Staff View: Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris

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...

Full description

Saved in:

Bibliographic Details
Main Authors:	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
Format:	Article
Published:	American Chemical Society 2018
Subjects:	Q Science (General) QD Chemistry R Medicine
Online Access:	http://eprints.um.edu.my/21582/ https://doi.org/10.1021/acs.orglett.8b03592
Tags:	Add Tag No Tags, Be the first to tag this record!

id	my.um.eprints.21582
record_format	eprints
spelling	my.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 https://doi.org/10.1021/acs.orglett.8b03592 doi:10.1021/acs.orglett.8b03592
institution	Universiti Malaya
building	UM Library
collection	Institutional Repository
continent	Asia
country	Malaysia
content_provider	Universiti Malaya
content_source	UM Research Repository
url_provider	http://eprints.um.edu.my/
topic	Q Science (General) QD Chemistry R Medicine
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
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.
format	Article
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
title	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_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_sort	alstoscholactine and alstolaxepine, monoterpenoid indole alkaloids with γ-lactone-bridged cycloheptane and oxepane moieties from alstonia scholaris
publisher	American Chemical Society
publishDate	2018
url	http://eprints.um.edu.my/21582/ https://doi.org/10.1021/acs.orglett.8b03592
_version_	1643691600688185344
score	13.211869

Alstoscholactine and Alstolaxepine, Monoterpenoid Indole Alkaloids with γ-Lactone-Bridged Cycloheptane and Oxepane Moieties from Alstonia scholaris

Similar Items