罗汉果果渣的化学成分及抗炎活性研究

Study on chemical constituents and anti-inflammatory activity of the pomace of Siraitia grosvenorii

研究罗汉果(Siraitia grosvenorii)水提果渣的化学成分及其体外抗炎活性。采用多种色谱方法对罗汉果果渣化学成分进行系统的分离纯化,得到了26个化合物,并结合MS、NMR等波谱学手段对其进行结构鉴定,分别为齐墩果酸28-O-β-D-吡喃葡萄糖苷(1)、齐墩果酸3-O-β-D-吡喃葡萄糖醛酸苷-6′-乙酯(2)、(3α)-3,29-dihydroxy-7-oxomultiflor-8-ene-3,29-diyl dibenzoate(3)、3,29-二苯甲酰基栝楼仁二醇(4)、isomultiflorenol(5)、curcasinlignan B(6)、urolignoside(7)、diospyrosin(8)、楝叶吴萸素B(9)、4′-羟基苯基乙基香草酸酯(10)、橙黄胡椒酰胺乙酸酯(11)、山柰酚-7-O-α-L-鼠李糖苷(12)、山柰苷(13)、山柰酚-3-O-β-D-吡喃葡萄糖基-7-O-α-L-鼠李糖苷(14)、山柰酚-3-O-α-L-鼠李糖苷-7-O-β-D-木糖苷(1→2)-O-α-L-鼠李糖苷(15)、sagittatin A(16)、葫芦烷-5,24-二烯-3β-醇(17)、balsaminol E(18)、大豆脑苷I(19)、β-谷甾醇(20)、β-胡萝卜苷(21)、胆甾-5-烯-3β,7α-二醇(22)、2 E-4-羟基-壬烯酸(23)、香兰素(24)、对羟基苯乙醇(25)、β-hydroxypropiovanillone(26)。化合物2、6~11为首次在葫芦科植物中分离得到,化合物1、3、4、14~16、18、19、22~26为首次从罗汉果属植物中分离得到。初步研究了化合物1~26的体外抗炎活性,化合物4、5、7、13、19和21能抑制TNF-α生成,化合物13和21能同时抑制IL-1β、IL-6的生成,化合物7、19、22能抑制IL-1β的生成,化合物5能抑制IL-6的生成。

The chemical constituents from the pomace fraction with water extract of Siraitia grosvenorii,and the anti-inflammatory activity in vitro were studied.The chemical constituents from the pomace fraction of Siraitia grosvenorii were isolated with various chromatographic separation techniques,and their structures were determined by entirely analyzing MS and NMR spectrums,there are oleanolic acid 28-O-β-D-glucopyranoside(1),oleanolic acid 3-O-β-D-glucuronyl-6′-ethyl ester(2),(3α)-7-oxomultiflor-8-ene-3,29-diol 3,29-dibenzoate(3),3,29-O-dibenzoyloxykarounidiol(4),isomultiflorenol(5),curcasinlignan B(6),urolignoside(7),diospyrosin(8),evofolin B(9),4′-hydroxyphenyl ethyl vanillate(10),aurantiamide(11),kaempferol-7-O-α-L-rhamnoside(12),kaempferitrin(13),kaempferol-3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside(14),kaempferol 3-O-α-L-rhamnoside-7-O-β-D-xylosyl(1→2)-O-α-L-rhamnoside(15),sagittatin A(16),cucurbita-5,24-diene-3β-ol(17),balsaminol E(18),soya-cerebrosideⅠ(19),β-sitosterol(20),β-daucosterol(21),7α-hydroxycholesterol(22),2 E-4-hydroxy-nonenoic acid(23),vanillain(24),p-hydroxy-benzeneethanol(25),β-hydroxypropiovanillone(26).Compounds 2 and 6-11 were first isolated from Cucurbitaceae and compounds 1,3,4,14-16,18,19 and 22-26 were first isolated from Siraitia.Compounds 1-26 were preliminarily examined for anti-inflammatory activity in vitro,compounds 4,5,7,13,19 and 21 suppressed the production of TNF-α,compounds 13 and 21 both inhibited the production of IL-1βand IL-6,compounds 7,19 and 22 inhibited the production of IL-1β,compound 5 inhibited the production of IL-6.