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Studies On The Chemical Constituents Of Kopsia Officinalis,Podocarpus Macrophyllus And Polyalthia Petelotii

Posted on:2017-01-16Degree:MasterType:Thesis
Country:ChinaCandidate:C Q YangFull Text:PDF
GTID:2284330503973279Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
The thesis mainly reported chemical constituents on three medicinal plants Kopsia officinalis, Podocarpus macrophyllus and Polyalthia petelotii. Totally 51 compounds were isolated and identified from the three plants, including three new compounds. Compound 38 displayed weak inhibitory activity to cytotoxicity.By solvent extraction, normal phase silica gel column chromatography,Sephadex LH-20 column chromatography, MCI column chromatography and HPLC etc. Seven compounds were isolated from the stem bark and leaves of Kopsia officinalis. Their structures were established on the basis of extensive spectroscopic analyses(1H-NMR,13C-NMR,1H-1H COSY, HSQC, HMBC and ROESY etc.), and they are(-)-19-oxo-eburnamonine(1),(+)-eburnamonine(2),(-)-kopsinine(3),(-)-12-methoxykopsinaline(4), 10-demethooxykopsidasinine(5),tetrahydroalstonine(6),(-)-N-methoxycarbonyl-11,12-methylenedioxy kopsinaline(7), compounds 1, 2, 5 were isolated from Kopsia officinalis for the first time.Compounds 1-3, 5-7 were assessed for their inflammation activity, and the result showed that they had no activity.The twigs of Podocarpus macrophyllus were extracted with Me OH, the Me OH extract isolated 13 compounds by solvent extraction, normal phase silica gel column chromatography, Sephadex LH-20 column chromatography, MCI column chromatography and HPLC etc. Their structures were established on the basis of extensive spectroscopic analyses, including diterpenoid, simple aromatic compounds,lignins and flavones etc. They are 7-oxodehydroabietic acid(8), 4’,8-dihydroxy-6-methoxy-5,7-dimethylflavone(9), kaempferol-7-methyl ether(10), syzalterin(11),(+)-piperitol(12),(-)-piperitol(13),(+)-pinoresinol(14),(-)-nortrachelogenin(15),stellerachama A(16), 2’-acetyl-4’,4-dimethoxybiphenyl-2-carbaldehyde(17),p-methoxybenzoic acid(18), 3,4-dihydroxy benzoic acid(19), p-hydroxybenzonic acid(20). Compounds 8, 9, 12-18 were isolated from the genus Podocarpus for the first time, compounds 10, 19 and 20 were isolated from Podocarpus macrophyllus forthe first time.The twigs of Polyalthia petelotii were extracted with Me OH, the Me OH extract isolated 31 compounds by solvent extraction, normal phase silica gel column chromatography, Sephadex LH-20 column chromatography, MCI column chromatography and HPLC etc. Their structures were established on the basis of extensive spectroscopic analyses, including alkaloids, sesquiterpenoids, diterpenoids,steroids, simple aromatic compounds and lignins etc. They are iso-petalinemethine(21), magnocurarine(22), spinosine(23),(-)-oliveroline-β-N-oxide(24), N-pcoumaroyltyramine(25), salicifoline(26), darienine(27), isooncodine(28),(-)-ethyl dihydrophaseate(29), 11-hydroxy-orientalol E(30), 10b,11bepoxyguaiane-1a,4a,7a-triol(31), acomadendrane-4b,10b-diol(32), 4a,7a-epoxyguaiane-10a,11-diol(33),4β,12-dihydroxyguaian-6,10-diene(34), 4α,7β,11-trihydroxy-1βH,5αH-guai-10(14)-ene(35), eudesm-4(15)-ene-7α,11-diol(36), 15-hydroxy-cis-ent-cleroda-3,13(E)-diene(37), 16α-hydroxycleroda-3,13(14)Z-dien-16,15-olide(38), 15-hydroxy-3-cleroden-2-one(39),(-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide(40), 2-oxo-kolavenic acid(41), rel-(3R,3’S,4R,4’S)-3,3’,4,4’-tetrahydro-6,6’-dimethoxy[3,3’-bi-2H-benzopyran]-4,4’-diol(42), a-onocerin(43), stigmasterol(44), β-sitosterol(45),(-)-syringaresinol(46), vanillin(47), syringlaldehyde(48),vanillic acid(49), syringic acid(50), thioacetic anhydride(51). Compounds 21, 29 and 30 are new compounds. Compounds 22, 23, 26, 31-37, 39-46, 48 and 51 were isolated from the genus Polyalthia for the first time, others were isolated from Polyalthia petelotii for the first time. Compounds 23, 24, 29, 36-38 and 47 were assessed for their cytotoxicity against five human tumor lines(HL-60, SMMC-7721,A-549, MCF-7 and SW-480), and the result showed that only 38 displayed weak inhibitory activity.In the last, chemical constituents and pharmacological studies of Polyalthia were reviewed, including 349 compounds and their names, structures, plant resources,biological activities and references were cited.
Keywords/Search Tags:Kopsia officinalis, Podocarpus macrophyllus, Polyalthia petelotii, Polyalthia, Chemical constituents
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