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Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma Cells

Three new iridoids, namely neonanin A (1), neonanin B (2) and neoretinin A (3), as well as twelve known compounds, 6-hydroxy-7-methyl-1-oxo-4-carbomethoxyoctahydrocyclopenta[c]pyran (4), 4-epi-alyxialactone (5), loganetin (6), loganin (7), phenylcoumaran-α′-aldehyde (8), cleomiscosin A (9), ficusal...

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Autores principales: Chang, Fang-Pin, Chao, Wei, Wang, Sheng-Yang, Huang, Hui-Chi, Sung, Ping-Jyun, Chen, Jih-Jung, Cheng, Ming-Jen, Huang, Guan-Jhong, Kuo, Yueh-Hsiung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225429/
https://www.ncbi.nlm.nih.gov/pubmed/30205569
http://dx.doi.org/10.3390/molecules23092297
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author Chang, Fang-Pin
Chao, Wei
Wang, Sheng-Yang
Huang, Hui-Chi
Sung, Ping-Jyun
Chen, Jih-Jung
Cheng, Ming-Jen
Huang, Guan-Jhong
Kuo, Yueh-Hsiung
author_facet Chang, Fang-Pin
Chao, Wei
Wang, Sheng-Yang
Huang, Hui-Chi
Sung, Ping-Jyun
Chen, Jih-Jung
Cheng, Ming-Jen
Huang, Guan-Jhong
Kuo, Yueh-Hsiung
author_sort Chang, Fang-Pin
collection PubMed
description Three new iridoids, namely neonanin A (1), neonanin B (2) and neoretinin A (3), as well as twelve known compounds, 6-hydroxy-7-methyl-1-oxo-4-carbomethoxyoctahydrocyclopenta[c]pyran (4), 4-epi-alyxialactone (5), loganetin (6), loganin (7), phenylcoumaran-α′-aldehyde (8), cleomiscosin A (9), ficusal (10), balanophonin (11), vanillic acid (12), p-coumaric acid (13), cis,trans-abscisic acid (14), and trans,trans-abscisic acid (15) were isolated from the stems of Neonauclea reticulata (Havil.) Merr. These new structures were determined by the detailed analysis of spectroscopic data and comparison with the data of known analogues. Compounds 1–13 were evaluated using an in-vitro MTT cytotoxic assay for hepatocellular carcinoma (HCC) cells, and the preliminary results showed that ficusal (10), balanophonin (11), and p-coumaric acid (13) exhibited moderate cytotoxic activity, with EC(50) values of 85.36 ± 4.36, 92.63 ± 1.41, and 29.18 ± 3.48 µg/mL against Hep3B cells, respectively.
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spelling pubmed-62254292018-11-13 Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma Cells Chang, Fang-Pin Chao, Wei Wang, Sheng-Yang Huang, Hui-Chi Sung, Ping-Jyun Chen, Jih-Jung Cheng, Ming-Jen Huang, Guan-Jhong Kuo, Yueh-Hsiung Molecules Article Three new iridoids, namely neonanin A (1), neonanin B (2) and neoretinin A (3), as well as twelve known compounds, 6-hydroxy-7-methyl-1-oxo-4-carbomethoxyoctahydrocyclopenta[c]pyran (4), 4-epi-alyxialactone (5), loganetin (6), loganin (7), phenylcoumaran-α′-aldehyde (8), cleomiscosin A (9), ficusal (10), balanophonin (11), vanillic acid (12), p-coumaric acid (13), cis,trans-abscisic acid (14), and trans,trans-abscisic acid (15) were isolated from the stems of Neonauclea reticulata (Havil.) Merr. These new structures were determined by the detailed analysis of spectroscopic data and comparison with the data of known analogues. Compounds 1–13 were evaluated using an in-vitro MTT cytotoxic assay for hepatocellular carcinoma (HCC) cells, and the preliminary results showed that ficusal (10), balanophonin (11), and p-coumaric acid (13) exhibited moderate cytotoxic activity, with EC(50) values of 85.36 ± 4.36, 92.63 ± 1.41, and 29.18 ± 3.48 µg/mL against Hep3B cells, respectively. MDPI 2018-09-08 /pmc/articles/PMC6225429/ /pubmed/30205569 http://dx.doi.org/10.3390/molecules23092297 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Chang, Fang-Pin
Chao, Wei
Wang, Sheng-Yang
Huang, Hui-Chi
Sung, Ping-Jyun
Chen, Jih-Jung
Cheng, Ming-Jen
Huang, Guan-Jhong
Kuo, Yueh-Hsiung
Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma Cells
title Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma Cells
title_full Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma Cells
title_fullStr Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma Cells
title_full_unstemmed Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma Cells
title_short Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma Cells
title_sort three new iridoid derivatives have been isolated from the stems of neonauclea reticulata (havil.) merr. with cytotoxic activity on hepatocellular carcinoma cells
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225429/
https://www.ncbi.nlm.nih.gov/pubmed/30205569
http://dx.doi.org/10.3390/molecules23092297
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