海巴戟（诺丽）果实中裂环烯醚萜苷、半萜苷和脂肪酸苷的黑色素生成抑制活性

Melanogenesis inhibitory activities of iridoid-, hemiterpene-, and fatty acid-glycosides from the fruits of Morinda citrifolia (Noni).

作者信息

Akihisa Toshihiro, Seino Ken-ichi, Kaneko Etsuyo, Watanabe Kensuke, Tochizawa Shun, Fukatsu Makoto, Banno Norihiro, Metori Koichi, Kimura Yumiko

机构信息

College of Science and Technology, Nihon University, Tokyo 101-8308, Japan.

出版信息

J Oleo Sci. 2010;59(1):49-57. doi: 10.5650/jos.59.49.

DOI:10.5650/jos.59.49

PMID:20032599

Abstract

A new iridoid glycoside, 9-epi-6alpha-methoxy geniposidic acid (4), three new hemiterpene glycosides, 3-methylbut-3-enyl 2'-O-(beta-D-glucopyranosyl)-beta-D-glucopyranoside (nonioside K) (6), 3-methylbut-3-enyl 6'-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside (nonioside L) (8), and 3-methylbut-3-enyl 6'-O-(beta-D-xylofuranosyl)-beta-D-glucopyranoside (nonioside M) (9), and two new saccharide fatty acid esters, 6'-O-(beta-D-glucopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside N) (16) and 6'-O-(beta-D-xylopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside O) (17), were isolated from a methanol extract of the fruits of Morinda citrifolia (noni), along with 11 known compounds, namely, three iridoid glycosides (1-3), two hemiterpene glycosides (5 and 7), and five saccharide fatty acid esters (10-15). Upon evaluation of compounds 1-17 on the melanogenesis in the B16 melanoma cells induced with alpha-melanocyte-stimulating hormone (alpha-MSH), 13 compounds (1, 3, 4, 6-14, and 17) exhibited marked inhibitory effects with 34-49% reduction of melanin content at 100 muM with no or almost no toxicity to the cells (91-116% of cell viability at 100 microM).

摘要

从巴戟天（诺丽果）果实的甲醇提取物中分离出一种新的环烯醚萜苷，9-表-6α-甲氧基栀子苷酸（4），三种新的半萜苷，3-甲基丁-3-烯基 2'-O-(β-D-吡喃葡萄糖基)-β-D-吡喃葡萄糖苷（诺尼苷 K）（6），3-甲基丁-3-烯基 6'-O-(β-D-吡喃木糖基)-β-D-吡喃葡萄糖苷（诺尼苷 L）（8），以及 3-甲基丁-3-烯基 6'-O-(β-D-呋喃木糖基)-β-D-吡喃葡萄糖苷（诺尼苷 M）（9），还有两种新的糖脂肪酸酯，6'-O-(β-D-吡喃葡萄糖基)-1'-O-[(2ξ)-2-甲基丁酰基]-β-D-吡喃葡萄糖（诺尼苷 N）（16）和 6'-O-(β-D-吡喃木糖基)-1'-O-[(2ξ)-2-甲基丁酰基]-β-D-吡喃葡萄糖（诺尼苷 O）（17），以及 11 种已知化合物，即三种环烯醚萜苷（1-3），两种半萜苷（5 和 7），以及五种糖脂肪酸酯（10-15）。在用α-黑素细胞刺激激素（α-MSH）诱导的 B16 黑素瘤细胞中评估化合物 1-17 对黑色素生成的影响时，13 种化合物（1、3、4、6-14 和 17）表现出显著的抑制作用，在 100 μM 时黑色素含量降低 34-49%，对细胞无毒性或几乎无毒性（在 100 μM 时细胞活力为 91-116%）。