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Identification and Evaluation of Apoptosis-Inducing Activity of Ipomone from Ipomoea nil: A Novel, Unusual Bicyclo-[3.2.1] Octanone Containing Gibberic Acid Diterpenoid

[Image: see text] Ipomone (1), a novel diterpenoid along with seven known compounds (2–8), was isolated for the first time from the acidified hydroalcoholic extract of Ipomoea nil seeds. The structures of the isolated compounds were elucidated via comprehensive NMR spectroscopic data. The absolute c...

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Autores principales: Goel, Bharat, Chatterjee, Essha, Dey, Biswajit, Tripathi, Nancy, Bhardwaj, Nivedita, Khattri, Arun, Guru, Santosh Kumar, Jain, Shreyans K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8015099/
https://www.ncbi.nlm.nih.gov/pubmed/33817484
http://dx.doi.org/10.1021/acsomega.0c06304
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author Goel, Bharat
Chatterjee, Essha
Dey, Biswajit
Tripathi, Nancy
Bhardwaj, Nivedita
Khattri, Arun
Guru, Santosh Kumar
Jain, Shreyans K.
author_facet Goel, Bharat
Chatterjee, Essha
Dey, Biswajit
Tripathi, Nancy
Bhardwaj, Nivedita
Khattri, Arun
Guru, Santosh Kumar
Jain, Shreyans K.
author_sort Goel, Bharat
collection PubMed
description [Image: see text] Ipomone (1), a novel diterpenoid along with seven known compounds (2–8), was isolated for the first time from the acidified hydroalcoholic extract of Ipomoea nil seeds. The structures of the isolated compounds were elucidated via comprehensive NMR spectroscopic data. The absolute configuration of 1 was ascertained through NOESY, NMR, and ECD analyses. Compound 1 was found to contain an unusual bicyclo-[3.2.1] octanone, which appeared first time in any natural product that might be an artifact resulting from the acid-catalyzed 1,2 alkyl shift/rearrangement. The novel compound was screened for cytotoxic activity against a panel of 12 human cancer cell lines and exhibited weak cytotoxicity with IC(50) values in the range of 34–86 μM (except for HEK-293 cells). Microscopic studies revealed that compound 1 induced apoptosis and autophagy in A549 cells. To further explore the signaling pathway involved, immunoblot analysis was performed that confirmed inhibition of apoptotic proteins PARP-1 and caspase-3 expression and upregulation of LC3B expression by compound 1. The compound was further subjected to molecular docking studies to evaluate its binding affinity with p110α, PARP-1, and caspase-3 proteins.
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spelling pubmed-80150992021-04-02 Identification and Evaluation of Apoptosis-Inducing Activity of Ipomone from Ipomoea nil: A Novel, Unusual Bicyclo-[3.2.1] Octanone Containing Gibberic Acid Diterpenoid Goel, Bharat Chatterjee, Essha Dey, Biswajit Tripathi, Nancy Bhardwaj, Nivedita Khattri, Arun Guru, Santosh Kumar Jain, Shreyans K. ACS Omega [Image: see text] Ipomone (1), a novel diterpenoid along with seven known compounds (2–8), was isolated for the first time from the acidified hydroalcoholic extract of Ipomoea nil seeds. The structures of the isolated compounds were elucidated via comprehensive NMR spectroscopic data. The absolute configuration of 1 was ascertained through NOESY, NMR, and ECD analyses. Compound 1 was found to contain an unusual bicyclo-[3.2.1] octanone, which appeared first time in any natural product that might be an artifact resulting from the acid-catalyzed 1,2 alkyl shift/rearrangement. The novel compound was screened for cytotoxic activity against a panel of 12 human cancer cell lines and exhibited weak cytotoxicity with IC(50) values in the range of 34–86 μM (except for HEK-293 cells). Microscopic studies revealed that compound 1 induced apoptosis and autophagy in A549 cells. To further explore the signaling pathway involved, immunoblot analysis was performed that confirmed inhibition of apoptotic proteins PARP-1 and caspase-3 expression and upregulation of LC3B expression by compound 1. The compound was further subjected to molecular docking studies to evaluate its binding affinity with p110α, PARP-1, and caspase-3 proteins. American Chemical Society 2021-03-15 /pmc/articles/PMC8015099/ /pubmed/33817484 http://dx.doi.org/10.1021/acsomega.0c06304 Text en © 2021 The Authors. Published by American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (https://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Goel, Bharat
Chatterjee, Essha
Dey, Biswajit
Tripathi, Nancy
Bhardwaj, Nivedita
Khattri, Arun
Guru, Santosh Kumar
Jain, Shreyans K.
Identification and Evaluation of Apoptosis-Inducing Activity of Ipomone from Ipomoea nil: A Novel, Unusual Bicyclo-[3.2.1] Octanone Containing Gibberic Acid Diterpenoid
title Identification and Evaluation of Apoptosis-Inducing Activity of Ipomone from Ipomoea nil: A Novel, Unusual Bicyclo-[3.2.1] Octanone Containing Gibberic Acid Diterpenoid
title_full Identification and Evaluation of Apoptosis-Inducing Activity of Ipomone from Ipomoea nil: A Novel, Unusual Bicyclo-[3.2.1] Octanone Containing Gibberic Acid Diterpenoid
title_fullStr Identification and Evaluation of Apoptosis-Inducing Activity of Ipomone from Ipomoea nil: A Novel, Unusual Bicyclo-[3.2.1] Octanone Containing Gibberic Acid Diterpenoid
title_full_unstemmed Identification and Evaluation of Apoptosis-Inducing Activity of Ipomone from Ipomoea nil: A Novel, Unusual Bicyclo-[3.2.1] Octanone Containing Gibberic Acid Diterpenoid
title_short Identification and Evaluation of Apoptosis-Inducing Activity of Ipomone from Ipomoea nil: A Novel, Unusual Bicyclo-[3.2.1] Octanone Containing Gibberic Acid Diterpenoid
title_sort identification and evaluation of apoptosis-inducing activity of ipomone from ipomoea nil: a novel, unusual bicyclo-[3.2.1] octanone containing gibberic acid diterpenoid
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8015099/
https://www.ncbi.nlm.nih.gov/pubmed/33817484
http://dx.doi.org/10.1021/acsomega.0c06304
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