Thesis
Phytochemical studies on some species of Rutaceae
Southern Cross University, School of Natural and Complementary Medicine
Doctor of Philosophy (PhD), Southern Cross University
2001
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Abstract
The major part of the work concerns the isolation and identification of secondary metabolites from plant species in the family Rutaceae. Within four species of examined plant, three of them belong to subtribe Triphasiinae, tribe Citreae, subfamily Aurantioideae, these being Paramignya grijfithii, Merope angulate and Luvunga scandens. The fourth species was Bouchardatia neurococca, tribe Zanthoxyleae, subfamily Rutoideae. A total of 26 compounds and a mixture of triterpenoid alcohol and peroxide were isolated.
Two novel furano flavanones, 3' ,4' -dihydroxy-7-methoxy-8-(3-methylbut-2-enyl)-furano ( 4' ',5'' :6,5)-flavanone and 3' ,4' -dihydroxy-7-methoxy-8-(3-methylbut-2-enyl)-2' '-(l-hydroxy-1-1-methylethyl)-furano ( 4' ',5'' :6,5)-flavanone, a known flavanone, amoradicin, a novel chromene, 6-(2-hydroxyethyl)-2,2-dimethyl-2H-1-benzopyran, a known triterpene, 3-oxo-tirucalla-7,24-diene-21-al and benzamide were isolated from P. griffithii. A known flavanone, sakuranetin, a known triterpene, friedelin, vanillin and methyl vanillate were isolated from M. angulate.
Two new triterpenes, (23E)-3~-hydroxy-25-hydroperoxytirucalla-7,23-diene-21-01c acid methyl ester and 21-hydroxy-24~-hydroperoxy-3-oxo-tirucalla-7,25-diene, a mixture of 3a,25-dihydroxytirucalla-7,23-diene-21-oic acid and its 25-hydroperoxide (both of them novel compounds), two known triterpenes, 3-oxo-tirucalla-7,24-diene-21-al and 3a-hydroxy-7,24-diene-21-oic acid, two known coumarins, ostruthin and 8-geranyl-7-hydroxycoumarin and two known acridone alkaloids, acrifoline and 5-hydroxy-1 demethylacronycine were isolated from L. scandens.
A new ~-indoloquinazoline alkaloid, 1,2-dihydroxyrutaecarpine, two known ~indoloquinazoline alkaloids, rutaecarpine and 1-hydroxy rutaecarpine, a novel catabolite of ~-indoloquinazoline, two new limonoids, 23-oxo-21 ~-hydroxy-21,23-dihydroveprisone and 21-oxo-23~-hydroxy-21,23-dihydroveprisone, a known limonoid, veprisone, a known furoquinoline alkaloid, dictamnine, a known ~-ionone derivative, boscialin and its epimer were isolated from B. neurococca.
Cytotoxicity testing of eight compounds isolated from Triphasiinae, including amoradicin (PG-1), 3-oxo-tirucalla-7,24-diene-21-al (PG-4), sakuranetin (MA-1), friedelin (MA-2), ostruthin (LS-1), acrifoline (LS-3), (23£)-3~-hydroxy-25-hydroperoxytirucalla-7,23-diene-21- oic acid methyl ester (LS-6) and 3a-hydroxy-7,24-diene-21-oic acid (LS-7) showed that five compounds exhibited cytotoxicity against mouse (P-388) lymphocytic leukemia cells, amoradicin (IC50 = 0.11 μM), (23£)-3~hydroxy-25-hydroperoxytirucalla-7,23-diene-2 l- oic acid methyl ester (IC50 = 1.29 μM), acrifoline (ICso = 1.57 μM), sakuranetin (IC50 = 1.73 μM) and 3a-hydroxy-7,24-diene-21-oic acid (ICso = 3.44 μM).
Finally a brief chemotaxonomic analysis of the subtribe Triphasiinae was discussed and the unusual chemical character of Bouchardatia was considered in the light of its supposed relationship.
Details
- Title
- Phytochemical studies on some species of Rutaceae
- Creators
- Chatchai Wattanapiromsakul
- Contributors
- Peter Waterman (Supervisor) - Southern Cross University
- Awarding Institution
- Southern Cross University; Doctor of Philosophy (PhD)
- Theses
- Doctor of Philosophy (PhD), Southern Cross University
- Publisher
- Southern Cross University, School of Natural and Complementary Medicine
- Number of pages
- xix, 219
- Identifiers
- 991012915700202368
- Copyright
- © Chatchai Wattanapiromsakul 2001
- Academic Unit
- Faculty of Health
- Resource Type
- Thesis