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Macrocephatriolides A and B: Two Guaianolide Trimers from Ainsliaea macrocephala as PTP1B Inhibitors and Insulin Sensitizers
Ren, Yong Mei1,2,3; Zhang, Rui1; Feng, Zheling4; Ke, Chang Qiang1; Yao, Sheng1; Tang, Chunping1; Lin, Ligen4; Ye, Yang1,2,3
2021-12-17
Source PublicationJournal of Organic Chemistry
ISSN0022-3263
Volume86Issue:24Pages:17782-17789
AbstractMacrocephatriolides A and B (1 and 2), two novel guaiane-type sesquiterpene lactone trimers possessing unique linkage patterns, were identified from the whole plant of Ainsliaea macrocephala. The trimeric architecture of 1 features a cyclohexene linkage and a methylene bridge, which were presumably constructed from three constitutive monomers via a Diels–Alder cycloaddition and a Michael addition, respectively. The three monomers of 2 were tethered by a 1,2-ethanediyl and a methylene linkage at the same time. Their complex structures were established by extensive analysis of spectroscopic data inclusive of band-selective CT-HSQC and CT-HMBC and time-dependent density functional theory (TDDFT) ECD calculations. Compound 2 showed potent inhibition against protein tyrosine phosphatase 1B (PTP1B) with an IC value of 26.26 ± 0.88 μM but not compound 1. In the kinetic study, compound 2 was disclosed as a competitive inhibitor of PTP1B with a K value of 16.34 ± 4.72 μM. In insulin-stimulated C2C12 myotubes, compound 2 dose-dependently enhanced glucose uptake by activating the insulin signaling pathway. Compound 2 might represent a new scaffold of insulin sensitizers.
DOI10.1021/acs.joc.1c01996
URLView the original
Language英語English
Scopus ID2-s2.0-85120725006
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Cited Times [WOS]:1   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Affiliation1.State Key Laboratory of Drug Research and Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China
2.University of Chinese Academy of Sciences, Beijing, 100049, China
3.School of Life Science and Technology, ShanghaiTech University, Shanghai, 201203, China
4.State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Taipa, Avenida da Universidade, 999078, Macao
Recommended Citation
GB/T 7714
Ren, Yong Mei,Zhang, Rui,Feng, Zheling,et al. Macrocephatriolides A and B: Two Guaianolide Trimers from Ainsliaea macrocephala as PTP1B Inhibitors and Insulin Sensitizers[J]. Journal of Organic Chemistry,2021,86(24):17782-17789.
APA Ren, Yong Mei,Zhang, Rui,Feng, Zheling,Ke, Chang Qiang,Yao, Sheng,Tang, Chunping,Lin, Ligen,&Ye, Yang.(2021).Macrocephatriolides A and B: Two Guaianolide Trimers from Ainsliaea macrocephala as PTP1B Inhibitors and Insulin Sensitizers.Journal of Organic Chemistry,86(24),17782-17789.
MLA Ren, Yong Mei,et al."Macrocephatriolides A and B: Two Guaianolide Trimers from Ainsliaea macrocephala as PTP1B Inhibitors and Insulin Sensitizers".Journal of Organic Chemistry 86.24(2021):17782-17789.
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