New and bioactive natural products from an endophyte of Panax notoginseng. Issue 60 (2nd August 2017)

• Record Type: Journal Article
• Authors: Xie, Jun; Wu, Ying-Ying; Zhang, Tian-Yuan; Zhang, Meng-Yue; Zhu, Wei-Wei; Gullen, Elizabeth A.; Wang, Zhao-Jie; Cheng, Yung-Chi; Zhang, Yi-Xuan
• Is Part Of: RSC advances. Volume 7:Issue 60(2017)
• Page Start: 38100
• Page End: 38109
• Publication Date: 2017-08-02
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7ra07060h
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Secondary metabolites with cytotoxic activity, antiviral activity and antimicrobial activity from the endophytic fungi of Panax notoginseng . Abstract : Five new derivatives of macrolide antibiotic Brefeldin A (BFA, 6), named as Brefeldin E1–E5 (1–5 ), along with Brefeldin A 7- O -acetate (7 ), mycotoxins (8–9 ) and mangrovamides A (10 ) were produced by an endophytic fungus, Penicillium sp., which was isolated from the healthy root of Panax notoginseng . The structures of1–5 were established on the basis of their spectroscopic data, while the absolute configurations were assigned using a modified Mosher's method. All compounds were evaluated for their cytotoxic, antiviral and antimicrobial activities. Compounds1–5 and8–10 displayed low or moderate cytotoxicity against a panel of cancer cell lines. Compounds1, 2, 4, 5, and8–10 showed moderate antimicrobial activity. Compound6 showed strong anticancer and antiviral properties. Additionally, it demonstrated broad-spectrum activity against human pathogenic bacteria and fungal pathogens that can cause root-rot disease in Panax notoginseng, including Escherichia coli, Staphylococcus aureus, Bacillus cereus, Klebsiella pneumonia, Candida albicans, Fusarium solani, Cylindrocarpon didynum and Alternaria panax . Compound7, which could be mediated by 6 through the acetylation at the 7-hydroxyl, showed similar bioactivities to compound6 . Further studies of the cellular mechanism of compounds6 and 7 showed that they arrested HepG2 cells at the S phase. Due to the similarities in the basic carbon skeleton and the chemical construction correlations between compounds1–7, the plausible biosynthetic pathway of the BFA series of compounds has been proposed and their structure–activity relationships are also discussed.