葳岩仙皂苷 A | 17184-21-3

• 物质功能分类: 天然产物 - 萜类
• 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
• 中文名称: 葳岩仙皂苷 A
• 中文别名: 牡丹草苷A；葳岩仙皂苷A
• 英文名称: prosapogenin
• 英文别名: hederagenin 3-O-α-L-arabinopyranoside；cauloside A；leontoside A；δ-hederin；3-O-α-L-arabinopyranosylhederagenin；fatsiaside B1；(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 17184-21-3
• 化学式: C₃₅H₅₆O₈
• 分子量: 604.825
• InChiKey: QUBNLZCADIYAFW-RITZIESXSA-N

物化性质

• 熔点：
  276-278℃
• 沸点：
  719.3±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  43
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

安全信息

• 储存条件：
  室温

制备方法与用途

生物活性方面，Cauloside A（又称Leontoside A）是从徐长卿根部提取的一种皂苷。研究显示，Cauloside A 具备显著的抗真菌效果。

反应信息

• 作为反应物：
  描述：

  葳岩仙皂苷 A 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以79 mg的产率得到常春藤皂苷元
  参考文献：
  名称：

  来自 Ficaria ranunculoides 块茎的三萜皂苷

  摘要：

  摘要 从毛茛的块茎中提取并发酵纯化的次要皂苷之一可能是 3-O-(α-arabinopyranosyl-1')28-O-[β-吡喃葡萄糖基 → 6″(α-rhamnopyranosyl-1‴ → 4″) β-吡喃葡萄糖基-1″]-hederagenin。在化学降解和光谱分析的基础上，提出了这种新型皂苷的结构。

  DOI：

  10.1016/0031-9422(84)83038-1
• 作为产物：
  描述：

  3-O-<β-D-xylopyranosyl-(1-2)-α-L-arabinopyranosyl>hederagenin 28-O-<β-D-glucopyranoside> 在 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 120.0h， 生成 葳岩仙皂苷 A
  参考文献：
  名称：

  Kim, Youn Chul; Higuchi, Ryuichi; Komori, Tetsuya, Liebigs Annalen der Chemie, 1992, # 5, p. 453 - 460

  摘要：

  DOI：

文献信息

• Studies on nepalese crude drugs. III. On the saponins of Hedera nepalensis K. Koch.
  作者：HARUHISA KIZU、SHINGO KITAYAMA、FUKIO NAKATANI、TSUYOSHI TOMIMORI、TSUNEO NAMBA

  DOI：10.1248/cpb.33.3324

  日期：——

  Twelve saponins, tentatively named HN-saponins A (I), B (II), D1 (III), D2 (IV), E (V), F (VI), H (VII), I (VIII), K (X), M (XII), N (XIII) and P (XIV), were isolated from the stem and bark of Hedera nepalensis K. KOCH. (Araliaceae). Compounds II, V, XII, XIII and XIV were identified as Kizuta saponins K3, K6, K10, K11 and K12, respectively, which have been isolated from Hedera rhombea BEAN. On the basis of chemical and physicochemical evidence, other saponins were identified as follows : I, a mixture of the β-D-glucopyranosides of campesterol (trace), stigmasterol and β-sitosterol ; III, hederagenin 3-O-β-D-glucopyranoside ; IV, oleanolic acid 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; VI, 3-O-α-L-arabinopyranosyl-hederagenin 28-O-β-D-glucopyranosyl ester ; VII, hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester ; VIII, oleanolic acid 3-O-β-D-glucuronopyranoside ; X, hederagenin 3-O-β-D-glucuronopyranoside. Compounds VI and VII were isolated from nature for the first time, though they had previously been derived from Akebia seed saponin D and Kizuta saponin K12, respectively, by partial hydrolysis.

  从常春藤（Hedera nepalensis K. KOCH.，五加科）的茎和树皮中分离出12种皂苷，暂时命名为HN-皂苷A（I）、B（II）、D1（III）、D2（IV）、E（V）、F（VI）、H（VII）、I（VIII）、K（X）、M（XII）、N（XIII）和P（XIV）。化合物II、V、XII、XIII和XIV分别被鉴定为木通皂苷K3、K6、K10、K11和K12，这些皂苷先前已从木通（Hedera rhombea BEAN）中分离得到。根据化学和物理化学证据，其他皂苷被鉴定如下：I，为菜油固醇（微量）、豆固醇和β-谷固醇的β-D-葡萄糖苷混合物；III，常春藤苷元3-O-β-D-葡萄糖苷；IV，齐墩果酸3-O-α-L-鼠李糖基-(1→2)-α-L-阿拉伯糖苷；VI，3-O-α-L-阿拉伯糖基-常春藤苷元28-O-β-D-葡萄糖苷酯；VII，常春藤苷元28-O-α-L-鼠李糖基-(1→4)-β-D-葡萄糖基-(1→6)-β-D-葡萄糖苷酯；VIII，齐墩果酸3-O-β-D-葡萄糖醛酸苷；X，常春藤苷元3-O-β-D-葡萄糖醛酸苷。化合物VI和VII虽曾分别通过部分水解木通籽皂苷D和木通皂苷K12获得，但这是它们首次从自然界中分离出来。
• Studies on the constituents of Hedera rhombea Bean. IV. On the hederagenin glycosides. (2)
  作者：HARUHISA KIZU、SATOSHI HIRABAYASHI、MIZUMI SUZUKI、TSUYOSHI TOMIMORI

  DOI：10.1248/cpb.33.3473

  日期：——

  On the basis of chemical and physicochemical evidence, the structures of two new hederagenin bisdesmosides, named Kizuta saponins K8 (X) and K11 (I), which were isolated from the stem and bark of Hedera rhombea BEAN (Araliaceae), were established to be as follows : X, 3-O-α-L-arabinopyranosyl-hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-6-O-acetyl-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester ; I, 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-α-L-rhamnopyranosyl (1→4)-6-O-acetyl-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester. A glucoside mixture (XIII) was considered to be a mixture of the β-D-glucopyranosides of campesterol (trace), stigmasterol and β-sitosterol based on chemical and physicochemical evidence.

  基于化学和物理化学证据，确定了从常春藤（Hedera rhombea BEAN，五加科）的茎和树皮中分离出的两种新的常春素双甙的结构，分别命名为Kizuta皂苷K8（X）和K11（I），其结构如下：X为3-O-α-L-阿拉伯呋喃糖基-常春素28-O-α-L-鼠李呋喃糖基-(1→4)-6-O-乙酰基-β-D-葡萄吡喃糖基-(1→6)-β-D-葡萄吡喃糖基酯；I为3-O-α-L-鼠李呋喃糖基-(1→2)-α-L-阿拉伯呋喃糖基-常春素28-O-α-L-鼠李呋喃糖基(1→4)-6-O-乙酰基-β-D-葡萄吡喃糖基-(1→6)-β-D-葡萄吡喃糖基酯。基于化学和物理化学证据，认为葡萄糖苷混合物（XIII）是油菜甾醇（微量）、豆甾醇和β-谷甾醇的β-D-葡萄吡喃糖苷混合物。
• Triterpene Glycosides from the Underground Parts of <i>Caulophyllum thalictroides</i>
  作者：Yukiko Matsuo、Kazuki Watanabe、Yoshihiro Mimaki

  DOI：10.1021/np900164b

  日期：2009.6.26

  A total of 22 triterpene glycosides, including 10 new compounds (1−10), were isolated from the underground parts of Caulophyllum thalictroides. The structures of the new glycosides were determined on the basis of extensive spectroscopic analyses, including two-dimensional (2D) NMR data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. All 22 compounds were evaluated

  共有22个三萜糖苷，包括10种新化合物（1 - 10），从地下部分分离红毛七属蕨。新糖苷的结构是在广泛的光谱分析（包括二维（2D）NMR数据）的基础上确定的，然后进行了水解裂解，然后进行了色谱或光谱分析。评价所有22种化合物对HL-60人白血病细胞的细胞毒性。基于齐墩果酸（三萜monodesmosides 1和11 - 16）显示出细胞毒性活性对HL-60细胞IC 50值其范围从3.4至15.9微克/毫升。
• Triterpene Glycosides from Kalopanax septemlobum. 1. Glycosides A, B, C, F, G1, G2, I2, H, and J from Leaves of Kalopanax septemlobum var. Maximowichii Introduced to Crimea
  作者：V. I. Grishkovets、D. A. Panov、V. V. Kachala、A. S. Shashkov

  DOI：10.1007/s10600-005-0110-2

  日期：2005.3

  Eight known glycosides of hederagenin and the new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin were isolated by chromatographic methods from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea. The known 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin was observed for the first time in Kalopanax septemlobum.

  从引入克里米亚的刺楸变种Kalopanax septemlobum var. maximowichii叶中，通过色谱方法分离出了已知的8种常春藤苷元和新的三萜皂苷3-O-β-D-吡喃木糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→2)-O-α-L-吡喃阿拉伯糖基-28-O-α-L-吡喃鼠李糖基-(1→4)-O-6-O-乙酰基-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基酯常春藤苷元。在鵺中首次观察到已知的3-O-α-L-吡喃阿拉伯糖基-28-O-α-L-吡喃鼠李糖基-(1→4)-O-6-O-乙酰基-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基酯常春藤苷元。
• Triterpenoid glycosides from Stauntonia hexaphylla
  作者：Huai-Bin Wang、Ralf Mayer、Gerhard Rücker

  DOI：10.1016/0031-9422(91)80035-y

  日期：1993.11

  On the basis of spectroscopic and chemical methods, the structures of two new bisdesmosidic triterpenoid glycosides, named staunoside D and E, which were isolated from Stauntonia hexaphylla, were established as 3-O-(beta-D-glucopyranosyl(1-->2)-[beta-D- glucopyranosyl(1-->3)]-beta-D-glucopyranosyl)-hederagenin-28- O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester and 28-O-[alpha-L-rhamnopyranosyl

  在光谱和化学方法的基础上，从六叶石蕊中分离出的两种新的双桥苷三萜糖苷，命名为 staunoside D 和 E 的结构被确定为 3-O-(beta-D-glucopyranosyl(1-->2 )-[β-D-吡喃葡萄糖基(1-->3)]-β-D-吡喃葡萄糖基)-hederagenin-28-O-[β-D-吡喃葡萄糖基(1-->6)-β-D-吡喃葡萄糖基]酯和 28-O-[α-L-吡喃鼠李糖基 (1-->4)-β-D-吡喃葡萄糖基(1-->6)-β-D-吡喃葡萄糖基]酯，分别。还分离了三种已知的三萜糖苷。从酯糖苷键的断裂中分离出一种新的糖苷原，并对其结构进行了表征。