quercetin 3-O-α-L-arabinopyranosyl-(1'''->6'')-β-D-galactopyranoside | 13241-30-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: quercetin 3-O-α-L-arabinopyranosyl-(1'''->6'')-β-D-galactopyranoside
• 英文别名: quercetin 3-O-α-L-arabinopyranosyl-(1->6)-β-D-galactopyranoside；quercetin-3-O-[α-L-arabinopyranosyl-(1-6)-β-D-galactopyranoside]；Quercetin-3-O-(6-O-α-L-arabinopyranosyl)-β-D-galaktopyranosid；quercetin 3-O-α-L-arabinopyranosyl(1-6)-β-D-galactopyranoside；quercetin 3-O-vicianoside；rumarin；2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• CAS: 13241-30-0；23284-18-6；142905-18-8
• 化学式: C₂₆H₂₈O₁₆
• 分子量: 596.499
• InChiKey: YNMFDPCLPIMRFD-XTXTUNRQSA-N

物化性质

• 熔点：
  252-253 °C(Solv: water (7732-18-5))
• 沸点：
  994.8±65.0 °C(Predicted)
• 密度：
  1.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  266
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  quercetin 3-O-α-L-arabinopyranosyl-(1'''->6'')-β-D-galactopyranoside 在 盐酸 作用下， 反应 2.0h， 生成 槲皮素
  参考文献：
  名称：

  Acylated flavonol glycosides as probing stimulants of a bean aphid, Megoura crassicauda, from Vicia angustifolia

  摘要：

  A bean aphid, Megoura crassicauda, which feeds selectively on the plant genus Vicia (Fabaceae), was found to be stimulated to probe an extract solution of the host plant, narrowleaf vetch, Vicia angustifolia L., depositing characteristic stylet sheaths on a parafilm membrane. Two acylated flavonol glycosides were isolated as the specific probing stimulants from the extracts and characterized as quercetin 3-O-alpha-L-arabinopyranosyl-(1-->6)-[2"-O-(E)-p-coumaroyl]-beta-D-glucopyranoside and quercetin 3-O-alpha-L-arabinopyranosyl-(1-->6)-[2"-O-(E)-p-coumaroyl]-beta-D-galactopyranoside. A mixture of these compounds in the same equivalency strongly induced the probing response from M. crassicauda, suggesting their kairomonal roles during host recognition. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(02)00226-1
• 作为产物：
  描述：

  quercetin 3-O-α-L-arabinopyranosyl-(1->6)-[2''-O-(E)-p-coumaroyl]-β-D-galactopyranoside 在 氢氧化钾 作用下， 反应 1.0h， 生成 quercetin 3-O-α-L-arabinopyranosyl-(1'''->6'')-β-D-galactopyranoside
  参考文献：
  名称：

  Acylated flavonol glycosides as probing stimulants of a bean aphid, Megoura crassicauda, from Vicia angustifolia

  摘要：

  A bean aphid, Megoura crassicauda, which feeds selectively on the plant genus Vicia (Fabaceae), was found to be stimulated to probe an extract solution of the host plant, narrowleaf vetch, Vicia angustifolia L., depositing characteristic stylet sheaths on a parafilm membrane. Two acylated flavonol glycosides were isolated as the specific probing stimulants from the extracts and characterized as quercetin 3-O-alpha-L-arabinopyranosyl-(1-->6)-[2"-O-(E)-p-coumaroyl]-beta-D-glucopyranoside and quercetin 3-O-alpha-L-arabinopyranosyl-(1-->6)-[2"-O-(E)-p-coumaroyl]-beta-D-galactopyranoside. A mixture of these compounds in the same equivalency strongly induced the probing response from M. crassicauda, suggesting their kairomonal roles during host recognition. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(02)00226-1

文献信息

• A new flavonol glycoside from Hylomecon vernalis
  作者：Seung Young Lee、Ki Hyun Kim、Il Kyun Lee、Kyu Ha Lee、Sang Un Choi、Kang Ro Lee

  DOI：10.1007/s12272-012-0303-8

  日期：2012.3

  Purification of a MeOH extract from the aerial parts of Hylomecon vernalis Maxim. (Papaveraceae) using column chromatography furnished a new acetylated flavonol glycoside (1), together with twenty known phenolic compounds (2–21). Structural elucidation of 1 was based on 1D- and 2D-NMR spectroscopy data analysis to be quercetin 3-O-[4‴-O-acetyl-α-L-arabinopyranosyl]-(1‴→6″)-β-D-galactopyranoside (1). The structures of compounds 2–21 were elucidated by spectroscopy and confirmed by comparison with reported data; quercetin 3-O-[2‴-O-acetyl-α-L-arabinopyranosyl]-(1‴→6″)-β -D-galactopyranoside (2), quercetin 3-O-α-L-arabinopyranosyl-(1‴→6″)-β-D-galactopyranoside (3), quercetin 3-O-β -D-galactopyranoside (4), kaempferol 3,7-O-α-L-dirhamnopyranoside (5), diosmetin 7-O-β -D-glucopyranoside (6), diosmetin 7-O-β -D-xylopyranosyl-(1‴→6″)-β-D-glucopyranoside (7), p-hydroxybenzoic acid (8), protocatechuic acid (9), caffeic acid (10), 6-hydroxy-3,4-dihydro-1-oxo-β -carboline (11), (Z)-3-hexenyl-β -D-glucopyranoside (12), (E)-2-hexenyl-β -D-glucopyranoside (13), (Z)-3-hexenyl-α-Larabinopyranosyl-(1″→6′)-β-D-glucopyranoside (14), oct-1-en-3-yl-α-L-arabinopyranosyl-(1″→6′)-β-D-glucopyranoside (15), benzyl-β-D-apiofuranosyl-(1″→6′)-β-D-glucopyranoside (16), benzyl-α-L-arabinopyranosyl-(1″→6′)-β-D-glucopyranoside (17), benzyl-β-D-xylopyranosyl-(1″→6′)-β-Dglucopyranoside (18), 2-phenylethyl-α-L-arabinopyranosyl-(1″→6′)-β-D-glucopyranoside (19), 2-phenylethyl-β-D-apiofuranosyl-(1″→6′)-β-D-glucopyranoside (20), and aryl-β-D-glucopyranoside (21). Compounds 2-21 were isolated for the first time from this plant. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay.

  使用柱层析法纯化了从 Hylomecon vernalis Maxim.(采用柱层析法从 Hylomecon vernalis Maxim（罂粟科）的气生部分中提取出了一种新的乙酰化黄酮醇苷（1），以及二十种已知的酚类化合物（2-21）。根据一维和二维核磁共振光谱数据分析，槲皮素 3-O-[4‴-O-乙酰基-α-L-阿拉伯吡喃糖基]-(1‴→6″)-β-D-吡喃半乳糖苷（1）的结构被阐明。化合物 2-21 的结构通过光谱分析得以阐明，并与已报道的数据进行了对比确认；槲皮素 3-O-[2‴-O-乙酰基-α-L-阿拉伯吡喃糖基]-(1‴→6″)-β-D-吡喃半乳糖苷（2）、槲皮素 3-O-α-L-阿拉伯吡喃糖基-(1‴→6″)-β-D-吡喃半乳糖苷（3）、槲皮素 3-O-β -D-吡喃半乳糖苷（4），山奈酚 3,7-O-α-L-dirhamnopyranoside （5），香叶木素 7-O-β -D-吡喃葡萄糖苷（6）、diosmetin 7-O-β -D-xylopyranosyl-(1‴→6″)-β-D-glucopyranoside (7)、对羟基苯甲酸 (8)、原儿茶酸 (9)、咖啡酸 (10)、6-羟基-3,4-二氢-1-氧代-β-咔啉（11）、(Z)-3-己烯基-β-D-吡喃葡萄糖苷（12）、(E)-2-己烯基-β-D-吡喃葡萄糖苷（13）、(Z)-3-己烯基-α-L-阿拉伯吡喃糖基-(1″→6′)-β-D-吡喃葡萄糖苷 (14)，辛-1-烯-3-基-α-L-阿拉伯吡喃糖基-(1″→6′)-β-D-吡喃葡萄糖苷 (15)、苄基-β-D-呋喃硫糖基-(1″→6′)-β-D-吡喃葡萄糖苷（16），苄基-α-L-阿拉伯吡喃糖基-(1″→6′)-β-D-吡喃葡萄糖苷（17）、苄基-β-D-吡喃木糖基-(1″→6′)-β-D-吡喃葡萄糖苷（18），2-苯基乙基-α-L-阿拉伯吡喃糖基-(1″→6′)-β-D-吡喃葡萄糖苷（19）、2-苯基乙基-β-D-呋喃硫代-(1″→6′)-β-D-吡喃葡萄糖苷（20）和芳基-β-D-吡喃葡萄糖苷（21）。化合物 2-21 是首次从这种植物中分离出来。利用磺胺 B 生物测定法，在体外测试了分离出的化合物对四种人类肿瘤细胞系的细胞毒性。