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Chemical And Bioactive Constituents Of Dalbergia Odorifera

Posted on:2015-01-09Degree:MasterType:Thesis
Country:ChinaCandidate:H WangFull Text:PDF
GTID:2284330467971149Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
The heartwood of Dalbergia odorifera T. Chen.(Leguminosae) has been used intraditional Chinese medicine. Results of chemical studies showed that D. odoriferamainly contained flavonoids and volatile oil, which showed a variety of biologicalactivities, such as anti-inflammatory, antioxidant, antimicrobial, antitumor andanti-platelet activity. In order to search new bioactive constituents, the ethanol extractof D. odorifera was systematically investigated.In our present study,63compounds, including19new compounds, were isolatedand identified from D. odorifera. The types of these compounds are mainly themonoterpenoids, sesquiterpenoids, triterpenoids, flavonoids, ligans and other phenoliccompounds. And the flavonoids cover pterocarpans, neoflavones, isoflavans,isoflavones, flavanones and isoflavanones etc. The new compounds are mainlybelonging to the sesquiterpenoids and phenols. The sesquiterpenoids most likely arebiotransformed from nerolidol, and a possible biogenetic pathway of these compoundswas proposed. All compounds were evaluated for their antibacterial activities andcytotoxicity, acetylcholinesterase inhibitory activity of some characteristic compoundswas assayed as well. The results showed that compounds3and4showed antibacterialactivity against Candida albicans; compound4showed antibacterial activity againstStaphylococcus aureus; compounds2,54,56,58and59showed antibacterial activityagainst Ralstonia solanacearum. Compound28exhibited cytotoxicity againstSGC-7901and BEL-7402tumor cell lines, respectively. Compound36,37and54exhibited inhibitory activities against AChE. The structure-activity relationship was studied in this paper.1.3,7-dimethyl-5,8-epoxy-3-hydroxyoct-1-en-8-one (1)*2. rel-(3S,6R,7S)-3,7-dimethyl-3,6;7,10-diepoxy-1-decanen-10-one (2)3. rel-(3R,6R,7S)-3,7,11-trimethyl-3,7-epoxy-1,10-dodecadien-6-ol (3)*4.6α-hydrocyclonerolidol (4)5. rel-(3S,6S,7R)-3,7,11-trimethyl-3,6-epoxy-1-dodecen-7,11-diol (5)*6. rel-(3S,6R,7S)-3,7,11-trimethyl-3,6-epoxy-1-dodecen-7,11-diol (6)*7. rel-(3S,6R,7S)-3,7,11-trimethyl-3,6-epoxy-1,10-dodecadien-7-ol (7)8. rel-(3S,6S,7R)-3,7,11-trimethyl-3,6-epoxy-1,10-dodecadien-7-ol (8)9. rel-(3S,6R,7S)-3,7,11-trimethyl-3,6-epoxy-1,9,11-dodecatrien-7-ol (9)*10. negunfurol (10)11. rel-(3S,7S,10S)-7,10-epoxy-3,7,11-trimethyldodec-1,5-diene-3,11-diol (11)*12. rel-(3S,7R,10S)-7,10-epoxy-3,7,11-trimethyldodec-1,5-diene-3,11-diol (12)13. rel-(3S,7S,10R)-7,10-epoxy-3,7,11-trimethyldodec-1,5-diene-3,11-diol (13)*14. neroplofurol (14)15.(3S,6R,7S,10R)-2,6,10-trimethyl-3,6;7,10-diepoxy-11-dodecen-2-ol (15)16. rel-(3S,6R,7S,10S)-2,6,10-trimethyl-3,6;7,10-diepoxy-11-dodecen-2-ol (16)*17.(3S,5E)-3,11-dimethyl-7-methylenedodaca-1,5,10-trien-3-ol (17)*18.7-methoxy-3,7,11-trimethyldodeca-1,5,10-trien-3-ol (18)*19.(Z)-3,11-dimethyl-7-methylene-9,14-epoxy-1,6,10-dodecatrien-3-ol (19)20. rel-(3S,6RS,7SR)-3.7.11-trimethyldodeca-1,10-diene-3,6,7-triol (20)21. rel-(S,E)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,10-dimethylundeca-5,9-dien-2-ol (21)22.(E)-7-hydroxy-6,10-dimethylundeca-5,9-dien-2-one (22)23. crocinervolide (23)24.3-acetvl oleanolic acid (24)25. vesticarpan (25)26.(6aR,11aR)-variabiin (26)27. meliotocarpan D (27) 28.(6aR,11aR)-6a,3,9-trimethoxypterocarpan (28)*29.4,9-dimethoxy-3-hydroxypterocarpan (29)30. meliotocarpan A (30)31.3,8-dihydroxy-9-methoxypterocarpan (31)32.3-methoxy-9-hydroxypterocarpan (32)33. medicarpin (33)34.3-hydroxy-9-methoxypterocarp-6a-ene (34)35.(6aR,11aR)-6a,9-dimethoxy-3-hydroxypterocarpan (35)*36. dalbergin (36)37. stevenin (37)38. mucronulatol (38)39.3′-hydroxy-8-methoxyvestitol (39)40.7-O-methylvestitol (40)41. pinocembrin (41)42.2′,4′,5-trihydroxy-7-methoxyisoflavone (42)43. sativanone (43)44. formononetin (44)45. koparin (45)46. prunetin (46)47.2′-hydroxyformononetin (47)48.2′,7-dihydroxy-4′,5′-dimethoxyisoflavone (48)49.7,2′,3′-trihydroxy-4′-methoxyisoflavan (49)50.3′-O-methylviolanone (50)51.(3R)-7,3′-dihydroxy-6,2′,4′-trimethoxyisoflavanone (51)*52.3,7-dihydroxy-2′,4′-dimethoxyisoflavanone (52)53. neokhriol A (53)54.6-methoxy-5,2′,4′-trihydroxy-3-benzoylbenzofuran (54)*55.6,7-dimethoxy-2-(4-methoxy-benzoquinonyl)-flavan (55)* 56.2-[2-(2,4-dimethoxyphenyl)-2-oxoethoxy]-4-hydrobenzoic acid (56)*57.2-(2,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl) ethanone (57)*58.2′,6-dihydroxy-4′-methoxy-2-arylbenzofuran (58)59.2,4-dihydroxy-5-methoxy-benzophenone (59)60.7-hydroxy-5′-methoxyspiro[benzo[d][1,3]dioxole-2′,3-chroman]-4-one (60)*61.2-[4,5-dimethoxy-5-(3-m-hydroxyphenyl-trans-allyl)cyclohexa-3,6-dien-2-on-1-ylmethyl]-5-hydroxy-6-methoxy-3-phenylbenzofuran.(61)*62. syringaresinol (62)63. lyoniresinol (63)NOTE:*new compound...
Keywords/Search Tags:Dalbergia odorifera T. Chen, sesquiterpenoid, flavonoid, bioactivity
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