3-O-{α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->2)]-β-D-glucuronopyranosyl}camelliagenin A

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-O-{α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->2)]-β-D-glucuronopyranosyl}camelliagenin A
• 英文别名: ternstroemiaside A；(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aS,9S,12aS,14aR,14bR)-8,9-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• 化学式: C₅₄H₈₈O₂₄
• 分子量: 1121.28
• InChiKey: BUIOZZJEVAFSTE-GABFKREGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  78
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  394
• 氢给体数：
  15
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  sanchakasaponin G 在 水 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 惕格酸 、 3-O-{α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->2)]-β-D-glucuronopyranosyl}camelliagenin A
  参考文献：
  名称：

  Medicinal Flowers. XXXVI.¹⁾ Acylated Oleanane-Type Triterpene Saponins with Inhibitory Effects on Melanogenesis from the Flower Buds of Chinese <i>Camellia japonica</i>

  摘要：

  从中国云南省栽培的茶花花蕾中分离得到4个酰化的齐墩果烷型三萜低聚糖苷——山茶皂苷E~H，以及4个已知的三萜低聚糖苷。通过化学和物理化学证据阐明了新三萜低聚糖苷的化学结构。研究了这些三萜低聚糖苷组分对茶碱刺激的B16黑色素瘤4A5细胞黑素生成的抑制作用。

  DOI：

  10.1248/cpb.60.752

文献信息

• Medicinal Flowers. XXXI. Acylated Oleanane-Type Triterpene Saponins, Sasanquasaponins I-V, with Antiallergic Activity from the Flower Buds of Camellia sasanqua
  作者：Hisashi Matsuda、Seikou Nakamura、Katsuyoshi Fujimoto、Ryo Moriuchi、Yuta Kimura、Noriko Ikoma、Yuki Hata、Osamu Muraoka、Masayuki Yoshikawa

  DOI：10.1248/cpb.58.1617

  日期：——

  The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia sasanqua THUNB. were found to show inhibitory activities on the release of β-hexosaminidase from rat basophile leukemia (RBL-2H3) cells. From the 1-butanol-soluble fraction, five new acylated oleanane-type triterpene saponins, sasanquasaponins I—V, were isolated together with a known saponin and their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The principal saponin constituents, sasanquasaponins I—III, with an acyl group at the 22-position of the aglycon part showed the inhibitory effects on the release of β-hexosaminidase and some structure–activity relationships were reported.

  从山茶花（Camellia sasanqua THUNB.）花蕾中提取的甲醇提取物及其1-丁醇可溶性馏分对大鼠嗜碱性白血病（RBL-2H3）细胞释放β-己糖胺酸酶具有抑制作用。从 1-丁醇可溶性馏分中分离出了五种新的酰化齐墩果烷型三萜皂苷，即 sasanquasaponins I-V，以及一种已知的皂苷，并根据化学和理化证据阐明了它们的化学结构。主要的皂苷成分--沙参皂苷 I-III，在苷元部分的 22 位上带有酰基，对 β-己糖胺酶的释放有抑制作用，并报告了一些结构-活性关系。