2025
Garcioblons A-F, polycyclic polyprenylated acylphloroglucinolswith diverse rearranged skeletons from Garcinia oblongifolia.
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Title:Garcioblons A-F, polycyclic polyprenylated acylphloroglucinolswith diverse rearranged skeletons from Garcinia oblongifolia.
Author(s):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*.
Journal Name, Year, Volume(Issue): Page range:
Organic Letters, 2025,27(13), 3273-3278.
DOI:10.1021/acs.orglett.5c00605
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[8.5.1.01,12.05,10]hexadecane motif, while 2–4 are its biogenetically related analogues. Compound 5 possesses a caged 6-oxatetracyclo[7.3.1.12,10.02,7]tetradecane new carbon skeleton, while compound 6 features a 4-oxatricyclo[7.4.0.01,5]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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