1,2-dilinolenoyl-3-β-galactosylglycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,2-dilinolenoyl-3-β-galactosylglycerol
• 英文别名: [(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• 化学式: C₄₅H₇₄O₁₀
• 分子量: 775.077
• InChiKey: QUZHZFAQJATMCA-XOOANFPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  55
• 可旋转键数：
  35
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2-dilinolenoyl-3-β-galactosylglycerol 在 boric acid-borax buffer 、 Rhizopus arrhizus lipase XI 、 Triton X-100 作用下， 反应 1.0h， 生成 Γ-十八碳三烯酸 、 [(2R)-2-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
  参考文献：
  名称：

  Polar Metabolites of the Tropical Green SeaweedCaulerpa taxifolia Which Is Spreading in the Mediterranean Sea: Glycoglycerolipids and Stable Enols (α\=Keto Esters)

  摘要：

  Examination of the polar components of the green seaweed Caulerpa taxifolia (VAHL) C. AGARDH, which is heavily spreading in the northeastern Mediterranean, led to two families of compounds. The new (2R)-3-O-beta-D-galactopyranosyl-1 -O-[(7Z,10Z,13Z)-hexadeca-7,10,13-trienoyl]-2-O-[(9Z,12Z,15Z)-octadeca-1,12,15-trienoyl]-sn-glycerol (2) was isolated in low abundance, like the analogues 1 and 3 already known from freshwater cyanobacteria. The acyl positions in 1 - 3 were determined by enzymatic methods and the absolute configuration from the O-galactosylglycerol obtained upon alcaline methanolysis. More abundant were the (4-hydroxyphenyl)- and (3,4-dihydroxyphenyl)pyruvic acid methyl esters, occurring in the enol (Z) forms 13a and 14a accompanied by very minor (E) forms 13b and 14b. The latter became predominant on UV irradiation of 13a or 14a, allowing the determination of the C=C configuration of these isolatable, stable enols from H-1,C-13 NMR couplings (larger H-C(3)/C(1) coupling constant in the (E) than in the (Z) isomer). Contrary to literature implications, the O-galactosylglycerolipids 1-3 lack any cholinergic or histaminegic activity; similarly, enols (= alpha-keto esters) 13 and 14 or terpenoids of this seaweed were also devoid of such biological activities (see Table).

  DOI：

  10.1002/(sici)1522-2675(19980909)81:9<1681::aid-hlca1681>3.0.co;2-4

文献信息

• Polar Metabolites of the Tropical Green SeaweedCaulerpa taxifolia Which Is Spreading in the Mediterranean Sea: Glycoglycerolipids and Stable Enols (α\=Keto Esters)
  作者：Ines Mancini、Graziano Guella、Andrea Defant、M. Luz Candenas、Cristina P. Armesto、Daniela Depentori、Francesco Pietra

  DOI：10.1002/(sici)1522-2675(19980909)81:9<1681::aid-hlca1681>3.0.co;2-4

  日期：1998.9.9

  Examination of the polar components of the green seaweed Caulerpa taxifolia (VAHL) C. AGARDH, which is heavily spreading in the northeastern Mediterranean, led to two families of compounds. The new (2R)-3-O-beta-D-galactopyranosyl-1 -O-[(7Z,10Z,13Z)-hexadeca-7,10,13-trienoyl]-2-O-[(9Z,12Z,15Z)-octadeca-1,12,15-trienoyl]-sn-glycerol (2) was isolated in low abundance, like the analogues 1 and 3 already known from freshwater cyanobacteria. The acyl positions in 1 - 3 were determined by enzymatic methods and the absolute configuration from the O-galactosylglycerol obtained upon alcaline methanolysis. More abundant were the (4-hydroxyphenyl)- and (3,4-dihydroxyphenyl)pyruvic acid methyl esters, occurring in the enol (Z) forms 13a and 14a accompanied by very minor (E) forms 13b and 14b. The latter became predominant on UV irradiation of 13a or 14a, allowing the determination of the C=C configuration of these isolatable, stable enols from H-1,C-13 NMR couplings (larger H-C(3)/C(1) coupling constant in the (E) than in the (Z) isomer). Contrary to literature implications, the O-galactosylglycerolipids 1-3 lack any cholinergic or histaminegic activity; similarly, enols (= alpha-keto esters) 13 and 14 or terpenoids of this seaweed were also devoid of such biological activities (see Table).