pp:1977-1989
Publication Date(Web):August 19, 2015
DOI:10.1021/acs.jnatprod.5b00331
Sixteen new lanostane triterpenes, ganoleucoins A–P (1–16), together with 10 known tripterpenes (17–26), were isolated from the cultivated fruiting bodies of Ganoderma leucocontextum, a new member of the Ganoderma lucidum complex. The structures of the new compounds were elucidated by extensive spectroscopic analysis and chemical transformation. The inhibitory effects of 1–26 on HMG-CoA reductase and α-glucosidase were tested in vitro. Compounds 1, 3, 6, 10–14, 17, 18, 23, 25, and 26 showed much stronger inhibitory activity against HMG-CoA reductase than the positive control atorvastatin. Compounds 13, 14, and 16 presented potent inhibitory activity against α-glucosidase from yeast with IC50 values of 13.6, 2.5, and 5.9 μM, respectively. In addition, the cytotoxicity of 1–26 was evaluated against the K562 and PC-3 cell lines by the MTT assay. Compounds 1, 2, 6, 7, 10, 12, 16, 18, and 25 exhibited cytotoxicity against K562 cells with IC50 values in the range 10–20 μM. Paclitaxel was used as the positive control with an IC50 value of 0.9 μM. This is the first report of secondary metabolites from this medicinal mushroom.
Co-reporter:Danfeng Xue, Quanxin Wang, Ziheng Chen, Lei Cai, Li Bao, Qiuyue Qi, Lei Liu, Xiaohui Wang, Haijing Jin, Jun Wang, Hao Wu, Hongwei Liu, Quan Chen
Bioorganic & Medicinal Chemistry Letters 2015 Volume 25(Issue 7) pp:1464-1470
Publication Date(Web):1 April 2015
DOI:10.1016/j.bmcl.2015.02.030
Autophagy is defined as an evolutionarily conserved process responsible for degradation of the cytoplasmic components including protein aggregates via the lysosomal machinery. Increasing evidence has linked defective autophagic degradation of protein aggregates with the pathogenesis of neurodegenerative disorders, and it is suggested that promotion of autophagy is regarded as a potential therapeutic for these diseases including Parkinson’s disease (PD). Here we identified, 3-anhydro-6-hydroxy-ophiobolin A (X15-2), an ophiobolin derivative from Bipolaris oryzae that can strongly induce autophagic degradation of α-synuclein, the major constituent of Lewy bodies. We showed that X15-2 induced autophagy is dependent on both Beclin1 and Beclin2. Knockout of ATG5 by CRISPER/Cas9 prevented X15-2 induced autophagy and degradation of α-synuclein. Mechanistically, we showed that X15-2 induces ROS and the activation of JNK signaling for the autophagic degradation of α-synuclein in PC12 cells.
Co-reporter:Kai Wang, Li Bao, Ke Ma, Ning Liu, Ying Huang, Jinwei Ren, Wenzhao Wang, Hongwei Liu
Tetrahedron 2015 Volume 71(Issue 51) pp:9557-9563
Publication Date(Web):23 December 2015
DOI:10.1016/j.tet.2015.10.068
Eight new alkaloids (1–8), were isolated from the solid culture of Hericium erinaceus. The structures of new metabolites were established by spectroscopic methods. The absolute configuration of 1 was determined by electronic circular dichroism (ECD) calculation. Compounds 5–8 showed inhibitory activities against both protein tyrosine phosphatase-1B (PTP1B) and α-glucosidase. In the cytotoxicity assay, compounds 1–4 showed moderate cytotoxicity against K562 cells with IC50 values in the range of 11.4–18.2 μM, and also weak cytotoxicity against doxorubicin resistant K562 cells.
Co-reporter:Ke Ma, Li Li, Li Bao, Luwei He, Chen Sun, Bing Zhou, Shuyi Si, Hongwei Liu
Tetrahedron 2015 Volume 71(Issue 12) pp:1808-1814
Publication Date(Web):25 March 2015
DOI:10.1016/j.tet.2015.02.002
Six new 3,4-seco-27-norlanostane triterpenes, ganoboninones A–F (1–6), as well as three known compounds ganoboninketals A–C (7–9), were isolated from the fruiting bodies of the medicinal mushroom Ganoderma boninense. The structures of 1–6 were established by extensive spectroscopic analysis. Compounds 1–6 are new 3,4-seco-27-norlanostane triterpenoids featuring with an interesting tetradecahydrobenzo[4,5]indeno[1,7a-c]furan backbone. The absolute configurations in 1–6 were determined by CD spectral analysis, and ECD calculation. In an in vitro anti-Plasmodium falciparum bioassay, compounds 1, 2, and 6 showed antimalarial effects with IC50 values of 27.36, 15.68, and 2.03 μM, respectively. In a transactivation assay, compounds 5, 7, 8, and 9 showed agonistic activity to LXRβ with EC50 value of 203.00, 8.32, 257.00, and 86.70 nM, respectively.
Co-reporter:Qiu-Yue Qi, Li Bao, Jin-Wei Ren, Jun-Jie Han, Zong-Yao Zhang, Yi Li, Yi-Jian Yao, Rui Cao, and Hong-Wei Liu
Organic Letters 2014 Volume 16(Issue 19) pp:5092-5095
Publication Date(Web):September 12, 2014
DOI:10.1021/ol502441n
Two new heterodimeric sesquiterpenes, sterhirsutins A (1) and B (2), and two new sesquiterpenes, hirsutic acids D–E (3 and 4), were identified from the culture of Stereum hirsutum. The absolute configurations in 1 and 2 were confirmed by single-crystal X-ray diffraction experiments and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 are likely biosynthesized from a hirsutane-type sesquiterpene and α-humulene by a hetero-Diels–Alder cycloaddition. Compounds 1–4 showed cytotoxicity against K562 and HCT116 cell lines.
Co-reporter:Ke Ma, Li Bao, Junjie Han, Tao Jin, Xiaoli Yang, Feng Zhao, Shaifei Li, Fuhang Song, Miaomiao Liu, Hongwei Liu
Food Chemistry 2014 Volume 143() pp:239-245
Publication Date(Web):15 January 2014
DOI:10.1016/j.foodchem.2013.07.124
•The edible and medicinal mushroom Stereum hirsutum was fermented on rice.•Two new benzoate esters and three new sesquiterpenes were purified and identified.•The absolute configuration of compound 3 was assigned by X-ray.•New benzoate esters (1 and 2) showed moderate antimicrobial activity.•New sesquiterenes (1 and 3) presented strong NO inhibitory activity and cytotoxicity.In addition to the fruiting bodies, mushroom mycelia can be used as functional foods and nutraceutical materials. In this study, two new benzoate derivatives (1 and 2) and three new sesquiterpenoids (3–5) were isolated from the mycelia of Stereum hirsutum. Their chemical structures were elucidated by NMR experiments. The absolute configuration in 3 was assigned by X-ray crystallographic analysis. In bioactivities evaluation, compounds 1 and 2 showed antimicrobial effects against methicillin-resistant Staphylococcusaureus, and S. aureus with the MIC values of 25.0 μg/mL; compounds 1 and 3 inhibited the NO overproduction in the LPS-induced macrophages with the IC50 values of 19.17 and 15.44 μM, and also displayed cytotoxicity against A549 and HepG2 with IC50 in the range of 10–50 μM. These results support the usage of the mycelia of S. hirsutum as a good functional food.
Co-reporter:Botao Wang, Junjie Han, Wei Xu, Yuhui Chen, Hongwei Liu
Food Chemistry 2014 Volume 152() pp:169-176
Publication Date(Web):1 June 2014
DOI:10.1016/j.foodchem.2013.11.137
•The nest fungus Cyathus gansuensis was fermented on rice.•Seven new cyathane diterpenes (Cyathins J–P) were purified and identified.•Their structures were elucidated by NMR and MS data analysis.•New diterpenes (Cyathins J, K and M) presented moderate NO inhibitory activity.Cyathane diterpenes are important bioactive substances produced by some edible and medicinal fungi. Seven new cyathane type diterpenes, named as cyathins J–P (1–7), together with two known diterpenes (8 and 9), were isolated from the solid culture of the bird’s nest fungus Cyathus gansuensis growing on cooked rice. The structures of the new secondary metabolites were elucidated by NMR experiments. Bioactivity screening indicated that compounds 1, 2, 4, and 8 showed moderate inhibitory activity against NO production in lipopolysaccharide-activated macrophages with an IC50 value of 42, 78, 80, and 16 μM, respectively. The fungus C. gansuensis is a promising source of bioactive secondary metabolites and has application potential in preparing healthy food.
Co-reporter:Ke Ma ; Junjie Han ; Li Bao ; Tiezheng Wei
Journal of Natural Products 2014 Volume 77(Issue 4) pp:942-947
Publication Date(Web):March 19, 2014
DOI:10.1021/np401026b
Edible mushrooms are known as an important source of natural antioxidants. The ethyl acetate extract of the edible mushroom Sarcodon leucopus (Zangzi mushroom) possesses strong antioxidative activity. Bioactivity-guided isolation afforded 10 compounds from its fruiting bodies, including two new sarcoviolins, sarcoviolin β (1) and episarcoviolin β (2), and one new p-terphenyl derivative (3) along with seven known compounds. The structures of the new compounds were elucidated by spectroscopic methods and comparison with the known compounds. Compounds 1–10 were found to have antioxidant effects in the DPPH scavenging assay, the total antioxidant capacity assay, the reducing power assay, and the lipid peroxidation assay. Further study indicated that they could protect DNA strands from free radical-induced cleavage at 200 μM. Compounds 1–10 also presented strong α-glucosidase inhibitory activity. Of all tested compounds, compound 1 exhibited the strongest inhibitory activity, with an IC50 value of 0.58 μM.
Co-reporter:Ke Ma ; Jinwei Ren ; Junjie Han ; Li Bao ; Li Li ; Yijian Yao ; Chen Sun ; Bing Zhou
Journal of Natural Products 2014 Volume 77(Issue 8) pp:1847-1852
Publication Date(Web):July 30, 2014
DOI:10.1021/np5002863
Three new nortriterpenes, ganoboninketals A–C (1–3), featuring rearranged 3,4-seco-27-norlanostane skeletons and highly complex polycyclic systems were isolated from the medicinal mushroom Ganoderma boninense. The structures of the new metabolites were established by spectroscopic methods. The absolute configurations in 1–3 were assigned by electronic circular dichroism (ECD) calculations. Compounds 1–3 showed antiplasmodial activity against Plasmodium falciparum with IC50 values of 4.0, 7.9, and 1.7 μM, respectively. Compounds 1 and 3 also displayed weak cytotoxicity against A549 cell line with IC50 values of 47.6 and 35.8 μM, respectively. Compound 2 showed weak cytotoxicity toward HeLa cell line with an IC50 value of 65.5 μM. Compounds 1–3 also presented NO inhibitory activity in the LPS-induced macrophages with IC50 values of 98.3, 24.3, and 60.9 μM, respectively.
Co-reporter:Qiu-Yue Qi;Li Huang;Lu-Wei He;Jun-Jie Han;Quan Chen;Lei Cai;Hong-Wei Liu
Chemistry & Biodiversity 2014 Volume 11( Issue 12) pp:1892-1899
Publication Date(Web):
DOI:10.1002/cbdv.201400106
Abstract
A new cochlioquinone derivative, cochlioquinone F (1), as well as three known compounds, anhydrocochlioquinone A (2), isocochlioquinone A (3), and isocochlioquinone C (4), were isolated from the PDB (potato dextrose broth) culture of the phytopathogenic fungus Bipolaris luttrellii. The structure of 1 was elucidated on the basis of NMR techniques. The apoptosis-inducing effects of compounds 1–4 were evaluated against HCT116 cancer cells. Compound 2 exhibited the strongest activity in inducing apoptosis on HCT116 cells within the range of 10–30 μM. In addition, the caspase activation, the release of cytochrome c from mitochondria, and the downregulation of Bcl-2 protein in HCT116 cells treated with compound 2 were detected.
Co-reporter:Quan-xin Wang, Qiu-yue Qi, Kai Wang, Li Li, Li Bao, Jun-jie Han, Miao-miao Liu, Li-xin Zhang, Lei Cai, and Hong-wei Liu
Organic Letters 2013 Volume 15(Issue 15) pp:3982-3985
Publication Date(Web):July 22, 2013
DOI:10.1021/ol401736z
Coicenals A–C (1–3) possessing a previously undescribed 10-(sec-butyl)-6-hydroxy-1,7,9-trimethyl-1,6,7,8,9,9a-hexahydro-1,4-methanobenzo[d]oxepin-2(4H)-ylidene)acetaldehyde skeleton and coicenal D (4) with a new 2-(sec-butyl)-5-hydroxy-1,6,8-trimethyl-2,5,6,7,8,8a-hexahydro-1H-4a,1-(epoxymethano)naphthalen-10-ylidene)acetaldehyde skeleton were isolated from the solid culture of the plant pathogenic fungus Bipolaris coicis. The absolute configurations in 1 and 4 were assigned by electronic circular dichroism (ECD) calculations. Compounds 1 and 2 were transformed into 4 and 5 by treatment with acetyl chloride, respectively. Compounds 1–4 showed moderate inhibitory activity against NO release with IC50 values of 16.34 ± 1.12, 23.55 ± 1.37, 10.82 ± 0.83, and 54.20 ± 2.82 μM, respectively.
Co-reporter:Jun-Jie Han ; Li Bao ; Lu-Wei He ; Xiao-Qing Zhang ; Xiao-Li Yang ; Shao-Jie Li ; Yi-Jian Yao ;Hong-wei Liu
Journal of Natural Products 2013 Volume 76(Issue 8) pp:1448-1453
Publication Date(Web):July 19, 2013
DOI:10.1021/np400234u
Five new hispidin derivatives, phaeolschidins A–E (1–5), as well as two known natural products, pinillidine (6) and hispidin (7), were isolated from the fruiting bodies of Phaeolus schweinitzii collected in the Tibetan Plateau. The structures of the new compounds were elucidated by spectroscopic methods. Phaeolschidins A–D (1–4) are new bishispidins. Phaeolschidin E (5) is a new class of hispidin derivative in which one pyrrolidin-2-one moiety was linked to C-3 of hispidin. The antioxidant activity of 1–7 was evaluated using three methods: the DPPH scavenging assay, the total antioxidant capacity assay, and the lipid peroxidation assay. Hispidin showed the strongest antioxidant activity of all tested compounds. This is the first report of secondary metabolites from the fungus P. schweinitzii.
Co-reporter:Yongxia Li, Li Bao, Bin Song, Junjie Han, Heran Li, Feng Zhao, Hongwei Liu
Food Chemistry 2013 Volume 141(Issue 3) pp:1614-1618
Publication Date(Web):1 December 2013
DOI:10.1016/j.foodchem.2013.04.133
The fruiting bodies or mycelia of mushrooms have been used as food and food-flavoring material for centuries due to their nutritional and medicinal value and the diversity of their bioactive components. The present research is the first to investigate the bioactive secondary metabolites from the solid culture of the edible mushroom Neolentinus lepideus. Two new secondary metabolites, 5-methoxyisobenzofuran-4,7(1H,3H)-dione (1) and 1,3-dihydroisobenzofuran-4,6-diol (2), as well as seven known compounds including one benzoquinone derivative (3) and six cinnamic acid derivatives (4–9) were obtained. Their structures were established by means of spectroscopic methods, including 1D and 2D NMR. The bioactivity on the nitric oxide production in lipopolysaccharide-induced macrophages was evaluated for all metabolites (1–9) isolated. Compound 1 showed strong NO inhibitory activity with the IC50 value of 6.2 μM. Compound 2 displayed moderate NO inhibitory activity with the IC50 value of 88.8 μM. In the DPPH scavenging assay, compound 2 displayed antioxidant activity with IC50 of 68.6 μM. The discovery of new NO production inhibitors from N. lepideus expands its usage as a functional food.•Two NO production inhibitors were isolated from the culture of Neolentinus lepideus.•The structure of 1 and 2 was elucidated by NMR and MS data analysis.•Compound 1 showed strong NO inhibitory activity with an IC50 value of 6.2 μM.•Compound 2 displayed moderates NO inhibitory activity with an IC50 value of 88.8 μM.
Co-reporter:Shao-juan Wang ; Li Bao ; Jun-jie Han ; Quan-xin Wang ; Xiao-li Yang ; Hua-an Wen ; Liang-dong Guo ; Shao-jie Li ; Feng Zhao ;Hong-wei Liu
Journal of Natural Products 2013 Volume 76(Issue 1) pp:45-50
Publication Date(Web):January 8, 2013
DOI:10.1021/np3006524
Five novel perhydrobenzannulated 5,5-spiroketal sesquiterpenes, namely, pleurospiroketals A–E (1–5), were isolated from the culture of the edible mushroom Pleurotus cornucopiae. Pleurospiroketals D (4) and E (5) were obtained as an isomeric mixture with a ratio of 5:4. Their structures were established by NMR, X-ray single-crystal diffraction, and CD data analysis. Pleurospiroketals A–E (1–5) are sesquiterpenoids with a unique benzannulated 5,5-spiroketal skeleton. Compounds 1–3 showed inhibitory activity against nitric oxide production in lipopolysaccharide-activated macrophages with IC50 values of 6.8, 12.6, and 20.8 μM, respectively.
Co-reporter:Shaojuan Wang, Li Bao, Feng Zhao, Quanxin Wang, Shaojie Li, Jinwei Ren, Li Li, Huaan Wen, Liangdong Guo, and Hongwei Liu
Journal of Agricultural and Food Chemistry 2013 Volume 61(Issue 21) pp:5122-5129
Publication Date(Web):May 7, 2013
DOI:10.1021/jf401612t
Edible mushroom is a profilic source of bioactive metabolites for the development of drugs and nutraceuticals. In this work, four new monoterpenoids (1–4) and one new sesquiterpenoid (6) were isolated from the mycelia of edible mushroom Pleurotus cornucopiae fermented on rice. Their structures were established by nuclear magnetic resonance, mass spectrometry, and circular dichroism (CD) data analysis. Compound 1 possesses an unusual spiro[benzofuran-3,2′-oxiran] skeleton. The absolute configuration of the 6,7-diol moieties in compounds 1, 2, and 6 was assigned using the in situ dimolybdenum CD method. Compounds 1–5, 7, and 8 showed moderate inhibitory activity against nitric oxide production in lipopolysaccaride-activated macrophages, with IC50 values in the range of 60–90 μM. Compounds 6 and 7 also exhibited slight cytotoxicity against HeLa and HepG2 cells.
Co-reporter:Quan-Xin Wang, Jian-Ling Yang, Qiu-Yue Qi, Li Bao, Xiao-Li Yang, Miao-Miao Liu, Pei Huang, Li-Xin Zhang, Ji-Long Chen, Lei Cai, Hong-Wei Liu
Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 12) pp:3547-3550
Publication Date(Web):15 June 2013
DOI:10.1016/j.bmcl.2013.04.034
A new ophiobolin derivative, 3-anhydro-6-hydroxy-ophiobolin A (1), as well as two known ophiobolin derivatives 3-anhydro-ophiobolin A (2) and 3-anhydro-6-epi-ophiobolin A (3) were isolated from the PDB culture of a phytopathogenic fungus Bipolaris oryzae. The structure of 1 was elucidated through 2D NMR and other spectroscopic techniques. Compound 1 exhibited strong antimicrobial activity against Bacille Calmette–Guerin, Bacillus subtilis, Staphylococcus aureus, and methicillin-resistant Staphylococcus aureus with MIC value of 12.5 μg/mL, and potent antiproliferative activity against cell lines HepG2 and K562 with IC50 of 6.49 μM and 4.06 μM, respectively. Further studies on the cytotoxicity of compound 1 against K562 cells demonstrated that it induced apoptosis, observed by flow cytometric method. Preliminary structure–activity relationships of these ophiobolins and the mechanism of apoptosis induced by 1 were analyzed.
Co-reporter:Shao-juan Wang, Yong-xia Li, Li Bao, Jun-jie Han, Xiao-li Yang, He-ran Li, Ya-qi Wang, Shao-jie Li, and Hong-wei Liu
Organic Letters 2012 Volume 14(Issue 14) pp:3672-3675
Publication Date(Web):July 6, 2012
DOI:10.1021/ol301519m
Eryngiolide A (1), the first member of C20 diterpenoids with the skeleton deriving from a cyclododecane core fused with two γ-lactone units, was isolated from the solid culture of the edible mushroom Pleurotus eryngii. The structure of 1 was elucidated by extensive analysis of NMR spectra. Compound 1 exhibited moderate cytotoxicity against two human cancer lines in vitro.
Co-reporter:Yaqi Wang, Li Bao, Xiaoli Yang, Li Li, Shaifei Li, Hao Gao, Xin-Sheng Yao, Huaan Wen, Hong-Wei Liu
Food Chemistry 2012 Volume 132(Issue 3) pp:1346-1353
Publication Date(Web):1 June 2012
DOI:10.1016/j.foodchem.2011.11.117
The edible mushroom Flammulina velutipes was cultivated on cooked rice. Six new cuparene sesquiterpenes, enokipodins E-J (1–6), and two new sterpurane sesquiterpenes, sterpurols A (10) and B (11), with four known sesquiterpenes, 2,5-cuparadiene-1,4-dione (7), enokipodins B (8) and D (9), and sterpuric acid (12), were isolated from the solid culture of F. velutipes. The structures of new metabolites were elucidated by NMR experiments. The absolute configurations in new compounds were assigned by X-ray crystallographic analysis, the modified Mosher method, and CD data analysis. Bioactivity screening indicated that compounds 5–9 displayed weak antibacterial activity against Bacillus subtilis; 2, 3, and 5 showed weak antifungal activity against Aspergilus fumigatus; 6–9 showed both moderate cytotoxicity against the human tumor cell lines (HepG2, MCF-7, SGC7901, and A549) and antioxidant activity in DPPH scavenging assay. These results suggest that the solid culture of F. velutipes on cooked rice could be a good functional food.Highlights► The edible mushroom Flammulina velutipes was cultivated on cooked rice. ► Eight new sesquiterpenes were purified and identified from its solid culture. ► The absolute configuration was assigned by X-ray, the Mosher and CD methods. ► Cuparene sesquiterpenes showed antimicrobial, cytotoxic and antioxidant activity. ► This is the first report of sterurane type sesquiterpene from this mushroom.
Co-reporter:Ya-Qi Wang;Li Bao;Xiao-Li Yang;Huan-Qin Dai;Hui Guo;Xin-Sheng Yao;Li-Xin Zhang;Hong-Wei Liu
Helvetica Chimica Acta 2012 Volume 95( Issue 2) pp:261-267
Publication Date(Web):
DOI:10.1002/hlca.201100289
Abstract
Flamvelutpenoids A–D (1–4), four new cuparene-type sesquiterpenes, were isolated from the solid culture of Flammulina velutipes. Their structures were elucidated by NMR experiments. The absolute configurations of 1 and 2 were assigned via the circular dichroism data of the [Rh2(OCOCF3)4] complex, whereas that of C(3) of 3 was determined by applying the octant rule for the α,β-unsaturated ketone moiety. Compounds 1–4 showed weak antibacterial activity against Escherichia coli, Bacillus subtilis, and methicillin-resistant Staphylococcus aureus with MIC values larger than 100 μM.
Co-reporter:Wen Wu, Huanqin Dai, Li Bao, Biao Ren, Jingcai Lu, Yuanming Luo, Liangdong Guo, Lixin Zhang, and Hongwei Liu
Journal of Natural Products 2011 Volume 74(Issue 5) pp:1303-1308
Publication Date(Web):March 23, 2011
DOI:10.1021/np100909y
Two new cyclic pentapeptides (1 and 2) and the known blazein (3), ganodesterone (4), ergosterin (5), cerevisterol (6), 24-methylcholesta-4,6,8(14),22-tetraen-3-one (7), 5,8-epidioxyergosta-6,22-dien-3-ol (8), 16-α-d-mannopyranosyloxyisopimar-7-en-19-oic acid (9), and 16-hydroxy isopimar-7-en-19-oic acid (10) have been isolated from the crude extract of an endolichenic Xylaria sp. The structures of 1 and 2 were elucidated primarily by NMR and MS methods. The absolute configurations of 1 and 2 were assigned using Marfey’s method on their acid hydrolysate. Compounds 1−10 were evaluated for activity against fungi and for synergistic antifungal activity. Compound 1 showed synergistic antifungal activity against Candida albicans SC5314 with 0.004 μg/mL ketoconazole.
Co-reporter:Wen Wu;Feng Zhao;Li Bao;Jin-Cai Lu;Hong-Wei Liu
Helvetica Chimica Acta 2011 Volume 94( Issue 11) pp:2020-2026
Publication Date(Web):
DOI:10.1002/hlca.201100100
Abstract
Two new drimane-type sesquiterpenoid ethers of isocitric acid, cryptoporic acids N (1) and O (6), were isolated from the fruiting bodies of Cryptoporus sinensis. Their structures were established by means of spectroscopic methods, including 1D- and 2D-NMR. The cytotoxic activity against a panel of cell lines (A549, MCF-7, PC-3, and PANC-1) was evaluated for all cryptoporic acid derivatives 1–12 isolated.
Co-reporter:Sha Yan;Saifei Li;Wen Wu;Feng Zhao;Li Bao;Rong Ding;Hao Gao;Hua-An Wen;Fuhang Song;Hong-Wei Liu
Chemistry & Biodiversity 2011 Volume 8( Issue 9) pp:1689-1700
Publication Date(Web):
DOI:10.1002/cbdv.201100026
Abstract
Three new sesquiterpene acids, xylaric acids A–C (1–3, resp.), and a new tetralone (=3,4-dihydronaphthalen-1(2H)-one) derivative, 4, along with nine known compounds, xylaric acid D (5), hydroheptelidic acid (6), gliocladic acid (7), chlorine heptelidic acid (8), trichoderonic acid A (9), 16-(α-D-mannopyranosyloxy)isopimar-7-en-19-oic acid (10), 16-(α-D-glucopyranosyloxy)isopimar-7-en-19-oic acid (11), 5-carboxymellein (12), and naphthalen-1,8-diol 1-O-α-D-glucopyranoside (13) have been isolated from the solid culture of the ascomycete fungus Xylaria sp. associated with termite nest. The structures of these compounds were elucidated primarily by NMR experiments. The absolute configurations of compounds 1–3 and 5–9 were determined by combination of X-ray data and CD spectral analysis. The absolute configuration of 4 was assigned by Snatzke's method. Compounds 8 and 11 showed slight cytotoxicities against two cell lines A549 and SGC7901.
Co-reporter:Li Bao;Manyuan Wang;Feng Zhao;Yisong Zhao
Chemistry & Biodiversity 2010 Volume 7( Issue 12) pp:
Publication Date(Web):
DOI:10.1002/cbdv.200900349
Abstract
Two new resorcinol derivatives, 4-hydroxy-2-methoxy-6-[(8Z)-pentadec-8-en-1-yl]phenyl acetate (1) and 4-hydroxy-2-methoxy-6-pentadecylphenyl acetate (2), together with known compounds ardisiphenol D (3), 5-tridecylresorcinol (4), 5-pentadecylresorcinol (5), 5-[(8Z)-pentadec-8-en-1-yl]resorcinol (6), belamcandaquinones C and D (7 and 8, resp.), ardisicrenoside A, ardisiacrispin B, (22E)-24-ethyl-5α-cholesta-7,22-dien-3-one, and (22E)-24-ethyl-5α-cholesta-7,22-dien-3β-ol were isolated from the MeOH extract of the roots of Ardisia brevicaulisDiels. Their structures were determined by spectroscopic analysis including ESI- and EI-MS, and NMR data. Cytotoxicities of 1–4 against cell lines A549, MCF-7, and PANC-1 were tested in vitro by the MTT (=3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide) method. Compounds 1–4 showed cytotoxic activity against all cell lines stronger than that of cisplatin against A549.
Co-reporter:Li Bao;Xiaofeng Ma;Xiaohong Song;Manyuan Wang
Chemistry & Biodiversity 2010 Volume 7( Issue 12) pp:
Publication Date(Web):
DOI:10.1002/cbdv.200900394
Abstract
Two new resveratrol tetramers, cajyphenol A (1) and cajyphenol B (2), together with two known resveratrol dimers, quadrangularin A (3) and pallidol (4), and resveratrol (5) were isolated from the stems of Cayratia japonica (Thunb.) Gagn. Their structures were established by means of NMR (1H,1H-COSY, 1H,13C-HSQC, HMBC, and NOESY) and ESI-MS analyses. Compounds 1–5 showed fast-binding inhibitory activities on fatty acid synthase with the IC50 values of 1.63±0.02, 1.49±0.03, 7.50±0.01, 11.1±0.01, and 10.2±0.01 μM, respectively. Compounds 1–5 also exhibited antioxidant activities in the ORAC assay.
Co-reporter:Li Bao, Xinsheng Yao, Jiekun Xu, Xiaoyu Guo, Hongwei Liu, Hiroshi Kurihara
Fitoterapia (September 2009) Volume 80(Issue 6) pp:349-353
Publication Date(Web):1 September 2009
DOI:10.1016/j.fitote.2009.04.009
The ethanol extract of Pithecellobium clypearia Benth (PCE) was characterized to be rich in polyphenols by HPLC analysis, and investigated for its anti-inflammatory and anti-allergic activities. In our assay, PCE showed anti-inflammatory activity in both acute and auto-immune inflammation animal models. Administration of PCE can effectively inhibit the croton oil-induced ear edema and capillary permeability, the carrageenin-induced paw edema, and the liver injury caused by propionibacterium acnes plus lipopolysaccharide. PCE was also found to possess anti-allergic activity in inhibiting the DNFB-induced delayed hypersensitivity reaction. Meanwhile, seven main components (1–7) from PCE were studied for their effect on histamine release stimulated by compound 48/80 from rat peritoneal mast cells in vitro. Compound 2 ((−)-epigallocatechin-7-gallate), 3 ((−)-5, 7, 3′, 4′, 5′-pentahydroxyflavan), and 5 ((−)-tetra hydroxyflavan-7-gallate) showed significant inhibition effect on histamine release.The ethanol extract of Pithecellobium clypearia Benth (PCE) was investigated for anti-inflammatory and anti-allergic activities. In our assay, PCE showed anti-inflammatory activity in both acute and auto-immune inflammation animal models. Meanwhile, the effect of compounds 1–7 isolated from P. clypearia on histamine release stimulated by compound 48/80 from rat peritoneal mast cells was tested. Compounds 2 ((−)-epigallocatechin-7-gallate), 3 ((−)-5, 7, 3′, 4′, 5′-pentahydroxyflavan), and 5 ((−)-tetra hydroxyflavan-7-gallate) showed significant inhibition effect on histamine release.Download full-size image
Co-reporter:Qiao-Qiao Tao, Ke Ma, Li Bao, Kai Wang, Jun-Jie Han, Jin-Xia Zhang, Chen-Yang Huang, Hong-Wei Liu
Fitoterapia (June 2016) Volume 111() pp:29-35
Publication Date(Web):1 June 2016
DOI:10.1016/j.fitote.2016.04.007
Nine new sesquiterpenoids, clitocybulol derivatives, clitocybulols G–O (1–9) and three known sesquiterpenoids, clitocybulols C–E (10 − 12), were isolated from the solid culture of the edible fungus Pleurotus cystidiosus. The structures of compounds 1–12 were determined by spectroscopic methods. The absolute configurations of compounds 1–9 were assigned via the circular dichroism (CD) data analysis. Compounds 1, 6 and 10 showed moderate inhibitory activity against protein tyrosine phosphatase-1B (PTP1B) with IC50 values of 49.5, 38.1 and 36.0 μM, respectively.Download high-res image (130KB)Download full-size image
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