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。
• Medicinal Flowers. XXXVI.&lt;sup&gt;1&lt;/sup&gt;&lt;sup&gt;)&lt;/sup&gt; Acylated Oleanane-Type Triterpene Saponins with Inhibitory Effects on Melanogenesis from the Flower Buds of Chinese &lt;i&gt;Camellia japonica&lt;/i&gt;
  作者：Seikou Nakamura、Katsuyoshi Fujimoto、Souichi Nakashima、Takahiro Matsumoto、Tomoko Miura、Kaoru Uno、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1248/cpb.60.752

  日期：——

  Four acylated oleanane-type triterpene oligoglycosides, sanchakasaponins E–H, were isolated from the flower buds of Camellia japonica cultivated in Yunnan province, China, together with four known triterpene oligoglycosides. The chemical structures of the new triterpene oligoglycosides were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the triterpene oligoglycoside constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were investigated.

  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。