Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity

[Image: see text] Seven previously undescribed compounds, including five pyranonaphthoquinones (ventilanones L–P) and two naphthoquinones (ventilanones Q and R), along with 15 known compounds were isolated from the stem bark of Ventilago harmandiana (Rhamnaceae). The structures were established by e...

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Autores principales: Saisin, Suwannee, Panthong, Kanda, Hongthong, Sakchai, Kuhakarn, Chutima, Thanasansurapong, Sariyarach, Chairoungdua, Arthit, Suksen, Kanoknetr, Akkarawongsapat, Radeekorn, Napaswad, Chanita, Prabpai, Samran, Nuntasaen, Narong, Reutrakul, Vichai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10043937/
https://www.ncbi.nlm.nih.gov/pubmed/36787536
http://dx.doi.org/10.1021/acs.jnatprod.2c00980
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author Saisin, Suwannee
Panthong, Kanda
Hongthong, Sakchai
Kuhakarn, Chutima
Thanasansurapong, Sariyarach
Chairoungdua, Arthit
Suksen, Kanoknetr
Akkarawongsapat, Radeekorn
Napaswad, Chanita
Prabpai, Samran
Nuntasaen, Narong
Reutrakul, Vichai
author_facet Saisin, Suwannee
Panthong, Kanda
Hongthong, Sakchai
Kuhakarn, Chutima
Thanasansurapong, Sariyarach
Chairoungdua, Arthit
Suksen, Kanoknetr
Akkarawongsapat, Radeekorn
Napaswad, Chanita
Prabpai, Samran
Nuntasaen, Narong
Reutrakul, Vichai
author_sort Saisin, Suwannee
collection PubMed
description [Image: see text] Seven previously undescribed compounds, including five pyranonaphthoquinones (ventilanones L–P) and two naphthoquinones (ventilanones Q and R), along with 15 known compounds were isolated from the stem bark of Ventilago harmandiana (Rhamnaceae). The structures were established by extensive analysis of their spectroscopic data. The absolute configuration of ventilanone L was established from single crystal X-ray crystallographic analysis using Cu Kα radiation and from its electronic circular dichroism data. Anti-HIV-1 activity using a syncytium inhibition assay and the cytotoxic activities of some isolated compounds were evaluated. Compounds 12, 13, 15, and 16 showed activity against syncytium formation with half maximal effective concentration (EC(50)) values ranging from 9.9 to 47 μM (selectivity index (SI) 2.4–4.5).
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spelling pubmed-100439372023-03-29 Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity Saisin, Suwannee Panthong, Kanda Hongthong, Sakchai Kuhakarn, Chutima Thanasansurapong, Sariyarach Chairoungdua, Arthit Suksen, Kanoknetr Akkarawongsapat, Radeekorn Napaswad, Chanita Prabpai, Samran Nuntasaen, Narong Reutrakul, Vichai J Nat Prod [Image: see text] Seven previously undescribed compounds, including five pyranonaphthoquinones (ventilanones L–P) and two naphthoquinones (ventilanones Q and R), along with 15 known compounds were isolated from the stem bark of Ventilago harmandiana (Rhamnaceae). The structures were established by extensive analysis of their spectroscopic data. The absolute configuration of ventilanone L was established from single crystal X-ray crystallographic analysis using Cu Kα radiation and from its electronic circular dichroism data. Anti-HIV-1 activity using a syncytium inhibition assay and the cytotoxic activities of some isolated compounds were evaluated. Compounds 12, 13, 15, and 16 showed activity against syncytium formation with half maximal effective concentration (EC(50)) values ranging from 9.9 to 47 μM (selectivity index (SI) 2.4–4.5). American Chemical Society and American Society of Pharmacognosy 2023-02-14 /pmc/articles/PMC10043937/ /pubmed/36787536 http://dx.doi.org/10.1021/acs.jnatprod.2c00980 Text en © 2023 The Authors. Published by American Chemical Society and American Society of Pharmacognosy https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Saisin, Suwannee
Panthong, Kanda
Hongthong, Sakchai
Kuhakarn, Chutima
Thanasansurapong, Sariyarach
Chairoungdua, Arthit
Suksen, Kanoknetr
Akkarawongsapat, Radeekorn
Napaswad, Chanita
Prabpai, Samran
Nuntasaen, Narong
Reutrakul, Vichai
Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity
title Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity
title_full Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity
title_fullStr Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity
title_full_unstemmed Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity
title_short Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity
title_sort pyranonaphthoquinones and naphthoquinones from the stem bark of ventilago harmandiana and their anti-hiv-1 activity
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10043937/
https://www.ncbi.nlm.nih.gov/pubmed/36787536
http://dx.doi.org/10.1021/acs.jnatprod.2c00980
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