山柰素A-D，高氧化海玛烷二萜，具有有效的抗炎活性。

IF 4.8 3区化学 Q1 CHEMISTRY, MEDICINAL Natural Products and Bioprospecting Pub Date : 2023-12-01 DOI:10.1007/s13659-023-00420-0

Orawan Jongsomjainuk, Jutatip Boonsombat, Sanit Thongnest, Hunsa Prawat, Paratchata Batsomboon, Sitthivut Charoensutthivarakul, Saroj Ruchisansakun, Kittipong Chainok, Jitnapa Sirirak, Chulabhorn Mahidol, Somsak Ruchirawat

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摘要

从山柰根茎中分离到4个高度氧化的海玛烷二萜。Kaemtakols a - c具有一个具有融合四氢吡喃基序或四氢呋喃基序的四环环。Kaemtakol D具有一个不寻常的重排的A/B环螺桥海马烷框架，具有一个C-10螺环结和一个相邻的1-甲基三环[3.2.1.02,7]辛烯环。利用光谱分析、DP4 +和ECD计算以及x射线晶体学对其进行了结构表征，并提出了其推测的生物合成途径。Kaemtakol B对一氧化氮的抑制作用显著，IC50值为0.69 μM。分子对接研究为研究卡木他酚B对iNOS蛋白的作用提供了新的思路。

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Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

Four highly oxidized pimarane diterpenoids were isolated from Kaempferia takensis rhizomes. Kaemtakols A–C possess a tetracyclic ring with either a fused tetrahydropyran or tetrahydrofuran motif. Kaemtakol D has an unusual rearranged A/B ring spiro-bridged pimarane framework with a C-10 spirocyclic junction and an adjacent 1-methyltricyclo[3.2.1.0^2,7]octene ring. Structural characterization was achieved using spectroscopic analysis, DP4 + and ECD calculations, as well as X-ray crystallography, and their putative biosynthetic pathways have been proposed. Kaemtakol B showed significant potency in inhibiting nitric oxide production with an IC₅₀ value of 0.69 μM. Molecular docking provided some perspectives on the action of kaemtakol B on iNOS protein.