异麦角甾苷 | 61303-13-7

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 异麦角甾苷
• 中文别名: 异毛蕊花糖苷；异类叶升麻苷
• 英文名称: Isoacteoside
• 英文别名: isoverbascoside；isoacetoside；[(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 61303-13-7
• 化学式: C₂₉H₃₆O₁₅
• 分子量: 624.596
• InChiKey: FNMHEHXNBNCPCI-QEOJJFGVSA-N

物化性质

• 熔点：
  220～230℃
• 沸点：
  942.9±65.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：≥ 48 mg/mL（76.85 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  15

安全信息

• 海关编码：
  29389090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

制备方法与用途

用途

肉苁蓉为肉苁蓉属植物干燥带鳞叶的肉质茎，主要用于治疗男子阳痿、女子不孕、血枯便秘等症状，有“沙漠人参”之称。近20年来的药理活性研究发现，肉苁蓉不仅能防治神经退行性疾病，还能显著上调α3和α7尼古丁受体蛋白质的表达水平。从肉苁蓉中分离得到的主要活性成分之一为异麦角甾苷。

生物活性

Isoacteoside是一种天然产物，能显著抑制糖基化终产物的形成。

化学性质

异麦角甾苷是白色结晶粉末，可溶于甲醇、乙醇和DMSO等有机溶剂，来源于肉苁蓉和地黄。

用途

异麦角甾苷具有抗炎作用，并可用于含量测定、鉴定及药理实验。此外，它还具有免疫调节、抗氧化、增强体力和抗疲劳等多种药理作用。

反应信息

• 作为反应物：
  描述：

  异麦角甾苷 在 sodium methylate 作用下， 反应 49.0h， 生成 methyl (E)-3-(3,4-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  来自 Harpagophytum Procumbens 的环烯醚萜和酚糖苷

  摘要：

  摘要 从Harpagophytum procumbens 的次生根中获得了一种新型生物苷β-(3',4'-二羟基苯基)乙基-O-α-L-吡喃鼠李糖基(1→3)-D-吡喃葡萄糖苷。它伴随着已知的环烯醚萜苷 harpagoside、procumbide 及其 6'-O-p-香豆酰酯，以及酚糖苷、acteoside 和 isoacteoside，后者对首次从 H. procumbens 中获得。这些代谢物的结构通过高分辨率 NMR 研究进行了区分，而生物苷的结构也得到了合成的支持。

  DOI：

  10.1016/s0031-9422(00)81833-6
• 作为产物：
  描述：

  毛蕊花糖苷 在 sodium hydroxide 作用下， 反应 2.0h， 以9.1 g的产率得到异麦角甾苷
  参考文献：
  名称：

  Schilling, Gerhard; Huegel, Michael; Mayer, Walter, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 12, p. 1633 - 1635

  摘要：

  DOI：

文献信息

• Studies on the acyl glycosides from Leucoseptrum japonicum (Miq.) Kitamura et Murata.
  作者：TOSHIO MIYASE、AKIRA KOIZUMI、AKIRA UENO、TADATAKA NORO、MASANORI KUROYANAGI、SEIGO FUKUSHIMA、YOSHIHIKO AKIYAMA、TSUNEMATSU TAKEMOTO

  DOI：10.1248/cpb.30.2732

  日期：——

  Two new acyl glycosides, leucosceptosides A (IV) and B (V), have been isolated from Leucosceptrum japonicum (MIQ.) KITAMURA et MURATA, together with martynoside (III), acteoside (I) and an acteoside isomer (II). The structures of IV and V were determined to be 2-(3, 4-dihydroxyphenylethyl) 1-O-α-L-rhamnopyranosyl-(1→3)-β-D-(4-O-caffeyl)-glucopyranoside and 2-(3-hydroxy-4-methoxyphenylethyl) 1-O-α-L-rhamnopyranosyl-(1→3)-O-[β-D-apiofuranosyl (1→6)]-β-D-glucopyranoside, respectively, on the basis of chemical and spectral data.

  从日本白头翁（Leucosceptrum japonicum (MIQ.) KITAMURA et MURATA）中分离出两种新的酰基糖苷，分别为白头翁苷A（IV）和白头翁苷B（V），同时还分离出了马尔丁苷（III）、阿克托苷（I）和阿克托苷异构体（II）。根据化学及光谱数据，IV和V的结构分别被确定为2-(3, 4-二羟基苯基乙基) 1-O-α-L-鼠李糖吡喃糖基-(1→3)-β-D-(4-O-咖啡酸)-葡萄糖吡喃糖苷和2-(3-羟基-4-甲氧基苯基乙基) 1-O-α-L-鼠李糖吡喃糖基-(1→3)-O-[β-D-阿糖苷[1→6]]-β-D-葡萄糖吡喃糖苷。
• Antiviral Phenylpropanoid Glycosides from the Medicinal Plant <i>Markhamia lutea</i>
  作者：Michael R. Kernan、Ambrose Amarquaye、Jian Lu Chen、Jody Chan、David F. Sesin、Nigel Parkinson、Zhi-jun Ye、Marilyn Barrett、Cheryl Bales、Cheryl A. Stoddart、Barbara Sloan、Phillipe Blanc、Charles Limbach、Salehe Mrisho、Edward J. Rozhon

  DOI：10.1021/np9703914

  日期：1998.5.1

  Three new phenylpropanoid glycosides, named luteoside A (3), luteoside B (4), and luteoside C (5), were isolated together with the known compounds verbascoside (1) and isoverbascoside (2) from the roots of the medicinal plant Markhamia lutea. The structures of the new compounds were determined to be 1-O-(3,4-dihydroxyphenyl)ethyl beta-D-apiofuranosyl(1-->2)-alpha-L-rhamnopyranosyl(1-->3)-4-O-caffeoyl-6-acetyl- beta-D-glucopyranoside, 1-O-(3,4-dihydroxyphenyl)ethyl beta-D-apiofuranosyl(1-->2)-alpha-L-rhamnopyranosyl(1-->3)-6-O-caffeoyl-beta-D-glucopyranoside, and 1-O-(3,4-dihydroxyphenyl)ethyl beta-D-apiofuranosyl(1-->2)-alpha-L-rhamnopyranosyl(1-->3)-6-O-feruloyl-beta-D-glucopyranoside, respectively, on the basis of chemical and spectroscopic data. All five phenylpropanoid glycosides exhibited potent in vitro activity against respiratory syncytial virus.
• Identification and occurrence of phenylethanoid and iridoid glycosides in six Polish broomrapes (Orobanche spp. and Phelipanche spp., Orobanchaceae)
  作者：Dariusz Jedrejek、Sylwia Pawelec、Renata Piwowarczyk、Łukasz Pecio、Anna Stochmal

  DOI：10.1016/j.phytochem.2019.112189

  日期：2020.2

  There are about 200 holoparasitic broomrapes (Orobanchaceae) known worldwide, however, only several species have been so far investigated phytochemically. Among Orobanche s.l. are both rare and endangered species, as well as onerous crop pests. This study aims to give a phytochemical description, both qualitative and quantitative, of six broomrape species (Orobanche and Phelipanche taxa) growing in Poland, including species that have not been tested in detail (O. caryophyllacea, O. linen, O. picridis, and P. arenaria). Sixteen metabolites, including 14 phenylethanoid glycosides (PhGs) and 2 iridoid glycosides (IrGs), were isolated and identified using NMR spectroscopy and hydrolysis, revealing the presence of two previously undescribed PhGs in P. ramosa, named ramoside A and 2'-acetylramoside A. In addition, in the example of O. caryophyllacea, we have reported as the first occurrence of IrGs in broomrapes. Concentrations of phenylethanoids, the main constituents of broomrapes, in the studied plant material (flowering shoots with haustoria) were determined using the UHPLC-PDA method. It was found that P. ramosa has been the richest source of PhGs. In addition, the differences between broomrapes have been visualized using principal component and cluster analysis. The results of the antiradical DPPH test of 13 PhGs confirmed previous findings on the relation of the antioxidant potential with the structure of phenolic moieties - phenolic acid and phenylethanoid unit.
• Antiparasitic antioxidant phenylpropanoids and iridoid glycosides from Tecoma mollis
  作者：Wael M. Abdel-Mageed、Enaam Y. Backheet、Azza A. Khalifa、Zedan Z. Ibraheim、Samir A. Ross

  DOI：10.1016/j.fitote.2011.12.025

  日期：2012.4

  A radical scavenging guided phytochemical study on the stem bark of Tecoma mollis afforded seven active phenylpropanoid glycosides (1-7), including a new one (4), and one iridoid (8). The structures of the isolated compounds were elucidated on the basis of spectroscopic evidences and correlated with known compounds. Compounds (1-7) displayed promising antioxidant activity (DPPH assay) in relation to ascorbic acid (positive control). The antimicrobial activity for compounds (1-8) was evaluated against five bacterial and five fungal strains. The isolated compounds exhibited nonselective weak to moderate antimicrobial activity. The highest antileishmanial activity against Leishmania donovani was observed for compound (7) with an IC50 value of 6.71 mu g/ml, using pentamidine and amphotericin B as drug controls. Compound (5) exhibited moderate antimalarial activity (45% inhibition) against chloroquine sensitive (D6) clones of Plasmodium falciparum. (C) 2012 Elsevier B.V. All rights reserved.
• Antioxidative Activities of Phenylethanoid Glycosides from <i>Ligustrum</i> <i>purpurascens</i>
  作者：Ivan Yuen Fan Wong、Zheng-Dan He、Yu Huang、Zhen-Yu Chen

  DOI：10.1021/jf0100604

  日期：2001.6.1

  Tea and kudingcha (bitter tea) are the two most popular beverages consumed in China. Tea derived from the leaves of Camellia sinensis has been well studied for its various health benefits, but there are very limited data on the biological activities of bitter tea derived from the leaves of Ligustrum purpurascens (LP). The present study was carried out to characterize the antioxidants present in the bitter tea brewed from the leaves of LP. It was found that the crude glycoside fraction possessed strong protection against oxidation of human low-density lipoprotein (LDL). The column chromatographic separation led to the isolatation of five phenylethanoid glycosides, namely, acteoside, ligupurpuroside A, cis-ligupurpuroside B, trans-ligupurpuroside B, and osmanthuside B. When acteoside was heated in the boiling water, it was isomerized to form isoacteoside. Acteoside, isoacteoside, and ligupurpuroside A purified from LP were protective, whereas cis-ligupurpuroside B, trans-ligupurpuroside B, and osmanthuside B exhibited no protection to human LDL from CU2+ medicated oxidation. Acteoside, isoacteoside, and ligupurpuroside A were also effective in preventing the peroxyl free radical-induced oxidation of alpha -tocopherol in human LDL. The antioxidant activities of acteoside, isoacteoside, and ligupurpuroside A were comparable to that observed for a green tea antioxidant, (-)-epicatechin gallate. The inhibitory effect of these three phenylethanoid glycosides on oxidation of human LDL and a-tocopherol was dose-dependent at concentrations of 5-40 muM. The present results suggest that the bitter tea beverage derived from LP contains effective antioxidants that may have an equal benefit as a green tea beverage.