Grewiifopenes A-K, bioactive clerodane diterpenoids from Casearia grewiifolia Vent.

IF 4.8 3区化学 Q1 CHEMISTRY, MEDICINAL Natural Products and Bioprospecting Pub Date : 2024-09-14 DOI:10.1007/s13659-024-00475-7

Phanruethai Pailee, Paratchata Batsomboon, Wiriya Yaosanit, Theerawat Thananthaisong, Chulabhorn Mahidol, Poonsakdi Ploypradith, Nanthawan Reuk-ngam, Panita Khlaychan, Supanna Techasakul, Somsak Ruchirawat, Vilailak Prachyawarakorn

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摘要

从盐肤木（Casearia grewiifolia Vent.，莎草科）的小枝和茎的二氯甲烷提取物中纯化了 11 个新的萜类化合物，即 grewiifopenes A-K（1-4 和 12-18），以及 9 个已知化合物（5-11、19 和 20）。研究人员利用核磁共振、HRESIMS 和电子圆二色性计算等光谱数据，完整地描述和阐明了这些化合物的化学结构和绝对构型。与其他化合物相比，具有一个 6-OH 基团且 C-7 没有被取代的萜类二萜具有更强的细胞毒活性，其 IC50 值介于 0.3 至 2.9 μM 之间。Isocaseamembrin E (7) 对金黄色葡萄球菌具有抗菌活性，而 isocaseamembrin E (7)、corymbulosin X (8)、caseargrewiin A (9)、kurzipene A (10) 和 balanspene F (11) 对蜡样芽孢杆菌具有抗菌活性。

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Grewiifopenes A–K, bioactive clerodane diterpenoids from Casearia grewiifolia Vent.

Eleven novel clerodane-type diterpenoids, grewiifopenes A–K (1–4 and 12–18), along with nine known compounds (5–11, 19, and 20) were purified from the dichloromethane extract of the twigs and stems of Casearia grewiifolia Vent. (Salicaceae). Their spectroscopic data, including the NMR, HRESIMS, and electronic circular dichroism calculations were employed to completely characterize and elucidate the chemical structures and absolute configurations. The clerodane diterpenoids possessing a 6-OH group and no substitution at C-7 exhibited greater cytotoxic activity than others, with their IC₅₀ values ranging from 0.3 to 2.9 μM. Isocaseamembrin E (7) exhibited antibacterial activity against Staphylococcus aureus, while isocaseamembrin E (7), corymbulosin X (8), caseargrewiin A (9), kurzipene A (10), and balanspene F (11) exhibited antibacterial activity against Bacillus cereus.