| Quercus serrata var.brevipetiolata is belongs to the species of the genus Quercus in Fagaceae family.Quercus is one of the earliest wild woody food crops in traditional Chinese society.It has been used for more than ten thousand years.Quercus has important medicinal value,which is recorded in Compendium of Materia Medica and Si-ku-quan-shu.Modern studies have shown that the chemical constituents of Quercus mainly include flavonoids,triterpenoids,tannins and so on,which have antioxidant,anti-cancer,anti-inflammatory,anti-bacterial and anti-virus pharmacological effects.In our preliminary study on the seeds of Q.serrata var.brevipetiolata,34 compounds were isolated and identified from the ethyl acetate fraction,including 30 triterpenoids.On the basis of our previous studies,the chemical constituents of the n-butanol fraction of 70% ethanol extract from the seeds of Q.serrata var.brevipetiolata were systematically studied by using various modern chromatographic methods and spectroscopic identification techniques.Sixty-five compounds were isolated and purified from the n-butanol fraction of 70% ethanol extract of Q.serrata var.brevipetiolata,including 27 triterpenes,10 jasmonates,10 glycosides and 18 other compounds.Their chemical names were:(1)Triterpenoids-(i.Oleanene type)3,23-O-Butylidene-2α,3β,19α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-β-Dglucopyranoside(1*),3β,23-Dihydroxy-24-oxo-olean-12-en-28-oic acid 28-O-β-D-glucopyranoside(2*),Arjunglucoside I(3),Arjunolic acid(4),2α,3β,19α,24-Tetrahydroxyolean-12-en-28-oic acid(5),Sericoside(6),Paradrymonin(7),Trachelosperoside D-1(8),Arjunglucoside II(9),28-β-D-Gucopyranosyl-2α,3β,19α-trihydroxyolean-12-ene-24,28-dioic acid(10),Bellericaside B(11),2α,3β,16α,19α,23-Pentahydroxyolean-12-en-28-oic acid-β-D-glucopyranoside(12),2α,3β,19α,23-Tetrahydroxy-11-oxo-olean-12-en-28-oic acid 28-O-β-D-glucopyranoside(13),Quadranoside III(14),Olean-12-en-28-oic acid-2α,19α,23-trihydroxy-3-{[O-(3,4,5-trihydroxybenzoyl)-β-D-glucopyranosyl]oxy]}-β-Dglucopyranoside(15);(ii.Ursane type)23-O-Galloyl-2α,3β,19α-trihydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranoside(16*),Asiatic acid(17),Niga-ichigosd F1(18),2α,3β,19α,24-Tetrahydroxyurs-12-en-28-oic acid-β-D-glucopyranoside(19),2α,3β,19α,23-Tetrahydroxyurs-12-en-28-oic Acid(20),6β,23-Dihydroxytormentic acid(21),3,23-O-Butylidene-2α,3β,19α,23-tetrahydroxy-urs-12-en-28-oic acid β-D-glucopyranoside(22),3-O-Galloyl-2α,19α,23-hydroxytormentic acid28-O-β-D-glucopyranoside(23),Quadranoside VIII(24),2α,3β,23-Trihydroxyurs-12,18-dien-28-oic acid 28-O-β-D-glucopyranoside(25),2α,3β,23-Trihydroxyursa-12,19-dien-28-oic acid β-D-glucopyranoside(26);(iii.Lupanes type)2α,3β,23-Trihydroxylup-20(29)-en-28-oic acid 28-O-β-D-glucopyranoside(27*);(2)Jasmonates :(1S,2R)-2-[(2′Z)-5-Hydroxy-2-penten-1-yl]-3-oxo-butyl ester(28*),Methyl {(1S,2S)-2-[4′-(β-D-glucopyransyloxy)-pent]cyclopentyl}-3-oxocyclopentaneacetate(29*),Methyl {(1S,2S,2′E)-2-[4′-(β-Dglucopyransyloxy)-pent-3′-enyl]cyclopentyl}-3-oxo-cyclopentaneacetate(30*),Methyl {(1S,2S,2′Z)-2-[4′-(β-D-glucopyransyloxy)-pent-3′-enyl] cyclopentyl}-3-oxo-cyclopentaneacetate(31*),Methyl {(1S,2S,3′Z)-2-[2′-(β-D-glucopyransyloxy)-pent-3′-enyl]cyclopentyl}-3-oxo-cyclopentaneacetate(32*),β-D-Glucopyranose-1-[(1S,2R)-3-oxo-2-(2Z)-2-penten-1-ylcyclopentanebutanoate](33),Methyl {(1R,2S,3S)-3-(β-Dglucopyranosyloxy)-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acete(34),Methyl {(1S,2S,2′Z)-2-[5′-(β-D-glucopyransyloxy)-pent-2′-enyl] cyclopentyl}-3-oxo-cyclopentaneacetate(35),4′(R)-Hydroxyjasmonic acid 4′-O-β-D-glucoside(36),(-)-5’-β-D-glucopyranosyloxyjasmonic acid(37)(3)Glycosides: Isopentyl-O-β-D-glucopyranosyl(1-6)-α-Larabinopyranosyl(38*),2-[β-D-Glucopyranosyl(1-6)-α-Larabinopyranosyl]-pentane(39*),n-Butyl-O-β-D-fructopyranoside(40),Isopentyl-O-β-D-glucopyranoside(41),2-Phenylethyl-β-D-glucopyranoside(42),2-O-β-D-Glucopyranosyl-(1S)-phenylethylene glycol(43),2-Phenemyl-8-O-(6′-O-α-L-arabinofuranosyl)-β-Dglucopyranoside(44),Viridoside(45),1-O-(9Z-12Z-15Z-Octadecatrienoyl-3-O-[α-D-galactopyranosyl-(1→6)-O-β-D-galactopyranosyl]glycerol(46),1-O-(9Z-12Z-Octadecatrienoyl-3-O-[α-D-galactopyranosyl-(1→6)-O-β-D-galactopyranosyl]glycerol(47)(4)Other type compounds: ent-7β,16β,17-Tetrahydroxykauran-19-oic acid-17-O-β-D-glucopyranoside(48*),β-Paucosterol(49),β-Stigmasterol(50),Phellodendric acid A(51),Butylmethyl succinate(52),(-)-Clovane-2,9-diol(53),Brevifolin(54),β-Sitiosterol(55),α-Cadinol(56),Aromadendra-4β,10α-diol(57),Junipediol(58),(25S)-5β-Spirostan-3β-ol-3-O-α-L-rhamnopyranoside(59),5-Hydroxymethylfurfural(60),Phenylglycol(61),3,4-Hydroxypyrrolidine acid-1-carboxylate(62),4-(5-Oxopyrrolidin-2-carbonyl)butanoic acid(63),1,2,6-Tri-O-galloyl-β-D-glucose(64),3-(4-Hydroxy-3-methoxyphenyl)-3-methoxypropane-1,2-diol(65).Among them,compounds 1,2,16,27,28-32,38,39 and 48 were 12 new compounds(marked with *).In addition,the anti-neuroinflammatory activities of some compounds isolated and purified from the seeds of Q serrata var.brevipetiolata were tested in vitro.Compared with the positive drug indomethacin(IC50 34.81+8.798 μmol/L),compounds 4,5,9,13,14,16-18,23,24,26 and 27 showed better inhibitory effects on LPS-induced NO release from BV-2 cells(IC50 12.44-27.05 μmol/L),showing stronger anti-neuroinflammatory activity. |
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