Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris
Two new monoterpenoid indole alkaloids, alstoscholactine (1) and alstolaxepine (2), were isolated from Alstonia scholaris. Compound 1 represents a rearranged stemmadenine alkaloid with an unprecedented C-6-C-19 connectivity, whereas compound 2 represents a 6,7-seco-angustilobine B-type alkaloid inco...
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| Format: | Article |
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American Chemical Society
2018
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| _version_ | 1796961466544291840 |
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| author | Krishnan, Premanand Lee, Fong Kai Chong, Kam Weng Mai, Chun Wai Muhamad, Azira Lim, Siew Huah Low, Yun Yee Ting, Kang Nee Lim, Kuan Hon |
| author_facet | Krishnan, Premanand Lee, Fong Kai Chong, Kam Weng Mai, Chun Wai Muhamad, Azira Lim, Siew Huah Low, Yun Yee Ting, Kang Nee Lim, Kuan Hon |
| author_sort | Krishnan, Premanand |
| collection | UM |
| description | Two new monoterpenoid indole alkaloids, alstoscholactine (1) and alstolaxepine (2), were isolated from Alstonia scholaris. Compound 1 represents a rearranged stemmadenine alkaloid with an unprecedented C-6-C-19 connectivity, whereas compound 2 represents a 6,7-seco-angustilobine B-type alkaloid incorporating a rare γ-lactone-bridged oxepane ring system. Their structures and absolute configurations were determined by spectroscopic analyses. Compound 1 was successfully semisynthesized from 19E-vallesamine. Compound 2 induced marked vasorelaxation in rat isolated aortic rings precontracted with phenylephrine. |
| first_indexed | 2024-03-06T05:54:32Z |
| format | Article |
| id | um.eprints-21582 |
| institution | Universiti Malaya |
| last_indexed | 2024-03-06T05:54:32Z |
| publishDate | 2018 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | um.eprints-215822019-07-09T04:46:58Z http://eprints.um.edu.my/21582/ Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris Krishnan, Premanand Lee, Fong Kai Chong, Kam Weng Mai, Chun Wai Muhamad, Azira Lim, Siew Huah Low, Yun Yee Ting, Kang Nee Lim, Kuan Hon Q Science (General) QD Chemistry R Medicine Two new monoterpenoid indole alkaloids, alstoscholactine (1) and alstolaxepine (2), were isolated from Alstonia scholaris. Compound 1 represents a rearranged stemmadenine alkaloid with an unprecedented C-6-C-19 connectivity, whereas compound 2 represents a 6,7-seco-angustilobine B-type alkaloid incorporating a rare γ-lactone-bridged oxepane ring system. Their structures and absolute configurations were determined by spectroscopic analyses. Compound 1 was successfully semisynthesized from 19E-vallesamine. Compound 2 induced marked vasorelaxation in rat isolated aortic rings precontracted with phenylephrine. American Chemical Society 2018 Article PeerReviewed Krishnan, Premanand and Lee, Fong Kai and Chong, Kam Weng and Mai, Chun Wai and Muhamad, Azira and Lim, Siew Huah and Low, Yun Yee and Ting, Kang Nee and Lim, Kuan Hon (2018) Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris. Organic Letters, 20 (24). pp. 8014-8018. ISSN 1523-7060, DOI https://doi.org/10.1021/acs.orglett.8b03592 <https://doi.org/10.1021/acs.orglett.8b03592>. https://doi.org/10.1021/acs.orglett.8b03592 doi:10.1021/acs.orglett.8b03592 |
| spellingShingle | Q Science (General) QD Chemistry R Medicine Krishnan, Premanand Lee, Fong Kai Chong, Kam Weng Mai, Chun Wai Muhamad, Azira Lim, Siew Huah Low, Yun Yee Ting, Kang Nee Lim, Kuan Hon Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris |
| title | Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris |
| title_full | Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris |
| title_fullStr | Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris |
| title_full_unstemmed | Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris |
| title_short | Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris |
| title_sort | alstoscholactine and alstolaxepine monoterpenoid indole alkaloids with γ lactone bridged cycloheptane and oxepane moieties from alstonia scholaris |
| topic | Q Science (General) QD Chemistry R Medicine |
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