New sesquiterpenes from the soft coral Litophyton arboreum

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL Journal of Natural Medicines Pub Date : 2024-10-22 DOI:10.1007/s11418-024-01843-w

Amany Hamouda Mahmoud, Sabry A. H. Zidan, Mamdouh Nabil Samy, Abdallah Alian, Mahmoud A. A. Ibrahim, Mostafa Ahmed Fouad, Mohamed Salah Kamel, Katsuyoshi Matsunami

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Abstract

Two new sesquiterpenes; 8α,11-dihydroxy-β-cyperon (2), and 5-epi-7α-hydroxy-( +)-oplopanone (3), were isolated from the soft coral Litophyton arboreum, together with nine known ones, including five sesquiterpenes; 11-hydroxy-8-oxo-β-cyperon (1), alismoxide (4), 5β,8β-epidioxy-11-hydroxy-6-eudesmene (5), chabrolidione B (6), 7-oxo-tri-nor-eudesm-5-en-4β-ol (7), two sterols; 7β-acetoxy-24-methyl-cholesta-5,24(28)-diene-3β,19-diol (8), nebrosteroid M (9), and two glycerol derivatives; chimyl alcohol (10) and batyl alcohol (11). The structures of the isolated compounds were characterized using spectroscopic techniques, predominately HR-ESI–MS, 1D, 2D-NMR, and ECD analyses. Compounds 1–11 were evaluated for their cytotoxic activity against three human cancer-cell lines (A549, MCF-7 and HepG2), and anti-leishmanial potential against the causal parasite, Leishmania major. Compounds 4, 8, and 9 exhibited potent cytotoxic activity against the A549 cell line (IC₅₀ = 17.0 ± 2.5, 13.5 ± 2.1, and 16.5 ± 1.3 μg/ml, respectively) as compared with the standard antitumor agent etoposide (IC₅₀ 28.4 ± 4.5 μg/ml). In addition, compound 9 exhibited remarkable cytotoxic activity against MCF-7 cell line (IC₅₀ = 24.7 ± 2.1 μg/ml: 22.2 ± 4.2 μg/mL for etoposide).

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来自软珊瑚 Litophyton arboreum 的新倍半萜。

从软珊瑚 Litophyton arboreum 中分离出两种新的倍半萜；8α,11-二羟基-β-cyperon (2) 和 5-epi-7α-hydroxy-( +)-oplopanone (3)，以及九种已知的倍半萜，其中包括五种倍半萜；11-hydroxy-8-oxo-β-cyperon (1)、alismoxide (4)、5β,8β-epidioxy-11-hydroxy-6-eudesmene (5)、chabrolidione B (6)、7-oxo-tri-nor-eudesm-5-en-4β-ol (7)、两种甾醇；7β-乙酰氧基-24-甲基-胆甾-5,24(28)-二烯-3β,19-二醇（8）、nebrosteroid M（9）和两种甘油衍生物：chimyl 醇（10）和 batyl 醇（11）。利用光谱技术，主要是 HR-ESI-MS、1D、2D-NMR 和 ECD 分析，对分离化合物的结构进行了表征。评估了化合物 1-11 对三种人类癌细胞系（A549、MCF-7 和 HepG2）的细胞毒性活性，以及对病原寄生虫大利什曼原虫的抗利什曼病潜力。与标准抗肿瘤药物依托泊苷（IC50 28.4 ± 4.5 μg/ml）相比，化合物 4、8 和 9 对 A549 细胞系具有很强的细胞毒性活性（IC50 分别为 17.0 ± 2.5、13.5 ± 2.1 和 16.5 ± 1.3 μg/ml）。此外，化合物 9 对 MCF-7 细胞株具有显著的细胞毒性活性（IC50 = 24.7 ± 2.1 μg/ml：依托泊苷为 22.2 ± 4.2 μg/ml）。

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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.