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环烯醚萜衍生物

环烯醚萜衍生物概述

环烯醚萜(Ring-Enol Terpenoids)是一类具有独特环状结构的天然产物,其特征是含有一个5或6元的氧杂环,通常由两个戊酸单元通过共轭双键相连形成。这类化合物广泛存在于植物界中,尤其在中药资源中有较多发现。

结构特点
  • 基本骨架:环烯醚萜的基本结构是由两个异戊二烯单位通过共轭的碳-碳双键连接形成的环状结构。
  • 氧杂环:含有一个5或6元的氧杂环(最常见的为5-乙酰基四环酮、6-甲氧基四环酮等)。
生物活性
  1. 抗炎作用:某些环烯醚萜衍生物能够抑制炎症反应,通过影响细胞因子和相关酶类的活动来发挥作用。
  2. 抗氧化性:这些化合物具有较强的清除自由基的能力,有助于对抗氧化应激损伤。
  3. 抗癌作用:部分环烯醚萜衍生物对多种癌细胞株表现出显著的抑制效果,可能与调节细胞增殖、凋亡及信号传导路径有关。
  4. 抗菌和抗病毒特性:这些天然产物能够抑制某些细菌或病毒感染,通过干扰病原体生长所需的关键代谢过程。
研究进展
  • 提取分离技术:近年来,随着高效液相色谱(HPLC)、气相色谱质谱联用(GC-MS)等先进分析手段的应用,从复杂天然产物中分离纯化环烯醚萜衍生物变得更加便捷。
  • 合成方法探索:化学家们正在尝试通过不同策略进行这些化合物的全合成,以期更好地理解其结构与活性之间的关系,并实现工业化生产。
应用前景

环烯醚萜及其衍生物由于其独特的结构和广泛的生物活性,在药物开发中展现出巨大潜力。未来的研究方向可能集中在优化现有候选药物分子、发现新的具有临床价值的化合物以及探索其作用机制等方面。

中文名称 英文名称 CAS号 化学式 结构式图片
—— [(1S,4S,6R,7R,9S)-4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.04,11]undecan-6-yl] 4-hydroxybenzoate 1390-72-3 C16H18O7
[(1S,4S,6R,7R,9S)-4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.04,11]undecan-6-yl] 4-hydroxybenzoate
—— methyl (1S,4aS,7R,7aS)-5'-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4'-[(1S)-1-[(E)-3-[4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxyethyl]spiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate 80396-57-2 C36H42O19
methyl (1S,4aS,7R,7aS)-5'-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4'-[(1S)-1-[(E)-3-[4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxyethyl]spiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
—— 10-O-Caffeoyl-6-epiferetoside 83348-22-5 C26H30O14
10-O-Caffeoyl-6-epiferetoside
—— Nuezhenide 39011-92-2 C31H42O17
Nuezhenide
—— Durantoside II 53526-66-2 C27H34O14
Durantoside II
—— [2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxybenzoate 6736-85-2 C22H26O12
[2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxybenzoate
—— methyl (1S,4aS,7R,7aS)-4'-[1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate 80416-52-0 C30H32O14
methyl (1S,4aS,7R,7aS)-4'-[1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
—— protoplumericin 80396-57-2 C36H42O19
protoplumericin
—— (2R,3S,4R,5R,6S)-2-[[(1R,2R,4R,5R,6S,10R)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol 2415-24-9 C15H22O10
(2R,3S,4R,5R,6S)-2-[[(1R,2R,4R,5R,6S,10R)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
—— [(1S,2S,4S,5S,6R)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxybenzoate 6736-85-2 C22H26O12
[(1S,2S,4S,5S,6R)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxybenzoate
—— musseanoside 64421-28-9 C17H26O11
musseanoside
—— gardenoside 24512-62-7 C17H24O11
gardenoside
—— (4a<i>S</i>,7<i>R</i>)-1<i>c</i>-β-D-glucopyranosyloxy-4'-((<i>S</i>)-1-hydroxy-ethyl)-5'-oxo-(4a<i>r</i>,7a<i>c</i>)-4a,7a-dihydro-1<i>H</i>,5'<i>H</i>-spiro[cyclopenta[<i>c</i>]pyran-7,2'-furan]-4-carboxylic acid 132586-69-7 C20H24O12
(4a<i>S</i>,7<i>R</i>)-1<i>c</i>-β-D-glucopyranosyloxy-4'-((<i>S</i>)-1-hydroxy-ethyl)-5'-oxo-(4a<i>r</i>,7a<i>c</i>)-4a,7a-dihydro-1<i>H</i>,5'<i>H</i>-spiro[cyclopenta[<i>c</i>]pyran-7,2'-furan]-4-carboxylic acid
—— (8Z)-ligstroside 35897-92-8 C25H32O12
(8Z)-ligstroside
—— Cyclopenta[c]pyran-4-carboxylicacid, 1,4a,5,6,7,7a-hexahydro-1,6-dihydroxy-7-methyl-, methyl ester,(1S,4aS,6S,7R,7aS)- 29748-10-5 C11H16O5
Cyclopenta[c]pyran-4-carboxylicacid, 1,4a,5,6,7,7a-hexahydro-1,6-dihydroxy-7-methyl-, methyl ester,(1S,4aS,6S,7R,7aS)-
—— (2a<i>S</i>)-4-acetoxymethyl-5<i>c</i>-β-D-glucopyranosyloxy-(2a<i>r</i>,4a<i>c</i>,7b<i>c</i>)-2a,4a,5,7b-tetrahydro-2,6-dioxa-cyclopent[<i>cd</i>]inden-1-one 14259-45-1 C18H22O11
(2a<i>S</i>)-4-acetoxymethyl-5<i>c</i>-β-D-glucopyranosyloxy-(2a<i>r</i>,4a<i>c</i>,7b<i>c</i>)-2a,4a,5,7b-tetrahydro-2,6-dioxa-cyclopent[<i>cd</i>]inden-1-one
—— methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-7-methyl-6-(3-phenylprop-2-enoyloxy)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate 53526-67-3 C26H32O13
methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-7-methyl-6-(3-phenylprop-2-enoyloxy)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
—— rehmaglutin C 103744-84-9 C9H13ClO4
rehmaglutin C
—— Catalpol 2415-24-9 C15H22O10
Catalpol
—— musseanosidic acid 29836-27-9 C16H24O11
musseanosidic acid
—— Lamiid 27856-54-8 C17H26O12
Lamiid
—— lamiide 27856-54-8 C17H26O12
lamiide
—— SHANZHISIDE METHYL ESTER 64421-28-9 C17H26O11
SHANZHISIDE METHYL ESTER
—— (Hydroxybenzoyl)catalpol; Catalpol 6-p-hydroxybenzoate 6736-85-2 C22H26O12
(Hydroxybenzoyl)catalpol; Catalpol 6-p-hydroxybenzoate
—— Dihydrovaltrate 18296-45-2 C22H32O8
Dihydrovaltrate
—— 2-[[5-Hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol 2415-24-9 C15H22O10
2-[[5-Hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
—— Cerberic Acid 65597-44-6 C11H8O5
Cerberic Acid