Alpha-常春藤苷 | 27013-91-8

• 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: Alpha-常春藤苷
• 中文别名: 常春藤皂甙；ALPHA-常春藤皂甙；Alpha-常春藤皂苷；a-常春藤皂苷
• 英文名称: α-hederin
• 英文别名: alpha-Hederin；sapindoside A；kalopanaxsaponin A；hederagenin 3-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside；hederagenin 3-O-2)-α-L-arabinopyranoside>；hederagenin-3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside；hederagenin 3-O-α-L rhamnopyranosyl-(1/2)-α-L-arabinopyranoside；dipsacoside A；(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 27013-91-8
• 化学式: C₄₁H₆₆O₁₂
• 分子量: 750.968
• InChiKey: KEOITPILCOILGM-LLJOFIFVSA-N

物化性质

• 熔点：
  215°C (dec.)
• 比旋光度：
  D20 +14.5° (c = 0.92 in methanol)
• 沸点：
  849.6±65.0 °C(Predicted)
• 密度：
  1.32
• 溶解度：
  DMF：10mg/mL； DMSO：10mg/mL；乙醇：5mg/mL
• LogP：
  8.370 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  53
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

安全信息

• 安全说明：
  S22,S24/25,S45
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  29389090
• 危险品运输编号：
  UN 1544
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性

alpha-Hederin (α-Hederin) 是一种单桥糖三萜皂苷，对多种肿瘤细胞表现出良好的抗肿瘤作用。它可通过激活线粒体依赖性途径抑制胃癌细胞的增殖，并诱导凋亡 (apoptosis)，同时伴随着谷胱甘肽减少和活性氧生成。

体外研究

alpha-Hederin (α-Hederin) 具有细胞毒性，在较低浓度下即可抑制细胞增殖。它还能降低处理细胞中的有丝分裂活动。

体内研究

在动物模型中，alpha-Hederin (α-Hederin) 显示出预防作用，类似于 thymoquinone 对敏感大鼠的效果。它可能通过干预 miRNA-126 的表达来影响 IL-13 分泌途径，从而减少炎症反应。

化学性质

白色结晶粉末状物质，溶于水、甲醇和乙醇，来源于预知子。

用途

α-常春藤皂苷具有抗抑郁的作用，并可用于含量测定、鉴定及药理实验。其表现出一定的细胞毒活性。

反应信息

• 作为反应物：
  描述：

  Alpha-常春藤苷 在 吡啶 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  皂苷衍生物及其药物组合物和应用

  摘要：

  本发明公开了一种皂苷衍生物及其药物组合物和应用。该皂苷衍生物的结构如式(I)所示，其中X为C＝O、C＝N‑OH、CH‑OH，Y为C或CH，或X‑Y为CH＝CH；Z为CH2或C＝O；或R2与Y之间通过共价键连接构成酯。该皂苷衍生物保留了较强的抗肿瘤活性，但其溶血毒性大大降低。

  公开号：

  CN108341850B
• 作为产物：
  描述：

  3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl hederagenin-28-O-β-D-galactopyranosyl-(1->6)-β-D-glucopyranosyl ester 在 potassium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 Alpha-常春藤苷
  参考文献：
  名称：

  Antimicrobially Active Hederagenin Glycosides from Cephalaria elmaliensis

  摘要：

  A phytochemical investigation of the aerial parts of Cephalaria elmaliensis resulted in the isolation of ten hederagenin-type triterpene saponins (1-10) including three new ones, elmalienoside A (1), elmalienoside B (2), elmalienoside C (3), and two known flavonoid glycosides (11-12). Their structures were identified by extensive spectroscopic techniques (1D and 2D NMR, HR ESIMS) and chemical evidence. The antimicrobial activity of the extracts and the pure compounds was evaluated by the MIC method. According to the results, all pure compounds including the new ones were found to be very active against both gram-positive and gram-negative bacteria.

  DOI：

  10.1055/s-0031-1298415

文献信息

• Molecular Complexes of Ivy Triterpene Glycosides with Cholesterol
  作者：L. A. Yakovishin、V. I. Grishkovets

  DOI：10.1134/s1068162019070136

  日期：2019.12

  ethanol at 25°С). The constants are calculated on the basis of isomolar curves. The complexes of cholesterol with ivy monodesmosidic glycosides are more stable. Intermolecular interaction in the complexes is carried out by hydrogen bonds formation of type –С=О⋅⋅⋅Н–О– (for monodesmosidic glycosides) and –(Н)О⋅⋅⋅Н–О– (for bisdesmosidic glycoside). Hydrophobic contacts of the aglycone part of glycosides (hederagenin)

  该论文报道了常春藤属常春藤（五加科）成员胆固醇与优势三萜皂苷的分子复合物的制备，即单线苷糖苷α-常春藤苷（hederagenin 3-O-α-L-rhamnopyranosyl-(1 →2)-O-α-L-arabinopyranoside) 和双桥糖苷常春藤皂苷 C（hederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosyl-28-О-α-L -rhamnopyranosyl-(1→4)-О-β-D-吡喃葡萄糖基-(1→6)-О-β-D-吡喃葡萄糖苷），以及少量的单链糖苷常春藤苷 F（hederagenin 3-О-β-D -吡喃葡萄糖基-(1→2)-О-β-D-吡喃葡萄糖苷)。已经通过分光光度法版本中的等摩尔系列方法和具有通用光学衰减全反射 (ATR) 附件的 FT-IR 光谱法研究了络合。已经表明，α-常春藤素、常春藤皂苷
• 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 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。
• Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis
  作者：Xiao-Yang Wang、Hui Gao、Wei Zhang、Yuan Li、Guang Cheng、Xiao-Li Sun、Hai-Feng Tang

  DOI：10.1016/j.bmcl.2013.08.006

  日期：2013.10

  extensive use of 1D and 2D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1–12, prosapogenins 4a, 5a, 10a–12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines

  所述的调查Ñ的根茎的提取物-BuOH海葵太白导致了五个新的齐墩果烷型三萜皂甙（隔离1 - 5），用七个已知皂苷（一起6 - 12）。通过广泛使用1 D和2 D NMR实验以及ESIMS分析和酸水解来确定其结构。的糖苷配基1，2和4被确定为siaresinolic酸，其据报道该属首次。皂苷1 – 12，促皂甙元的细胞毒性分别评估了4a，5a，10a – 12a和皂苷元唾液酸树脂（SA），齐墩果酸（OA），二十碳皂素（HE）针对五种人类癌细胞系，包括HepG2，HL-60，A549，HeLa和U87MG。所述monodesmosidic皂苷6 - 8，5A，10A - 12A和皂苷元SA，OA，HE表现出细胞毒性活性对所有癌细胞系，用IC 50个值范围为2.25至57.28微米。值得注意的是，双糖苷皂苷1 –图4和9显示了对U87MG细胞的选择性细胞毒性。
• Antifungal Activity of Modified Hederagenin Glycosides from the Leaves of Kalopanax pictum var. chinense.
  作者：Min-Won LEE、Sung Uk KIM、Dug-Ryoung HAHN

  DOI：10.1248/bpb.24.718

  日期：——

  Monodesmosides which were obtained from the partial degradation of hederagenin bisdesmosides exhibited significant antifungal effect against Microsporum canis, Coccidioides immitis, Trichophyton mentagrophytes, Cryptococcus neoformans, and Candida albicans at the minimal inhibitory concentrations of 6.25—25 μm/ml. The hederagenin glycosides were isolated from the leaves of Kalopanax pictum var. chinense.

  从常春藤甙元的双甙部分降解物中得到的单甙对犬小孢子菌、粗球孢子菌、须毛癖菌、新型隐球菌和白色念珠菌表现出显著的抗真菌效应，其最低抑制浓度为6.25—25μm/ml。这些常春藤甙是从刺揪中国变种的叶中分离得到的。