(±)-Talapyrones A-F: six pairs of dimeric polyketide enantiomers with unusual 6/6/6 and 6/6/6/5 ring systems from Talaromycesadpressus.
10.1016/S1875-5364(25)60928-9
- Author:
Meijia ZHENG
1
;
Xinyi ZHAO
2
;
Chenxi ZHOU
3
;
Hong LIAO
2
;
Qin LI
2
;
Yuling LU
2
;
Bingbing DAI
2
;
Weiguang SUN
2
;
Ying YE
2
;
Chunmei CHEN
4
;
Yonghui ZHANG
5
;
Hucheng ZHU
6
Author Information
1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: 1074560710@qq.com.
2. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
3. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China; School of Pharmacy, Shenyang Pharmaceutical University, Shenyang 110016, China.
4. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: chenchuanmei@hust.edu.cn.
5. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: zhangyh@mails.tjmu.edu.cn.
6. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: zhuhucheng@hust.edu.cn.
- Publication Type:Journal Article
- Keywords:
Biosynthetic pathways;
Enantiomers;
Polyketides;
Structure elucidation;
Talaromyces adpressus
- MeSH:
Polyketides/isolation & purification*;
Talaromyces/chemistry*;
Stereoisomerism;
Molecular Structure;
Circular Dichroism;
Pyrones/chemistry*
- From:
Chinese Journal of Natural Medicines (English Ed.)
2025;23(8):932-937
- CountryChina
- Language:English
-
Abstract:
(±)-Talapyrones A-F (1-6), six pairs of dimeric polyketide enantiomers featuring unusual 6/6/6 and 6/6/6/5 ring systems, were isolated from the fungus Talaromyces adpressus. Their structures were determined by spectroscopic analysis and HR-ESI-MS data, and their absolute configurations were elucidated using a modified Mosher's method and electronic circular dichroism (ECD) calculations. (±)-Talapyrones A-F (1-6) possess a 6/6/6 tricyclic skeleton, presumably formed through a Michael addition reaction between one molecule of α-pyrone derivative and one molecule of C8 poly-β-keto chain. In addition, compounds 2/3 and 4/5 are two pairs of C-18 epimers, respectively. Putative biosynthetic pathways of 1-6 were discussed.
