Phaeosphspirone (1/1 '), a pair of unique polyketide enantiomers with an unusual 6/5/5/6 tetracyclic ring from the desert plant endophytic fungus Phaeosphaeriaceae sp.

doi:10.1016/j.phytochem.2021.112969

KIB OpenIR

	Phaeosphspirone (1/1 '), a pair of unique polyketide enantiomers with an unusual 6/5/5/6 tetracyclic ring from the desert plant endophytic fungus Phaeosphaeriaceae sp.
	Xu,Zhen-Lu ; Yan,Dao-Jiang ; Tan,Xiang-Mei ; Niu,Shu-Bin ; Yu,Meng ; Sun,Bing-Da ; Ding,Cai-Feng ; Zhang,Yong-Gang ; Ding,Gang
	2022
发表期刊	PHYTOCHEMISTRY
ISSN	0031-9422
卷号	194 页码:112969
摘要	Phaeosphspirone, an undescribed polyketide with a unique 6/5/5/6-fused tetracyclic system, and two known analogues, herbarin and O-methylherbarin, were purified from the endophytic fungus Phaeosphaeriaceae sp. isolated from the desert plant Bassia dasyphylla. The connectivity and relative configuration of phaeosphspirone was elucidated by comprehensive HR-ESI-MS and NMR analysis together with a computer-assisted structure elucidation (CASE) method. A pair of enantiomers existing in phaeosphspirone were separated by HPLC chromatography after reacting with chiral reagents, from which the absolute configuration of phaeosphspirone was simultaneously determined based on Mosher's rule. This tandem strategy provides a useful approach for the separation and stereochemical determination of enantiomers possessing secondary hydroxyl groups. The structural feature of phaeosphspirone, herbarin and O-methylherbarin together with gene cluster analysis suggested their polyketide biosynthetic origin. Herbarin and O-methylherbarin exhibited moderate cytotoxicity against three cancer cell lines.
关键词	Phaeosphspirone Phaeosphaeriaceae Absolute configurations Biosynthetic pathway Cytotoxicity ASSISTED STRUCTURE ELUCIDATION BIOSYNTHESIS REVISION
DOI	10.1016/j.phytochem.2021.112969
WOS记录号	WOS:000737602700001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/73721
专题	中国科学院昆明植物研究所
作者单位	1.[Xu, Zhen-Lu 2.Tan, Xiang-Mei 3.Yu, Meng 4.Peking Union Med Coll & Chinese Acad Med Sci, Key Lab Bioact Subst & Resources Utilizat Chinese, Minist Educ, Inst Med Plant Dev, Beijing 100193, Peoples R China 5.Qilu Univ Technol, Biol Inst, Shandong Acad Sci, Jinan 250103, Shandong, Peoples R China 6.Shandong Normal Univ, Coll Life Sci, Jinan 250014, Shandong, Peoples R China 7.Chinese Acad Med Sci & Peking Union Med Coll, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China 8.Beijing City Univ, Sch Biol Med, Beijing 450046, Peoples R China 9.Chinese Acad Sci, Inst Microbiol, Beijing 100101, Peoples R China 10.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
推荐引用方式 GB/T 7714	Xu,Zhen-Lu,Yan,Dao-Jiang,Tan,Xiang-Mei,et al. Phaeosphspirone (1/1 '), a pair of unique polyketide enantiomers with an unusual 6/5/5/6 tetracyclic ring from the desert plant endophytic fungus Phaeosphaeriaceae sp.[J]. PHYTOCHEMISTRY,2022,194:112969.
APA	Xu,Zhen-Lu.,Yan,Dao-Jiang.,Tan,Xiang-Mei.,Niu,Shu-Bin.,Yu,Meng.,...&Ding,Gang.(2022).Phaeosphspirone (1/1 '), a pair of unique polyketide enantiomers with an unusual 6/5/5/6 tetracyclic ring from the desert plant endophytic fungus Phaeosphaeriaceae sp..PHYTOCHEMISTRY,194,112969.
MLA	Xu,Zhen-Lu,et al."Phaeosphspirone (1/1 '), a pair of unique polyketide enantiomers with an unusual 6/5/5/6 tetracyclic ring from the desert plant endophytic fungus Phaeosphaeriaceae sp.".PHYTOCHEMISTRY 194(2022):112969.