isoacteoside peracetate | 83529-65-1

• 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
• 英文名称: isoacteoside peracetate
• 英文别名: Isoverbascoside Noaacetate；[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-6-[2-(3,4-diacetyloxyphenyl)ethoxy]-4-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-diacetyloxyphenyl)prop-2-enoate
• CAS: 83529-65-1
• 化学式: C₄₇H₅₄O₂₄
• 分子量: 1002.93
• InChiKey: TZOYRGIJINVJQD-IZPHFZRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  71
• 可旋转键数：
  29
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  300
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  isoacteoside peracetate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以96%的产率得到(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-6-[2-(3,4-dihydroxy-phenyl)-ethoxy]-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Antiviral Phenylpropanoid Glycosides from the Medicinal Plant Markhamia lutea

  摘要：

  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.

  DOI：

  10.1021/np9703914
• 作为产物：
  描述：

  乙酸酐 、 异麦角甾苷 在 吡啶 作用下， 以90 mg的产率得到isoacteoside peracetate
  参考文献：
  名称：

  Studies on the acyl glycosides from Leucoseptrum japonicum (Miq.) Kitamura et Murata.

  摘要：

  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。

  DOI：

  10.1248/cpb.30.2732

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。
• Kobayashi, Hiromi; Oguchi, Hiroko; Takizawa, Nobuo, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 8, p. 3309 - 3314
  作者：Kobayashi, Hiromi、Oguchi, Hiroko、Takizawa, Nobuo、Miyase, Toshio、Ueno, Akira、el al.

  DOI：——

  日期：——
• 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.