desacyl-jegosaponin | 53962-19-9

• 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: desacyl-jegosaponin
• 英文别名: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8,9,10-trihydroxy-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
• CAS: 53962-19-9
• 化学式: C₅₄H₈₈O₂₅
• 分子量: 1137.28
• InChiKey: RYALPQKRBGXULF-FBWIGKGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  79
• 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：
  415
• 氢给体数：
  16
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  desacyl-jegosaponin 以650 mg的产率得到
  参考文献：
  名称：

  Kitagawa, Isao; Yoshikawa, Masayuki; Kobayashi, Katsuya, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 296 - 300

  摘要：

  DOI：
• 作为产物：
  描述：

  21,22-di-O-tigloyl barringtogenol 3-O-β-D-glucopyranosyl(1->2)[α-L-rhamnopyranosyl(1->2)-β-D-galactopyranosyl(1->3)]-β-D-glucopyranosiduronic acid 在 氢氧化钾 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以4 mg的产率得到desacyl-jegosaponin
  参考文献：
  名称：

  Medicinal Flowers. XXVI. Structures of Acylated Oleanane-Type Triterpene Oligoglycosides, Yuchasaponins A, B, C, and D, from the Flower Buds of <i>Camellia oleifera</i>&mdash;Gastroprotective, Aldose Reductase Inhibitory, and Radical Scavenging Effects&mdash;

  摘要：

  山茶花（Camellia oleifera ABEL）花蕾的甲醇提取物及其丁醇可溶部分对大鼠乙醇和吲哚美辛诱导的胃黏膜损伤显示出抑制作用。乙酸乙酯和丁醇可溶部分还表现出对大鼠晶状体醛糖还原酶的抑制作用以及对1,1-二苯基-2-苦基肼自由基和超氧自由基的清除效果。从丁醇可溶部分中分离出四种新的酰化齐墩果烷型三萜寡糖苷，命名为玉茶皂苷A、B、C和D，其结构根据化学和物理化学证据得以阐明。另一方面，从乙酸乙酯和丁醇可溶部分中分离出槲皮素3-O-α-L-鼠李糖苷和山柰酚3-O-α-L-鼠李糖苷作为主要成分，并对其胃保护作用进行了研究。

  DOI：

  10.1248/cpb.57.269

文献信息

• 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。
• Kitagawa, Isao; Kamigauchi, Toshiyuki; Ohmori, Hidenobu, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 10, p. 3078 - 3086
  作者：Kitagawa, Isao、Kamigauchi, Toshiyuki、Ohmori, Hidenobu、Yoshikawa, Masayuki

  DOI：——

  日期：——
• Medicinal Flowers. XXVI. Structures of Acylated Oleanane-Type Triterpene Oligoglycosides, Yuchasaponins A, B, C, and D, from the Flower Buds of &lt;i&gt;Camellia oleifera&lt;/i&gt;&amp;mdash;Gastroprotective, Aldose Reductase Inhibitory, and Radical Scavenging Effects&amp;mdash;
  作者：Sachiko Sugimoto、Guihua Chi、Yasuyo Kato、Seikou Nakamura、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1248/cpb.57.269

  日期：——

  The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia oleifera ABEL were found to exhibit inhibitory effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. The ethyl acetate- and 1-butanol-soluble fractions also showed inhibitory effects on rat lens aldose reductase and scavenging effects on 1,1-diphenylpicryl-2-hydrazyl radical and superoxide. From the 1-butanol-soluble fraction, four new acylated oleanane-type triterpene oligoglycosides, yuchasaponins A, B, C, and D, were isolated and their structures were elucidated on the basis of chemical and physicochemical evidence. On the other hand, quercetin 3-O-α-L-rhamnopyranoside and kaempferol 3-O-α-L-rhamnopyranoside were isolated from the ethyl acetate- and 1-butanol-soluble fractions as the principal constituents, and their gastroprotective effects were examined.

  山茶花（Camellia oleifera ABEL）花蕾的甲醇提取物及其丁醇可溶部分对大鼠乙醇和吲哚美辛诱导的胃黏膜损伤显示出抑制作用。乙酸乙酯和丁醇可溶部分还表现出对大鼠晶状体醛糖还原酶的抑制作用以及对1,1-二苯基-2-苦基肼自由基和超氧自由基的清除效果。从丁醇可溶部分中分离出四种新的酰化齐墩果烷型三萜寡糖苷，命名为玉茶皂苷A、B、C和D，其结构根据化学和物理化学证据得以阐明。另一方面，从乙酸乙酯和丁醇可溶部分中分离出槲皮素3-O-α-L-鼠李糖苷和山柰酚3-O-α-L-鼠李糖苷作为主要成分，并对其胃保护作用进行了研究。
• Kitagawa, Isao; Yoshikawa, Masayuki; Kobayashi, Katsuya, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 296 - 300
  作者：Kitagawa, Isao、Yoshikawa, Masayuki、Kobayashi, Katsuya、Imakura, Yasuhiro、Im, Kwang Sik、Ikenishi, Yuji

  DOI：——

  日期：——