标题:Smardaesidins A-G, isopimarane and 20-nor-isopimarane diterpenoids from Smardaea sp., a fungal endophyte of the moss Ceratodon purpureus.
作者:Wang, X. N.;Bashyal, B. P.;Wijeratne, E. M. K.;U\'Ren, J. M.;Liu, M. X.;Gunatilaka, M. K.;Arnold, A. E.;Gunatilaka, A. A. L.
作者机构:[Wang, X.-N] SW Center for Natural Products Research and Commercialization, College of Agriculture and Life Sciences, University of Arizona, 250 E. Va 更多
通讯作者:Gunatilaka, AAL
通讯作者地址:[Gunatilaka, AAL]Univ Arizona, SW Ctr Nat Prod Res & Commercializat, Sch Nat Resources & Environm, Coll Agr & Life Sci, 250 E Valencia Rd, Tucson, AZ 更多
来源:Journal of natural products
出版年:2011
卷:74
期:10
页码:2052-2061
DOI:10.1021/np2000864
关键词:adenocarcinoma;antineoplastic properties;breast cancer;cell lines;chemical composition;chemical structure;cytotoxic compounds;cytotoxicity;diterpenoids;endophytes;fibroblasts;hydrogenation;in vitro;reduction;Bryophyta;man;Pezizales;plants;mosses;Bryophyta;eukaryotes;Homo;Hominidae;Primates;mammals;vertebrates;Chordata;animals;Pezizomycetes;Pezizomycotina;Ascomycota;fungi;anti-neoplastic properties;cancers;Ceratodon;Ceratodon purpureus;Dicranales;Ditrichaceae;fungus;Smardaea
摘要:Five new isopimarane diterpenes, smardaesidins A-E (1-5) and two new 20-nor-isopimarane diterpenes, smardaesidins F (6) and G (7), together with sphaeropsidins A (8) and C-F (10-13) were isolated from an endophytic fungal strain, Smardaea sp. AZ0432, occurring in living photosynthetic tissue of the moss Ceratodon purpureus. Of these, smardaesidins B (2) and C (3) were obtained as an inseparable mixture of isomers. Chemical reduction of sphaeropsidin A (8) afforded sphaeropsidin B (9), whereas catalytic hydrogenation of 8 yielded 7-O-15,16-tetrahydrosphaeropsidin A (14) and its new derivative, 7-hydroxy-6-oxoisopimara-7-en-20-oic acid (15). The acetylation and diazomethane reaction of sphaeropsidin A (8) afforded two of its known derivatives, 6-O-acetylsphaeropsidin A (16) and 8,14-methylenesphaeropsidin A methyl ester (17), respectively. Methylation of 10 yielded sphaeropsidin C methyl ester (18). The planar structures and relative configurations of the new compounds 1-7 and 15 were elucidated using MS and 1D and 2D NMR experiments, while the absolute configurations of the stereocenters of 4 and 6-8 were assigned using a modified Mosher\'s ester method, CD spectra, and comparison of specific rotation data with literature values. Compounds 1-18 were evaluated for their potential anticancer activity using several cancer cell lines and cells derived from normal human primary fibroblasts. Of these, compounds 8, 11, and 16 showed significant cytotoxic activity. More importantly, sphaeropsidin A (8) showed cell-type selectivity in the cytotoxicity assay and inhibited migration of metastatic breast adenocarcinoma (MDA-MB-231) cells at subcytotoxic concentrations.Digital Object Identifier http://dx.doi.org/10.1021/np2000864
收录类别:SCOPUS;SCIE
WOS核心被引频次:32
Scopus被引频次:35
资源类型:期刊论文
原文链接:https://www.scopus.com/inward/record.uri?eid=2-s2.0-80055097832&doi=10.1021%2fnp2000864&partnerID=40&md5=9fea125e8aafa77208083ed470ba01cf
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