Tripodalsporormielones A–C, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems

A chemical investigation on Sporormiella sp. led to the isolation and structural elucidation of tripodalsporormielones A–C (1–3), a new class of polyketide possessing unprecedented cage-like skeletons with polyvdent bridged and fused ring systems. These polyketides with cage-like skeletons were char...

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Autores principales:	Guodong Chen, Bingxin Zhao, Meijuan Huang, Jia Tang, Yanbing Li, Liangdong Guo, Rongrong He, Dan Hu, Xinsheng Yao, Hao Gao
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2021
Materias:	Tripodalsporormielones Cage-like polyketides 3-Methylorcinaldehyde Alzheimer's disease Therapeutics. Pharmacology RM1-950
Acceso en línea:	https://doaj.org/article/9f94b2b8e0734ccea424e40560e6b48b
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spelling	oai:doaj.org-article:9f94b2b8e0734ccea424e40560e6b48b2021-12-02T05:01:23ZTripodalsporormielones A–C, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems2211-383510.1016/j.apsb.2021.05.001https://doaj.org/article/9f94b2b8e0734ccea424e40560e6b48b2021-11-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S2211383521001635https://doaj.org/toc/2211-3835A chemical investigation on Sporormiella sp. led to the isolation and structural elucidation of tripodalsporormielones A–C (1–3), a new class of polyketide possessing unprecedented cage-like skeletons with polyvdent bridged and fused ring systems. These polyketides with cage-like skeletons were characterized as a high non-protonated carbon-containing system, which resulted in few HMBC correlations observed and made the accurate structures hard to be obtained by NMR. Especially, some signals of non-protonated sp2 carbons are weak and even unobservable in compound 1. In order to establish the structure of 1, the calculated NMR with DP4 evaluation was applied to determine the structure from the plausible structure candidates obtained from the detailed NMR analysis. Based on NMR experiments and calculated NMR, the structures of isolated compounds were established and confirmed by X-ray technology. Through chiral isolation, the optically pure enantiomers of 1 and 3 were obtained, and their absolute configurations were determined based on ECD quantum chemical calculation. Based on the isolated compounds and our previous work, 1–3 would be derived from 3-methylorcinaldehyde, and their plausible biosynthetic mechanism was proposed. Furthermore, 1 exhibited obvious short-term memory improvement activity on an Alzheimer's disease fly model.Guodong ChenBingxin ZhaoMeijuan HuangJia TangYanbing LiLiangdong GuoRongrong HeDan HuXinsheng YaoHao GaoElsevierarticleTripodalsporormielonesCage-like polyketides3-MethylorcinaldehydeAlzheimer's diseaseTherapeutics. PharmacologyRM1-950ENActa Pharmaceutica Sinica B, Vol 11, Iss 11, Pp 3648-3654 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Tripodalsporormielones Cage-like polyketides 3-Methylorcinaldehyde Alzheimer's disease Therapeutics. Pharmacology RM1-950
spellingShingle	Tripodalsporormielones Cage-like polyketides 3-Methylorcinaldehyde Alzheimer's disease Therapeutics. Pharmacology RM1-950 Guodong Chen Bingxin Zhao Meijuan Huang Jia Tang Yanbing Li Liangdong Guo Rongrong He Dan Hu Xinsheng Yao Hao Gao Tripodalsporormielones A–C, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems
description	A chemical investigation on Sporormiella sp. led to the isolation and structural elucidation of tripodalsporormielones A–C (1–3), a new class of polyketide possessing unprecedented cage-like skeletons with polyvdent bridged and fused ring systems. These polyketides with cage-like skeletons were characterized as a high non-protonated carbon-containing system, which resulted in few HMBC correlations observed and made the accurate structures hard to be obtained by NMR. Especially, some signals of non-protonated sp2 carbons are weak and even unobservable in compound 1. In order to establish the structure of 1, the calculated NMR with DP4 evaluation was applied to determine the structure from the plausible structure candidates obtained from the detailed NMR analysis. Based on NMR experiments and calculated NMR, the structures of isolated compounds were established and confirmed by X-ray technology. Through chiral isolation, the optically pure enantiomers of 1 and 3 were obtained, and their absolute configurations were determined based on ECD quantum chemical calculation. Based on the isolated compounds and our previous work, 1–3 would be derived from 3-methylorcinaldehyde, and their plausible biosynthetic mechanism was proposed. Furthermore, 1 exhibited obvious short-term memory improvement activity on an Alzheimer's disease fly model.
format	article
author	Guodong Chen Bingxin Zhao Meijuan Huang Jia Tang Yanbing Li Liangdong Guo Rongrong He Dan Hu Xinsheng Yao Hao Gao
author_facet	Guodong Chen Bingxin Zhao Meijuan Huang Jia Tang Yanbing Li Liangdong Guo Rongrong He Dan Hu Xinsheng Yao Hao Gao
author_sort	Guodong Chen
title	Tripodalsporormielones A–C, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems
title_short	Tripodalsporormielones A–C, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems
title_full	Tripodalsporormielones A–C, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems
title_fullStr	Tripodalsporormielones A–C, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems
title_full_unstemmed	Tripodalsporormielones A–C, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems
title_sort	tripodalsporormielones a–c, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems
publisher	Elsevier
publishDate	2021
url	https://doaj.org/article/9f94b2b8e0734ccea424e40560e6b48b
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Tripodalsporormielones A–C, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems

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