(±) Benzomalvins E isolated from Penicillium sp. SYPF 8411 in the rhizosphere soil of Codonopsis clematidea.
Autor: Feng, Qing-Mei; Feng, Yuan; Zhang, Tian-Yuan; Wang, Hai-Feng; Zhang, Meng-Yue; Wu, Ying-Ying; Chen, Gang; Zhang, Yi-Xuan; Pei, Yue-Hu
Publication year: 2020
Natural product research
issn:1478-6427 1478-6419
doi: 10.1080/14786419.2019.1569004
Abstract:
(+) Benzomalvins E (1) and (-) Benzomalvins E (2), a pair of epimeric derivatives, together with three known benzomalvins (3-5), were isolated from solid cultures of a interrhizospheric fungus Penicillium sp. SYPF 8411. The planar structure of (+) Benzomalvins E (1) has been previously reported. While, the absolute configuration of compound 1 was established by X-ray crystallographic analysis for the first time. The planar structure of the new compound 2 were elucidated by detailed interpretation of their HR ESI-TOF MS and NMR spectroscopic data. The absolute configuration of compound 2 was established by Rh(2)(OCOCF(3))(4)-induced CD spectral data and the electronic circular dichroic (ECD) method. Furthermore, the epimerization induced by pH, temperature and H(2)O was revealed. Benzomalvins (1-3, 5), a type of indoximod, enhanced the cytotoxic capability of 5-fluorouracil against A549.
Language: eng
Rights:
Pmid: 30760040
Tags: Humans; Magnetic Resonance Spectroscopy; A549 Cells; Cytotoxins/isolation & purification/pharmacology; Molecular Conformation; Crystallography, X-Ray; Penicillium sp.; Penicillium/*chemistry; *Rhizosphere; Benzodiazepine alkaloid; Benzodiazepines/chemistry/*isolation & purification/pharmacology; benzomalvin; Codonopsis/*microbiology; cytotoxic capability; Soil/chemistry; X-ray crystallography
Link: https://pubmed.ncbi.nlm.nih.gov/30760040/
