A new 3,4-seco-isopimarane and three new isopimarane diterpenoids from Kaempferia champasakensis collected from Vietnam and their cytotoxic activities

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines Pub Date : 2024-03-22 DOI:10.1007/s11418-024-01789-z

Kiep Minh Do, Shotaro Hoshino, Takeshi Kodama, Hien Minh Nguyen, Son Van Le, Naotaka Ikumi, Hiroyasu Onaka, Hiroyuki Morita

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Abstract

A phytochemical investigation of Kaempferia champasakensis rhizomes led to the isolation of a new 3,4-seco-isopimarane diterpene, kaempferiol A (1), and three new isopimarane diterpenes, kaempferiols B–D (2–4), together with six known isopimarane diterpenes (5–10). The structures of 1–4 were elucidated by extensive spectroscopic analyses, including HR-ESI–MS, UV, IR, and 1D and 2D NMR. The absolute configurations of 1, 3, and 4 were determined by ECD calculations, while that of 2 was established using the modified Mosher method. All isolated compounds were tested for cytotoxicity against three human cancer cell lines, lung cancer (A549), cervical cancer (HeLa), and breast cancer (MCF-7). Among them, 6 and 7 showed moderate cytotoxic activities against the three tested cell lines, with IC₅₀ values ranging from 38.04 to 27.77 μM, respectively.

Graphical abstract

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从越南采集的Kaempferia champasakensis中发现的一种新的3,4-seco-isopimarane和三种新的isopimarane二萜类化合物及其细胞毒性活性。

通过对山奈根茎进行植物化学研究，分离出了一种新的 3,4-seco-isopimarane（山奈酚）二萜，即山奈酚 A（1）和三种新的异山奈酚二萜，即山奈酚 B-D（2-4），以及六种已知的异山奈酚二萜（5-10）。通过广泛的光谱分析，包括 HR-ESI-MS、紫外光谱、红外光谱以及一维和二维核磁共振，阐明了 1-4 的结构。1、3 和 4 的绝对构型是通过 ECD 计算确定的，而 2 的绝对构型则是通过改进的 Mosher 方法确定的。所有分离出的化合物都对三种人类癌细胞系（肺癌（A549）、宫颈癌（HeLa）和乳腺癌（MCF-7））进行了细胞毒性测试。其中，6 号和 7 号化合物对三种受试细胞株具有中等程度的细胞毒性活性，IC50 值分别为 38.04 至 27.77 μM。

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来源期刊

Journal of Natural Medicines 医学-药学

CiteScore

6.90

自引率

3.00%

发文量

审稿时长

1.7 months

期刊介绍： The Journal of Natural Medicines is an international journal publishing original research in naturally occurring medicines and their related foods and cosmetics. It covers: -chemistry of natural products -biochemistry of medicinal plants -pharmacology of natural products and herbs, including Kampo formulas and traditional herbs -botanical anatomy -cultivation of medicinal plants. The journal accepts Original Papers, Notes, Rapid Communications and Natural Resource Letters. Reviews and Mini-Reviews are generally invited.