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Garsubelone A, the First Dimeric Polycyclic Polyprenylated Acylphloroglucinols with Complicated Heptacyclic Architecture from Garcinia subelliptica.

Authors :
Wang YL
Ye YS
Fu WW
Wu R
Xiang Q
Lao YZ
Yang JL
Tan HS
Yang XW
Yang BC
Xu HX
Xu G
Source :
Organic letters [Org Lett] 2019 Mar 01; Vol. 21 (5), pp. 1534-1537. Date of Electronic Publication: 2019 Feb 18.
Publication Year :
2019

Abstract

Garsubelone A (1), the first dimeric polycyclic polyprenylated acylphloroglucinols type metabolite featuring a complicated 6/6/6/6/6/6/6 heptacyclic architecture containing 10 stereogenic centers, was isolated from Garcinia subelliptica. Biogenetically, this compound was constructed by the plausible monomeric precursor, garsubelone B (2) and secohyperforin, via a key Diels-Alder cycloaddition to form an unique 2-oxabicyclo[3.3.1]nonane core. Their structures and absolute configurations were determined by comprehensive spectroscopic and X-ray diffraction techniques. The cytotoxic activities of these isolates were also evaluated.

Details

Language :
English
ISSN :
1523-7052
Volume :
21
Issue :
5
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
30775925
Full Text :
https://doi.org/10.1021/acs.orglett.9b00388