Garcioblons A–F, Polycyclic Polyprenylated Acylphloroglucinols with Diverse Rearranged Skeletons from Garcinia oblongifolia

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-20 DOI:10.1021/acs.orglett.5c00605

Qiang Lin, Hua-Yan Xie, Qing Tang, Hai-Shan Zhang, Min-Jing Cheng, Zhao-Chun Zhan, Hong-Xiao Wang, Yao-Lan Li, Hao Wang, Guo-Cai Wang, Yu-Bo Zhang

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Abstract

Garcioblons A–F (1–6), six unprecedented polycyclic polyprenylated acylphloroglucinols (PPAPs) formed via intramolecular Diels–Alder (IMDA) reactions from monocyclic polyprenylated acylphloroglucinols (MPAPs), were isolated from Garcinia oblongifolia. Their structures were elucidated through spectroscopic analysis and quantum calculations. Structurally, compound 1 is the first PPAP characterized by an unprecedented 6/6/5/7/6/5/6/5 octacyclic ring system with a 11-oxatetracyclo[8.5.1.0^1,12.0^5,10]hexadecane motif, while 2–4 are its biogenetically related analogues. Compound 5 possesses a caged 6-oxatetracyclo[7.3.1.1^2,10.0^2,7]tetradecane new carbon skeleton, while compound 6 features a 4-oxatricyclo[7.4.0.0^1,5]tridecane structure. Additionally, compound 1 demonstrated notable antitumor activities by inhibiting autophagic flux and stimulating oxidative stress, which collectively resulted in reduced cell proliferation and induced apoptosis.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.