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Structurally diverse diterpenoids from Isodon pharicus

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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… Click to show full 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.

Keywords: isodon pharicus; diverse diterpenoids; epoxy ent; pharicus; pharicus structurally; structurally diverse

Journal Title: Organic chemistry frontiers
Year Published: 2018

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