Griseofulvin enantiomers and bromine-containing griseofulvin derivatives with antifungal activity produced by the mangrove endophytic fungus Nigrospora ***1

作     者：Ge Zou Wencong Yang Tao Chen Zhaoming Liu Yan Chen Taobo Li Gulab Said Bing Sun Bo Wang Zhigang She 

作者机构：School of ChemistrySun Yat-sen UniversityGuangzhou 510275China State Key Laboratory of Applied Microbiology Southern ChinaGuangdong Provincial Key Laboratory of Microbial Culture Collection and ApplicationInstitute of MicrobiologyGuangdong Academy of SciencesGuangzhou 510070China School of PharmacyAnhui Medical UniversityHefei 230032China Department of ChemistryWomen University SwabiSwabi 23430Pakistan 

出 版 物：《Marine Life Science & Technology》 (海洋生命科学与技术（英文）)

年 卷 期：2024年第6卷第1期

页      面：102-114页

核心收录：

学科分类：0710[理学-生物学] 070703[理学-海洋生物学] 07[理学] 0707[理学-海洋科学] 

基　　金：funded by the Guangdong Marine Economy Development Special Project(GDNRC35,GDNRC39) the National Natural Science Foundation of China(U20A2001,42276114) 

主　　题：Mangrove endophytic fungus Nigrospora sp. Griseofulvin Antifungal activity 

摘      要：Marine microorganisms have long been recognized as potential sources for drug *** was one of the first antifungal natural products and has been used as an antifungal agent for *** this study,12 new griseofulvin derivatives[(±)-1-2,(+)-3,(±)-4,10-12,and 14-15]and two new griseofulvin natural products(9 and 16)together with six known analogues[(-)-3,5-8,and 13]were isolated from the mangrove-derived fungus Nigrospora ***1 treated with 0.3%NaCl or 2%NaBr in rice solid *** 2D structures and absolute configurations were established by extensive spectroscopic analysis(1D and 2D NMR,HRESIMS),ECD spectra,computational calculation,DP4+analysis,and X-ray single-crystal *** 1-4 represent the first griseofulvin enantiomers with four absolute configurations(2S,6 S;2R,6 R;2S,6 R;2R,6 S),and compounds 9-12 represent the first successful production of brominated griseofulvin derivatives from fungi via the addition of NaBr to the culture *** the antifungal assays,compounds 6 and 9 demonstrated significant inhibitory activities against the fungi Colletotrichum truncatum,Microsporum gypseum,and Trichophyton mentagrophyte with inhibition zones varying between 28 and 41 mm(10μg/disc).The structure-activity relationship(SAR)was analyzed,which showed that substituents at C-6,C-7,C-6 and the positions of the carbonyl and double bond of griseofulvin derivatives significantly affected the antifungal activity.