Stereochemical determination of new cytochalasans from the plant endophytic fungus Trichoderma gamsii.

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Abstract

Three new cytochalasans, trichalasins E (1), F (2) and H (7), together with four known analogues, trichalasin C (3), aspochalasin K (4), trichalasin G (5) and aspergillin PZ (8), were isolated from one endophytic fungus Trichoderma gamsii inhabiting in the traditional medicinal plant Panax notoginseng (BurK.) F.H. Chen. Trichalasins E (1) contains a unique hydroperoxyl group, which is the first report in all known analogues, whereas trichalasin H (7) possesses the rare 6/5/6/6/5 pentacyclic skeleton with 12-oxatricyclo [6.3.1.0(2,7)] moiety as that of aspergillin PZ (8). The relative configurations of the new compounds were characterized by analysis of coupling constants and ROESY correlations, and the absolute configurations of trichalasins E (1), H (7) and aspergillin PZ (8) were determined by modified Mosher's reaction. In addition, compounds 1-5, 7 and 8 were tested cytotoxic activities against several cancer cell lines.

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Journal

Journal ID (iso-abbrev): Fitoterapia

Title: Fitoterapia

Publisher: Elsevier BV

ISSN (Electronic): 1873-6971

ISSN (Print): 0367-326X

Publication date (Electronic): Jul 2014

Volume: 96

Affiliations

[1 ] Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, PR China. Electronic address: lchenchina@163.com.

[2 ] Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, PR China.

[3 ] Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, PR China; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, PR China. Electronic address: gding@implad.ac.cn.

[4 ] Institute of Microbiology. Chinese Academy of Sciences, Beijing, PR China.

[5 ] Syngenta Jealott's Hill International Research Center, Bracknell, Berkshire RG42 6EY, United Kingdom.

[6 ] Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, PR China. Electronic address: zmzou@implad.ac.cn.

Article

Publisher Item ID: S0367-326X(14)00111-7

DOI: 10.1016/j.fitote.2014.04.009

PubMed ID: 24752139

SO-VID: 11865b98-6e84-490b-8a02-8fbf83add1ab

History

Keywords: Stereochemistry,Cytochalasans,Endophytes,Trichoderma gamsii

Data availability:

Keywords: Stereochemistry, Cytochalasans, Endophytes, Trichoderma gamsii

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