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Issue 15, 2018
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Structurally diverse diterpenoids from Isodon pharicus

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Abstract

Twenty-one diterpenoids with diverse structures, including twelve new compounds (1–12), were isolated from the aerial parts of Isodon pharicus. Structurally, pharicusin A (1), composed of a benzoyl group coupled to a 7α,20-epoxy-ent-kauranoid, represents an unprecedented C27 meroditerpenoid; pharicusin B (2) is a novel trinorditerpenoid with an unreported 15,16,17-trinor-7α,20-epoxy-ent-kaurane skeleton; pharicusin C (4) represents the first example of 7α,20-epoxy-ent-atisane diterpenoids. Their structures were elucidated based on spectroscopic analysis, wherein the absolute configurations of 2 and 3 were further confirmed by single-crystal X-ray diffraction and computational analysis of the optical rotatory dispersion (ORD). Selected sixteen isolates were evaluated for their in vitro cytotoxicity against a small panel of human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480), and compounds 9, 10, 13, 16, and 18 exhibited significant inhibitory effects against all five cell lines, with IC50 values in the range of 0.37–6.03 μM.

Graphical abstract: Structurally diverse diterpenoids from Isodon pharicus

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Publication details

The article was received on 14 May 2018, accepted on 01 Jul 2018 and first published on 02 Jul 2018


Article type: Research Article
DOI: 10.1039/C8QO00477C
Citation: Org. Chem. Front., 2018,5, 2379-2389
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    Structurally diverse diterpenoids from Isodon pharicus

    Z. Hu, H. Xu, K. Hu, M. Liu, X. Li, X. Li, X. Du, Y. Zhang, P. Puno and H. Sun, Org. Chem. Front., 2018, 5, 2379
    DOI: 10.1039/C8QO00477C

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