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1.
Antibacterial Δ1‐3‐Ketosteroids from the South China Sea Gorgonian Coral Subergorgia rubra
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Three new Δ1‐3‐ketosteroids characterized with a 9‐OH, subergosterones A–C ( 1 – 3 ), together with five known analogs 4 – 8 , were obtained from the gorgonian coral Subergorgia rubra collected from the South China Sea. The structures of 1 – 3 , including their absolute configurations, were determined by comprehensive spectroscopic methods and electronic circular dichroism (ECD) experiments. Compounds 2 and 3 exhibited inhibitory antibacterial activities against Bacillus cereus with MIC values of 1.56 μM . 相似文献
2.
Three New Phenylpropanoids from the Roots of Piper taiwanense and Their Inhibitory Activities on Platelet Aggregation and Mycobacterium tuberculosis
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Si Chen Ming‐Jen Cheng Chin‐Chung Wu Chien‐Fang Peng Hung‐Yi Huang Hsun‐Shuo Chang Chyi‐Jia Wang Ih‐Sheng Chen 《化学与生物多样性》2014,11(5):792-799
Bioassay‐guided fractionation of the active AcOEt‐soluble fraction from the roots of Piper taiwanense has led to the isolation of two new phenylpropanoids, taiwanensols A and B ( 1 and 2 , resp.), a new natural product, taiwanensol C ( 3 ), and 3‐acetoxy‐4‐hydroxy‐1‐allylbenzene ( 4 ). The compounds were obtained as two isomer mixtures ( 1 / 2 and 3 / 4 , resp.). Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR spectroscopy and mass spectrometry, and by the comparison of their NMR data with those of related compounds. Compounds 1 – 4 were evaluated for their antiplatelet and antitubercular activities. The mixtures 1 / 2 and 3 / 4 showed potent inhibitory activities against platelet aggregation induced by collagen, with IC50 values of 35.2 and 8.8 μM , respectively. In addition, 1 / 2 and 3 / 4 showed antitubercular activities against Mycobacterium tuberculosis H37Rv, with MIC values of 30.0 and 48.0 μg/ml, respectively. 相似文献
3.
Hui Chen Shuang‐Gang Ma Zhen‐Feng Fang Jian Bai Shi‐Shan Yu Xiao‐Guang Chen Qi Hou Shao‐Peng Yuan Xia Chen 《化学与生物多样性》2013,10(4):695-702
Three new tirucallane triterpenoids, brumollisols A–C ( 1 – 3 , resp.), together with five known analogues, (23R,24S)‐23,24,25‐trihydroxytirucall‐7‐ene‐3,6‐dione ( 4 ), piscidinol A ( 5 ), 24‐epipiscidinol A ( 6 ), 21α‐methylmelianodiol ( 7 ), and 21β‐methylmelianodiol ( 8 ), were isolated from an EtOH extract of the stems of Brucea mollis. Their structures were elucidated by means of spectroscopic methods including 1D‐ and 2D‐NMR techniques and mass spectrometry. In the in vitro assays, compound 6 exhibited significant cytotoxic activity against A549 and BGC‐823 cancer cells with IC50 values of 1.16 and 3.01 μM , respectively. At a concentration of 10 μM , compounds 1 – 5, 7 , and 8 were found to inhibit NO production in mouse peritoneal macrophages with inhibitory ratios ranging from 39.8±7.7 to 68.2±4.5%. 相似文献
4.
Ren Ren Chao‐Jun Chen Sha‐Sha Hu Hui‐Ming Ge Wen‐Yong Zhu Ren‐Xiang Tan Rui‐Hua Jiao 《化学与生物多样性》2015,12(3):371-379
Three new drimane sesquiterpenoids, astellolides C–E ( 1 – 3 , resp.), four new drimane sesquiterpenoid p‐hydroxybenzoates, astellolides F–I ( 4 – 7 , resp.), together with two known compounds astellolides A and B ( 8 and 9 , resp.), have been isolated from the liquid culture of Aspergillus oryzae (strain No. QXPC‐4). Their structures were established by comprehensive analysis of spectroscopic data. The relative and absolute configurations were determined on the basis of NOESY and CD data, together with single‐crystal X‐ray diffraction analyses of compounds 1 – 3 . The metabolites were evaluated for their cytotoxic activities, however, no compounds showed a significant cytotoxicity against the tested cell lines at a concentration of 20 μM . 相似文献
5.
Wei‐Guang Wang Zhao‐Yuan Wu Rui Chen Hai‐Zhou Li Hong‐Mei Li Yuan‐Dan Li Rong‐Tao Li Huai‐Rong Luo 《化学与生物多样性》2013,10(6):1061-1071
Four highly acylated diterpenoids, designated as pierisformotoxins A–D ( 1 – 4 , resp.), along with 26 known compounds, were isolated from the flowers of Pieris formosa. Among them, pierisformotoxins A and B ( 1 and 2 , resp.) were new highly acylated grayanane diterpenoids, of which the five‐membered ring A has undergone an oxidative cleavage between C(3) and C(4), followed by lactonization, to give rise to a five‐membered lactone ring between C(3) and C(5), differing from the previously reported grayanane diterpenoids with a 5/7/6/5 ring system. Results of the cAMP‐regulation‐activity assay showed that pierisformotoxin C ( 3 ) at 10 μM (inhibitory ratio (IR): 10.1%) or 2 μM (9.8%), and pierisformotoxin B ( 2 ) at 50 μM (13.9%) significantly decreased the cAMP level in N1E‐115 neuroblastoma cells (p<0.05). 相似文献
6.
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 . 相似文献
7.
Antimicrobial‐directed phytochemical investigation of the MeOH extract of Drypetes staudtii afforded two new compounds, 4,5‐(methylenedioxy)‐o‐coumaroylputrescine ( 1 ), 4,5‐(methylenedioxy)‐o‐coumaroyl‐4′‐N‐methylputrescine ( 2 ), along with seven known natural products 4α‐hydroxyeremophila‐1,9‐diene‐3,8‐dione ( 3 ), drypemolundein B ( 4 ), friedelan‐3β‐ol ( 5 ), erythrodiol ( 6 ), ursolic acid ( 7 ), p‐coumaric acid ( 8 ), and β‐sitosterol ( 9 ). Structures of compounds 1 – 9 were elucidated with the aid of extensive NMR and mass spectral studies. All of the isolates exhibited antibacterial activity against Gram‐positive and Gram‐negative bacteria with minimum inhibitory concentration (MIC) in the range of 8 – 128 μg/ml. Compounds 1 – 2 were also moderately active against Candida albicans with an MIC value of 32 μg/ml. 相似文献
8.
Six new triterpene saponins, ilexasprellanosides A–F ( 1 – 6 , resp.), together with eleven known compounds were isolated from the roots of Ilex asprella. The new saponins were characterized as ursa‐12,18‐dien‐28‐oic acid 3‐O‐β‐D ‐xylopyranoside ( 1 ), 19α‐hydroxyursolic acid 3‐O‐β‐D ‐(2′‐O‐acetylxylopyranoside) ( 2 ), 19α‐hydroxyursolic acid 3‐O‐β‐D ‐glucuronopyranoside ( 3 ), 3β,19α‐dihydroxyolean‐12‐en‐23,28‐dioic acid 28‐O‐β‐D ‐glucopyranoside ( 4 ), 19α‐hydroxyoleanolic acid 3‐O‐β‐D ‐(2′‐O‐acetylxylopyranoside) ( 5 ), 19α‐hydroxyoleanolic acid 3‐O‐β‐D ‐glucuronopyranoside ( 6 ). The structures of the new compounds were elucidated by analysis of their spectroscopic data and chemical degradation. Compounds 2, 4 , oleanolic acid 3‐O‐β‐D ‐glucuronopyranoside, 3‐β‐acetoxy‐28‐hydroxyurs‐12‐ene, and pomolic acid showed significant cytotoxic activities against human tumor cell line A549 (IC50 values of 1.87, 2.51, 1.41, 3.24, and 5.63 μM , resp.). 相似文献
9.
Seven new polyoxygenated cembranoids possessing an α‐methylene‐γ‐lactone group, crassocolides G–M ( 1 – 7 , resp.), have been isolated from the AcOEt extract of the Formosan soft coral Sarcophyton crassocaule. The structures of compounds 1 – 7 were established by detailed spectroscopic analyses, including 2D‐NMR spectroscopy (1H,1H‐COSY, HMQC, HMBC, and NOESY), while the absolute configuration of 1 was determined using a modified reaction of Mosher's method. The cytotoxicity of compounds 1 – 7 against a limited panel of cancer cell lines was also determined. 相似文献
10.
Ya‐Long Zhang Jian‐Guang Luo Chuan‐Xing Wan Zhong‐Bo Zhou Ling‐Yi Kong 《化学与生物多样性》2015,12(11):1768-1776
Four new flavonoids, mortatarins A–D ( 1 – 4 , resp.), along with eight known flavonoids ( 5 – 12 ) were isolated from the root bark of Morus alba var. tatarica. Their structures were established on the basis of spectroscopic data analysis, and the absolute configuration of 4 was determined by analysis of its CD spectrum. All isolates were tested for inhibitory activities against α‐glucosidase. Compounds 4, 7 , and 8 exhibited a significant degree of inhibition with IC50 values of 5.0±0.3, 7.5±0.5, and 5.9±0.2 μM , respectively. 相似文献
11.
Six new triterpenoids, meliasenins S–X ( 1 – 6 , resp.), were isolated from the stem bark of Melia toosendan. Their structures were elucidated by mass spectrometry, NMR experiments, and comparison with the known compounds. Particularly, the absolute configuration at C(24) in new compounds was determined through their CD spectra of the [Pr(FOD)3] complex (fod=1,1,1,2,2,3,3,7,7,7‐decafluoroheptane‐4,6‐dione) in CCl4, as well as by using Mosher's method. 相似文献
12.
Toshihiro Akihisa Shun Tochizawa Nami Takahashi Ayako Yamamoto Jie Zhang Takashi Kikuchi Makoto Fukatsu Harukuni Tokuda Nobutaka Suzuki 《化学与生物多样性》2012,9(6):1172-1187
Five new saccharide fatty acid esters, named nonioside P ( 3 ), nonioside Q ( 4 ), nonioside R ( 8 ), nonioside S ( 10 ), and nonioside T ( 14 ), and one new succinic acid ester, butyl 2‐hydroxysuccinate (=4‐butoxy‐3‐hydroxy‐4‐oxobutanoic acid) ( 31 ), were isolated, along with 26 known compounds, including eight saccharide fatty acid esters, 1, 2, 5, 6, 7, 9, 12 , and 13 , three hemiterpene glycosides, 15, 17 , and 18 , six iridoid glycosides, 21 – 25 , and 27 , and nine other compounds, 20, 28, 29 , and 32 – 37 , from a MeOH extract of the fruit of Morinda citrifolia (noni). Upon evaluation of these and five other glycosidic compounds, 11, 16, 19, 26 , and 30 , from M. citrifolia fruit extract for their inhibitory activities against melanogenesis in B16 melanoma cells induced with α‐melanocyte‐stimulating hormone (α‐MSH), most of the saccharide fatty acid esters, hemiterpene glycosides, and iridoid glycosides showed inhibitory effects with no or almost no toxicity to the cells. These compounds were further evaluated with respect to their cytotoxic activities against two human cancer cell lines (HL‐60 and AZ521) and their inhibitory effects on Epstein? Barr virus early antigen (EBV‐EA) activation induced with 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells. 相似文献
13.
Characteristic Steroids from the South China Sea Gorgonian Muricella sibogae and Their Cytotoxicities
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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. 相似文献
14.
Wannapha Molee Anuchit Phanumartwiwath Chatchai Kesornpun Sanya Sureram Nattaya Ngamrojanavanich Kornkanok Ingkaninan Chulabhorn Mahidol Somsak Ruchirawat Prasat Kittakoop 《化学与生物多样性》2018,15(3)
New naphthalene derivatives ( 1 and 2 ) and a new isomer ( 3 ) of ventilagolin, together with known anthraquinones, chrysophanol ( 4 ), physcion or emodin 3‐methyl ether ( 5 ), and emodin ( 6 ), were isolated from vines of Ventilago denticulata. The isolated compounds exhibited cytotoxic activity with IC50 values of 1.15 – 40.54 μg/ml. Compounds 1 – 3 selectively exhibited weak antibacterial activity (MIC values of 200.0 – 400.0 μg/ml), while emodin ( 6 ) displayed moderate antibacterial activity with MIC value of 25.0 μg/ml. The isolated compounds showed nitric oxide and DPPH radical scavenging activities. Compounds 1 – 3 and 6 exhibited weak xanthine oxidase inhibitory activity, while emodin ( 6 ) acted as an aromatase inhibitor with the IC50 value of 10.1 μm . Compounds 1 and 2 exhibited phosphodiesterase 5 inhibitory activity with IC50 values of 8.28 μm and 6.48 μm , respectively. 相似文献
15.
Zhiying Wang Peng Fu Peipei Liu Pei Wang Jiabo Hou Wenjun Li Weiming Zhu 《化学与生物多样性》2013,10(2):281-287
Two new pyran‐2‐ones, nocardiopyrones A and B ( 1 and 2 , resp.), along with four known compounds, pyridinols 3 – 5 , and 1‐acetyl‐β‐carboline ( 6 ) were isolated from the alkalophilic actinomycete Nocardiopsis alkaliphila sp. nov. YIM‐80379. Their structures were established on the basis of spectroscopic analysis, CD spectra, and the quantum‐chemical ECD calculation. Pyridinols 3 – 5 were isolated from a natural source for the first time. Compounds 1 and 2 showed weak antibacterial activities against Pseudomonas aeruginosa, Enterobacter aerogenes, and Escherichia coli with MIC values of 20–48 μM . Compound 2 showed weak antimicrobial activities against Candida albicans and Staphylococcus aureus with MIC values of 24 and 48 μM , respectively. 相似文献
16.
You‐Heng Gao Zhi‐Xiong Wei Yi Cheng Teng‐Hua Wang Lin Ni Xiao‐Hong Zhou Li‐Yuan Zhang 《化学与生物多样性》2013,10(8):1487-1493
Four new ent‐kaurane diterpenoids, rabdonervosins G–J ( 1 – 4 , resp.), were isolated from the leaves and stems of Isodon nervosus. Their structures were elucidated by extensive spectroscopic analyses, including 1D‐, 2D‐NMR and HR mass spectra. Compound 2 showed potent cytotoxicity against the HepG2 and PC‐9/ZD cell lines with IC50 values of 2.36 and 6.07 μM , respectively, and compound 3 exhibited cytotoxicity against the HepG2 and CNE2 cell lines with IC50 values of 8.64 and 9.77 μM , respectively. 相似文献
17.
Yu‐Xin Yan Jie‐Qing Liu Hong‐Wei Wang Jin‐Xiong Chen Jian‐Chao Chen Li Chen Lin Zhou Ming‐Hua Qiu 《化学与生物多样性》2015,12(7):1040-1046
Four new limonoids, azadiraindins A–D ( 1 – 4 , resp.), together with seven known analogs, were isolated from the MeOH extract of Azadirachta indica. The structures of 1 – 4 were elucidated by NMR and MS spectroscopic analyses, and the relative configuration of 1 was determined by single‐crystal X‐ray crystallography. The compounds isolated in comparatively large amount were evaluated for their antifeedant activities against Plutella xylostella; the antifeedant rate of 10 was 90.6% and the corrected mortality of 8 was 79.2%. 相似文献
18.
Hai‐Xue Kuang Zhi‐Bin Wang Qiu‐Hong Wang Bing‐You Yang Hong‐Bin Xiao Yoshihito Okada Tohru Okuyama 《化学与生物多样性》2013,10(4):703-710
Three new triterpene glucosides, named congmuyenosides C–E ( 1 – 3 , resp.), along with four known ones, were isolated from an EtOH extract of Aralia elata (Miq .) Seem . leaves. The structures of the new compounds were identified as 3‐O‐{β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐glucopyranosyl}caulophyllogenin ( 1 ), 3‐O‐{β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐glucopyranosyl}hederagenin 28‐O‐β‐D ‐glucopyranosyl ester ( 2 ), 3‐O‐{β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐glucopyranosyl}echinocystic acid 28‐O‐β‐D ‐glucopyranosyl ester ( 3 ) on the basis of spectral analyses, including MS, 1H‐NMR, 13C‐NMR, DEPT, HSQC, HMBC, NOESY, and HSQC‐TOCSY experiments. All isolates obtained were evaluated for their cytotoxic activities against three human tumor cell lines (HepG2, SKOV3, and A549). Compound 3 showed significant cytotoxicity against A549 cell line (IC50 9.9±1.5 μM ). 相似文献
19.
Bernhard Biersack Randi Diestel Carsten Jagusch Georg Rapp Florenz Sasse Rainer Schobert 《化学与生物多样性》2008,5(11):2423-2430
The marine tetramic acid (=1,5‐dihydro‐4‐hydroxy‐2H‐pyrrol‐2‐ones) derivatives melophlin P, Q, and R ( 1p – 1r , resp.) were synthesized for the first time in only four steps. Together with the congenerous melophlins A–C and G, they were also tested for antimicrobial and cytotoxic effects. Melophlins B, C, P, Q, and R, which share a 5‐Me residue, showed some antibacterial activity, mainly in Gram‐positive bacteria. Melophlins B, C, and R, which have Me‐branched 3‐acyl side chains in common, inhibited the growth of cells of human KB‐3‐1 cervix carcinoma, A‐498 kidney carcinoma, and U‐937 leukemia with IC50 values <10 μM . They were similar in activity to cisplatin. Melophlin Q, also Me‐branched, was astoundingly specific in inhibiting A‐498 kidney cancer cells, while melophlin P inhibited U‐937 leukemia cells particularly well. The position of the Me branch is decisive for the magnitude of the antiproliferative effect of the melophlin couples B/C and R/Q. 相似文献
20.
Inhibition of NO Production by Grindelia argentina and Isolation of Three New Cytotoxic Saponins
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Natalia P. Alza Eva‐Maria Pferschy‐Wenzig Sabine Ortmann Nadine Kretschmer Olaf Kunert Gerald N. Rechberger Rudolf Bauer Ana P. Murray 《化学与生物多样性》2014,11(2):311-322
A bioassay‐guided phytochemical analysis of the ethanolic extract of Grindelia argentina Deble & Oliveira ‐Deble (Asteraceae) allowed the isolation of a known flavone, hispidulin, and three new oleanane‐type saponins, 3‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester ( 2 ), 3‐O‐β‐D ‐glucopyranosyl‐2β,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester, ( 3 ) and 3‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐2β,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester ( 4 ), named grindeliosides A–C, respectively. Their structures were determined by extensive 1D‐ and 2D‐NMR experiments along with mass spectrometry and chemical evidence. The isolated compounds were evaluated for their inhibitory activities against LPS/IFN‐γ‐induced NO production in RAW 264.7 macrophages and for their cytotoxic activities against the human leukemic cell line CCRF‐CEM and MRC‐5 lung fibroblasts. Hispidulin markedly reduced LPS/IFN‐γ‐induced NO production (IC50 51.4 μM ), while grindeliosides A–C were found to be cytotoxic, with grindelioside C being the most active against both CCRF‐CEM (IC50 4.2±0.1 μM ) and MRC‐5 (IC50 4.5±0.1 μM ) cell lines. 相似文献