Biologically active indole and bisindole alkaloids from Leuconotis and Kopsia / Gan Chew Yan
Two Malaysian plants viz., Leuconotis griffithii and Kopsia pauciflora, and one fungi strain (Penicillium sp. (CDA p48.3)) were investigated for their alkaloidal content and the results are summarized below (Table). A total of 107 alkaloids were isolated and characterized from these sources. Of thes...
| Main Author: | |
|---|---|
| Format: | Thesis |
| Published: |
2013
|
| Subjects: | |
| Online Access: | http://studentsrepo.um.edu.my/4963/ http://studentsrepo.um.edu.my/4963/1/Final_Thesis_17042013.pdf |
| _version_ | 1848772765470949376 |
|---|---|
| author | Gan, Chew Yan |
| author_facet | Gan, Chew Yan |
| author_sort | Gan, Chew Yan |
| building | UM Research Repository |
| collection | Online Access |
| description | Two Malaysian plants viz., Leuconotis griffithii and Kopsia pauciflora, and one fungi strain (Penicillium sp. (CDA p48.3)) were investigated for their alkaloidal content and the results are summarized below (Table). A total of 107 alkaloids were isolated and characterized from these sources. Of these, 37 are new alkaloids. Leuconotis griffithii yielded a total of 24 new alkaloids, of which sixteen, viz., the tetracyclic ring-opened oxindole leucolusine (1), the strychnan alkaloids, leuconicines AG (28), the ring-C contracted rhazinilam alkaloid, nor-rhazinicine (22), the unprecedented eburnanequinoline dimer, leucophyllidine (36), the eburnanesarpagine bisindole, leuconoline (37), the aspidospermatanaspidospermatan bisindole, leucofoline (38), and the StrychnosStrychnos bisindoles, leucoridines AD (3942), are notable for incorporating novel or intriguing molecular skeletons. The stem-bark and leaf extracts of Kopsia pauciflora gave a total of 10 new alkaloids. These new alkaloids are the seco-leuconoxine alkaloid, compound 62, the eburnane alkaloids, 6364, the corynanthean oxindole alkaloids, 6971, the corynanthean pseudoindoxyl alkaloid, tetrahydroalstonine pseudoindoxyl (73), the aspidofractinine alkaloid, 11,12-dimethoxykopsinaline (77), and the andransinine alkaloids, andransinine (90) and compound 91. The culture broth extract of a Penicillium sp. (CDA p48.3) gave three new variotin derivatives, viz., compounds 101103. Among the new alkaloids, 5,21-dihydrorhazinilam N-oxide (23), leucophyllidine (36), and leucoridine A (39) showed pronounced cytotoxic effects against human KB cells (IC50 0.572.95 g/mL), while leuconodine B (10), leuconodine D (12), nor-rhazinicine (22), leuconoline (37), leucofoline (38), and leucoridines BD (4042) showed only moderate to weak activity (IC50 7.0617.90 g/mL). Leuconicines AB (23), compound 70, and andransinine
iii
(90) were found to be effective in circumventing MDR in vincristine-resistant KB cells (IC50 1.612.75 g/mL), while leuconicines CE (46), leuconodine E (13), and compounds 62, 64, and 91, showed only moderate to weak activity (IC50 3.8618.13 g/mL). |
| first_indexed | 2025-11-14T13:31:43Z |
| format | Thesis |
| id | um-4963 |
| institution | University Malaya |
| institution_category | Local University |
| last_indexed | 2025-11-14T13:31:43Z |
| publishDate | 2013 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | um-49632015-04-01T02:15:54Z Biologically active indole and bisindole alkaloids from Leuconotis and Kopsia / Gan Chew Yan Gan, Chew Yan Q Science (General) Two Malaysian plants viz., Leuconotis griffithii and Kopsia pauciflora, and one fungi strain (Penicillium sp. (CDA p48.3)) were investigated for their alkaloidal content and the results are summarized below (Table). A total of 107 alkaloids were isolated and characterized from these sources. Of these, 37 are new alkaloids. Leuconotis griffithii yielded a total of 24 new alkaloids, of which sixteen, viz., the tetracyclic ring-opened oxindole leucolusine (1), the strychnan alkaloids, leuconicines AG (28), the ring-C contracted rhazinilam alkaloid, nor-rhazinicine (22), the unprecedented eburnanequinoline dimer, leucophyllidine (36), the eburnanesarpagine bisindole, leuconoline (37), the aspidospermatanaspidospermatan bisindole, leucofoline (38), and the StrychnosStrychnos bisindoles, leucoridines AD (3942), are notable for incorporating novel or intriguing molecular skeletons. The stem-bark and leaf extracts of Kopsia pauciflora gave a total of 10 new alkaloids. These new alkaloids are the seco-leuconoxine alkaloid, compound 62, the eburnane alkaloids, 6364, the corynanthean oxindole alkaloids, 6971, the corynanthean pseudoindoxyl alkaloid, tetrahydroalstonine pseudoindoxyl (73), the aspidofractinine alkaloid, 11,12-dimethoxykopsinaline (77), and the andransinine alkaloids, andransinine (90) and compound 91. The culture broth extract of a Penicillium sp. (CDA p48.3) gave three new variotin derivatives, viz., compounds 101103. Among the new alkaloids, 5,21-dihydrorhazinilam N-oxide (23), leucophyllidine (36), and leucoridine A (39) showed pronounced cytotoxic effects against human KB cells (IC50 0.572.95 g/mL), while leuconodine B (10), leuconodine D (12), nor-rhazinicine (22), leuconoline (37), leucofoline (38), and leucoridines BD (4042) showed only moderate to weak activity (IC50 7.0617.90 g/mL). Leuconicines AB (23), compound 70, and andransinine iii (90) were found to be effective in circumventing MDR in vincristine-resistant KB cells (IC50 1.612.75 g/mL), while leuconicines CE (46), leuconodine E (13), and compounds 62, 64, and 91, showed only moderate to weak activity (IC50 3.8618.13 g/mL). 2013 Thesis NonPeerReviewed application/pdf http://studentsrepo.um.edu.my/4963/1/Final_Thesis_17042013.pdf Gan, Chew Yan (2013) Biologically active indole and bisindole alkaloids from Leuconotis and Kopsia / Gan Chew Yan. PhD thesis, University of Malaya. http://studentsrepo.um.edu.my/4963/ |
| spellingShingle | Q Science (General) Gan, Chew Yan Biologically active indole and bisindole alkaloids from Leuconotis and Kopsia / Gan Chew Yan |
| title | Biologically active indole and bisindole alkaloids from
Leuconotis and Kopsia / Gan Chew Yan
|
| title_full | Biologically active indole and bisindole alkaloids from
Leuconotis and Kopsia / Gan Chew Yan
|
| title_fullStr | Biologically active indole and bisindole alkaloids from
Leuconotis and Kopsia / Gan Chew Yan
|
| title_full_unstemmed | Biologically active indole and bisindole alkaloids from
Leuconotis and Kopsia / Gan Chew Yan
|
| title_short | Biologically active indole and bisindole alkaloids from
Leuconotis and Kopsia / Gan Chew Yan
|
| title_sort | biologically active indole and bisindole alkaloids from
leuconotis and kopsia / gan chew yan |
| topic | Q Science (General) |
| url | http://studentsrepo.um.edu.my/4963/ http://studentsrepo.um.edu.my/4963/1/Final_Thesis_17042013.pdf |