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Study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of Millettia pyrrhocarpa Mattapha, Forest & Hawkins, sp. Nov

BACKGROUND: M. pyrrhocarpa is a new plant in the Fabaceae: Faboideae family that is found in Thailand. A literature search revealed that the Milletia genus is rich in bioactive compounds possessing a wide range of biological activities. In this study, we aimed to isolate novel bioactive compounds an...

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Autores principales: Sananboonudom, Suda, Kaewnoi, Atchara, Pompimon, Wilart, Narakaew, Samroeng, Jiajaroen, Suwadee, Chainok, Kittipong, nuntasaen, Narong, Suksen, Kanoknetr, Chairoungdua, Arthit, Limthongkul, Jitra, Naparswad, Chanita, Pikulthong, Suttiporn, Meepowpan, Puttinan, Wingwon, Boonthawan, Charoenphakinrattana, Nichapa, Udomputtimekakul, Phansuang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: BioMed Central 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10161675/
https://www.ncbi.nlm.nih.gov/pubmed/37143007
http://dx.doi.org/10.1186/s12906-023-03963-4
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author Sananboonudom, Suda
Kaewnoi, Atchara
Pompimon, Wilart
Narakaew, Samroeng
Jiajaroen, Suwadee
Chainok, Kittipong
nuntasaen, Narong
Suksen, Kanoknetr
Chairoungdua, Arthit
Limthongkul, Jitra
Naparswad, Chanita
Pikulthong, Suttiporn
Meepowpan, Puttinan
Wingwon, Boonthawan
Charoenphakinrattana, Nichapa
Udomputtimekakul, Phansuang
author_facet Sananboonudom, Suda
Kaewnoi, Atchara
Pompimon, Wilart
Narakaew, Samroeng
Jiajaroen, Suwadee
Chainok, Kittipong
nuntasaen, Narong
Suksen, Kanoknetr
Chairoungdua, Arthit
Limthongkul, Jitra
Naparswad, Chanita
Pikulthong, Suttiporn
Meepowpan, Puttinan
Wingwon, Boonthawan
Charoenphakinrattana, Nichapa
Udomputtimekakul, Phansuang
author_sort Sananboonudom, Suda
collection PubMed
description BACKGROUND: M. pyrrhocarpa is a new plant in the Fabaceae: Faboideae family that is found in Thailand. A literature search revealed that the Milletia genus is rich in bioactive compounds possessing a wide range of biological activities. In this study, we aimed to isolate novel bioactive compounds and to study their bioactivities. METHODS: The hexane, ethyl acetate, and methanol extracts from the leaves and twigs of M. pyrrhocarpa were isolated and purified using chromatography techniques. These extracts and pure compounds were tested in vitro for their inhibitory activities against nine strains of bacteria, as well as their anti-HIV-1 virus activity and cytotoxicity against eight cancer cell lines. RESULTS: Three rotenoids, named 6aS, 12aS, 12S-elliptinol (1), 6aS, 12aS, 12S-munduserol (2), dehydromunduserone (3), and crude extracts were evaluated for antibacterial, anti-HIV, and cytotoxic activities. It was found that compounds 1–3 inhibited the growth of nine strains of bacteria, and the best MIC/MBC values were obtained at 3/ > 3 mg/mL. The hexane extract showed anti-HIV-1 RT with the highest %inhibition at 81.27 at 200 mg/mL, while 6aS, 12aS, 12S-elliptinol (1) reduced syncytium formation in 1A2 cells with a maximum EC(50) value of 4.48 μM. Furthermore, 6aS, 12aS, 12S-elliptinol (1) showed cytotoxicity against A549 and Hep G2 cells with maximum ED(50) values of 2.27 and 3.94 μg/mL. CONCLUSION: This study led to the isolation of constituents with potential for medicinal application, providing compounds (1–3) as lead compounds against nine strains of bacteria. The hexane extract showed the highest %inhibition of HIV-1 virus, Compound 1 showed the best EC(50) in reducing syncytium formation in 1A2 cells, and it also showed the best ED(50) against human lung adenocarcinoma (A549) and human hepatocellular carcinoma (Hep G2). The isolated compounds from M. pyrrhocarpa offered significant potential for future medicinal application studies. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s12906-023-03963-4.
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spelling pubmed-101616752023-05-06 Study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of Millettia pyrrhocarpa Mattapha, Forest & Hawkins, sp. Nov Sananboonudom, Suda Kaewnoi, Atchara Pompimon, Wilart Narakaew, Samroeng Jiajaroen, Suwadee Chainok, Kittipong nuntasaen, Narong Suksen, Kanoknetr Chairoungdua, Arthit Limthongkul, Jitra Naparswad, Chanita Pikulthong, Suttiporn Meepowpan, Puttinan Wingwon, Boonthawan Charoenphakinrattana, Nichapa Udomputtimekakul, Phansuang BMC Complement Med Ther Research BACKGROUND: M. pyrrhocarpa is a new plant in the Fabaceae: Faboideae family that is found in Thailand. A literature search revealed that the Milletia genus is rich in bioactive compounds possessing a wide range of biological activities. In this study, we aimed to isolate novel bioactive compounds and to study their bioactivities. METHODS: The hexane, ethyl acetate, and methanol extracts from the leaves and twigs of M. pyrrhocarpa were isolated and purified using chromatography techniques. These extracts and pure compounds were tested in vitro for their inhibitory activities against nine strains of bacteria, as well as their anti-HIV-1 virus activity and cytotoxicity against eight cancer cell lines. RESULTS: Three rotenoids, named 6aS, 12aS, 12S-elliptinol (1), 6aS, 12aS, 12S-munduserol (2), dehydromunduserone (3), and crude extracts were evaluated for antibacterial, anti-HIV, and cytotoxic activities. It was found that compounds 1–3 inhibited the growth of nine strains of bacteria, and the best MIC/MBC values were obtained at 3/ > 3 mg/mL. The hexane extract showed anti-HIV-1 RT with the highest %inhibition at 81.27 at 200 mg/mL, while 6aS, 12aS, 12S-elliptinol (1) reduced syncytium formation in 1A2 cells with a maximum EC(50) value of 4.48 μM. Furthermore, 6aS, 12aS, 12S-elliptinol (1) showed cytotoxicity against A549 and Hep G2 cells with maximum ED(50) values of 2.27 and 3.94 μg/mL. CONCLUSION: This study led to the isolation of constituents with potential for medicinal application, providing compounds (1–3) as lead compounds against nine strains of bacteria. The hexane extract showed the highest %inhibition of HIV-1 virus, Compound 1 showed the best EC(50) in reducing syncytium formation in 1A2 cells, and it also showed the best ED(50) against human lung adenocarcinoma (A549) and human hepatocellular carcinoma (Hep G2). The isolated compounds from M. pyrrhocarpa offered significant potential for future medicinal application studies. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s12906-023-03963-4. BioMed Central 2023-05-04 /pmc/articles/PMC10161675/ /pubmed/37143007 http://dx.doi.org/10.1186/s12906-023-03963-4 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/ (https://creativecommons.org/publicdomain/zero/1.0/) ) applies to the data made available in this article, unless otherwise stated in a credit line to the data.
spellingShingle Research
Sananboonudom, Suda
Kaewnoi, Atchara
Pompimon, Wilart
Narakaew, Samroeng
Jiajaroen, Suwadee
Chainok, Kittipong
nuntasaen, Narong
Suksen, Kanoknetr
Chairoungdua, Arthit
Limthongkul, Jitra
Naparswad, Chanita
Pikulthong, Suttiporn
Meepowpan, Puttinan
Wingwon, Boonthawan
Charoenphakinrattana, Nichapa
Udomputtimekakul, Phansuang
Study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of Millettia pyrrhocarpa Mattapha, Forest & Hawkins, sp. Nov
title Study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of Millettia pyrrhocarpa Mattapha, Forest & Hawkins, sp. Nov
title_full Study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of Millettia pyrrhocarpa Mattapha, Forest & Hawkins, sp. Nov
title_fullStr Study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of Millettia pyrrhocarpa Mattapha, Forest & Hawkins, sp. Nov
title_full_unstemmed Study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of Millettia pyrrhocarpa Mattapha, Forest & Hawkins, sp. Nov
title_short Study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of Millettia pyrrhocarpa Mattapha, Forest & Hawkins, sp. Nov
title_sort study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of millettia pyrrhocarpa mattapha, forest & hawkins, sp. nov
topic Research
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10161675/
https://www.ncbi.nlm.nih.gov/pubmed/37143007
http://dx.doi.org/10.1186/s12906-023-03963-4
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