(-)-olivil 4',4''-di-O-β-D-glucopyranoside | 99633-10-0

分子结构分类

有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷

中文名称

——

中文别名

——

英文名称

(-)-olivil 4',4''-di-O-β-D-glucopyranoside

英文别名

(-)-olivil-4',4"-di-O-β-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-[4-[[(3S,4R,5S)-3-hydroxy-4-(hydroxymethyl)-5-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]oxolan-3-yl]methyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

(-)-olivil 4',4''-di-O-β-D-glucopyranoside化学式

CAS

99633-10-0

化学式

C₃₂H₄₄O₁₇

mdl

——

分子量

700.691

InChiKey

ZOHABIUWJOPCKZ-LVCPPOIXSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

-1.7
重原子数：

49
可旋转键数：

12
环数：

5.0
sp3杂化的碳原子比例：

0.62
拓扑面积：

267
氢给体数：

10
氢受体数：

17

反应信息

作为反应物：

描述：

(-)-olivil 4',4''-di-O-β-D-glucopyranoside 在 β-glucosidase 作用下，以 various solvent(s) 为溶剂，反应 72.0h，生成橄榄树脂素

参考文献：

名称：

The constituents of Eucommia ulmoides OLIV. II. Isolation and structures of three new lignan glycosides.

摘要：

从杜仲（Eucommia ulmoides OLIV.(杜仲科）树皮中分离出三种新的木质素苷。根据化学证据和光谱研究，它们的结构被确定为(-)-olivil 4'，4"-di-O-β-D-吡喃葡萄糖苷（1）、(+)-1-hydroxypinoresinol 4'，4"-di-O-β-D-吡喃葡萄糖苷（2）和(+)-medioresinol 4'-O-β-D-吡喃葡萄糖苷（命名为杜仲素 A）（3）。此外，还分离出一种已知的木质素苷，(+)-syringaresinol O-β-D-glucopyranoside（4）。

DOI：

10.1248/cpb.33.3651

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文献信息

Inhibition of adenosine 3',5'-cyclic monophosphate phosphodiesterase by lignan glucosides of Eucommia bark.

作者：TAKESHI DEYAMA、SANSEI NISHIBE、SHIZUKA KITAGAWA、YUKIO OGIHARA、TADAHIRO TAKEDA、TAICHI OHMOTO、TAMOTSU NIKAIDO、USHIO SANKAWA

DOI：10.1248/cpb.36.435

日期：——

Studies were conducted on adenosine 3', 5'-cyclic monophosphate (cyclic AMP) phosphodiesterase inhibition by lignan glucosides from bark of Eucommia ulmoides OLIV. (Eucommiaceae). Various lignan diglucosides. (+)-syringaresinol di-O-β-D-glucopyranoside (1c), (+)-medioresinol di-O-β-D-glucopyranoside (2c), (+)-pinoresinol di-O-β-D-glucopyranoside (3c) and (+)-1-hydroxy-pinoresinol 4', 4"-di-O-β-D-glucopyranoside (4d), showed strong inhibitory activity.The structure-inhibitory activity relationships of the aglycone and its glucosides are discussed. The order of inhibitory effect was diglucoside ≩︀ aglycone > monoglucoside.

同类化合物

鹅掌楸碱罗汉松树脂酚-4'-O-β-龙胆二糖苷络石苷元-4'-O-BETA-龙胆二糖苷络石苷牛蒡苷牛蒡子苷元-4'-O-Β-龙胆二糖苷柑属苷B 松脂醇二葡萄糖苷松脂醇-4-O-beta-D-吡喃葡萄糖苷松脂醇 beta-D-吡喃葡萄糖苷木須皮苷异落叶松脂素9'-BETA-D-吡喃木糖苷异落叶松脂素-9'-O-beta-D-吡喃葡萄糖苷开环异落叶松脂素BETA-D-葡糖苷地菲林葡萄糖苷去甲络石苷南烛木糖甙刺五加苷D 刺五加甙E 刺五加甙 E 刺五加提取物丁香树脂醇双葡萄糖苷 b-D-吡喃葡萄糖苷,4-[(1R,2R)-1,3-二羟基-2-[4-[(1E)-3-羟基-1-丙烯-1-基]-2-甲氧基苯氧基]丙基]-2-甲氧苯基 Ssioriside; (2S,3S)-4-羟基-2,3-双[(4-羟基-3,5-二甲氧基苯基)甲基]丁基 beta-D-吡喃木糖苷 8-羟基松脂醇二葡萄糖苷 8-O-(α-阿拉伯呋喃糖)-β-àpeltatin 4-[(5S,5aR,8aS)-10-羟基-6-羰基-5,5a,6,8,8a,9-六氢呋喃并[3',4':6,7]萘并[2,3-d][1,3]二噁唑-5-基]-2,6-二甲氧苯基α-L-呋喃阿拉伯糖苷 4-(1,3-苯并二氧戊环-5-基)-9-[(2S,3R,4S,5R)-3,4-二甲氧基-5-[(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基四氢吡喃-2-基]氧基-6,7-二甲氧基-1H-苯并[f][2]苯并呋喃-3-酮 4-(1,3-苯并二氧戊环-5-基)-6,7-二甲氧基-9-[(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-1H-苯并[f][2]苯并呋喃-3-酮 3-[2,3-二氢-6-羟基-2-(1-羟基-1-甲基乙基)苯并呋喃-5-基]-8-(beta-D-吡喃葡萄糖基)-2,3-二氢-5,7-二羟基-4H-1-苯并吡喃-4-酮 2,3-双(3-甲氧基-4-羟基苄基)丁烷-1,4-二醇 1,4-二葡萄糖甙 (3S,4R)-4-(苯并[1,3]二氧杂环戊烯-5-基甲基)-3-[(S)-[(2R,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-(3,4,5-三甲氧基苯基)甲基]四氢呋喃-2-酮 (3R,4S)-3-[[4-(beta-D-吡喃葡萄糖基氧基)-3-甲氧基苯基]甲基]-4,5-二氢-4-[(4-羟基-3-甲氧基苯基)甲基]呋喃-2(3H)-酮 (3-苯甲酰氧基-2-羟基-4,5-二苯基-四氢-[2]呋喃基)-苯基酮 (2S)-5,7-二羟基-2-[4-[2,4,6-三羟基-3-[(E)-3-(4-羟基苯基)丙-2-烯酰基]-5-[(2S,3R,4R,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]苯氧基]苯基]色满-4-酮 (-)-异落叶松脂素-9'-O-BETA-D-吡喃葡萄糖苷 (+)-南烛木树脂酚9'-O-葡萄糖甙 4-O-[6-O-(5-O-syringoyl-β-D-apiofuranosyl)-β-D-glucopyranosyl]-(+)-(7S,7'R,8R,8'R)-4'-hydroxy-3,3',5,5'-tetramethoxy-7,9':7',9-diepoxylignane (+)-1-hydroxypinoresinol 4'-O-β-glucopyranoside hexaacetate (+)-1-hydroxypinoresinol 4''-O-β-glucopyranoside 2''',3''',4''',4',6'''-O-pentaacetate (+)-1-hydroxypinoresinol 4''-O-β-glucopyranoside hexaacetate Acetic acid (3R,4S,5R)-2-(9-benzo[1,3]dioxol-5-yl-8-oxo-6,8-dihydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy)-4,5-dimethoxy-tetrahydro-pyran-3-yl ester (+)-1-hydroxypinoresinol 4'-O-β-glucopyranoside 2''',3''',4''',4'',6'''-O-pentaacetate 4'-acetoxy-6-C-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)-8-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,7-dihydroxyflavan (2S,3R,4S,5S,6R)-2-[4-[(2R,3R)-4-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(hydroxymethyl)butyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(5S,5aR,8aR)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-ylsulfanyl]-tetrahydro-pyran-3-yl ester 2,2-difluoro-N-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2-((2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetamide 2,2-difluoro-N-((5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2-((2R,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetamide 2,2-difluoro-N-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2-((2R,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetamide