Phytochemicals variation between hydrochloric and tartaric acid-derived alkaloidal extracts of Erythrina fusca Lour. Leaves: A proton NMR-based approach

Erythrina fusca Lour. (Fabaceae) has been used traditionally to relieve toothache and migraine headaches, cleansing putrid ulcers, and reducing skin inflammations and irritation. Interestingly, most of the reported biological activities on the plant are attributed to its Erythrina alkaloids which ar...

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Published in:SOUTH AFRICAN JOURNAL OF BOTANY
Main Authors: Azmi, Adiez Sapura; Mediani, Ahmed; Abidin, Wan Abdul Muiz Wan Zainal; Othman, Wan Nurul Nazneem Wan; Cordell, Geoffrey A.; Salim, Fatimah
Format: Article
Language:English
Published: ELSEVIER 2024
Subjects:
Online Access:https://www-webofscience-com.uitm.idm.oclc.org/wos/woscc/full-record/WOS:001217769000001
author Azmi
Adiez Sapura; Mediani
Ahmed; Abidin
Wan Abdul Muiz Wan Zainal; Othman
Wan Nurul Nazneem Wan; Cordell
Geoffrey A.; Salim
Fatimah
spellingShingle Azmi
Adiez Sapura; Mediani
Ahmed; Abidin
Wan Abdul Muiz Wan Zainal; Othman
Wan Nurul Nazneem Wan; Cordell
Geoffrey A.; Salim
Fatimah
Phytochemicals variation between hydrochloric and tartaric acid-derived alkaloidal extracts of Erythrina fusca Lour. Leaves: A proton NMR-based approach
Plant Sciences
author_facet Azmi
Adiez Sapura; Mediani
Ahmed; Abidin
Wan Abdul Muiz Wan Zainal; Othman
Wan Nurul Nazneem Wan; Cordell
Geoffrey A.; Salim
Fatimah
author_sort Azmi
spelling Azmi, Adiez Sapura; Mediani, Ahmed; Abidin, Wan Abdul Muiz Wan Zainal; Othman, Wan Nurul Nazneem Wan; Cordell, Geoffrey A.; Salim, Fatimah
Phytochemicals variation between hydrochloric and tartaric acid-derived alkaloidal extracts of Erythrina fusca Lour. Leaves: A proton NMR-based approach
SOUTH AFRICAN JOURNAL OF BOTANY
English
Article
Erythrina fusca Lour. (Fabaceae) has been used traditionally to relieve toothache and migraine headaches, cleansing putrid ulcers, and reducing skin inflammations and irritation. Interestingly, most of the reported biological activities on the plant are attributed to its Erythrina alkaloids which are usually extracted through the acid -base method. While the selection of acids for the extraction process is crucial, there is limited information on comparing the efficacy of strong organic and inorganic acids in extracting Erythrina alkaloids, and, more broadly, other types of alkaloids. In this study, comparison between hydrochloric acid (HCl) and tartaric acid (H 2 T) was made to extract the Erythrina alkaloids. From the same mass (10 g) of the crude methanolic leaf extract, a significantly higher (9-fold) alkaloidal yield was obtained using H 2 T compared to the HCl. The alkaloidal extracts displayed different proton nuclear magnetic resonance ( 1 H NMR) profile where identification of their phytochemical constituents was done extensively through comparison with respective data of previously isolated compounds from the Erythrina species. Forty-seven phytochemicals were identified in the HCl extract and they were mostly alkaloids. While the H 2 T extract not only contained alkaloids, but also flavonoids, and pterocarpans. Cumulatively, 83 phytochemicals were identified from the extracts, including 35 alkaloids, 18 flavonoids, 14 pterocarpans, 9 terpenes, 3 phenols, and 4 saponins. Based on multivariate analysis (MVDA), the alkaloids erysodine (1), erysovine (2), erysopine (3), warangalone (39), calopocarpin (53), and dolichin A (60) were found in both alkaloidal extracts. The PLS-DA model further identified the variation in the two extracts where the HCl extract was characterized by the flavonoids lupinifolin (41) and erythrisenegalone (43). Conversely, the H 2 T extract contained a broader range of phytochemicals, including the alkaloids glucoerysodine (21) and erythratidinone (28), the flavonoids 5,3 ' -dihydroxy-4 ' -methoxy-5 ' -(3- methyl-1,3-butadienyl)-2 '' ,2 '' dimethylpyrano-[5,6:6,7]-isoflavanone (51), 5,3 ' -dihydroxy-5 ' -(3-hydroxy-3- methyl-1-butenyl)-4 ' -methoxy-2 '' ,2 '' dimethylpyrano-[5,6:6,7]-isoflavanone (52), and catechin (82), the pterocarpans calopocarpin (53) and sandwicensin (63), the terpenes loliolide (70), ursolic acid (80), propyloxyamyrin (83), and stigmast-3-en-4-one (73), the saponins sigmoisides A, B, and E (75, 76, and 77), and the phenol methyl gallate (81). The present findings highlight the value of targeting the extraction process for alkaloids, in this instance Erythrina alkaloids, using different type of acids. Furthermore, these compounds may be considered potential markers that were selectively extracted through the acid -base extraction process. (c) 2024 SAAB. Published by Elsevier B.V. All rights reserved.
ELSEVIER
0254-6299
1727-9321
2024
168

10.1016/j.sajb.2024.03.040
Plant Sciences

WOS:001217769000001
https://www-webofscience-com.uitm.idm.oclc.org/wos/woscc/full-record/WOS:001217769000001
title Phytochemicals variation between hydrochloric and tartaric acid-derived alkaloidal extracts of Erythrina fusca Lour. Leaves: A proton NMR-based approach
title_short Phytochemicals variation between hydrochloric and tartaric acid-derived alkaloidal extracts of Erythrina fusca Lour. Leaves: A proton NMR-based approach
title_full Phytochemicals variation between hydrochloric and tartaric acid-derived alkaloidal extracts of Erythrina fusca Lour. Leaves: A proton NMR-based approach
title_fullStr Phytochemicals variation between hydrochloric and tartaric acid-derived alkaloidal extracts of Erythrina fusca Lour. Leaves: A proton NMR-based approach
title_full_unstemmed Phytochemicals variation between hydrochloric and tartaric acid-derived alkaloidal extracts of Erythrina fusca Lour. Leaves: A proton NMR-based approach
title_sort Phytochemicals variation between hydrochloric and tartaric acid-derived alkaloidal extracts of Erythrina fusca Lour. Leaves: A proton NMR-based approach
container_title SOUTH AFRICAN JOURNAL OF BOTANY
language English
format Article
description Erythrina fusca Lour. (Fabaceae) has been used traditionally to relieve toothache and migraine headaches, cleansing putrid ulcers, and reducing skin inflammations and irritation. Interestingly, most of the reported biological activities on the plant are attributed to its Erythrina alkaloids which are usually extracted through the acid -base method. While the selection of acids for the extraction process is crucial, there is limited information on comparing the efficacy of strong organic and inorganic acids in extracting Erythrina alkaloids, and, more broadly, other types of alkaloids. In this study, comparison between hydrochloric acid (HCl) and tartaric acid (H 2 T) was made to extract the Erythrina alkaloids. From the same mass (10 g) of the crude methanolic leaf extract, a significantly higher (9-fold) alkaloidal yield was obtained using H 2 T compared to the HCl. The alkaloidal extracts displayed different proton nuclear magnetic resonance ( 1 H NMR) profile where identification of their phytochemical constituents was done extensively through comparison with respective data of previously isolated compounds from the Erythrina species. Forty-seven phytochemicals were identified in the HCl extract and they were mostly alkaloids. While the H 2 T extract not only contained alkaloids, but also flavonoids, and pterocarpans. Cumulatively, 83 phytochemicals were identified from the extracts, including 35 alkaloids, 18 flavonoids, 14 pterocarpans, 9 terpenes, 3 phenols, and 4 saponins. Based on multivariate analysis (MVDA), the alkaloids erysodine (1), erysovine (2), erysopine (3), warangalone (39), calopocarpin (53), and dolichin A (60) were found in both alkaloidal extracts. The PLS-DA model further identified the variation in the two extracts where the HCl extract was characterized by the flavonoids lupinifolin (41) and erythrisenegalone (43). Conversely, the H 2 T extract contained a broader range of phytochemicals, including the alkaloids glucoerysodine (21) and erythratidinone (28), the flavonoids 5,3 ' -dihydroxy-4 ' -methoxy-5 ' -(3- methyl-1,3-butadienyl)-2 '' ,2 '' dimethylpyrano-[5,6:6,7]-isoflavanone (51), 5,3 ' -dihydroxy-5 ' -(3-hydroxy-3- methyl-1-butenyl)-4 ' -methoxy-2 '' ,2 '' dimethylpyrano-[5,6:6,7]-isoflavanone (52), and catechin (82), the pterocarpans calopocarpin (53) and sandwicensin (63), the terpenes loliolide (70), ursolic acid (80), propyloxyamyrin (83), and stigmast-3-en-4-one (73), the saponins sigmoisides A, B, and E (75, 76, and 77), and the phenol methyl gallate (81). The present findings highlight the value of targeting the extraction process for alkaloids, in this instance Erythrina alkaloids, using different type of acids. Furthermore, these compounds may be considered potential markers that were selectively extracted through the acid -base extraction process. (c) 2024 SAAB. Published by Elsevier B.V. All rights reserved.
publisher ELSEVIER
issn 0254-6299
1727-9321
publishDate 2024
container_volume 168
container_issue
doi_str_mv 10.1016/j.sajb.2024.03.040
topic Plant Sciences
topic_facet Plant Sciences
accesstype
id WOS:001217769000001
url https://www-webofscience-com.uitm.idm.oclc.org/wos/woscc/full-record/WOS:001217769000001
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