Daphnane diterpenoid orthoesters with an odd-numbered aliphatic side chain from Daphne pedunculata

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines Pub Date : 2024-05-23 DOI:10.1007/s11418-024-01826-x

Lingjian Tan, Kouharu Otsuki, Takashi Kikuchi, Di Zhou, Ning Li, Li Huang, Chin-Ho Chen, Wei Li

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Abstract

Daphnane diterpenoids were recognized for their extensive range of potent biological activities. In the present study, phytochemical investigation including LC–MS/MS analysis resulted in the identification of five daphnane diterpenoid orthoesters (1–5). Among the five daphnane diterpenoids, two previously unreported compounds, daphnepedunins I and J (2 and 4) were isolated from Daphne pedunculata. The structure of new compounds was elucidated with extensive physicochemical and spectroscopic analyses. Their structure was characterized by the presence of an unusual odd-numbered aliphatic chain connected to an orthoester. The isolated compounds were evaluated for their anti-HIV activity against HIV-1 infection of MT4 cells, and the results indicated that compound 1 showed the most potent anti-HIV activity with an IC₅₀ value of 0.82 nM.

Graphical Abstract

Abstract Image

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Daphnane diterpenoid orthoesters with an odd-numbered aliphatic side chain from Daphne pedunculata.

水飞萘二萜类化合物因其广泛的强效生物活性而得到认可。在本研究中，通过植物化学调查（包括 LC-MS/MS 分析），确定了五种水飞萘二萜原酯（1-5）。在这五种水飞萘二萜类化合物中，从 Daphnne pedunculata 中分离出了两种以前未报道过的化合物，即水飞萘素 I 和 J（2 和 4）。通过大量的理化和光谱分析，阐明了新化合物的结构。它们的结构特征是存在一条与正交酯相连的奇数脂肪链。结果表明，化合物 1 的抗 HIV 活性最强，其 IC50 值为 0.82 nM。

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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.