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决明子种子中的两个新萘内酯糖苷。

Two new naphthalenic lactone glycosides from Cassia obtusifolia L. seeds.

机构信息

Department of Food and Life Science, Pukyong National University, Busan, 48513, Republic of Korea.

Drug Research and Development Center, College of Pharmacy, Daegu Catholic University, Gyeongbuk, 38430, Republic of Korea.

出版信息

Arch Pharm Res. 2018 Jul;41(7):737-742. doi: 10.1007/s12272-018-1044-0. Epub 2018 Jun 8.

Abstract

Two new naphthalenic lactone glycosides, (3S)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-benzo[g]isochromene-3-carboxylic acid 9-O-β-D-glucopyranoside (1) and (3R)-cassialactone 9-O-β-D-glucopyranoside (2) were isolated from seeds of Cassia obtusifolia Linn., along with five known compounds: (3R)-cassialactone 9-O-β-D-gentiobioside (3), emodin 1-O-β-gentiobioside (4), 1-hydroxyl-2-acetyl-3,8-dimethoxy-naphthalene 6-O-β-D-apiofuranosyl-(1 → 2)-β-D-glucopyranoside (5), rubrofusarin 6-O-β-D-gentiobioside (6), rubrofusarin 6-O-β-D-triglucoside (7). Structures of 1 and 2 were elucidated by NMR and HR-ESI-MS spectroscopic analysis. Their stereochemistry was determined by CD experiment. All compounds were tested for their ability to inhibit the formation of advanced glycation end-products in vitro. Compounds 1, 2, 3, 5, and 6 showed significant in vitro inhibitory activities (IC values of 11.63, 23.40, 7.32, 89.03, and 38.89 µM, respectively).

摘要

从决明子种子中分离得到了两个新的萘内酯糖苷,(3S)-9,10-二羟基-7-甲氧基-3-甲基-1-氧代-3,4-二氢-1H-苯并[g]异色烯-3-羧酸 9-O-β-D-吡喃葡萄糖苷(1)和(3R)-卡西亚内酯 9-O-β-D-吡喃葡萄糖苷(2),以及五个已知化合物:(3R)-卡西亚内酯 9-O-β-D-龙胆二糖苷(3)、大黄素 1-O-β-龙胆二糖苷(4)、1-羟基-2-乙酰基-3,8-二甲氧基萘 6-O-β-D-阿魏酰基-(1 → 2)-β-D-吡喃葡萄糖苷(5)、红紫素 6-O-β-D-龙胆二糖苷(6)、红紫素 6-O-β-D-三糖苷(7)。通过 NMR 和 HR-ESI-MS 光谱分析确定了 1 和 2 的结构。通过 CD 实验确定了它们的立体化学。所有化合物均测试了其体外抑制晚期糖基化终产物形成的能力。化合物 1、2、3、5 和 6 表现出显著的体外抑制活性(IC 值分别为 11.63、23.40、7.32、89.03 和 38.89 µM)。

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