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

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...

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Published inOrganic letters Vol. 21; no. 5; pp. 1534 - 1537
Main Authors Wang, Yong-Ling, Ye, Yan-Song, Fu, Wen-Wei, Wu, Rong, Xiang, Qian, Lao, Yuan-Zhi, Yang, Jin-Ling, Tan, Hong-Sheng, Yang, Xing-Wei, Yang, Bai-Can, Xu, Hong-Xi, Xu, Gang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.03.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
HYPERFORIN
BENZOPHENONES
DERIVATIVES
OBLONGIFOLIN C
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00388