Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one
The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the a...
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| Format: | Article |
| Language: | English |
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MDPI AG
2008-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/13/12/2935/ |
| _version_ | 1818134551088594944 |
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| author | Surachai Nimgirawath Phansuang Udomputtimekakul Samathi Pongphuttichai Thongchai Taechowisan Asawin Wanbanjob |
| author_facet | Surachai Nimgirawath Phansuang Udomputtimekakul Samathi Pongphuttichai Thongchai Taechowisan Asawin Wanbanjob |
| author_sort | Surachai Nimgirawath |
| collection | DOAJ |
| description | The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the aporphines by a radical-intiated cyclisation. Both (±)-laurelliptinhexadecan-1-one (1a) and (±)-laurelliptinoctadecan-1-one (1b) were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028. |
| first_indexed | 2024-12-11T09:10:25Z |
| format | Article |
| id | doaj.art-a0caa087c87c4e76a63f5e3079e74583 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T09:10:25Z |
| publishDate | 2008-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a0caa087c87c4e76a63f5e3079e745832022-12-22T01:13:31ZengMDPI AGMolecules1420-30492008-11-0113122935294710.3390/molecules13122935Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-oneSurachai NimgirawathPhansuang UdomputtimekakulSamathi PongphuttichaiThongchai TaechowisanAsawin WanbanjobThe structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the aporphines by a radical-intiated cyclisation. Both (±)-laurelliptinhexadecan-1-one (1a) and (±)-laurelliptinoctadecan-1-one (1b) were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028.http://www.mdpi.com/1420-3049/13/12/2935/AlkaloidAmidic aporphineIsoquinolineSynthesisAntimicrobial activity |
| spellingShingle | Surachai Nimgirawath Phansuang Udomputtimekakul Samathi Pongphuttichai Thongchai Taechowisan Asawin Wanbanjob Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one Molecules Alkaloid Amidic aporphine Isoquinoline Synthesis Antimicrobial activity |
| title | Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one |
| title_full | Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one |
| title_fullStr | Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one |
| title_full_unstemmed | Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one |
| title_short | Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one |
| title_sort | total synthesis and antimicrobial activity of a a laurelliptinhexadecan 1 one and a a laurelliptinoctadecan 1 one |
| topic | Alkaloid Amidic aporphine Isoquinoline Synthesis Antimicrobial activity |
| url | http://www.mdpi.com/1420-3049/13/12/2935/ |
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