School of Biosciences, University of Nottingham Malaysia, Jalan Broga, 43500, Semenyih, Selangor, Malaysia.
School of Pharmacy, University of Nottingham Malaysia, Jalan Broga, 43500, Semenyih, Selangor, Malaysia.
Phytochemistry. 2022 Jan;193:112988. doi: 10.1016/j.phytochem.2021.112988. Epub 2021 Oct 27.
Four undescribed cucurbitacins, designated as petiolaticins A-D, and four known cucurbitacins were isolated from the bark and leaves of Elaeocarpus petiolatus (Jack) Wall. Their chemical structures were elucidated based on detailed analyses of the NMR and MS data. The absolute configuration of petiolaticin A was also determined by X-ray diffraction analysis. Petiolaticin A represents a cucurbitacin derivative incorporating a 3,4-epoxyfuranyl-bearing side chain, while petiolaticin B possesses a furopyranyl unit fused to the tetracyclic cucurbitane core structure. Petiolaticins A, B, and D were evaluated in vitro against a panel of human breast, pancreatic, and colorectal cancer cell lines. Petiolaticin A exhibited the greatest cytotoxicity against the MDA-MB-468, MDA-MB-231, MCF-7, and SW48 cell lines (IC 7.4, 9.2, 9.3, and 4.6 μM, respectively). Additionally, petiolaticin D, 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one, and 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one 3-O-β--glucopyranoside were tested for their ability to inhibit cell entry of a pseudotyped virus bearing the hemagglutinin envelope protein of a highly pathogenic avian influenza virus. Petiolaticin D showed the highest inhibition (44.3%), followed by 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one (21.0%), and 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one 3-O-β--glucopyranoside showed limited inhibition (9.0%). These preliminary biological assays have demonstrated that petiolaticins A and D possess anticancer and antiviral properties, respectively, which warrant for further investigations.
从 Elaeocarpus petiolatus（Jack）Wall 的树皮和叶子中分离得到了四个未描述的葫芦素，分别命名为 petiolaticin A-D，以及四个已知的葫芦素。根据 NMR 和 MS 数据的详细分析，阐明了它们的化学结构。通过 X 射线衍射分析还确定了 petiolaticin A 的绝对构型。Petiolaticin A 代表了一种葫芦素衍生物，其中包含带有 3,4-环氧呋喃基的侧链，而 petiolaticin B 具有与四环葫芦烷核心结构融合的呋喃基单元。在体外，对一系列人乳腺癌、胰腺癌和结直肠癌细胞系进行了 petiolaticin A、B 和 D 的评估。Petiolaticin A 对 MDA-MB-468、MDA-MB-231、MCF-7 和 SW48 细胞系的细胞毒性最大（IC 7.4、9.2、9.3 和 4.6 μM）。此外，16α,23α-环氧-3β,20β-二羟基-10αH,23βH-葫芦-5,24-二烯-11-酮、16α,23α-环氧-3β,20β-二羟基-10αH,23βH-葫芦-5,24-二烯-11-酮 3-O-β--葡萄糖苷和 16α,23α-环氧-3β,20β-二羟基-10αH,23βH-葫芦-5,24-二烯-11-酮 3-O-β--葡萄糖苷被测试其抑制高致病性禽流感病毒血凝素包膜蛋白假型病毒进入细胞的能力。Petiolaticin D 显示出最高的抑制率（44.3%），其次是 16α,23α-环氧-3β,20β-二羟基-10αH,23βH-葫芦-5,24-二烯-11-酮（21.0%），而 16α,23α-环氧-3β,20β-二羟基-10αH,23βH-葫芦-5,24-二烯-11-酮 3-O-β--葡萄糖苷显示出有限的抑制作用（9.0%）。这些初步的生物学检测表明，petoilaticin A 和 D 分别具有抗癌和抗病毒特性，值得进一步研究。
