糙叶树果实中的 2-乙酰氧基-ω-苯戊烯脂肪酸三糖苷：Berchemiosides A-C。

Berchemiosides A-C, 2-Acetoxy-ω-phenylpentaene Fatty Acid Triglycosides from the Unripe Fruits of Berchemia berchemiifolia.

机构信息

College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University , Seoul 08826, Republic of Korea.

出版信息

J Nat Prod. 2017 Oct 27;80(10):2778-2786. doi: 10.1021/acs.jnatprod.7b00602. Epub 2017 Oct 3.

DOI:10.1021/acs.jnatprod.7b00602

PMID:28972762

Abstract

Three compounds in a new class of 2-acetoxy-ω-phenylpentaene fatty acid triglycosides, berchemiosides A-C (1-3), and a biosynthetically related phenolic glycoside (4) were isolated from the unripe fruits of Berchemia berchemiifolia, along with three flavonoid 5-O-diglycosides (5-7) and three known flavonoids (8-10). Their chemical structures including absolute configurations were determined by spectroscopic analysis in combination with chemical derivatization. The pentaene group of 1 was found to have (6E,8E,10Z,12Z,14E)-geometry, whereas those of 2 and 3 exhibited all-E geometries. The isolated compounds were examined for their cytotoxicity and xanthine oxidase (XO) inhibitory activity; only compound 7 showed weak XO inhibitory activity.

摘要

从未成熟的破布木果实中分离得到三种新的 2-乙酰氧基-ω-苯基戊烯脂肪酸三糖苷，分别命名为贝切米亚苷 A-C（1-3），以及一个生物合成相关的酚糖苷（4），此外还分离得到三种黄酮类 5-O-二糖苷（5-7）和三种已知的黄酮类化合物（8-10）。通过光谱分析结合化学衍生化确定了它们的化学结构，包括绝对构型。化合物 1 的戊烯部分具有（6E,8E,10Z,12Z,14E）-几何构型，而化合物 2 和 3 则表现出全 E 几何构型。对分离得到的化合物进行了细胞毒性和黄嘌呤氧化酶（XO）抑制活性的测试，只有化合物 7 表现出较弱的 XO 抑制活性。