橄榄苦苷,又称橄榄苦甙,是一种天然植物提取物,主要来源于油橄榄树叶。油橄榄树属于木犀科木犀榄属的常绿乔木,是世界著名的木本油料兼果用树种。栽培品种具有较高的食用价值,含有丰富的优质食用植物油——橄榄油。
橄榄叶的主要成分
橄榄叶中含有的主要活性成分为橄榄苦苷及其苷、黄酮及其苷、双黄酮及其苷和低分子单宁等裂环烯醚萜类化合物。其中,橄榄苦苷(Oleuropein)是一种无毒的裂环烯醚萜苷类多酚化合物,广泛存在于木犀科的多种植物中。
理化性质
微小结晶(乙酸乙酯),熔点87~89℃,易吸湿,旋光度-147°(c=1,水、乙醇或丙醇),呈变旋作用。旋光度在9小时后变为-127°(水中)。橄榄苦苷极易溶于乙醇、丙酮和冰醋酸,并可溶于5%NaOH溶液及水、丁醇、乙酸乙酯、醋酸丁酯,几乎不溶于乙醚、石油醚、氯仿或四氯化碳。暴露在空气和阳光下会分解,建议在避光条件下低温密封保存。
提取方法
常用的橄榄苦苷提取方法包括浸提法、超声波辅助提取法、微波辅助提取法、超临界CO2萃取法、分散液-液微萃取法、过热液体提取法及低温减压沸腾蒸馏提取法。谢普军等研究表明,超声波与低温减压的组合是一种适合工业化生产且操作简易、效率高、能耗低的方法。
未来的研究趋势可能包括将天然产物提取装置直接联用HPLC、GC-MS等分析技术以实现在线检测,提高分析速度并控制产品质量。
测定方法
党建章等人建立了HPLC含量测定方法,使用色谱柱ZORBAX Eclipse XDB-C18(4.6mm*250mm, 5um),流动相为0.01mol/L磷酸溶液-乙腈(79:21),流速为0.8ml.min-1,检测波长254nm。
郑媛媛建立了一种UV-VIS差减法测定油橄榄叶提取物中橄榄苦苷含量的方法,并指出这种方法准确度高且成本低廉,可以替代现有的HPLC方法。
药理作用
橄榄苦苷具有多种生物活性,包括抗病毒、抗肿瘤、抗氧化、抑菌和降糖等。在护肤品中,高含量的橄榄苦苷可用于保护皮肤细胞不受紫外线伤害,维持肌肤柔嫩与弹性。Microherb80%为高含量产品,专门设计用于化妆品配方。
化学性质
来源于油橄榄树
用途
主要用于含量测定、鉴定及药理实验等;具有强力抗细菌和抗病毒特性,并具备极强的抗氧化能力。
药理作用
主要表现为降血压、抗氧化、抗微生物和抗癌等。
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
—— | demethyloleuropein | 52077-55-1 | C24H30O13 | 526.494 |
女贞甙 | ligstroside | 35897-92-8 | C25H32O12 | 524.522 |
—— | demethylligstroside, (2''R)-and (2"S)-2"-hydroxyoleuropeins, fraxamoside and frameroside | —— | C24H30O12 | 510.495 |
—— | (E)-methyl 4-(2-(3,4-dimethoxyphenethoxy)-2-oxoethyl)-3-ethylidene-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate | —— | C27H36O13 | 568.575 |
—— | (E)-methyl 3-ethylidene-4-(2-oxo-2-phenethoxyethyl)-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate | —— | C25H32O11 | 508.522 |
—— | (E)-methyl 4-(2-(3-(3,4-dimethoxyphenyl)propoxy)-2-oxoethyl)-3-ethylidene-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate | —— | C28H38O13 | 582.602 |
—— | (E)-methyl 4-(2-ethoxy-2-oxoethyl)-3-ethylidene-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate | —— | C19H28O11 | 432.425 |
—— | (E)-methyl 4-(2-butoxy-2-oxoethyl)-3-ethylidene-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate | —— | C21H32O11 | 460.478 |
—— | (E)-methyl 3-ethylidene-4-(2-(isopentyloxy)-2-oxoethyl)-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate | —— | C22H34O11 | 474.505 |
木樨榄苷-11-甲酯 | 4-carboxymethyl-5-ethylidene-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester | 60539-23-3 | C17H24O11 | 404.371 |
—— | Oleoside dimethyl ester | 30164-95-5 | C18H26O11 | 418.398 |
—— | oleoside 11-methyl ester | —— | C17H24O11 | 404.371 |
—— | (E)-methyl 4-(2-(benzyloxy)-2-oxoethyl)-3-ethylidene-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate | —— | C24H30O11 | 494.496 |
—— | (E)-methyl 4-(2-(2-cyclohexylethoxy)-2-oxoethyl)-3-ethylidene-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate | —— | C25H38O11 | 514.57 |
Oleoside; (2S,3E,4S)-5-羧基-3-亚乙基-2-(beta-D-吡喃葡萄糖氧基)-3,4-二氢-2H-吡喃-4-乙酸 | oleoside | 178600-68-5 | C16H22O11 | 390.344 |
—— | (E)-methyl 4-(2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methoxy)-2-oxoethyl)-3-ethylidene-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate | —— | C26H32O13 | 552.532 |
—— | 5-ethylidene-4-[3-hydroxy-2-(2-hydroxy-1-methyl-ethyl)-5-methylcyclopentylmethoxycarbonylmethyl]-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester | —— | C27H42O13 | 574.623 |
—— | (2S,3S,4R,5S,6R)-2-(acetoxymethyl)-6-(((E)-4-(2-butoxy-2-oxoethyl)-3-ethylidene-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | —— | C29H40O15 | 628.628 |
—— | (E)-3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-(((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylic acid | —— | C25H32O15 | 572.52 |
—— | (2S,3S,4R,5S,6R)-2-(acetoxymethyl)-6-(((E)-3-ethylidene-5-(methoxycarbonyl)-4-(2-((3-methylbut-3-en-1-yl)oxy)-2-oxoethyl)-3,4-dihydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | —— | C30H40O15 | 640.639 |
—— | (2S,3S,4R,5S,6R)-2-(acetoxymethyl)-6-(((E)-3-ethylidene-4-(2-(furan-2-ylmethoxy)-2-oxoethyl)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | —— | C30H36O16 | 652.606 |
—— | oleuropeinol | 119329-51-0 | C16H26O9 | 362.377 |
—— | oleuropein aglycone | 31773-95-2 | C19H22O8 | 378.379 |
—— | (2R,3S,4S)-4-{[2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-3-formyl-3,4-dihydro-2H-pyran-5-acetic acid methyl ester | —— | C19H22O8 | 378.379 |
—— | methyl (2S,4S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-3-formyl-2-methyl-3,4-dihydro-2H-pyran-5-carboxylate | 1372175-04-6 | C19H22O8 | 378.379 |
—— | 1-(3,4-dihydroxyphenyl)-ethan-2-ol elenolic acid ester | 50915-70-3 | C19H22O8 | 378.379 |
—— | Secoiridoid | —— | C11H14O6 | 242.229 |