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

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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Abstract

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.

Graphical Abstract

Abstract Image

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山柰素A-D，高氧化海玛烷二萜，具有有效的抗炎活性。

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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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.