| Gardenia jasminoides is an evergreen shrub distributed widely in south regions of People's Republic of China,including Jiangxi,Hunan,Sichuan,Zhejiang,and Taiwan Provinces.Its dried ripe fruit was used to extract natural food colorants and as one of the most important crude drugs frequently listed in prescriptions of traditional Chinese medicine(TCM)for its diuretic,detoxification effects.Previous chemical investigations of the fruit of G.jasminoides showed the presence of iridoids and their glycosides,monocyclic monoterpenoids and their glycosides,flavonoids,crocetin and its glycosides,quinic acid derivatives and vanillic acid glycosides.In the present study,63 compounds were isolated from the fruit of Gardenia jasminoides.On the basis of chemical evidences and spectral analysis,the structures of 63 compounds were elucidated as follows:6"-O-trans-caffeoylgenipin gentiobioside(1),genipin 1-O-?-D-apiofuranosyl(1?6)-?-D-glucopyranoside(2),genipin 1-O-a-D-xylopyranosyl(1?6)-?-D-glucopyranoside(3),geniposide(4),6?-hydroxygeniposide(5),6a-hydroxygeniposide(6),6-O-methylscandoside methyl ester(7),6-O-methyldeacetylasperulosidic acid methyl ester(8),gardenoside(9),8-O-methylmonotrope in methyl ester(10),shanzhiside(11),gardoside(12),6'-acetylgeniposide(13),10-acetylgeniposide(14),genipin 1-O-?-D-gentiobioside(15),genipin 1-O-?-D-isomaltoside(16),genipin 1-O-a-L-rhamnopyranosyl(1?6)-?-D-glucopyranoside(17),genameside D(18),genameside C(19),6"-O-trans-sinapoylgenipin gentiobioside(20),6"-O-traps-p-coumaroylgenipin gentiobioside(21),10-O-E-sinapoylgeniposide(22),jasminoside R(23),jasminoside S(24),jasminoside T(25),rehmapicrogenin(26),jasminoside C(27),jasminoside G(28),jasminoside B(29),jasminoside K(30),jasminoside I(31),epijasminoside H(32),jasminoside H(33),6'-O-sinapoyljasminoside C(34),6'-O-trans-sinapoyl jasminoside L(35),(6S,7E,9R)-6,9-dihydroxy-4,7-megastiymadien-3-one-9-O-[a-L-arabinopyranosyl-(1?6)-?-D-gluc opyranoside](36),trans-crocetin di(?-D-gentiobioyl)ester(37),trans-crocetin(?-D-glucopyranosyl)-(?-D-gentiobioyl)ester(38),crocetin(39),5-hydroxy-7,3',4',5'-tetramethoxyl flavone(40),5-hydroxy-6,7,3',4',5'-pentamethoxyl flavone(41),luteolin-7-O-?-D-glucopyranoside(42),kaempferol-3-O-rutinoside(43),1,2,3,4-tetrahydroxy-2-methylbutane-4-O-(6-O-trans-sinapoyl)-?-D-glucopyranoside(44),1,2,3,4-tetrahydroxy-2-methylbutane-1-O-(6-O-trans-sinapoyl)-?-D-glucopyranoside(45),1-sinapoyl-?-D-glucopyranoside(46),1,6-di-O-E-sinapoyl-glucopyranose(47),3,4-dihydroxy benzoic aldehyde(48),3,4-dihydroxy benzoic acid(49),caffeic acid(50),methyl caffeate(51),ferulic acid(52),sinapic acid(53),7-O-?-D-apiofuranosyl(1?6)-?-D-glucopyranosyl-6-methoxy-coumarin(54),(1R,7R,8S,10R)-7,8,11-trihydroxyguai-4-en-3-one(55),methyl-3,5-di-O-caffeoylglutaroylquinate(56),methyl-3-O-sianpoyl-5-O-caffeoylglutaroylquinate(57),methyl-4-O-sianpoyl-5O-caffeoylglutaroylquinate(58),methyl-3,5-di-O-caffeoyl-4-O-(3-hydroxy-3-methyl)glutaroylquinate(59),D-mannitol(60),methyl-a-D-fructofuranoside(61),methyl-?-D-fructofuranoside(62),ursolic acid(63).Eight of them were new compounds,including 3 new iridoid glycosides(1-3),three new monocyclic monoterpenoids(23-25),two new phenolic glucosides(44-45).Compounds 17-19,26,36,42,43,61,62 were isolated from this plant for the first time.All of the compounds isolated from the fruit of Gardenia jasminoides were assayed against NO production on LPS activated macrophages by Griess method.Among the tested compounds,the aglycones of iridoid glycosides(4a,5a,12a),the aglycons of monocyclic mo no terpenoids(26)and the aglycones of crocetin derivatives(39)showed strong inhibition of NO production.Some of the quinic acid derivatives(56,58,59)showed middle/weak activity.The antioxidant potentials of the isolates were evaluated with 1,1-dphenyl-2-picrylhydrazyl(DPPH)radical and hydroxyl radical.Several compounds exhibited weak antioxidant capacities. |
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