Staff View: Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia

Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia

Nine new alkaloids, eugeniinalines A-H (1-8) and (+)-eburnamenine N-oxide (9), comprising one quinoline, six indole, and two isogranatanine alkaloids, were isolated from the stem-bark extract of the Malayan Leuconotis eugeniifolia. The structures and absolute configurations of these alkaloids were e...

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Main Authors:	Tan, Yi-Sheng, Ng, Min-Phin, Tan, Chun-Hoe, Tang, Wai-Kit, Sim, Kae-Shin, Yong, Kien-Thai, Krishnan, Premanand, Lim, Kuan-Hon, Lim, Siew-Huah, Low, Yun-Yee
Format:	Article
Published:	American Chemical Society 2024
Subjects:	QD Chemistry RM Therapeutics. Pharmacology RS Pharmacy and materia medica SB Plant culture
Online Access:	http://eprints.um.edu.my/45735/ https://doi.org/10.1021/acs.jnatprod.3c00960
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spelling	my.um.eprints.457352024-11-11T04:16:35Z http://eprints.um.edu.my/45735/ Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia Tan, Yi-Sheng Ng, Min-Phin Tan, Chun-Hoe Tang, Wai-Kit Sim, Kae-Shin Yong, Kien-Thai Krishnan, Premanand Lim, Kuan-Hon Lim, Siew-Huah Low, Yun-Yee QD Chemistry RM Therapeutics. Pharmacology RS Pharmacy and materia medica SB Plant culture Nine new alkaloids, eugeniinalines A-H (1-8) and (+)-eburnamenine N-oxide (9), comprising one quinoline, six indole, and two isogranatanine alkaloids, were isolated from the stem-bark extract of the Malayan Leuconotis eugeniifolia. The structures and absolute configurations of these alkaloids were established based on the analysis of the spectroscopic data, GIAO NMR calculations, DP4+ probability analysis, TDDFT-ECD method, and X-ray diffraction analysis. Eugeniinaline A (1) represents a new pentacyclic quinoline alkaloid with a 6/6/5/6/7 ring system. Eugeniinaline G (7) and its seco-derivative, eugeniinaline H (8), were the first isogranatanine alkaloids isolated as natural products. The known alkaloids leucolusine (10) and melokhanine A (11) were found to be the same compound, based on comparison of the spectroscopic data of both compounds, with the absolute configuration of (7R, 20R, 21S). Eugeniinalines A and G (1 and 7) showed cytotoxic activity against the HT-29 cancer cell line with IC50 values of 7.1 and 7.2 mu M, respectively. American Chemical Society 2024-01 Article PeerReviewed Tan, Yi-Sheng and Ng, Min-Phin and Tan, Chun-Hoe and Tang, Wai-Kit and Sim, Kae-Shin and Yong, Kien-Thai and Krishnan, Premanand and Lim, Kuan-Hon and Lim, Siew-Huah and Low, Yun-Yee (2024) Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia. Journal of Natural Products, 87 (2). pp. 286-296. ISSN 0163-3864, DOI https://doi.org/10.1021/acs.jnatprod.3c00960 <https://doi.org/10.1021/acs.jnatprod.3c00960>. https://doi.org/10.1021/acs.jnatprod.3c00960 10.1021/acs.jnatprod.3c00960
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	QD Chemistry RM Therapeutics. Pharmacology RS Pharmacy and materia medica SB Plant culture
spellingShingle	QD Chemistry RM Therapeutics. Pharmacology RS Pharmacy and materia medica SB Plant culture Tan, Yi-Sheng Ng, Min-Phin Tan, Chun-Hoe Tang, Wai-Kit Sim, Kae-Shin Yong, Kien-Thai Krishnan, Premanand Lim, Kuan-Hon Lim, Siew-Huah Low, Yun-Yee Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia
description	Nine new alkaloids, eugeniinalines A-H (1-8) and (+)-eburnamenine N-oxide (9), comprising one quinoline, six indole, and two isogranatanine alkaloids, were isolated from the stem-bark extract of the Malayan Leuconotis eugeniifolia. The structures and absolute configurations of these alkaloids were established based on the analysis of the spectroscopic data, GIAO NMR calculations, DP4+ probability analysis, TDDFT-ECD method, and X-ray diffraction analysis. Eugeniinaline A (1) represents a new pentacyclic quinoline alkaloid with a 6/6/5/6/7 ring system. Eugeniinaline G (7) and its seco-derivative, eugeniinaline H (8), were the first isogranatanine alkaloids isolated as natural products. The known alkaloids leucolusine (10) and melokhanine A (11) were found to be the same compound, based on comparison of the spectroscopic data of both compounds, with the absolute configuration of (7R, 20R, 21S). Eugeniinalines A and G (1 and 7) showed cytotoxic activity against the HT-29 cancer cell line with IC50 values of 7.1 and 7.2 mu M, respectively.
format	Article
author	Tan, Yi-Sheng Ng, Min-Phin Tan, Chun-Hoe Tang, Wai-Kit Sim, Kae-Shin Yong, Kien-Thai Krishnan, Premanand Lim, Kuan-Hon Lim, Siew-Huah Low, Yun-Yee
author_facet	Tan, Yi-Sheng Ng, Min-Phin Tan, Chun-Hoe Tang, Wai-Kit Sim, Kae-Shin Yong, Kien-Thai Krishnan, Premanand Lim, Kuan-Hon Lim, Siew-Huah Low, Yun-Yee
author_sort	Tan, Yi-Sheng
title	Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia
title_short	Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia
title_full	Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia
title_fullStr	Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia
title_full_unstemmed	Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia
title_sort	quinoline, indole, and isogranatanine alkaloids from malayan leuconotis eugeniifolia
publisher	American Chemical Society
publishDate	2024
url	http://eprints.um.edu.my/45735/ https://doi.org/10.1021/acs.jnatprod.3c00960
_version_	1816130451665846272
score	13.223943

Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia

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