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Study On The Bioactive Constituents Of Alocasia Macrorrhiza

Posted on:2018-12-20Degree:MasterType:Thesis
Country:ChinaCandidate:W J HuangFull Text:PDF
GTID:2334330533967341Subject:Pharmacy
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Giant taro(Alocasia macrorrhiza(L.)Schott),a perennial herb from the Alocasia of the family Araceae,widely distributes in the tropic and subtropical regions of Asia,such as Guangdong,Yunnan,Taiwan,Hainan provinces in China.As a common folk medicine,Alocasia macrorrhiza is widely used in treating nasopharyngeal carcinoma,appendicitis,tuberculosis,influenza,joint disorders,snake-bite,and so on.Besides,some modern medical researches indicated that giant taro exhibited anti-cancer,anti-inflammatory,anti-nociceptive,and anti-febrile activities,and so on.Since the 1950 s,more than 40 compounds were isolated and identified from Alocasia macrorrhiza,including 21 alkaloids,5 flavonoids,4 phenols and 11 other kinds of components.In this study,various chromatographic methods and spectroscopic methods were applied to the separation,purification,identification of the chemical constituents of the rhizome of Alocasia macrorrhiza.As a result,71 compounds were successfully isolated and identified,including 34 alkaloids,(E)-3-(2-(3-hydroxy-5-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydrobenzofuran-5-yl)-N-(4-hydroxyphenethyl)acrylamide(1*),(E)-3-(2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydrobenzofuran-5-yl)-N-(4-hydroxyphenethyl)acrylamide(2*),(Z)-3-(2-(3-hydroxy-5-methoxyphenyl)-3-(hydroxy methyl)-7-methoxy-2,3-dihydrobenzofuran-5-yl)-N-(4-hydroxyphenethyl)acrylamide(3*),(Z)-3-(2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydrobenzo furan-5-yl)-N-(4-hydroxyphenethyl)acrylamide(4*),grossamide(5),cis-grossamide(6#),(±)-(4-(ethoxy(4-hydroxy-3-methoxyphenyl)methyl)-2-(4-hydroxy-3-methoxyphenyl)-N-(4-hydroxylphenethyl)tetrahydrofuran-3-carboxamide(7*),(2S,3R,6R)-2-methyl-6-(1-phenyl nonan-4-one-9-yl)piperidin-3-ol(8*),(2R,3S,6S)-2-methyl-6-(1-phenylnonan-5-one-9-yl)piperidin-3-ol(9*),(2S,3R,6R)-2-methyl-6-(9-phenylnonyl)piperidin-3-ol(10*),(2R,3R,4S,6S)-2-methyl-6-(9-phenylnonyl)piperidine-3,4-diol(11*),(2S,3S,6S)-2-methyl-6-(9-phenyl nonyl)piperidin-3-ol(12*),(2R,3R,5R,6R)-2-methyl-6-(9-phenylnonyl)piperidine-3,5-diol(13*),1-(2-(5-hydroxy-1H-indol-3-yl)-2-oxoethyl)-1H-pyrrole-3-carbaldehyde(14*),hyrtiosin B(15),5-hydroxy-1H-indole-3-glyoxylate methyl ester(16#),5-hydroxy-1H-indole-3-glyoxylate ethyl ester(17#),1H-indole-3-carbaldehyde(18#),1H-indole-3-carboxylic acid(19#),5-hydroxy-1H-indole-3-carbaldehyde(20#),5-hydroxy-1H-indole-3-carboxylic acid ethyl ester(21#),7,8-dimethylbenzo[g]pteridine-2,4(1H,3H)-dione(22#),cyclo-(L-Val-L-Pro)(23#),L-pyroglutamicacid methyl ester(24#),(R)-5-hydroxypyrrolidin-2-one(25#),uracil(26),5-methyluracil(27#),thymidine(28#),adenosine(29#),trans-N-feruloyltyranine(30),cis-N-feruloyltyranine(31#),(E)-ferulamide(32#),5-hydroxypyridine(33#),methyl-5-hydroxy-2-pyridinecarboxylate(34#).Eight terpenoids,(6S,7E)-6-hydroxy-4,7-megastigmadien-3,9-dione(35#),(6R,9R)-blumenol B(36#),blumenol A(37#),(E)-6-hydroxy-2,6-dimethylocta-2,7-dienoicacid(38#),(+)-sporogen AO-2(39#),phaseic acid(40#),cannabiside D(41#),ursolic acid(42#);Five lignans,(+)-lyoniresinol-3?-O-?-D-glucopyranoside(43#),(+)-lyoniresinol(44#),(+)-lyoniresin-4-yl ?-D-glucopyranoside(45#),syringaresinol(46#),8,8'-bisdihydro siringenin glucoside(47#).Nine phenylpropanoids,siringenin(48#),dihydrosiringenin(49#),dihydroconiferin(50#),threo-1-C-syringylglycerol(52#),?-hydroxypropiovanillone(53#),trans-cinnamic acid(54#),dihydroferulic acid methyl ester(55#),dihydroferulic acid(56#),ferulic acid(57#);Seven phenolics,2,6-dimethoxy p-hydroquinone 1-O-?-D-glucopyranoside(51#),3-methoxy-4-hydroxybenzoic acid(63),3,4-dihydroxybenzoic acid(64),syringic acid(65#),phydroxy benzaldehyde(66#),p-hydroxybenzoic acid(67),anisic acid(68#).Eight others,icariside F2(58#),isopentenol 1-O-?-D-apiofuranosyl-(1?6)-?-Dglucopyranoside(59#),5?,8?-epidioxyergosta-6,22-diene-3?-ol(60#),decumbic acid(61#),5-(hydroxymethyl)furan-2-carbaldehyde(62#),butanedioic acid monoethyl ester(69#),(9Z,12 Z,15Z)-2,3-dihydroxypropyl octadecadienoate(70#),(9Z,12Z)-2,3-dihydroxy-propyl octadecadienoate(71#).Compounds 1–4,7 were five new lignanamides,compounds 8–13 were six new lignanamides,and compound 14 was a new monoindoles.Besides,52 compounds(6,16–25,27–29,31–62,65–66,68–71)were obtained from the genus of Alocasia for the first time.The isolated compounds were tested for the cytotoxicity against CNE-1,Detroit 562,Fadu,MGC-803 and MCF-7 cell lines by MTT method,and the anti-inflammatory activity.As a result,compounds 8–10,39 and 42 showed significant cytotoxicity against five cancer cells.Compounds 1–6 exhibited significant anti-inflammatory activity with the IC50 values of 13.33,2.35,17.79,9.20,7.96 and 3.45 ?M,respectively.
Keywords/Search Tags:Alocasia macrorrhiza, Chemical constituents, Anti-inflammatory activity, Cytotoxicity
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