| Murraya koenigii is a plant which belongs to Murraya of Rutaceae. Its another name is curry leaf. Murraya koenigii has calm, antiphlogosis functions in folk. Modern pharmacological found that Murraya koenigii had many kinds of pharmacological activities. The chemical constituents of Murraya koenigii were studied, and biological activities of the isolated compounds were evaluated by several pharmacological models in this paper. The study provided theoretical support of pharmacodynamical material basis, clinical applications and rational exploitation of resources.Active fractions were determined by pharmacological screening, and the chemical constituents of the active fractionswere studied. By using a variety of chromatographic techniques and spectroscopic methods,136compounds (1*-136) were isolated and structurally determined from the bioactive fractions. Among them, compounds1*-20*are new ones, compounds21#-28#are new natural products, compounds29-136are known ones. These compounds include35alkaloids (1*-6*,16*,18*and28#-54),19sesquiterpenes (7*-9*and55-70),29phenylpropanoids (10*,11*,23#-25#and71-94),13phenolic glycosides (21#,22#and95-105),9lignans (106-114),2coumarins (115and116),3rutinosides (12*,13*and117),5olefines (14*,15*,17*,122and123),12armatic compounds (26#,27#and127-136),9other compounds (19*,20*,118-121and124-126). Among them, compounds1*and2*are the N-9of benzyl-substituted carbazole alkaloids for the first time. These compounds are listed as follows: N-benzyl carbazole-A(1*),N-benzylcarbazole-B(2*),Iso-koenidine(3*),Iso-koenigine(4*),3-Formyl e-7-hydroxy-9H-carbazole-1-O-β-D-glucopyranoside(5*),(1’R,R,6’S)-Endocycliom urrayamine-A(6*),(3R,5S,6R)-3,5,6-Trihydroxy-1,1,5-trimethylcyclohexyl-8-butyn-9-one (7*),(8E,9R)-Ethyl-7-(3S,5R,6S)-3,6-dihydroxy-1,1,5-trimethylcyclohexyl)-9-hydroxybut-8-enoate(8*),(3R)-3-O-O-β-D-Glucoside-6’-D-apiose-β-ionone(9*),(7R)-2,6-Dimethoxyph enyl)-7,9-propanediol-1-O-β-D-glucopyranoside(10*),(7’E,8S)-9’-Hydroxy-7’-propen-3’,5’-dimethoxyphenyl-3-methoxyphenyl-7,9-propanediol-4-O-β-D-glucopyranoside(11*),4-O-β-D-Rutinose-3-methoxyphenyl-1-propanone(12*),1-O-β-D-Rutinose-2(R)-ethyl-l-pe ntanol(13*),(3S,4E,6E,10R)-2,10-Dihydroxy-2-methylethyl-6,10-dimethy1-4,6,11-sencol aninic-3-β-D-glucopyranoside(14*),(6E,10E)-3,7,11-Trimethyl-1,6,10-dodecatriene-3,5,8-triol(15*),5-Amino-(2Z,4Z)-1,2,3-trihydroxybuta-2,4-dienyloxy-pentane-6,7,8,9-tetraol (16*),(3E,7E)-Octadeca-3,7-diene-6,9,10,11,17-pentaol(17*),4’-Hydroxyphenyl-6-ethyl-1H-pyrrole-2-carboxaldehyde(18*),(2’R,4’R,7S)-2’,4-Dihydroxy-3-methoxyphenyl-4’-hyd roxymethyl-tetrahydro-1H-pyran-1-one(19*),(1R,10S)-1-Hydroxy-7-(10-hydroxybutyl)-2 ,3-dihydrobenzofuran-8(6H)-one(20*),6-β-D-Glucopyranoside-3-hydroxymethyl-benzoat e(21#),Isovanillylalcohol-3-β-D-glucopyranoside(22#),(2R)-2-Hydroxypropyl-2,6-dimeth oxyphenol(23#),Guaiacylglycerol-β-ethylferuloylether(24#),(3S)-4’-Hydroxyphenyl-3-hyd roxypropionicacidethylester(25#),4-Methoxy-2-pentyl-phenol(26#),2-Ethoxy-6-hydroxy-4-methyl-benzoicacid(27#),4-Hydroxyphenoxy-N-methyl-propanamide(28#),Girinimbine (29),Koenine(30),Koenigine(31),Koenimbine(32),Iso-koenine(33),Koenidine(34),Murray anine(35),O-demethylmurrayanine(36),3-Formylcarbazole(37),l-Methoxy-carbazole-3-m ethanol(38),3-Hydroxymethyl-9-H-carbazole(39),N-methoxy-3-hydroxymethyl-9H-carba zole(40),Mahanimbine(41),Mahanine(42),8,8’-Biskoenigine(43),Cyclomahanimbine(44), Murrayazolinine(45),2-Formyl-5-hydroxymethyl-pyrrole(46),5-Hydroxymethyl-l-methyl pyrrole-2-carboxaldehyde(47),Pyrrolezanthine(48),Pyrrolezanthine-6-methylether(49),3-Formyl-1H-indole(50),Nicotilamide(51),Piconol(52),3-Hydroxy-4-amino-benzaldehyde(53),Crotonine(54),(R)-(-)-Dehydrovomifoliol(55),Blumenol-C(56),Blumenol-A(57),Icari side-B1(58),Icariside-B1aglycon(59),(3S,5R,6R,8E)-3,5,6-Trihydroxy-1,1,5-trimethylcyc lohexyl-8-buten-9-one(60),(4R)-4-Hydroxy-2,6,6-trimethyl-l-cyclohexene-l-methanol(61),(8E)-3(R)-O-β-D-glucopyranosyloxy-1,5,5-trimethyl-7-cyclohexen-8-buten-7-one(62),3β-Glucopyranosyloxy-β-ionone(63),3β-Hydroxy-5a,6a-epoxy-7-megastigmen-9-one(64),3-O-β-D-Glucopyranosyloxy-5a,6a-epoxy-7-megastigmen-9-one(65),Loliolide(66),(-)-Epiloliolide(67),(3R,6R,7E)-3-Hydroxy-a-ionone(68),5,6-Dihydrovomifoliol(69),(3S,9R)-9-Hydroxy-7-butynyl-1,1,5-trimethyl-5-cyclohexen-3-ol(70),(1E)-2,6-Dimethoxy-1-pro penylphenyl-4-O-β-D-glucopyranoside(71),4-Allyl-2,6-dimethoxyphenylglucoside(72),S yringoside(73),4-O-β-D-Glucopyranosyloxy-3,5-dimethoxyphenyl-7-propenal(74),Dihyd rosyringin(75),Dihydrosyringin(75),(E)-Coniferin(76),3,4’-Dihydroxy-3’-methoxypropio phenone(77),1-Hydroxy-2-methoxy-hydrocinnamicacid(78),3-Hydroxy-4’-hydroxy-3’,5’-dimethoxyphenyl-1-propanone(79),(E)-3’,4’-Dimethoxycinnamylalcohol(80),(7S,8R)-4-H ydroxy-3-methoxyphenyl-7,8,9-propanetriol(81),(7S,8R)-4-Hydroxy-3,5-dimethoxyphen y1-7,8,9-propanetriol(82),C-veratroylglycol(83),(1’R)-4-O-β-D-Glucopyranoside-3,5-dim ethoxyphenyl-1’-propanol(84),(7S,8S)-1’-Hydroxy-3’,5’-dimethoxyphenoxy-4-hydroxy-3-Methoxyphenyl-7,9-propanediol(85),(7’E’,7S,8S)-9’-Hydroxy-7’-propen-3’-methoxyphenyl-4-hydroxy-3-methoxyphenyl-7,9-propanediol(86),(1S,2R)-4,4’-Hydroxy-3,3’-methoxyph enyl-1,3-propanediol(87),(7S,8R)-4,4’-Dihydroxy-3,3’-dimethoxyphenyl-7-ethoxy-9-prop anol(88),(7S,8S)-4-Hydroxy-3-methoxy-7,8-(2’,1’-O-β-D-glucopyranosyl)phenyl-propane triol(89),CitrusinB(90),(7S,7’SS,8S,8’R)-4,4",7’,9’-Tetrahydroxy-3,3’,3"-trimethoxyphenyl-7,9-propanediol(91),Lariciresinol-4-O-β-D-glucopyranoside(92),(7’R,8’R,8E)-4’,7’-Dihyd roxy-3’-methoxyphenyl-8’-hydroxymethyl-ethoxy-3,5-dimethoxyphenyl-8-propenoic acidmethylester(93),(2R)-4’-Hydroxy-3’-methoxyphenyl-2-butanol(94),Methylsyringate-4-O-β-D-glucopyranoside(95),4-Hydroxymethyl-2,6-dimethoxyphenyl-1-O-β-D-glucopy ranoside(96),3,5-Dimethoxyphenylalcohol-4-O-β-D-glucopyranoside(97),4-Hydroxy-2-methoxyphenyl-1-0-β-D-glucopyranoside(98),Methylsalicylate-3-O-β-D-glucopyranosid e(99),4-Hydroxy-3-methoxyphenyl-1-O-β-D-glucopyranoside(100),4-Hydroxy-3,5-dimet hoxyphenyl-1-O-β-D-glucopyranoside(101),Benzyl-2-O-β-D-glucopyranoside(102),4"-H ydroxy-3"-methoxy-6-benzoate-4’-hydroxy-2’,6’-dimethoxyphenyl-1’-O-β-D-glucopyrano side(103),4"-Hydroxy-3"/5"-dimethoxy-6-benzoate-4’-hydroxy-6’-methoxyphenyl-l’-O-β-D-glucopyranoside(104),4"-Hydroxy-3"/5"-dimethoxy-6-benzoate-4’-hydroxy-2’/6’-dime thoxyphenyl-1’-O-β-D-glucopyranoside(105),Isoeucommin-A(106),(+)-Pinoresinol-4’-O-β-D-glucopyranoside(107),(±)-Syringaresinol(108),(+)-Pinoresinol(109),(+)-Syringaresin ol-4-O-β-glucopyranoside(110),Hedyotisol-A(111),(7"R,8"R)-8"-Syringaresinol-4"-hydro xy-3",5"-dimethoxyphenyl-7",9"-propanediol(112),(+)-Isolariciresinol(113),(+)-Lyoniresi nol(114),Seselin(115),Isoscopoletin(116),8-Phenylethyl-O-β-D-rutinoside(117),β-Sitoster ol(118),Apigenin-4’-O-β-D-glucopyranoside(119),n-Butylphthalate(120),n-Octylphthalat e(121),(2E,6R)-2,6-Dimethyl-2,7-octadiene-1,6-diol(122),(7E)-6,9,10-trihydroxy-7-octad ecenoicacid(123),Neoandrographolide(124),Aromadendrane-4β,10α-diol(125),(4S)-4-Hy droxy-2,3-dimethyl-4-pentyl-1(4H)-furanone(126),Parahydroxybenzaldehyde(127),3-Me thoxy-4-hydroxybenzaldehyde(128),1,3,5-Trimethoxybenzene(129),o-Acetylphenol(130),5-Hydroxymethyl-2-methoxyphenol(131),4-Hydroxy-benzeneethanol(132),4-Hydroxy-3-methoxy-benzeneethanol(133),4-Ethoxy-benzenemethanol(134),Phenol(135),p-Methylp henol(136).(*New compounds,#New natural compounds).These compounds were screened by several pharmacological models. Compounds4*,29,35,36,44and49(10μM) exhibited protective activity against a damage of hepatocyte, with significance compared to the blank control group. Compounds41,42and43showed obvious hyperglycemic activities withr IC50values of1.773,1.875and2.286μM, respectively. Compounds41,42and43displayed certain cytotoxicity activities. Furthermore, Compounds34,41,42and43showed significant anti-inflammatory functions. |
PDF Full Text Request