Calabanones A‒H, chromanone derivatives from the stem bark of Calophyllum calaba and their cytotoxic activities against cancer cells

IF 4.9 3区化学 Q1 CHEMISTRY, MEDICINAL

Natural Products and Bioprospecting Pub Date : 2026-03-04 DOI:10.1007/s13659-026-00603-5

Sutin Kaennakam, Fadjar Mulya, Manussada Ratanasak, Kitiya Rassamee, Pongpun Siripong, Yasuteru Shigeta, Preecha Phuwapraisirisan, Edwin R. Sukandar

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Abstract

The genus Calophyllum (Calophyllaceae), distributed mainly in tropical regions, is rich in chromanone derivatives with diverse molecular structures that exhibit potential antimicrobial and anticancer effects. Phytochemical investigation of the stem bark of C. calaba collected in Thailand led to the discovery of eight previously undescribed chromanones, calabanones A–H (1‒8), and two known analogs, (‒)-isocalomembranone P (9) and (‒)-calomembranone P (10). The chemical structures of undescribed compounds were elucidated using spectroscopic analyses, particularly NMR and HRESIMS, while their absolute configurations were determined through ECD and NMR calculations combined with DP4+ probability analysis. Compounds 7 and 8 were identified as chromanone–steroid hybrids linked via an ester bond, representing the first report of such structures in plants. Cytotoxic evaluation of the isolated specialized metabolites revealed that compounds 6 and 9 displayed moderate activity against KB and HeLa S3 cancer cell lines, with IC₅₀ values ranging from 12.71 to 25.50 μM, while compounds 3‒5 selectively inhibited the growth of KB cells, with IC₅₀ values in the range of 18.77‒27.06 μM.

Graphical abstract

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Calophyllum calaba茎皮中的Calabanones A-H、chromanone衍生物及其对癌细胞的细胞毒活性

Calophyllum （Calophyllaceae）属植物，主要分布于热带地区，含有丰富的铬甾酮衍生物，分子结构多样，具有潜在的抗菌和抗癌作用。对在泰国采集的calaba茎皮进行植物化学研究，发现了8种以前未描述的激素，calabanones A-H(1-8)，以及2种已知的类似物，(-)- isocalembranone P(9)和(-)-calomembranone P（10）。未描述化合物的化学结构通过波谱分析，特别是核磁共振和hresms来阐明，而它们的绝对构型通过ECD和核磁共振计算结合DP4+概率分析来确定。化合物7和8被鉴定为通过酯键连接的激素-类固醇杂交种，这是首次在植物中报道这种结构。化合物6和9对KB和HeLa S3癌细胞具有中等抑制作用，IC50值在12.71 ~ 25.50 μM之间；化合物3-5对KB细胞具有选择性抑制作用，IC50值在18.77 ~ 27.06 μM之间。图形抽象

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.