Co-reporter:Min Zhao, Zhuo-Ma Da-Wa, Yu-Cheng Gu, Da-Le Guo, ... Yan Zhou
Phytochemistry Letters 2017 Volume 20(Volume 20) pp:
Publication Date(Web):1 June 2017
DOI:10.1016/j.phytol.2017.04.037
•Three new chlorinated phenolic glycosides were isolated from Przewalskia tangutica.•Their structures were elucidated by NMR analysis and chemical methods.•Przewatangoside A showed weak cytotoxicity against SMMC-7721.Three new chlorinated phenolic glycosides, namely przewatangosides A-C (1-3), along with one known compound, globosumoside A (4), were isolated from the whole plants of Przewalskia tangutica. Their structures were unequivocally determined by extensive spectroscopic analysis and chemical method. The cytotoxic activities of the isolated phenolic glycosides (1-4) were evaluated against the five human cancer cell lines A549, MCF-7, SMMC-7721, HepG2 and HL-60. Przewatangoside A (1) exhibited weak cytotoxicity against SMMC-7721 with the IC50 value of 38.1 μM. All the tested compounds were inactive (IC50 > 50 μM) to the normal human hepatocyte cell line (L02).Download high-res image (306KB)Download full-size image
Co-reporter:Min Zhao, Da-Le Guo, Lv-Yi Yuan, Yu-Cheng Gu, ... Yan Zhou
Phytochemistry Letters 2017 Volume 19(Volume 19) pp:
Publication Date(Web):1 March 2017
DOI:10.1016/j.phytol.2016.11.010
•Three new labdane diterpenes were isolated from Loxocalyx urticifolius.•Their structures were elucidated by NMR analysis and chemical method.•The absolute configuration of 1 was confirmed by X-ray crystallographic analysis.•Compound 3 exhibited weak cytotoxicity against A549 and MCF-7.Three new labdane diterpenes, namely loxocalyxin D (1), loxocalyxin E (2) and 13-epiloxocalyxin E (3), were isolated from the whole plants of Loxocalyx urticifolius Hemsl. Their structures were elucidated by extensive spectral analysis and chemical methods. The absolute configuration of loxocalyxin D (1) was confirmed by X-ray crystallographic analysis. The cytotoxic activities of the isolated labdane diterpenes were evaluated against the four human cancer cell lines A549, HepG2, HL-60 and MCF-7. 13-epiloxocalyxin E (3) exhibited selective cytotoxicity against A549 and MCF-7 with the IC50 values of 22.4 and 47.3 μM, respectively.Download high-res image (96KB)Download full-size image
Co-reporter:Zhi-Zhou He, Li-Sheng Ding, Rui-Hong Xu, Bo Wan, Shu-Lin Peng, Hao-Huai Liu, Yuan Zeng
Biochemical Systematics and Ecology 2015 Volume 61() pp:118-120
Publication Date(Web):August 2015
DOI:10.1016/j.bse.2015.06.006
•Fourteen compounds were firstly isolated from Cremanthodium brunneo-pilosum.•Sesquiterpenoids could be used as chemotaxonomic markers of Cremanthodium brunneo-pilosum.•Cremanthodium is in a lower position in the evolutionary advancement of Compositae.Fourteen compounds were isolated from Cremanthodium brunneo-pilosum, including two steroids (1 and 14), five sesquiterpenoids (2–6), six flavonoids (7–12) and one isoflavone (13). Graveolide (2) was obtained from a plant for the first time. 5,7-Dihydroxy-3,6,3′,4′-tetramethoxy-flavone (9), centaureidin (10) and tectoridin (13) have not been isolated from the family Compositae. The chemotaxonomic data support the relationship between this species and others in the family Compositae.
Co-reporter:Shi-Ji Xiao, Fang Chen, Li-Sheng Ding, Yan Zhou
Chinese Chemical Letters 2014 Volume 25(Issue 3) pp:463-464
Publication Date(Web):March 2014
DOI:10.1016/j.cclet.2013.11.053
Two new eupodienone lignans, named gymnothelignan T (1) and gymnothelignan U (2) were isolated from the whole plants of endemic medicinal plant of Gymnotheca chinensis (Saururaceae). The structures of the new compounds were elucidated by means of HRMS, 1D and 2D NMR. Compound 1 was tested for cytotoxic activity in HCT15, HCT116, A549, MCF-7 and HepG2 cells and exhibited no appreciable activity against these tested cell lines with IC50 values above 50 μmol/L.Two new eupodienone lignans, named gymnothelignan T (1) and gymnothelignan U (2) were isolated from the whole plants of endemic medicinal plant of Gymnotheca chinensis (Saururaceae). Compound 1 was tested for cytotoxic activity in HCT15, HCT116, A549, MCF-7 and HepG2 cells and exhibited no appreciable activity against these tested cell lines with IC50 values above 50 μmol/L.
Co-reporter:Shi-Ji Xiao, Xin-Xiang Lei, Bing Xia, Hong-Ping Xiao, Da-Hai He, Dong-Mei Fang, Hua-Yi Qi, Fang Chen, Li-Sheng Ding, Yan Zhou
Tetrahedron Letters 2014 Volume 55(Issue 17) pp:2869-2871
Publication Date(Web):23 April 2014
DOI:10.1016/j.tetlet.2014.03.091
Two novel norlignans, gymnothedelignans A and B were isolated from the whole plants of Gymnotheca chinensis. These norlignans possess a rare 2/5 epoxy benzocycloheptanone skeleton. Their structures were established on the basis of 1D and 2D NMR spectral data analysis, and the absolute stereochemistry of gymnothedelignans A and B was further confirmed by single crystal X-ray diffraction analysis.
Co-reporter:Shi-Ji Xiao, Xin-Xiang Lei, Bing Xia, Dan-Qing Xu, Hong-Ping Xiao, Hong-Xi Xu, Fang Chen, Li-Sheng Ding, Yan Zhou
Tetrahedron Letters 2014 Volume 55(Issue 43) pp:5949-5951
Publication Date(Web):22 October 2014
DOI:10.1016/j.tetlet.2014.09.044
Two novel lignans, gymnothespirolignans A (1) and B (2), possessing a rare polycyclic spiro skeleton, were isolated from the endemic plant of Gymnotheca involucrata Pei. Their structures were determined by spectroscopic evidences and the absolute configurations were confirmed by single crystal X-ray diffraction analysis. Compounds 1 and 2 showed promising antiviral activities against RSV with an IC50 value of 31.87 and 17.51 μM, respectively.
Co-reporter:Shi-Ji Xiao, Yuan-Zhi Lao, Fang Chen, Hong-Xi Xu, Li-Sheng Ding, Yan Zhou
Phytochemistry Letters 2014 Volume 8() pp:38-40
Publication Date(Web):May 2014
DOI:10.1016/j.phytol.2014.01.007
•Two new lignans were isolated from Gymnotheca chinensis Decne.•Compound 1 exhibited moderate cytotoxicity against five human cancer cell lines.•Compound 2 exhibited weak cytotoxicity against the A549 cancer cell line.Two new lignans, gymnothelignans V (1) and W (2), were isolated from a methanol extraction of Gymnotheca chinensis Decne. Their structures were established on the basis of extensive 1D and 2D NMR spectroscopy. Compound 1 exhibited moderate cytotoxicity against the HCT116, HCT15, A549, MCF-7 and HepG2 cancer cell lines with IC50 values of 45.1 μM, 26.9 μM, 49.6 μM, 30.0 μM and 49.7 μM, respectively. Compound 2 exhibited weak cytotoxicity against the A549 cancer cell line with an IC50 value of 41.3 μM.
Co-reporter:Shiji Xiao;Dahai He;Dongmei Fang;Fang Chen;Lisheng Ding;Yan Zhou
Helvetica Chimica Acta 2014 Volume 97( Issue 4) pp:499-506
Publication Date(Web):
DOI:10.1002/hlca.201300208
Abstract
Four new biphenyl lignans, 1–4, with a tetrahydrofuran moiety were isolated from the MeOH extract of the whole plant of Gymnotheca chinensis. Their chemical structures were established by means of spectroscopic analysis, including 1D and 2D NMR spectroscopy and comparison with previously reported data. Compounds 1–4 occur as mixtures of atropisomers as revealed by variable-temperature NMR experiments.
Co-reporter:Dahai He;Xuemin Xu;Yan Zhou;Wenlong Deng;Bin Xia;Lisheng Ding
Helvetica Chimica Acta 2012 Volume 95( Issue 7) pp:1136-1143
Publication Date(Web):
DOI:10.1002/hlca.201100478
Abstract
Two new diterpenoids, loxocalyxin A (1) and 13-epiloxocalyxin A (2), and two new sesquiterpenoids, loxocalyxins B and C (3 and 4, resp.), together with three known compounds, were isolated from the MeOH extract of the whole plant of Loxocalyx urticifolius Hemsl. The structures of the new compounds were established by means of spectroscopic analysis including one- and two-dimensional NMR spectroscopy. All new structures were confirmed by X-ray crystallographic analysis. Their absolute configurations were established.
Co-reporter:Zhi-Jun Song, Xue-Min Xu, Wen-Long Deng, Shu-Lin Peng, Li-Sheng Ding, and Han-Hong Xu
Organic Letters 2011 Volume 13(Issue 3) pp:462-465
Publication Date(Web):December 21, 2010
DOI:10.1021/ol102796k
An unprecedented dimeric triterpenoid, designated dibelamcandal A, with a six-membered ring linking two iridal type triterpenoid nuclei, was isolated from the rhizome of Belamcanda chinensis. Its structure was determined by extensive spectroscopic measurements, including IR, ESI-MS, HR-ESI-MS, and 1D and 2D NMR. It demonstrated significant molluscicide activity against Pomacea canaliculata.
Co-reporter:Yan-Hui Li;Yan Zhou;Gesang Suolang;Ciren Bianba;Hui Feng
Helvetica Chimica Acta 2011 Volume 94( Issue 3) pp:474-480
Publication Date(Web):
DOI:10.1002/hlca.201000237
Abstract
From the aerial parts of Senecio dianthus, four new eremophilenolides (1–4, resp.) and one new eremophilenolide alkaloid (5), of the relatively uncommon eremophilenoid-type sesquiterpenoid lactones, were isolated together with three known sesquiterpenoid lactones, 10β-hydroxyeremophil-7(11)-en-12,8α-olide (6), 8β,10β-dihydroxyeremophil-7(11)-en-12,8α-olide (7), and 10α-hydroxy-1-oxoeremophila-7(11),8(9)-dien-12,8-olide (8). On the basis of IR, MS, and NMR data, particularly 2D-NMR analyses, the structures of the new compounds were established as: 2β-(angeloyloxy)-10β-hydroxyeremophil-7(11)-en-12,8α-olide (1), 6β-(angeloyloxy)-10β-hydroxyeremophil-7(11)-en-12,8α-olide (2), 2β-(angeloyloxy)-8β,10β-dihydroxyeremophil-7(11)-en-12,8α-olide (3), 2β-(angeloyloxy)-8α-hydroxyeremophila-7(11),9(10)-dien-12,8β-olide (4), and 8β-amino-10β-hydroxyeremophil-7(11)-en-12,8α-olide (5). In addition, the relative configuration of 1 was corroborated by X-ray diffraction analysis.
Co-reporter:Kaijie Xu, Shunyuan Jiang, Yan Zhou, Yanxia Zhang, Bing Xia, Xuemin Xu, Yi Zhou, Yufei Li, Mingkui Wang, Lisheng Ding
Journal of Pharmaceutical and Biomedical Analysis 2011 56(5) pp: 1089-1093
Publication Date(Web):
DOI:10.1016/j.jpba.2011.07.034
Co-reporter:Qiong Yu Zou, Na Li, Chun Dan, Wen Long Deng, Shu Lin Peng, Li Sheng Ding
Chinese Chemical Letters 2010 Volume 21(Issue 9) pp:1091-1093
Publication Date(Web):September 2010
DOI:10.1016/j.cclet.2010.05.002
A new ent-labdane diterpenoid, 19-O-β-d-glucopyranosyl-ent-labda-8(17),13-dien-15,16,19-triol, together with six known ent-labdane diterpenoids, was isolated from the aerial parts of Andrographis paniculata. The structure of the new compound was elucidated by extensive spectral analysis.
Co-reporter:Zhi-Zhou He, Ju-Fang Yan, Zhi-Jun Song, Fei Ye, Xun Liao, Shu-Lin Peng and Li-Sheng Ding
Journal of Natural Products 2009 Volume 72(Issue 6) pp:1198-1201
Publication Date(Web):May 28, 2009
DOI:10.1021/np800643n
Four new compounds including three bicoumarins, arteminorins A−C (1−3), and one neolignan, arteminorin D (4), together with 31 known ones were isolated from the aerial parts of Artemisia minor. Their structures were established on the basis of spectroscopic data and comparison with those of the related known compounds. Ethyl caffeate (27) showed in vitro cytotoxicity against the HepG2 cancer cell line. Arteminorin C (3) and luteolin (19) showed inhibitory activity on xanthine oxidase (XOD), and caffeic acid (28) exhibited inhibitory activity on protein tyrosine phosphatase 1B (PTP1B).
Co-reporter:Zhuoma Dawa;Yang Bai;Yan Zhou;Suolang Gesang;Ping A
Journal of Natural Medicines 2009 Volume 63( Issue 3) pp:327-330
Publication Date(Web):2009 July
DOI:10.1007/s11418-009-0320-1
The chemical constituents of the traditional Tibetan medicine of Saussurea medusa Maxim. (Compositae) were investigated and a new flavonoid glucoside, together with 14 known compounds, was isolated. The structure of the new compound was established as 6″-O-crotonoylhomoplantaginin by using one- and two-dimensional nuclear magnetic resonance spectroscopy and mass spectrometry analyses.
Co-reporter:Yan Zhou, Xin Liu, Jing Yang, Quan-Bin Han, Jing-Zheng Song, Song-Lin Li, Chun-Feng Qiao, Li-Sheng Ding, Hong-Xi Xu
Analytica Chimica Acta 2008 Volume 629(1–2) pp:104-118
Publication Date(Web):23 November 2008
DOI:10.1016/j.aca.2008.09.044
On-line ultra high-performance liquid chromatography (UHPLC) coupled with electrospray quadrupole time-of-flight tandem mass spectrometry (ESI–QTOF–MS/MS/MS) has been developed for the analysis of a series of caged xanthones in the resin of Garcinia hanburyi. The fragmentation of protonated molecular ions for 12 known cadged xanthones was carried out using low-energy collision-induced electrospray ionization tandem mass spectrometry. It was found that Retro-Diels-Alder rearrangement occurred in the CID processes and produced the characteristic fragment ions, which are especially valuable for the identification of this class of xanthones. The fragmentation differential between some cis-, trans-isomers was uncovered. Computation methods were utilized to rationalize the observed MS behaviors. On-line UHPLC-ESI-MS/MS/MS method has proved to be rapid and efficient in that within 6 min, 15 caged scaffold xanthones, including three pairs of epimers and four pairs of isomers in gamboges, were effectively separated and identified. Among them, two known, namely isogambogenin (13) and isomorellinol (14) and one likely new caged Garcinia xanthones from the Garcinia hanburyi were tentatively characterized based on the tandem mass spectra of known ones.
Co-reporter:Zhi Jun Song, Fan Luo, Yan Zhou, Bin Ru Bai, Shu Lin Peng, Li Sheng Ding
Chinese Chemical Letters 2007 Volume 18(Issue 6) pp:694-696
Publication Date(Web):June 2007
DOI:10.1016/j.cclet.2007.04.004
Two new isoflavonoids, 6-methoxy-5,7,8,4′-tetrahydryoxyisoflavone (1) and 4′-methoxy -5,6-dihydroxyisoflavone-7-O-β-d-glucopyranoside (2), were isolated from the rhizomes of Belamcanda chinensis (L.) DC. Their structures were elucidated by extensive spectroscopic evidence including 1D NMR, 2D NMR, MS and IR spectra.
Co-reporter:Ying-Tong Di;Yan Zhou;Suolang Gesang;Shu-Lin Peng
Helvetica Chimica Acta 2006 Volume 89(Issue 1) pp:94-102
Publication Date(Web):19 JAN 2006
DOI:10.1002/hlca.200690016
From the MeOH extract of the aerial parts of Swertia mileensis, four new secoiridoid glycosides were isolated, 4′-O-[(E)-caffeoyl]swertiamarin (1), 4′-O-[(Z)-coumaroyl]swertiamarin (7), 6′-O-[(E)-coumaroyl]swertiamarin (8), and 6′-O-[(Z)-coumaroyl]swertiamarin (9), together with five known compounds. Their structures were elucidated by NMR spectroscopy and tandem mass spectrometry. Detailed HPLC/MS analyses and MS/MS fragmentation pathways are discussed for the identification of the swertiamarin-derived (E)/(Z) isomers 6/7 and 8/9.
Co-reporter:Qi-Fa Li;Kai-Bei Yu;Xiao-Ling Wang;Yan Zhou;Shu-Lin Peng
Helvetica Chimica Acta 2006 Volume 89(Issue 11) pp:2738-2744
Publication Date(Web):21 NOV 2006
DOI:10.1002/hlca.200690245
Four new pregnane glycosides, tenacigenosides A–D (1–4), along with six known pregnane aglycones and five known pregnane glycosides, were isolated from the stems of Marsdenia tenacissima (Roxb.) Wight et Arn. (Asclepiadaceae). The chemical structures of the new compounds were established by 1D- and 2D-NMR as well as HR-MS analyses. The absolute configuration of 1 was confirmed by X-ray crystallography.
Co-reporter:Min Cai, Yan Zhou, Suolang Gesang, Ciren Bianba, Li-Sheng Ding
Journal of Chromatography B 2006 Volume 844(Issue 2) pp:301-307
Publication Date(Web):5 December 2006
DOI:10.1016/j.jchromb.2006.07.043
A high-performance liquid chromatography–diode array detection–tandem mass spectrometry (HPLC–DAD–MSn) method has been firstly developed for chemical fingerprint analysis of rhizomes of Gymnadenia conopsea R. Br. and rapid identification of major compounds in the fingerprints. Comparing the UV and MS spectra with those of reference compounds, seven main peaks in the fingerprints were identified as adenosine (1), 4-hydroxybenzyl alcohol (2), 4-hydroxybenzyl aldehyde (3), dactylorhin B (4), loroglossin (5), dactylorhin A (6) and militarine (7). Compounds 4–7 were succinate derivative esters and firstly discovered from this species. The Computer Aided Similarity Evaluation System (CASES) for chromatographic fingerprint of traditional Chinese medicine was employed to evaluate the similarities of 10 samples of the rhizomes of G. conopsea collected from Sichuan, Qinghai and Hebei provinces, Tibet autonomous region of China, and Nepal. These samples from different sources had similar chemical fingerprints. This method is specific and may serve for quality identification and comprehensive evaluation of this traditional Tibetan remedy.
Co-reporter:Li Bang-Jing;Gao Bao-Chun;Peng Shu-Lin;Liao Xun;Ding Li-Sheng
Chinese Journal of Chemistry 2005 Volume 23(Issue 7) pp:
Publication Date(Web):16 AUG 2005
DOI:10.1002/cjoc.200590933
A novel nortriterpene, acanthochlamic acid (6), along with 18 known compounds has been isolated from the whole plants of Acanthochlamys bracteata P. C. Kao, a single species in family Acanthochlamydaceae which is endemic to the southwest of China. The structure of the novel nortriterpene was elucidated as 3,4-seco-3-nor-lup-4(23),20(29)-dien-2,28-dioic acid by spectroscopic techniques including 1D and 2D NMR spectroscopy and confirmed by X-ray crystallography.
Co-reporter:Hui Dou;Xun Liao;Shu-Lin Peng;Yuan-Jiang Pan
Helvetica Chimica Acta 2003 Volume 86(Issue 8) pp:2797-2804
Publication Date(Web):28 AUG 2003
DOI:10.1002/hlca.200390230
The new rearranged-abietane diterpene 1, the four new triterpenoids 2–5, and the new aminoethylphenyl oligoglycoside 6, besides 19 known compounds, were isolated from the roots of Schnabelia tetradonta, a Chinese endemic herb. The structures of the new compounds were elucidated on the basis of spectroscopic evidence as 12,17-epoxy-11,14,16-trihydroxy-17(1516)-abeo-abieta-8,11,13,15-tetraen-7-one (1), 21β-(β-D-glucopyranosyloxy)-2α,3α-dihydroxyolean-12-en-28-oic acid (2), 2β,3β,16β-trihydroxy-15-oxo-28-norolean-12-en-23-oic acid (3), 3β-[(4-O-acetyl-β-D-glucopyranuronosyl)oxy]-2β,16β-dihydroxy-28-norolean-15-oxo-12-en-23-oic acid (4), 3β-[(4-O-acetyl-6-O-methyl-β-D-glucopyranuronosyl)oxy]-2β,16β-dihydroxy-15-oxo-28-norolean-12-en-23-oic acid (5), and 4-[2-(acetylamino)ethyl]phenyl O-6-O-[(Z)-p-methoxycinnamoyl]-β-D-glucopyranosyl-(12)]-O-[β-D-glucopyranosyl-(13)]-4-O-acetyl-α-L-rhamnopyranoside (6), respectively.