Immunosuppresive Sesterterpenoids and Norsesterterpenoids from Colquhounia coccinea var. mollis

A pair of new C-14 epimeric sesterterpenoids, colquhounoid D (1) and 14-epi-colquhounoid D (2), and five degradation products featuring new C20 and C21 frameworks, norcolquhounoids A–E (3–7), were isolated from Colquhounia coccinea var. mollis. Their structures were elucidated by comprehensive spect...

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Veröffentlicht in:Journal of organic chemistry 2021-08, Vol.86 (16), p.11169-11176
Hauptverfasser: Jing, Shu-Xi, Fu, Ran, Li, Chun-Huan, Zhou, Ting-Ting, Liu, Yan-Chun, Liu, Yan, Luo, Shi-Hong, Li, Xiao-Nian, Zeng, Fang, Li, Sheng-Hong
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Sprache:eng
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Zusammenfassung:A pair of new C-14 epimeric sesterterpenoids, colquhounoid D (1) and 14-epi-colquhounoid D (2), and five degradation products featuring new C20 and C21 frameworks, norcolquhounoids A–E (3–7), were isolated from Colquhounia coccinea var. mollis. Their structures were elucidated by comprehensive spectroscopic analysis and single-crystal X-ray diffraction. Degradation of the C25 skeleton to the C21 skeleton was also achieved using aqueous NaIO4 and RuCl3. Compounds 1 and 2 showed significant immunosuppressive activity on the cytokine IFN-γ secretion of mouse splenocytes induced by anti-CD3/CD4 monoclonal antibodies, with IC50 of 8.38 and 5.79 μM, respectively, and compounds 5 and 6 were moderately active.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00374