Qin-Shi Zhao

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Name: 赵勤实
Organization: Chinese Academy of Sciences , China
Department: Kunming Institute of Botany
Title: NULL(PhD)
Co-reporter:Zhi-Jun Zhang, Yin Nian, Qin-Feng Zhu, Xiao-Nian Li, Jia Su, Xing-De Wu, Jian Yang, and Qin-Shi Zhao
Organic Letters September 1, 2017 Volume 19(Issue 17) pp:
Publication Date(Web):August 22, 2017
DOI:10.1021/acs.orglett.7b02293
Lycoplanine A (1), a Lycopodium alkaloid with a 6/9/5 tricyclic ring skeleton fused with the γ-lactone ring and featuring an unusual 1-oxa-6-azaspiro[4.4]nonane moiety and an unprecedented 3-azabicyclo[6.3.1]dodecane unit, was isolated from the club moss Lycopodium complanatum. The structure and absolute configuration of 1 were identified by a combination of NMR spectroscopic analysis and single-crystal X-ray diffraction. Biological studies showed that 1 is a potent Cav3.1 T-type calcium channel (TTCC) inhibitor with an IC50 value of 6.06 μM.
Co-reporter:Xin Shi, Zhen-Tao Deng, Yu Zhu, Ying Bao, Li-Dong Shao, and Qin-Shi Zhao
The Journal of Organic Chemistry October 20, 2017 Volume 82(Issue 20) pp:11110-11110
Publication Date(Web):October 3, 2017
DOI:10.1021/acs.joc.7b02073
A practical synthesis of (±)-cermizine B was achieved. The nine-step synthesis mainly comprised two uninterrupted Michael additions including a highly diastereoselective 1,4-addition of 2-picoline to methyl 4-methyl-6-oxocyclohex-1-ene-1-carboxylate, Krapcho decarboxylation, a double reductive amination that resulted in ring closure and dearomatization of pyridine in 24% overall yield.
Co-reporter:Yu-Chen Liu;Zhi-Jun Zhang;Jia Su;Li-Yan Peng
Natural Products and Bioprospecting 2017 Volume 7( Issue 5) pp:405-411
Publication Date(Web):25 July 2017
DOI:10.1007/s13659-017-0140-z
Three new lycodine-type Lycopodium alkaloids, namely 1-methyllycodine (1), 8α-hydroxy-15,16-dehydro-des-N-methyl-α-obscurine (2), N-methyl-16-hydroxyhuperzine B (3), and one new natural lycodine-type Lycopodium alkaloid, N-methylhuperzine A (4), along with 11 known analogues (5–15), were isolated from the whole plants of club moss Huperzia serrata. The structures of 1–4 were elucidated on the basis of NMR spectroscopic and mass spectrometry data. Among them, compound 1 was the first lycodine-type alkaloid possessing a methyl group at C-1. In addition, the structure of 5 was confirmed by the single-crystal X-ray crystallography data and its 13C NMR was reported for the first time in current study. Compounds 1–5 were tested their BACE1 inhibitory activity.
Co-reporter:Min Fan, Ying Bao, Zhi-Jun Zhang, Hong-Bin Zhang, Qin-Shi Zhao
Fitoterapia 2017 Volume 123(Volume 123) pp:
Publication Date(Web):1 November 2017
DOI:10.1016/j.fitote.2017.09.013
Five new neo-clerodane diterpenoids, tiliifolins A–E (1–5), along with ten known ones, were isolated from the aerial part of Salvia tiliifolia. Their structures were proposed based on 1D and 2D NMR spectroscopic data analysis. All new compounds were evaluated for their neurotrophic activity on PC12 cells and cytotoxicity against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW480), and compound 5 showed statistically significant neuroprotective effect in vitro assay.Download high-res image (215KB)Download full-size image
Co-reporter:Li-Dong Shao, Ying Bao, Yu Shen, Jia Su, Ying Leng, Qin-Shi Zhao
European Journal of Medicinal Chemistry 2017 Volume 135(Volume 135) pp:
Publication Date(Web):28 July 2017
DOI:10.1016/j.ejmech.2017.04.059
•35 dammarane-type derivatives are prepared focusing on rings A and D.•10 compounds are selectively active to human or mouse 11β-HSD1.•One compound is selectively active to the both human and mouse 11β-HSD1.Inspired by natural 11β-HSD1 inhibitors hupehenols A - E, a ring-focused strategy was applied for the synthesis of 35 structurally diverse dammarane-type derivatives. These derivatives were effectively prepared from protopanaxadiol based on the modification of rings A and D. Among these compounds, ten were identified as selective 11β-HSD1 inhibitors (IC50 range: 101–1047 nM, SI range: 8–169) which exhibited inhibitory activities against human or mouse 11β-HSD1. Otherwise, we found 23a could selectively inhibit both human and mouse 11β-HSD1 with IC50 value of 994 and 213 nM (SI > 10 and > 47), respectively. Additionally, the molecular modelling results of 23a docking into the human and mouse 11β-HSD1 were in good agreement with the results from the enzyme inhibitory experiment. Moreover, valuable structural-activity relationship (SAR) information of dammarane-type 11β-HSD1 inhibitor was summarized.Download high-res image (176KB)Download full-size image
Co-reporter:Liao-Bin Dong, Xing-De Wu, Xin Shi, Zhi-Jun Zhang, Jing Yang, and Qin-Shi Zhao
Organic Letters 2016 Volume 18(Issue 18) pp:4498-4501
Publication Date(Web):September 1, 2016
DOI:10.1021/acs.orglett.6b02065
Five new Lycopodium alkaloids, phleghenrines A–D (1–4) and neophleghenrine A (5), were isolated from Phlegmariurus henryi (Baker) Ching. The structures and absolute configurations of 1–5 were determined using extensive spectroscopic data coupled with computational calculations and revealed 1–4 possess a bicyclo[3.2.2]nonane core, whereas 5 possesses an unprecedented 9-azaprotoadamantane core. Compounds 1 and 4 showed potent acetylcholinesterase (AChE) inhibitory activities, and 4 is a good lead natural product for the treatment of Alzheimer’s disease.
Co-reporter:Xing-De Wu, Dan Luo, Wen-Chao Tu, Zhen-Tao Deng, Xue-Jiao Chen, Jia Su, Xu Ji, and Qin-Shi Zhao
Organic Letters 2016 Volume 18(Issue 24) pp:6484-6487
Publication Date(Web):December 1, 2016
DOI:10.1021/acs.orglett.6b03388
Three rearranged labdane-type diterpenoids, hypophyllins A–C (1–3), and a caged labdane diterpenoid possessing a 8,9-dioxatricyclic[4.2.1.13,7]decane moiety, hypophyllin D (4), as well as two new biogenetically related diterpernoids, hypophyllins E (5) and F (6), were isolated from the aerial parts of Hypoestes phyllostachya “Rosea”. The absolute configurations of 1–4 were determined by X-ray diffraction analysis. The plausible biogenetic pathway for 1–4 was also proposed. Compounds 4 and 5 showed potent vasorelaxant activity on endothelium-intact thoracic aorta rings precontracted with KCl.
Co-reporter:Jian Ren, Xin Shi, Xiao-Nian Li, Lai-Wei Li, Jia Su, Li-Dong Shao, and Qin-Shi Zhao
Organic Letters 2016 Volume 18(Issue 16) pp:3948-3951
Publication Date(Web):August 3, 2016
DOI:10.1021/acs.orglett.6b01654
An efficient reaction tool box was developed for the synthesis of skeletally diverse and stereochemically complex templates for a small-molecule library based on the common synthon Q, which was prepared from hemslecin A in four steps. The reaction tool box comprises three acid-promoted rearrangements: semipinacol, Wagner–Meerwein, and cyclopropylmethyl cation rearrangements. More importantly, a Mn-mediated C–H oxidation was developed to achieve a high level of complexity, which provides a new entry for C–H functionalization of inert angular methyl groups in the chemistry of triterpenes. Our reaction-discovery strategy based on hemslecin A provides a basis for the inherent chemistry of triterpenes and could be applied for the further transformation of triterpenes.
Co-reporter:Jun Xu, Li-Dong Shao, Xin Shi, Jian Ren, Chengfeng Xia and Qin-Shi Zhao  
RSC Advances 2016 vol. 6(Issue 68) pp:63131-63135
Publication Date(Web):28 Jun 2016
DOI:10.1039/C6RA12766E
A collective formal synthesis approach to bioactive oxindole alkaloids, including (±)-rhynchophylline, (±)-isorhynchophylline, (±)-mitraphylline, (±)-formosanine, (±)-isomitraphylline, and (±)-isoformosanine, is completed in a protecting-group free manner. Besides multigram-scaled operations, the notable feature of the synthesis is the application of two one-pot, sequential transformations. Namely, two key tetracyclic intermediates pyridinium salt 9 and monoester 14 were prepared by a one-pot N-alkylation/cross-dehydrogenative coupling sequence and a one-pot Michael/Karpocho sequence with minimal purification, respectively.
Co-reporter:Li-Dong Shao, Jun Xu, Xiao-Nian Li, Zhi-Jun Zhang, Xin Shi, Jian Ren, Juan He, Yu Zhao, Ying Leng, Chengfeng Xia and Qin-Shi Zhao  
RSC Advances 2016 vol. 6(Issue 42) pp:35792-35803
Publication Date(Web):04 Apr 2016
DOI:10.1039/C6RA04236H
Hupehenols A–E (3–7) are bioactive octanordammarane triterpenoids, among which hupehenols B (4) and E (7) are the most potent and selective human 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors (IC50 = 15 and 34 nM, respectively). Herein, the hupehenols were synthesized from protopanaxadiol, the main component of Panax notoginseng. The different synthetic attempts resulted in the stereoselective synthesis of hupehenols A, B, and E for further biological exploration. Notable features of the synthesis included a regioselective epoxide-opening reaction, regioselective acetylation, and a late-stage stereoselective oxa-Michael addition. Semi-synthetic derivatization of these natural products led to the determination of their absolute configurations, a better understanding of their inherent reactivity patterns, and the required C-17 configuration for murine 11β-HSD1 inhibition. These studies provide the basis for the synthesis of 11β-HSD1 inhibitors as potential targets for the treatment of type 2 diabetes.
Co-reporter:Jin-Tang Cheng;Zhi-Jun Zhang;Xiao-Nian Li
Natural Products and Bioprospecting 2016 Volume 6( Issue 6) pp:279-284
Publication Date(Web):2016 December
DOI:10.1007/s13659-016-0111-9
Two rare lyconadin-type Lycopodium alkaloids, lyconadins G (1) and H (2), together with four known ones (3–6), were isolated from Lycopodium complanatum. The structures were determined on the basis of their spectroscopic analyses, and the absolute configuration of 1 was established by an X-ray crystallographic analysis. It is the first time to establish the absolute configuration of lyconadin-type Lycopodium alkaloid by an X-ray diffraction experiment. In addition, these findings may provide more information for the biosynthesis of lyconadins.
Co-reporter:Xing-De Wu, Lin-Fen Ding, Wen-Chao Tu, Hui Yang, Jia Su, Li-Yan Peng, Yan Li, Qin-Shi Zhao
Phytochemistry 2016 Volume 129() pp:68-76
Publication Date(Web):September 2016
DOI:10.1016/j.phytochem.2016.07.008
•Twenty-seven sesquiterpenoids were isolated from the flowers of Inula japonica.•Nine previously undescribed sesquiterpenoids were characterized.•Nine compounds exhibited potent cytotoxicity against five cancer cell lines.•Six compounds exhibited inhibition against NO production.Phytochemical investigation of the flowers of Inula japonica led to isolation of nine sesquiterpenoids, inujaponins A-I, as well as eighteen known ones. These sesquiterpenoids belong to six skeletal-types, including eudesmane, 1,10-seco-eudesmane, germacrane, guaiane, 4,5-seco-guaiane, and pseudoguaiane sesquiterpenoids. Their structures were established by extensive spectroscopic analysis. The absolute configurations of inujaponin A, eupatolide, and deacetylovatifolin were determined by Cu-Kα X-ray crystallographic analysis. Most of the isolated compounds exhibited potent cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cancer cell lines, with IC50 values ranging from 1.57 to 22.58 μM. Some selected compounds also possessed significant inhibitory activity against LPS-induced NO production in RAW264.7 macrophages with IC50 values ranging from 1.42 to 8.99 μM.Nine sesquiterpenoids, inujaponins A-I, along with eighteen known ones, were isolated from the flowers of Inula japonica. Their cytotoxicity and inhibitory effect against LPS-induced NO production in RAW264.7 macrophages were evaluated.
Co-reporter:Yong-Jun Jiang, Jia Su, Xin Shi, Xing-De Wu, Xuan-Qin Chen, Juan He, Li-Dong Shao, Xiao-Nian Li, Li-Yan Peng, Rong-Tao Li, Qin-Shi Zhao
Tetrahedron 2016 Volume 72(Issue 35) pp:5507-5514
Publication Date(Web):1 September 2016
DOI:10.1016/j.tet.2016.07.037
Ten new neo-clerodane derivatives (1–10) and 10 known diterpenoids were identified from the aerial parts of Salvia leucantha. The structures of 1–10 were established by 1D and 2D NMR spectroscopic data analysis. The absolute configurations of 1, 3, 6, and 7 were determined by X-ray diffraction data. Compound 16 exhibited cytotoxicity against HCT116, BT474, and HepG2 cancer cell lines and was identified as a heat shock protein 90 inhibitor. Compounds 8, 15, and 16 exhibited moderate acetyl cholinesterase inhibitory activity.
Co-reporter:Xuan-Qin Chen; Li-Dong Shao; Mahesh Pal; Yu Shen; Xiao Cheng; Gang Xu; Li-Yan Peng; Kou Wang; Zheng-Hong Pan; Ming-Ming Li; Ying Leng; Juan He
Journal of Natural Products 2015 Volume 78(Issue 2) pp:330-334
Publication Date(Web):January 15, 2015
DOI:10.1021/np500896n
Five selective 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) competitive inhibitors, hupehenols A–E (1–5), were isolated from Viburnum hupehense. The structure elucidation indicated that compounds 1–5 are new 20,21,22,23,24,25,26,27-octanordammarane triterpenoids. Their structures were established on the basis of NMR spectroscopic and mass spectrometric analysis. Hupehenols A–E (1–5) showed inhibition against human 11β-HSD1, with hupehenols B (2) and E (5) having IC50 values of 15.3 and 34.0 nM, respectively. Moreover, hupehenols C (3) and D (4) are highly selective inhibitors of human 11β-HSD1 when compared to murine 11β-HSD1.
Co-reporter:Yong-Jun Jiang, Yu Zhang, Juan He, Xing-De Wu, Li-Dong Shao, Xiao-Nian Li, Jia Su, Li-Yan Peng, Rong-Tao Li, Qin-Shi Zhao
Tetrahedron Letters 2015 Volume 56(Issue 40) pp:5457-5459
Publication Date(Web):30 September 2015
DOI:10.1016/j.tetlet.2015.08.022
(+)-Salviaprione and (−)-salviaprione, a pair of unprecedented abietane-type diterpeniods having an unprecedented 5/6/6 tricyclic ring system with a unique five membered ring A formed by a new C-2/C-11 bond, were isolated from the whole plant of Salvia prionitis. The enantiomeric separation was achieved by HPLC on a chiral column. Their structures and absolute configurations were determined on the basis of 1D and 2D NMR spectra, X-ray diffraction, and electronic circular dichroism (ECD). The possible biogenesis for (±)-salviaprione was also postulated.
Co-reporter:Jun Xu ; Li-Dong Shao ; Dashan Li ; Xu Deng ; Yu-Chen Liu ; Qin-Shi Zhao ;Chengfeng Xia
Journal of the American Chemical Society 2014 Volume 136(Issue 52) pp:17962-17965
Publication Date(Web):December 15, 2014
DOI:10.1021/ja5121343
A facile and straightforward method was developed to construct the fused tetracyclic 3-spirooxindole skeleton, which exists widely in natural products. The formation of the tetracyclic 3-spirooxindole structure was achieved through a transition-metal-free intramolecular cross-dehydrogenative coupling of pyridinium, which were formed in situ by the condensation of 3-(2-bromoethyl)indolin-2-one derivatives with 3-substituted pyridines. As examples of the application of this new methodology, two potentially medicinal natural products, (±)-corynoxine and (±)-corynoxine B, were efficiently synthesized in five scalable steps.
Co-reporter:Liao-Bin Dong, Ya-Nan Wu, Shi-Zhi Jiang, Xing-De Wu, Juan He, Yu-Rong Yang, and Qin-Shi Zhao
Organic Letters 2014 Volume 16(Issue 10) pp:2700-2703
Publication Date(Web):April 29, 2014
DOI:10.1021/ol500978k
Cernupalhine A (1) is a trace Lycopodium alkaloid (0.7 mg) possessing a new C17N skeleton with an unusual hydroxydihydrofuranone motif newly isolated from Palhinhaea cernua L. Its complete structural assignment, including absolute stereochemistry, was established through a combination of high-field NMR techniques and computational methods and further unequivocal confirmation by the first asymmetric total synthesis. Following the first total synthesis of lobscurinine (3), 1 was achieved via regio- and stereoselective cyanide ion addition and subsequent acid treatment.
Co-reporter:Xiu Gao, Li-Dong Shao, Liao-Bin Dong, Xiao Cheng, Xing-De Wu, Fei Liu, Wei-Wei Jiang, Li-Yan Peng, Juan He, and Qin-Shi Zhao
Organic Letters 2014 Volume 16(Issue 3) pp:980-983
Publication Date(Web):January 22, 2014
DOI:10.1021/ol403707a
Vibsatins A (1) and B (2), a pair of 14,15,16,17-tetranorvibsane-type diterpenoids that feature a bicyclo[4.2.1]nonane moiety formed by a new C-13/C-2 bond, were isolated from the twigs and leaves of Viburnum tinus cv. variegatus. The structures and absolute configurations were elucidated by a combination of NMR spectra, optical rotation, and X-ray diffraction experiments. A possible biogenetic pathway is also proposed. Moreover, vibsatin A (1) enhanced the neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 μM.
Co-reporter:Yanghe Luo, Xingren Li, Juan He, Jia Su, Liyan Peng, Xingde Wu, Runan Du, Qinshi Zhao
Food Chemistry 2014 Volume 164() pp:30-35
Publication Date(Web):1 December 2014
DOI:10.1016/j.foodchem.2014.04.103
•For the first time chufa peels were researched for its flavonoids profile.•Twenty flavonoids included six new ones were isolated and identified from it.•Chufa peels can be regarded as an excellent source of natural antioxidants.•Chufa peels should be a good additive in the beverage and canning.In this paper, chufa peels (Eleocharis tuberosa) were researched for the flavonoid profile for the first time. Twenty flavonoids were isolated and identified, including six new ones, named eleocharins A–F (1–6). Their structures were characterised by spectroscopic methods and compared with published data. The antioxidant activity of the acetone extract, EtOAc fraction, and nBuOH fraction of chufa peels as well as the isolated flavonoids were assessed by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical bioassay. The results showed that chufa peels can be regarded as an excellent source of natural antioxidants (mainly flavonoids) and a good additive in the beverage and canning.
Co-reporter:Zhi-Jun Zhang, Jing Yang, Juan He, Xing-De Wu, Li-Dong Shao, Yan Li, Sheng-Xiong Huang, Rong-Tao Li, Qin-Shi Zhao
Tetrahedron Letters 2014 Volume 55(Issue 47) pp:6490-6494
Publication Date(Web):19 November 2014
DOI:10.1016/j.tetlet.2014.10.011
Two new monoterpenoid indole alkaloids, vincamajorines A (1) and B (2), were isolated from Vinca major. Their structures were elucidated by means of 1D and 2D NMR, and HREIMS spectroscopic data. The relative and absolute configurations were deduced by comparing the experimental 13C NMR, ECD spectra, and OR data with those theoretically calculated. Vincamajorine A (1) represents a new C20 carbon skeleton arranged compactly in seven rings, and vincamajorine B (2) is an alkaloid with an unprecedented 6/5/7/5/6 pentacyclic ring system. A possible biosynthetic pathway was also proposed for the formation of 1 and 2.
Co-reporter:Li-Dong Shao, Jun Xu, Xiu Gao, Juan He, Yu Zhao, Li-Yan Peng, Huai-Rong Luo, Chengfeng Xia, Qin-Shi Zhao
Tetrahedron Letters 2014 Volume 55(Issue 23) pp:3414-3417
Publication Date(Web):4 June 2014
DOI:10.1016/j.tetlet.2014.04.061
Intramolecular hetero-DA reaction and unexpected retro-aldol like ring opening reaction were performed. As a result, six derivatives with different skeletons of vibsane-type diterpenoids were synthesized from vibsanin B within three steps. Moreover, compounds 2, 3, and 6 enhanced the neurite outgrowth of NGF-mediated PC12 cells.Graphical abstract
Co-reporter:Yan-Hong Li;Juan He;Yan Li;Xing-De Wu;Li-Yan Peng;Ru-Nan Du;Xiao Cheng;Rong-Tao Li
Helvetica Chimica Acta 2014 Volume 97( Issue 11) pp:1481-1486
Publication Date(Web):
DOI:10.1002/hlca.201300449

Abstract

A phytochemical study of the CHCl3 extract of the dried unripe fruits of Evodia rutaecarpa (Juss.) Benth. (Rutaceae) resulted in the isolation of three new alkaloids, evollionines A–C (13, resp.), together with two known compounds, evodianinine and wuzhuyumide I. The structures of the new compounds were elucidated on the basis of detailed spectroscopic evidence and confirmed in the case of compound 1 by single-crystal X-ray analysis.

Co-reporter:Juan He;Xing-De Wu;Fei Liu;Yu-Cheng Liu
Natural Products and Bioprospecting 2014 Volume 4( Issue 4) pp:213-219
Publication Date(Web):2014 August
DOI:10.1007/s13659-014-0027-1
Three new lycopodine-type alkaloids, 4α-hydroxyanhydrolycodoline (1), 4α,6α-dihydroxyanhydrolycodoline (2), and 6-epi-8β-acetoxylycoclavine (3), and an artifact, lycoposerramine G nitrate (4), along with seventeen related known compounds, were isolated from the club moss Lycopodiumjaponicum Thunb. ex Murray (Lycopodiaceae). Their structures were elucidated by extensive spectroscopic methods as well as X-ray analysis. Compounds 1–4 were evaluated for their acetylcholine esterase inhibitory activity.
Co-reporter:Fei Liu;Yu-Cheng Liu;Wei-Wei Jiang;Juan He
Natural Products and Bioprospecting 2014 Volume 4( Issue 4) pp:221-225
Publication Date(Web):2014 August
DOI:10.1007/s13659-014-0030-6
Carinatine A (1), a C16N2-type Lycopodium alkaloid possessing a 5/6/6/6 ring system formed by a new C-4/C-12 bond, and carinatine B (2), the first derivative of lycojaponicumin C, along 16 known compounds, were isolated from the whole plant of Phlegmariurus carinatus. Their structures were elucidated based on the spectroscopic data. The two new isolates were no inhibitory activity for the acetylcholinesterase (AChE).
Co-reporter:Li-Dong Shao;Ya-Nan Wu;Jun Xu;Juan He;Yu Zhao
Natural Products and Bioprospecting 2014 Volume 4( Issue 3) pp:181-188
Publication Date(Web):2014 June
DOI:10.1007/s13659-014-0022-6
A small focused library which comprised of l-AA lactone derivatives was built with a facile method. This reported method was optimized by modifying the acidity of the solvent. As a result, 12 l-AA lactones were synthesized. Among these lactones, lactones 8–12 were new compounds. The cytotoxicity of these synthetic compounds were investigated.
Co-reporter:Jin-Tang Cheng, Fei Liu, Xiao-Nian Li, Xing-De Wu, Liao-Bin Dong, Li-Yan Peng, Sheng-Xiong Huang, Juan He, and Qin-Shi Zhao
Organic Letters 2013 Volume 15(Issue 10) pp:2438-2441
Publication Date(Web):May 6, 2013
DOI:10.1021/ol400907v
Lycospidine A (1), the first example of a Lycopodium alkaloid which contains an unprecedented five-membered A ring, was isolated from Lycopodium complanatum. The unique five-membered A ring in 1 indicates that carbons 2–5 in 1 are presumably derived from proline instead of the lysine biosynthetically, which suggests that 1 represent a new class of Lycopodium alkaloid. In addition, the unique structural feature and biosynthetic origin of 1 shed new insight into the structural diversity of Lycopodium alkaloid analogue libraries potentially accessible by engineered biosynthesis.
Co-reporter:Liao-Bin Dong, Xiu Gao, Fei Liu, Juan He, Xing-De Wu, Yan Li, and Qin-Shi Zhao
Organic Letters 2013 Volume 15(Issue 14) pp:3570-3573
Publication Date(Web):July 1, 2013
DOI:10.1021/ol401411m
A new pentacyclic (5/6/6/6/7) Lycopodium alkaloid named isopalhinine A (1), which possesses a sterically congested architecture built with a tricyclo[4.3.1.03,7]decane (isotwistane) moiety and a 1-azabicyclo[4.3.1]decane moiety, and palhinines B (2) and C (3) were isolated from Palhinhaea cernua. The structure and absolute configuration of 1 were elucidated by a combination of NMR spectra, optical rotation calculation, and X-ray diffraction experiment. A possible biogenetic pathway was also proposed.
Co-reporter:Yu Zhao ; Jia Su ; Masuo Goto ; Susan L. Morris-Natschke ; Yan Li ; Qin-Shi Zhao ; Zhu-Jun Yao ;Kuo-Hsiung Lee
Journal of Medicinal Chemistry 2013 Volume 56(Issue 11) pp:4749-4757
Publication Date(Web):May 31, 2013
DOI:10.1021/jm400479p
Taxchinin A, with a 11(15→1)-abeo-taxane skeleton, is a major, but inactive taxoid contained in leaves of Taxus chinensis. In our design of dual-functional antitumor abeo-taxane derivatives, two fragments from antitumor agents with different molecular targets (the N-acyl-3′-phenylisoserine side chain from the antimitotic agent paclitaxel and an α,β-unsaturated carbonyl system from NF-κB inhibitors) were incorporated into the scaffold of taxchinin A. The resulting compounds displayed broad inhibitory effects against proliferation of tumor cell lines, with notable selectivity toward colon cancer, melanoma, and renal cancer, when evaluated in the NCI-60 human tumor cell line screening panel. On the basis of the NCI-60 assay data, structure–activity relationship (SAR) correlations were elucidated. Mechanistic studies indicated that this new compound type can both destabilize microtubules and inhibit NF-κB activation, thereby inducing tumor cell apoptosis. This first report of the dual-functional taxoid-core compounds thus provides new opportunities for future drug development based on natural axoid scaffolds.
Co-reporter:Xing-De Wu ; Juan He ; Xing-Yao Li ; Liao-Bin Dong ; Xun Gong ; Liu-Dong Song ; Yan Li ; Li-Yan Peng
Journal of Natural Products 2013 Volume 76(Issue 6) pp:1032-1038
Publication Date(Web):May 21, 2013
DOI:10.1021/np400010c
Five new isopimarane diterpenoids, fokihodgins A–E (1–5), four new labdane diterpenoids, fokihodgins F–I (6–9), and one new icetexane diterpenoid, fokihodgin J (10), as well as 18 known diterpenoids were isolated from Fokienia hodginsii. The structures of the new compounds were determined on the basis of their spectroscopic analysis, and the absolute configurations of 1 and 6 were established by X-ray crystallographic analysis. Compound 9 showed moderate cytotoxicity against HL-60 and SMMC-7721 cell lines, with IC50 values of 9.10 and 7.50 μM, respectively.
Co-reporter:Xu Deng, Yu Shen, Jing Yang, Juan He, Yu Zhao, Li-Yan Peng, Ying Leng, Qin-Shi Zhao
European Journal of Medicinal Chemistry 2013 Volume 65() pp:403-414
Publication Date(Web):July 2013
DOI:10.1016/j.ejmech.2013.05.010
•The discovery of ent-kaurane diterpenoids 1b as novel selective 11β-HSD1 inhibitors was reported.•Thirty-six structurally diverse analogs derived from the leads 1b and 2 were designed and synthesized.•The potency and selectivity of the derivatives were evaluated using SPA.•Seven urea derivatives exhibited significantly improved potency and selectivity.The biological screening of a collection of nature occurring diterpenoids against 11β-HSD1 resulted in the discovery of the lead compound 1b, which pointed to the therapeutic potential for type 2 diabetes. Subsequently, an optimization project was initiated. Starting from compound 1b and its counterpart 2, the hemi-synthesis was performed on kaurenic acid scaffolds yielding 36 derivatives. Further evaluations on both human and mouse 11β-HSD revealed that seven urea derivatives exhibited significant improved potency and selectivity. Especially, the urea 19a has an IC50 (human 11β-HSD1) = 9.4 nM and selectivity index (human 11β-HSD) > 10,649. The 2D and 3D binding models of the complex 19a/11β-HSD1 were generated using docking simulations. Based on the results, the structural–activity relationships (SARs) of compounds 1b and 2 were also discussed.Thirty-six structurally diverse analogs derived from ent-kaurane diterpenoids were designed and synthesized as selective 11β-HSD1 inhibitors. The 2D and 3D binding schemes of complex 19a/human 11β-HSD1 were also generated.
Co-reporter:Fei Liu, Xing-De Wu, Juan He, Xu Deng, Li-Yan Peng, Huai-Rong Luo, Qin-Shi Zhao
Tetrahedron Letters 2013 Volume 54(Issue 34) pp:4555-4557
Publication Date(Web):21 August 2013
DOI:10.1016/j.tetlet.2013.06.083
A phytochemical study on Lycopodium casuarinoides has led to the isolation of two new C16N2-type Lycopodium alkaloids, casuarine A (1), a cage-like structure featured with a fused 6/6/6/6/6 pentacyclic ring system, and casuarine B (2). Their structures were elucidated based on the spectroscopic data and further confirmed by X-ray analysis. In vitro acetylcholinesterase (AChE) inhibitory activity assay showed that compound 2 exhibited moderate anti-AChE activity with IC50 46.40 μM.
Co-reporter:Lan-Chun Zhang, Xing-De Wu, Juan He, Yan Li, Rong-Ping Zhang, Qin-Shi Zhao
Phytochemistry Letters 2013 Volume 6(Issue 3) pp:364-367
Publication Date(Web):August 2013
DOI:10.1016/j.phytol.2013.04.003
•Three new abietane diterpenoids were isolated from the twigs and leaves of Podocarpus fleuryi.•Fourteen known compounds were isolated.•The diterpenois were tested cytotoxic activity against five human cancer cell lines.•Fleuryinol B (2) and 19-hydroxyferruginol (4) exhibited moderate cytotoxic activities against some cell lines.Three new abietane diterpenoids, fleuryinols A–C (1–3), together with fourteen known compounds, were isolated from the twigs and leaves of Podocarpus fleuryi. Their structures were established by spectroscopic analysis, including 1D- and 2D-NMR spectroscopic techniques. Compounds 1–8 were tested cytotoxic activity against five human cancer cell lines, HL-60, SMMC-772, A-549, MCF-7, and SW480, of which fleuryinol B (2) and 19-hydroxyferruginol (4) exhibited moderate cytotoxic activity against some cell lines.
Co-reporter:Zhi-Jun Zhang;Juan He;Yan Li;Xing-De Wu;Xiu Gao;Li-Yan Peng;Xiao Cheng;Rong-Tao Li
Helvetica Chimica Acta 2013 Volume 96( Issue 4) pp:732-737
Publication Date(Web):
DOI:10.1002/hlca.201200289

Abstract

A new eremophilane sesquiterpene, (2β)-2-deoxo-2-methoxytessaric acid (1), and two new eudesmane sesquiterpenes, (3β,10α)-3-methoxyleudesma-4,11(13)-dien-12-oic acid (2) and (3α,4β,8α)-4-(acetyloxy)-3-(2,3-dihydroxy)-2-methyl-1-oxobutoxy-8-hydroxyeudesm-7(11)-eno-12,8-lactone (3), along with the ten known compounds 413 were isolated from the aerial parts of Laggera pterodonta. The structures of the new compounds were elucidated by spectroscopic analyses, including 2D-NMR data.

Co-reporter:Xing-De Wu;Lei Wang;Juan He;Xing-Yao Li;Liao-Bin Dong;Xun Gong;Xiu Gao;Liu-Dong Song;Yan Li;Li-Yan Peng
Helvetica Chimica Acta 2013 Volume 96( Issue 12) pp:2207-2213
Publication Date(Web):
DOI:10.1002/hlca.201300050

Abstract

Two new indole alkaloids, 5-oxodolichantoside (1) and deglycocadambine (2), were isolated from the twigs and leaves of Emmenopterys henryi, together with four known indole alkaloids and five known iridoids. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses, including 1D- and 2D-NMR experiments, and confirmed by single-crystal X-ray diffraction studies. This is the first report on the isolation of indole alkaloids from this species. The indole alkaloids were evaluated for their cytotoxic activities against five human cancer lines.

Co-reporter:Ming-Ming Li;Kou Wang;Juan He;Li-Yan Peng
Natural Products and Bioprospecting 2013 Volume 3( Issue 2) pp:38-42
Publication Date(Web):2013 April
DOI:10.1007/s13659-012-0022-3
Four new labdane-type diterpenoid glycosides, laevissiosides A-D (1–4) were isolated from the 95% ethanol extract of Diplopterygium laevissimum (Christ) Nakai, along with two known analogues, 18- β-D-glucopyranosyl ester-sclareol (5) and 18-hydroxy-sclareol (6). The structures of compounds 1–4 were elucidated by extensive 1D and 2D NMR spectroscopy as well as high-resolution MS analyses. All isolated compounds were evaluated for their cytotoxic effects.
Co-reporter:Xue-Yuan Zhang;Liao-Bin Dong;Fei Liu;Xing-De Wu
Natural Products and Bioprospecting 2013 Volume 3( Issue 2) pp:52-55
Publication Date(Web):2013 April
DOI:10.1007/s13659-013-0015-x
Co-reporter:Liao-Bin Dong, Jing Yang, Juan He, Huai-Rong Luo, Xing-De Wu, Xu Deng, Li-Yan Peng, Xiao Cheng and Qin-Shi Zhao  
Chemical Communications 2012 vol. 48(Issue 72) pp:9038-9040
Publication Date(Web):20 Jul 2012
DOI:10.1039/C2CC34676A
A novel sterically congested Lycopodium alkaloid named lycopalhine A (1) that possesses a fused hexacyclic (5/5/5/6/6/6) ring system comprising a 5,9-diaza-tricyclo[6.2.1.04,9]undecane moiety and a tricyclo[5.2.1.04,8]decane moiety was isolated from Palhinhaea cernua L. The structure and absolute configuration were determined by spectroscopic and computational methods.
Co-reporter:Xing-De Wu, Juan He, Yu Shen, Liao-Bin Dong, Zheng-Hong Pan, Gang Xu, Xun Gong, Liu-Dong Song, Ying Leng, Yan Li, Li-Yan Peng, Qin-Shi Zhao
Tetrahedron Letters 2012 Volume 53(Issue 7) pp:800-803
Publication Date(Web):15 February 2012
DOI:10.1016/j.tetlet.2011.12.004
Three novel triterpenoids, pseudoferic acids A and B (1 and 2) possessed a unique 16,24-cyclo-26-norlanostane skeleton, and pseudoferic acid C (3) featured a cis-fused D/E-ring system, were isolated from the root bark of Pseudolarix kaempferi. Their structures were elucidated on the basis of extensive spectroscopic analysis. Compounds 2 and 3 exhibited weak inhibitory activities against 11β-HSD1 (11β-hydroxysteroid dehydrogenase 1) with IC50 values of 0.44 (mouse 11β-HSD1) and 0.75 μM (human 11β-HSD1), respectively.
Co-reporter:Jin-Tang Cheng;Juan He;Xing-Yao Li;Xing-De Wu;Li-Dong Shao;Liao-Bin Dong;Xu Deng;Xiu Gao;Li-Yan Peng;Xiao Cheng;Yan Li
Helvetica Chimica Acta 2012 Volume 95( Issue 7) pp:1158-1163
Publication Date(Web):
DOI:10.1002/hlca.201100515

Abstract

Three new monosubstituted sucrose fatty acid esters, 13, were isolated from Equisetum hiemale L., together with nine known compounds, 412. Their structures were elucidated by spectroscopic analyses. Compounds 5, 6, and 1012 were isolated from the title plant for the first time. All these compounds were evaluated for their cytotoxic activity. However, none of them was cytotoxic.

Co-reporter:Xu Deng;Ling-Mei Kong;Yu Zhao;Juan He
Natural Products and Bioprospecting 2012 Volume 2( Issue 5) pp:210-216
Publication Date(Web):2012 October
DOI:10.1007/s13659-012-0071-7
A potential strategy for drug lead identification and in-active natural products re-discovery is elaborated. Starting from fifteen structurally diverse natural products, a focused library featured by Michael acceptors is constructed with IBX mediated oxidation. Biological assay on five tumor cell lines indicates that four Michael acceptors, 8a, 11a, 12a, 14a, are with improved cytotoxicity (3–10 folds more potent than the parent compounds), which merit further investigations. Further thiol-sensitive assay of the active hit 8a revealed that it was an irreversible Michael acceptor. The results suggest that the strategy is not only effective and relatively high discovery rate (28%), but also resource saving.
Co-reporter:Kou Wang, Xiao-Yu Zhou, Yuan-Yuan Wang, Ming-Ming Li, Yin-Shan Li, Li-Yan Peng, Xiao Cheng, Yan Li, Yi-Ping Wang, and Qin-Shi Zhao
Journal of Natural Products 2011 Volume 74(Issue 1) pp:12-15
Publication Date(Web):November 11, 2010
DOI:10.1021/np1004938
An unusual oxindole alkaloid inner salt, macrophyllionium (1), and a pair of new tetracyclic oxindole alkaloids, macrophyllines A (2) and B (3), together with six known alkaloids, were isolated from the aerial parts of Uncaria macrophylla. Corynantheidine (8) exhibited moderate cytotoxicity against HL-60 and SW480 cells with IC50 values of 13.96 and 23.28 μM, respectively. Dihydrocorynantheine (9) exhibited significant vasodilating activity against phenylephrine-induced contraction in rat thoracic aorta rings (IC50 = 6.73 μg/mL). In addition, compounds 2, 6, and 9 showed weak inhibitory action on KCl-induced contraction.
Co-reporter:Xu Deng, Jia Su, Yu Zhao, Li-Yan Peng, Yan Li, Zhu-Jun Yao, Qin-Shi Zhao
European Journal of Medicinal Chemistry 2011 Volume 46(Issue 9) pp:4238-4244
Publication Date(Web):September 2011
DOI:10.1016/j.ejmech.2011.06.028
Cheliensisin A is a natural styryl-lactone isolated from Goniothalamus cheliensis Hu in considerably large quantity with putative anticancer activities. However, its poor water solubility and chemical instability have precluded cheliensisin A as a potential drug candidate. To explore the strategy to overcome these problems, 21 novel derivatives of cheliensisin A with different substitutions at C-7 and C-8 positions were designed and synthesized. Inhibition of proliferation against five tumors cell lines indicates that eight new derivatives with embedment of oxazole or oxazoline exhibit improved cytotoxicity on SK-BR-3 and PANC-1, and compounds 2d and 2g show 5–8 folds higher potency than cisplatin. HPLC investigation of representative compounds indicates that oxazole and oxazoline analogs exhibit much improved chemical stability than their natural parent.Highlights► 21 novel cheliensisin A analogs were synthesized and evaluated against five tumor cell lines. ► Most oxazoline/oxazole containing analogs exhibited improved potency and chemical stability. ► Cis-configuration and reasonable rigid conformation were found to favor the bioactivities.
Co-reporter:Liao-Bin Dong, Juan He, Yuan-Yuan Wang, Xing-De Wu, Xu Deng, Zheng-Hong Pan, Gang Xu, Li-Yan Peng, Yu Zhao, Yan Li, Xun Gong, and Qin-Shi Zhao
Journal of Natural Products 2011 Volume 74(Issue 2) pp:234-239
Publication Date(Web):January 12, 2011
DOI:10.1021/np100694k
Four new terpenoids, metaseglyptorin A (1), metasequoic acid C (2), 12α-hydroxy-8,15-isopimaradien-18-oic acid (3), and (−)-acora-2,4(14),8-trien-15-oic acid (4), and three new norlignans, metasequirins D−F (5−7), were isolated from Metasequoia glyptostroboides, together with 15 known compounds. Structures of the new compounds were determined by analysis of their spectroscopic data, and the absolute configuration of 7 was established by the modified Mosher method. All of the compounds were evaluated for cytotoxicity against five human tumor cell lines.
Co-reporter:Yu Zhao, Hong-Bin Zhang, Ji-Kai Liu, Jia Su, Yan Li, Zhu-Jun Yao, Qin-Shi Zhao
Tetrahedron Letters 2011 Volume 52(Issue 1) pp:139-142
Publication Date(Web):5 January 2011
DOI:10.1016/j.tetlet.2010.11.008
Two interesting unprecedented fragmentations of 13-oxo-taxyunnansin A (3), initiated by treatment with tBuOK and Red-Al, respectively, have been discovered, optimized and successfully applied to the synthesis of novel abeo-paclitaxel and abeo-docetaxel derivatives. Eight new derivatives of abeo-paclitaxel and abeo-docetaxel possessing the structurally simplified 11 (15→1)-abeo-taxane skeleton with an oxetane ring and π bond conjugate system were accordingly prepared for the further evaluation of anticancer activities.
Co-reporter:Zheng-Hong Pan;Jin-Tang Cheng;Juan He;Yuan-Yuan Wang;Li-Yan Peng;Gang Xu;Wei-Bang Sun
Helvetica Chimica Acta 2011 Volume 94( Issue 3) pp:417-422
Publication Date(Web):
DOI:10.1002/hlca.201000203

Abstract

Three new clerodane diterpenoids, splendidins A–C (13, resp.), were isolated from Salvia splendens, together with six known ones. Their structures were elucidated by extensive spectroscopic analysis. Splendidin C (3) was the first diterpenoid glucoside reported from this plant. These compounds were evaluated for their cytotoxic activity; however, none of them were cytotoxic.

Co-reporter:Jiang Hu;Xuan-Qin Chen
Helvetica Chimica Acta 2011 Volume 94( Issue 6) pp:1085-1090
Publication Date(Web):
DOI:10.1002/hlca.201000337

Abstract

Two new diterpenoids, (3β,13S)-3-O-[6-O-acetyl-β-D-glucopyranosyl]-13-O-α-L-rhamnopyranosyllabda-8(17),14-diene (1) and (4R,13S)-18-O-β-D-glucopyranosyllabda-8(17),14-dien-13-ol (2) have been isolated from the 95% EtOH extract of the dry fronds of Diplopterygium rufopilosum. Their structures were characterized by spectroscopic methods, including 1D-NMR, 2D-NMR, and HR-ESI-MS.

Co-reporter:Liao-Bin Dong;Juan He;Xing-Yao Li;Xing-De Wu
Natural Products and Bioprospecting 2011 Volume 1( Issue 1) pp:41-47
Publication Date(Web):2011 August
DOI:10.1007/s13659-011-0007-7
Co-reporter:Li-Yan Peng;Juan He;Gang Xu;Xing-De Wu
Natural Products and Bioprospecting 2011 Volume 1( Issue 2) pp:101-103
Publication Date(Web):2011 October
DOI:10.1007/s13659-011-0021-9
Co-reporter:Zheng-Hong Pan, Yuan-Yuan Wang, Ming-Ming Li, Gang Xu, Li-Yan Peng, Juan He, Yu Zhao, Yan Li and Qin-Shi Zhao
Journal of Natural Products 2010 Volume 73(Issue 6) pp:1146-1150
Publication Date(Web):June 1, 2010
DOI:10.1021/np100250w
Nine new germacrane sesquiterpenes, trijugins A−I (1−9), a new lupane triterpenoid, 3α-O-acetyl-20(29)-lupen-2α-ol (10), and 24 known terpenoids were isolated from Salvia trijuga. The structure of compound 1 was confirmed by single-crystal X-ray diffraction. Compounds 1−10 and 32 were evaluated for their cytotoxicity against five human tumor cell lines. Compounds 9 and 32 exhibited moderate toxicity effects against several cell lines.
Co-reporter:Gang Xu, Jing Yang, Yuan-Yuan Wang, Li-Yan Peng, Xian-Wen Yang, Zheng-Hong Pan, En-De Liu, Yan Li, and Qin-Shi Zhao
Journal of Agricultural and Food Chemistry 2010 Volume 58(Issue 23) pp:12157-12161
Publication Date(Web):November 12, 2010
DOI:10.1021/jf103366g
Salvia digitaloides, belonging to the economically and medicinally important genus Salvia, is distributed in the northwest of Yunnan Province, People's Republic of China. The roots of this plant were soaked in alcohol by local Tibetans to make a special traditional “red wine”, and many local people like to drink this traditional “red wine” to strengthen physical health. To investigate the bioactive diterpenoid constituents of the roots, a detailed phytochemical study was carried out, and 13 diterpenoids including two new norditerpenoids, dihydroneotanshinlactone (1) and 16,17-dinorpisferal A (2), were isolated. Their structures were established on the basis of detailed spectroscopic analysis. In addition, computational methods were applied to validate the stereochemistry of compound 1. For the bioassay to inhibit the growth of five tumor cell lines, neotanshinlactone (3) exhibited selective cytotoxic activity toward the human breast cancer cell line SK-BR-3, while the other four tanshinones (4−7) showed significant toxicity effects against all of the tested five cell lines.
Co-reporter:Zheng-Hong Pan, Juan He, Yan Li, Yu Zhao, Xing-De Wu, Kou Wang, Li-Yan Peng, Gang Xu, Qin-Shi Zhao
Tetrahedron Letters 2010 Volume 51(Issue 38) pp:5083-5085
Publication Date(Web):22 September 2010
DOI:10.1016/j.tetlet.2010.07.107
Castanolide (1) and epi-castanolide (2), two novel diterpenoids possessing a unique seco-norabietane skeleton, were isolated from Salviacastanea Diels f. pubescens Stib. Their structures and relative stereochemistry were elucidated by extensive NMR analysis and confirmed by single-crystal X-ray diffraction study. A possible biosynthetic pathway of these two compounds was also proposed.Abstract
Co-reporter:Gang Xu;Li-Yan Peng;Xiao-Ling Shen
Helvetica Chimica Acta 2010 Volume 93( Issue 9) pp:
Publication Date(Web):
DOI:10.1002/hlca.200900453

Abstract

Two new eudesmanolide sesquiterpenoids containing a hemiacetal function, castanins G and H (1 and 2), were obtained as a pair of interconvertible isomers from the aerial parts of Salvia castaneaDiels f. tomentosaStib., and separated as their uninterconvertible acetates 3 and 4. Their structures were elucidated by unequivocal interpretation and comparative analysis of the NMR and MS data of the mixture 1/2 and of their acetates 3 and 4, respectively. The inhibitory activity of 3 and 4 toward MCF-7, HeLa, and HepG2 cell lines was also evaluated.

Co-reporter:Yan Zhou, Gang Xu, Franky Fung Kei Choi, Li-Sheng Ding, Quan Bin Han, Jing Zheng Song, Chun Feng Qiao, Qin-Shi Zhao, Hong-Xi Xu
Journal of Chromatography A 2009 Volume 1216(Issue 24) pp:4847-4858
Publication Date(Web):12 June 2009
DOI:10.1016/j.chroma.2009.04.017
An on-line ultra-high-performance liquid chromatography (UHPLC) coupled with photodiode-array detection and quadrupole time-of-flight tandem mass spectrometry (QTOF-MS/MS) method has been optimized and established for the qualitative and quantitative analysis of the important diterpenoids in the methanol extracts of 12 Salvia species. Specific marker components were identified for the classification of the Salvia samples by principal component analysis. The accurate mass measurement within 3 ppm error for all the protonated molecules and subsequent fragment ions offers higher quality structural information for interpretation of fragmentation pathways of various groups of diterpenoids. Thus, a total of 21 diterpenoids from different Salvia species were separated within 10 min, and were unequivocally or tentatively identified via comparisons with authentic standards and literature. This UHPLC-QTOF-MS/MS method was validated to be sensitive, precise and accurate with the limit of detections at 3.0–16 ng/ml, and the overall intra-day and the inter-day variations less than 3%. The recovery of the method was in the range of 96.2–101.8%, with relative standard deviation (RSD) less than 3.0%. The results demonstrated that the qualitative and quantitative differences in diterpenoids were not only useful for chemotaxonomy in some Salvia species but also for the standardization and differentiation of large numbers of similar samples.
Co-reporter:Gang Xu;Li-Yan Peng;Lin Tu;Xiao-Li Li;Yu Zhao;Peng-Tao Zhang
Helvetica Chimica Acta 2009 Volume 92( Issue 2) pp:
Publication Date(Web):
DOI:10.1002/hlca.200800293
Co-reporter:Lin Tu;Gang Xu;Yu Zhao;Li-Yan Peng;Juan He;Na Guo
Helvetica Chimica Acta 2009 Volume 92( Issue 7) pp:1324-1332
Publication Date(Web):
DOI:10.1002/hlca.200800420

Abstract

Seven new phenolic glucosides, 2′-O-acetylhenryoside (1), 2′,3′-di-O-acetylhenryoside (2), 2′,6′-di-O-acetylhenryoside (3), 2′,3′,6′-tri-O-acetylhenryoside (4), 2′,3′,4′,6′-tetra-O-acetylhenryoside (5), 2-[(2,3-di-O-acetyl-β-D-glucopyranosyl)oxy]-6-hydroxybenzoic acid (6), and 6-hydroxy-2-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]benzoic acid (7), were isolated from the leaves and stems of Viburnum cylindricum, along with 26 known compounds (henryoside=2-(β-D-glucopyranosyloxy)-6-hydroxybenzoic acid [2-(β-D-glucopyranosyloxy)phenyl]methyl ester). The structures of the new compounds were established on the basis of chemical and spectroscopic evidences.

Co-reporter:Xiu Gao, Juan He, Xing-De Wu, Li-Yan Peng, Li-Dong Shao, Yan Li, Xiao Cheng, Qin-Shi Zhao
Fitoterapia (January 2017) Volume 116() pp:116-120
Publication Date(Web):1 January 2017
DOI:10.1016/j.fitote.2016.11.018
Sauruchinenols A (1) and B (2), two novel monocyclic diterpenes with unique carbon skeleton, as well as two new structurally related diterpenes, sauruchinenols C (3) and D (4), were isolated from the aerial part of Saururus chinensis. Their structures were elucidated based on the analysis of spectroscopic data. A hypothetical biogenetic pathway for sauruchinenols A and B was proposed.Download high-res image (278KB)Download full-size image
Co-reporter:Liao-Bin Dong, Jing Yang, Juan He, Huai-Rong Luo, Xing-De Wu, Xu Deng, Li-Yan Peng, Xiao Cheng and Qin-Shi Zhao
Chemical Communications 2012 - vol. 48(Issue 72) pp:NaN9040-9040
Publication Date(Web):2012/07/20
DOI:10.1039/C2CC34676A
A novel sterically congested Lycopodium alkaloid named lycopalhine A (1) that possesses a fused hexacyclic (5/5/5/6/6/6) ring system comprising a 5,9-diaza-tricyclo[6.2.1.04,9]undecane moiety and a tricyclo[5.2.1.04,8]decane moiety was isolated from Palhinhaea cernua L. The structure and absolute configuration were determined by spectroscopic and computational methods.
Pierreione B
(2S)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-methyl-4H-1-benzopyran-4-one
Lushanrubescensin H
sculponeatin E
Xerophilusin G
Enanderianin B
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethenyl ester, (2E)- (9CI)
(S)-2-(3-Hydroxy-4-methoxyphenyl)chroman-7-ol