verbascoside nonaacetate | 86495-62-7

• 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: verbascoside nonaacetate
• 英文别名: per-O-acetyl-verbascoside；[(2R,3R,4S,5R,6R)-5-acetyloxy-2-(acetyloxymethyl)-6-[2-(3,4-diacetyloxyphenyl)ethoxy]-4-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-diacetyloxyphenyl)prop-2-enoate
• CAS: 86495-62-7
• 化学式: C₄₇H₅₄O₂₄
• 分子量: 1002.93
• InChiKey: JQWLTUXXXNYBQJ-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：

  verbascoside nonaacetate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以72%的产率得到(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-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-3-yl 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：

  [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate 生成 verbascoside nonaacetate
  参考文献：
  名称：

  ENDO, KATSUYA;TAKAHASHI, KAZUHIRO, HETEROCYCLES, 30,(1990) N, C. 291-294

  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。
• Identitätsprüfung von Verbenae Herba: Verbascosid als Leitstoff
  作者：Rudolf Hänsel、Susann Kallmann

  DOI：10.1002/ardp.19863190306

  日期：——

  Aus Verbena‐officinalis‐Kraut wurde Verbascosid (1), β‐(3′,4′‐Dihydroxyphenyl)ethyl‐O‐α‐L‐rhamnopyranosyl(1→3)‐β‐D(4‐O‐caffeoyl)‐glucopyranosid, isoliert. Seine Menge in der Droge beträgt nach HPLC‐Bestimmung 0,8 %. Das Verbascosid‐nonaacetat (2) wurde erstmalig rein dargestellt und spektroskopisch untersucht. Verbascosid kommt im Pflanzenreich verhältnismäßig selten vor1–12), so daß sein Nachweis

  Aus Verbena-officinalis-Kraut wurde Verbascosid (1), β-(3',4'-Dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1→3)-β-D(4-O-caffeoyl)-glupyranosid ，孤立无援。Seine Menge in der Droge beträgt nach HPLC-Bestimmung 0,8 %。Das Verbascosid-nonaacetat (2) wurde erstmalig rein dargestellt und spektroskopisch untersucht。Verbascosid kommt im Pflanzenreich verhältnismäßig selten vor1–12)，所以 daß sein Nachweis im Verbenenkraut
• Kobayashi, Hiromi; Karasawa, Hiroko; Miyase, Toshio, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 10, p. 3880 - 3885
  作者：Kobayashi, Hiromi、Karasawa, Hiroko、Miyase, Toshio、Fukushima, Seigo

  DOI：——

  日期：——
• Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds
  作者：Jabeena Khazir、Intizar Ali、Inshad Ali Khan、Halmuthur Mahabalarao Sampath Kumar

  DOI：10.1080/14786419.2014.984181

  日期：2015.4.18

  Enzymatic acylation of verbascoside, a polyhydroxylated natural product, has been reported in this study using five different commercial lipases and taking p-nitrophenyl alkanoates as acyl donors. Out of these enzymes, the immobilised Candida antarctica lipase B was found as the enzyme of choice. Mono- and di-acylated products were formed, with mono as major product indicating high regioselective nature of such transformations. A series of acyl esters of verbascoside have been synthesised by this enzymatic transesterification methodology. The lipophilicity of the synthesised analogues was also checked. The analogues were further subjected to synergistic antifungal activity with amphotericin B (AmB) against Candida albicans. Fourfold reduction in minimum inhibitory concentration of AmB was observed with few synthesised analogues such as verbascoside 4 ''-octanoate (3b), verbascoside 4 ''-palmitate (3d) and verbascoside 4 '',4 '-dipalmitate (4d) at a concentration of 0.5 mu g/mL.
• Kobayashi, Hiromi; Karasawa, Hiroko; Miyase, Toshio, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 8, p. 3009 - 3014
  作者：Kobayashi, Hiromi、Karasawa, Hiroko、Miyase, Toshio、Fukushima, Seigo

  DOI：——

  日期：——