Co-reporter:Mei-Jun Chu, Xu-Li Tang, Guo-Fei Qin, Nicole J. de Voogd, ... Guo-Qiang Li
Chinese Chemical Letters 2017 Volume 28, Issue 6(Volume 28, Issue 6) pp:
Publication Date(Web):1 June 2017
DOI:10.1016/j.cclet.2017.01.009
Three new non-brominated pyrrole alkaloids, nakamurines A–C (1–3) were isolated from the South China Sea sponge Agelas nakamurai. Their structures were elucidated on the basis of spectroscopic data. Compound 2 showed weak antimicrobial activity against Candida albicans with MIC of 60 μg/mL.Download high-res image (93KB)Download full-size imageThree new pyrrole alkaloids, nakamurines A–C were isolated from the South China Sea sponge Agelas nakamurai.
Co-reporter:Liang An;Wenjuan Song;Xuli Tang;Nicole J. de Voogd;Qi wang;Meijun Chu;Pinglin Li;Guoqiang Li
RSC Advances (2011-Present) 2017 vol. 7(Issue 24) pp:14323-14329
Publication Date(Web):2017/03/03
DOI:10.1039/C6RA27026C
A chemical investigation of the South China Sea sponge Agelas aff. nemoechinata yielded three pairs of new enantiotopic pyrrole alkaloids nemoechines A–C (1–3), one new diterpene-adenine alkaloid nemoechine D (8), and one new polyketide nemoechioxide A (10), together with nine known analogues (4–7, 9, 11–14). Compounds 1–3 were initially obtained as racemates and were further separated by chiral HPLC chromatography to afford the three pairs of enantiomers. Their structures including absolute configurations of compounds 1–3 were elucidated on the basis of comprehensive spectroscopic analysis and quantum chemical calculation. Nemoechine A (1), possessing an unusual cyclopentane-fused imidazole ring system, represents the first monomeric precursor of nagelamide J. Compounds 8 and 9 showed cytotoxicity against HL-60 cell lines with IC50 values of 9.9 and 0.9 μM, respectively, and compound 9 was also cytotoxic against HeLa cell lines with IC50 value of 8.9 μM.
Co-reporter:Zongjiang Yu; Weizhi Sun; Weibing Peng; Rilei Yu; Guoqiang Li;Tao Jiang
Molecular Pharmaceutics 2016 Volume 13(Issue 5) pp:1699-1710
Publication Date(Web):March 28, 2016
DOI:10.1021/acs.molpharmaceut.6b00129
Oleanolic acid (OA) is a well-known pentacyclic triterpenoid compound, which has been used as a dietary supplement and is supplied as an over-the-counter drug for the treatment of human liver diseases. These are reasons for the low bioavailability of OA which have restricted its wider application. In this study, two OA prodrugs (1,3-cyclic propanyl phosphate esters of OA) were designed and synthesized. The hepatoprotective effects of these prodrugs were evaluated against carbon tetrachloride (CCl4) induced liver injury in mice; the levels of alanine aminotransferase (ALT), lactic dehydrogenase (LDH), and aspartate aminotransferase (AST) were significantly increased, and the level of the hepatic malondialdehyde (MDA) was increased. The metabolism, in vitro, of the prodrugs was studied by incubation in rat liver microsome; the plasma pharmacokinetics and the biodistribution in vivo after intravenous (iv) injection to six rats were investigated, respectively. The prodrugs diminished gradually with time; most of the parent drugs were released within 30 min in vitro, and the presumed mechanism of the in vitro metabolism was confirmed. The plasma–concentration data in vivo was analyzed by a compartmental method: both the prodrugs and the corresponding released parent drugs existed at up to 48 h in rats. The t1/2 improved after intravenous administration in rats compared with direct injection of the parent drugs. All analyte concentrations were highest in the liver, and most of the prodrugs were excreted in feces (>47.11%). Therefore, 1,3-cyclic propanyl phosphate esters of OA can serve as a promising lead candidate for drugs.
Co-reporter:Tao Li, Bin Wang, Nicole J. de Voogd, Xu-Li Tang, Qi Wang, Mei-Jun Chu, Ping-Lin Li, Guo-Qiang Li
Chinese Chemical Letters 2016 Volume 27(Issue 7) pp:1048-1051
Publication Date(Web):July 2016
DOI:10.1016/j.cclet.2016.05.017
Two new N-methyladenine-containing diterpenes, nemoechines F (1) and G (2), were isolated from the South China Sea sponge Agelas aff. nemoechinata. The structures were assigned on the basis of spectroscopic date. Compound 2 showed weak activity against Jurkat cell lines with IC50 of 17.1 μmol/L.Two new N-methyladenine-containing diterpenes, nemoechines F and G, were isolated from the South China Sea Sponge Agelas aff. nemoechinata.
Co-reporter:Xing-Wang Zhang;Xu-Li Tang;Bao-Sheng Liu;Ping-Lin Li
Chemistry & Biodiversity 2016 Volume 13( Issue 2) pp:233-237
Publication Date(Web):
DOI:10.1002/cbdv.201500093
Abstract
Twenty-four steroid-based natural products, 9,10-secosteroids (1–10), 1,4-dien-3-one steroids (11–19), and 4-en-3-one steroids (20–24), containing varying side-chains, were isolated from the South China Sea gorgonian Muricella sibogae. The structures of one new 9,10-secosteroid, sibogol D (1), and two new 1,4-dien-3-one steroids, sibogols E and F (11 and 12), were elucidated by extensive spectroscopic analyses and by comparison with the literature data. Cytotoxicities for all the isolates were evaluated against four selected tumor cell lines, HL-60, HCT116, K562, and P388. Compounds 3, 9, and 13 exhibited potent cytotoxic activities against the HL-60 cell line, with IC50 values ranging from 1.27 to 10.05 μM, and compound 3 was also cytotoxic against HCT116 with an IC50 value of 5.8 μM. The bioassay results also indicated a potential relationship between structural patterns and activity. The newly presented series of 1,4-dien-3-one and 4-en-3-one types of steroids relating to the unique 9,10-secosteroids in biogenesis were found in this species for the first time, which is of considerable chemotaxonomic significance.
Co-reporter:Qi Wang, Xuli Tang, Xiangchao Luo, Nicole J. de Voogd, Pinglin Li, and Guoqiang Li
Organic Letters 2015 Volume 17(Issue 14) pp:3458-3461
Publication Date(Web):June 30, 2015
DOI:10.1021/acs.orglett.5b01503
A pair of novel bisheterocyclic quinoline-imidazole alkaloids, (+)- and (−)-spiroreticulatine (1), were isolated from the South China Sea sponge Fascaplysinopsis reticulata. The structures and absolute configurations were elucidated by comprehensive spectroscopic analysis, single-crystal X-ray diffraction, and quantum chemical calculation methods. Spiroreticulatine is the first example of a sponge-derived natural spiro quinoline-imidazole alkaloid that may derive from tryptophan and 1,3-dimethylurea. Compound 1 showed inhibitory activity on IL-2 production but inactive against normal tumor cell lines.
Co-reporter:Nai-Xia Zhang;Xu-Li Tang;Leen vanOfwegen;Lei Xue;Wen-Juan Song;Ping-Lin Li
Chemistry & Biodiversity 2015 Volume 12( Issue 2) pp:273-283
Publication Date(Web):
DOI:10.1002/cbdv.201400044
Abstract
Four new polyhydroxylated steroids, 1–4, and the racemic form of cyclopentenone 9, together with four known steroids, 5–8, one known cyclopentenone derivative, 10, and one known butenolide derivative, 11, were isolated from the soft coral Sinularia acuta collected from Weizhou Island of Guangxi Province, P. R. China. Their structures were elucidated on the basis of spectroscopic analyses and by comparison of the corresponding data with those previously reported. The cytotoxicities of the isolates 1–11 in vitro against the selected tumor cell lines HL-60, HeLa, and K562 were evaluated. Compounds 2 and 5 showed potent cytotoxicities against HL-60 cell lines with IC50 values of 7.3 and 9.9 μM, respectively. Compounds 5 and 6 showed moderate activities against K562 cell lines with IC50 values of 10.9 and 11.7 μM, respectively, while compounds 1, 2, and 6 showed weak activities against HeLa cell lines with respective IC50 values of 44.8, 27.1, and 18.2 μM. This is the first report on chemical and bioactivity research of S. acuta.
Co-reporter:Ji-Yong Chen ; Ping-Lin Li ; Xu-Li Tang ; Shu-Jiang Wang ; Yong-Tao Jiang ; Li Shen ; Ben-Ming Xu ; Yong-Liang Shao
Journal of Natural Products 2014 Volume 77(Issue 9) pp:1997-2005
Publication Date(Web):August 19, 2014
DOI:10.1021/np500249v
A phytochemical study on the rhizomes of Cimicifuga foetida resulted in the isolation of two new cycloartane triterpenoids (1 and 2), eight new cycloartane glycosides (3–10), and six known cycloartane glycoside analogues (11–16). The structures of 1–10 were determined by application of spectroscopic methods, with the absolute configuration of 1 determined by X-ray crystallography. Compounds 1–6, as three pairs of epimers at C-10 and C-24, belong to a seven-membered-ring variant of 9,10-seco-9,19-cycloartane triterpenoids, and glycosides 3–10 were found to be 3-O-β-d-xylopyranosides. The cytotoxicity of the isolates was evaluated against five selected human tumor cell lines, and the known compounds 15 and 16 showed cytotoxicity against the hepatocellular carcinoma SMMC-7721 cell line with IC50 values of 5.5 and 6.3 μM, respectively.
Co-reporter:Lei Xue, Ping-Lin Li, Zhen Liang, Xu-Li Tang, Guo-Qiang Li
Biochemical Systematics and Ecology 2014 Volume 57() pp:48-51
Publication Date(Web):December 2014
DOI:10.1016/j.bse.2014.06.010
•Seven compounds were obtained from the genus Echinogorgia for the first time.•New compound 1 was elucidated by spectroscopic and chemical calculation methods.•The chemotaxonomic importance of the isolates was discussed.Three guaiane-type sesquiterpenoids (1−3) and five steroids with 3β-hydroxy-5-en-7-one moiety (4−8) were obtained from gorgonian Echinogorgia sassapo reticulata collected from the South China Sea. Among them, new compound 1 was identified as (1S,5S,8S)-8-methoxy-menelloide B by spectroscopic methods including IR, HRESIMS, 1D and 2D NMR, and ECD spectra. All compounds except for 3 were obtained for the first time from the genus Echinogorgia. The chemotaxonomic significance of these compounds was summarized.
Co-reporter:Jinrong Zhang, Xuli Tang, Jing Li, Peifeng Li, Nicole J. de Voogd, Xiaoqin Ni, Xiaojie Jin, Xiaojun Yao, Pinglin Li, and Guoqiang Li
Journal of Natural Products 2013 Volume 76(Issue 4) pp:600-606
Publication Date(Web):March 25, 2013
DOI:10.1021/np300771p
Five new polyketides, plakortoxides A (1) and B (2), simplextones C (3) and D (4), and plakorsin D (5), together with six known analogues (6–11) were isolated from the South China Sea sponge Plakortis simplex. Their structures were identified by spectroscopic and chemical methods, including NMR, MS, and IR. Experimental and calculated ECD spectra and the modified Mosher’s method were used to determine the absolute configurations. Structurally, both plakortoxides A and B feature a butenolide coupled to an epoxide moiety, while simplextones C and D consist of γ-butyrolactone and cyclopentane moieties, and plakorsin D is a furan acetic acid polyketide. The cytotoxic activities of the isolates were tested, and compounds 8, 10, and 11 showed potent cytotoxicity against both K562 and HeLa tumor cell lines with IC50 values ranging from 0.8 to 5.3 μM. Compound 3 showed significant inhibitory activity against c-Met kinase.
Co-reporter:Can-Ling Cheng, Zhong-Zhao Wang, Ping-Lin Li, Xing-Wang Zhang, Rong-Cui Wu, Hong-Yan Zhu, Xu-Li Tang, Guo-Qiang Li
Chinese Chemical Letters 2013 Volume 24(Issue 12) pp:1080-1082
Publication Date(Web):December 2013
DOI:10.1016/j.cclet.2013.07.011
A continuing phytochemical study on the semi-mangrove plant Hibiscus tiliaceus yielded two new tetracyclic triterpenoids (3β,24S)-19(10→9)-abeo-8α,9β,10α-eupha-5,25(26)-dien-3,24-diol (tiliacol A, 1), and (3β,23Z)-19(10→9)-abeo-8α,9β,10α-tircalla-5,23-dien-3,25-diol (tiliacol B, 3), together with one known analog (2). Their structures were elucidated on the basis of extensive spectral analyses (MS, IR, 1D NMR and 2D NMR) and comparison with literature compounds. Compound 2 showed potent cytotoxicity against both P388 and HeLa cells with IC50 values of 11.2 μmol/L and 11.5 μmol/L, respectively.Two new tetracyclic triterpenoids (3β,24S)-19(10→9)-abeo-8α,9β,10α-eupha-5,25(26)-dien-3,24-diol (tiliacol A, 1), and (3β,23Z)-19(10→9)-abeo-8α,9β,10α-tircalla-5,23-dien-3,25-diol (tiliacol B, 3), together with one known analogue (2), were isolated from Hibiscus tiliaceus. Compound 2 showed potent cytotoxicity against both P388 and HeLa cells with IC50 values of 11.2 μmol/L and 11.5 μmol/L, respectively.
Co-reporter:Ting-Ting Li;Xu-Li Tang;Can-Ling Chen;Xing-Wang Zhang;Rong-Cui Wu;Hong-Yan Zhu;Ping-Lin Li
Helvetica Chimica Acta 2013 Volume 96( Issue 6) pp:1188-1196
Publication Date(Web):
DOI:10.1002/hlca.201200489
Abstract
Bioactivity-guided isolation of the rare gorgonian Muricella sibogae (Nutting) yielded the two new eunicellin diterpenes sibogin A and B (1 and 2), the three new 9,10-secosteroids sibogol A–C (6–8), together with the three known eunicellin diterpenes 3–5 and the five known 9,10-secosteroids 9–13. Their structures were established by extensive spectral analysis (1D- and 2D-NMR, IR, and MS). The cytotoxicity of the isolates 1–13 was evaluated in vitro against the selected tumor cell lines P388 and BEL-7402. All the compounds showed only weak activity against P388 cell lines, with an inhibition rate ranging from 10 to 60% at a concentration of 50 μg/ml, whereas the were inactive against BEL-7402 cell lines.
Co-reporter:Caixia Liu, Xuli Tang, Pinglin Li, and Guoqiang Li
Organic Letters 2012 Volume 14(Issue 8) pp:1994-1997
Publication Date(Web):April 3, 2012
DOI:10.1021/ol3004589
Suberitine A–D (1–4), four new bis-aaptamine alkaloids with two aaptamine skeleton units, 8,9,9-trimethoxy-9H-benzo[de][1,6]-naphthyridine and demethyl(oxy)-aaptamine, linked through a rare C-3–C-3′ or C-3–C-6′ σ-bond between the 1,6-naphthyridine rings, together with two known monomers 5 and 6, were isolated from the marine sponge Aaptos suberitoides. Their structures were elucidated using NMR spectroscopy. Compounds 2 and 4 showed potent cytotoxicity against P388 cell lines, with IC50 values of 1.8 and 3.5 μM, respectively.
Co-reporter:Jin-Rong Zhang;Ping-Lin Li;Xu-Li Tang;Xin Qi
Chemistry & Biodiversity 2012 Volume 9( Issue 10) pp:2218-2224
Publication Date(Web):
DOI:10.1002/cbdv.201100374
Abstract
Nine achiral tetraprenylated alkaloids, including three new compounds, named malonganenones I–K (1–3, resp.), together with six known analogs, 4–9, were isolated from the gorgonian Euplexaura robusta collected from Weizhou Island of Guangxi Province, China. The structures of compounds 1–3 were elucidated by extensive spectral analyses, especially of their 1D- and 2D-NMR data. Compounds 1, 4, 6, and 7 showed moderate cytotoxicities against K562 and HeLa tumor cell lines with IC50 values ranging from 0.35 to 10.82 μM. Compound 6 also showed moderate inhibitory activity against c-Met kinase at a concentration of 10 μM.
Co-reporter:Bin Wang;Yang-Bai Zhang;Hua-Shi Guan;Guo-Zhong Tong
Chromatographia 2009 Volume 70( Issue 5-6) pp:811-816
Publication Date(Web):2009 September
DOI:10.1365/s10337-009-1230-9
For the first time a validated liquid chromatography method coupled with hierarchical clustering analysis has been developed for the study of fingerprint chromatograms of extracts from the Radix Glehniae of Glehnia littorali. Liquid chromatography with gradient elution was performed on extracts from 23 plant samples collected from different geographical locations. Ten of twenty-three plant samples were selected using hierarchical clustering analysis and employed to establish the fingerprint. The fingerprint was established and ten chromatographic peaks were selected as characteristic peaks and panaxynol was used as reference standard compounds. The fingerprint chromatograms had a good stability, precision, and reproducibility. This method is a very reliable and useful method for assessment of the quality of Radix Glehniae.
Co-reporter:Gang Zhang, Xuli Tang, Canling Cheng, Kaikai Gong, Xingwang Zhang, Hongyan Zhu, Rongcui Wu, Pinglin Li, Guoqiang Li
Steroids (September 2013) Volume 78(Issue 9) pp:845-850
Publication Date(Web):1 September 2013
DOI:10.1016/j.steroids.2013.05.009
•Ten new 9,11-secosteroids were isolated from the gorgonian Subergorgia suberosa.•Their structures were elucidated by analysis of MS, 1D and 2D NMR data.•All the isolates possess the same 3β,6α,11-trihydroxy-7-en-9-one-5α-9,11- secosteroidal nucleus.•Compounds 9 and 10 showed significant cytotoxic activities..Ten new 9,11-secosteroids, subergorgols A–J (1–10), including two pairs of epimers (3/4, and 6/7), along with three known analogues (11–13) were isolated from the South China Sea gorgonian Subergorgia suberosa. The structures of these compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with the literature data. The cytotoxicities in vitro against three selected human tumor cell lines for all the compounds were evaluated. Compound 9 showed significant cytotoxicities toward both K562 and MDA-MB-231 cell lines with IC50 values of 5.5 and 6.2 μM, respectively, and compound 10 also showed inhibitory activity against K562 cell line with an IC50 value of 6.5 μM.Download full-size image
Co-reporter:Guo Qiang Li, Yang Bai Zhang, Hua Shi Guan
Fitoterapia (April 2008) Volume 79(Issue 3) pp:238-239
Publication Date(Web):1 April 2008
DOI:10.1016/j.fitote.2008.01.002
A new isoxazol derivative, 9,9a-dihydro-naphtho [2, 3-c] isoxazol-3(1H)-one (Naphthisoxazol A) (1, Fig. 1) was isolated from the roots of the traditional Chinese medicine Glehnia littoralis. The structure has been elucidated on the basis of MS and extensive NMR analysis.