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

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), cleomisc...

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Main Authors: Fang-Pin Chang, Wei Chao, Sheng-Yang Wang, Hui-Chi Huang, Ping-Jyun Sung, Jih-Jung Chen, Ming-Jen Cheng, Guan-Jhong Huang, Yueh-Hsiung Kuo
Format: Article
Language:English
Published: MDPI AG 2018-09-01
Series:Molecules
Subjects:
Neonauclea reticulate
iridoid
neonanin
Hep3B
Online Access:http://www.mdpi.com/1420-3049/23/9/2297
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spelling doaj-6e8c61fde2dc4e22af0437e53fc621bd2020-11-25T02:16:54ZengMDPI AGMolecules1420-30492018-09-01239229710.3390/molecules23092297molecules23092297Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma CellsFang-Pin Chang0Wei Chao1Sheng-Yang Wang2Hui-Chi Huang3Ping-Jyun Sung4Jih-Jung Chen5Ming-Jen Cheng6Guan-Jhong Huang7Yueh-Hsiung Kuo8The Ph.D Program for Cancer Biology and Drug Discovery, China Medical University and Academia Sinica, Taichung 404, TaiwanGraduate Institute of Medical Sciences, College of Medicine, Taipei Medical University, Taipei 250, TaiwanDepartment of Forestry, National Chung Hsing University, Taichung 402, TaiwanDepartment of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, TaiwanNational Museum of Marine Biology and Aquarium, Pingtung 912, TaiwanFaculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei 112, TaiwanBioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, TaiwanDepartment of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, TaiwanThe Ph.D Program for Cancer Biology and Drug Discovery, China Medical University and Academia Sinica, Taichung 404, TaiwanThree 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 EC50 values of 85.36 ± 4.36, 92.63 ± 1.41, and 29.18 ± 3.48 µg/mL against Hep3B cells, respectively.http://www.mdpi.com/1420-3049/23/9/2297Neonauclea reticulateiridoidneonaninHep3B
collection DOAJ
language English
format Article
sources DOAJ
author Fang-Pin Chang
Wei Chao
Sheng-Yang Wang
Hui-Chi Huang
Ping-Jyun Sung
Jih-Jung Chen
Ming-Jen Cheng
Guan-Jhong Huang
Yueh-Hsiung Kuo
spellingShingle Fang-Pin Chang
Wei Chao
Sheng-Yang Wang
Hui-Chi Huang
Ping-Jyun Sung
Jih-Jung Chen
Ming-Jen Cheng
Guan-Jhong Huang
Yueh-Hsiung Kuo
Three New Iridoid Derivatives Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Cytotoxic Activity on Hepatocellular Carcinoma Cells
Molecules
Neonauclea reticulate
iridoid
neonanin
Hep3B
author_facet Fang-Pin Chang
Wei Chao
Sheng-Yang Wang
Hui-Chi Huang
Ping-Jyun Sung
Jih-Jung Chen
Ming-Jen Cheng
Guan-Jhong Huang
Yueh-Hsiung Kuo
author_sort Fang-Pin Chang
title 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_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_sort three new iridoid derivatives have been isolated from the stems of neonauclea reticulata (havil.) merr. with cytotoxic activity on hepatocellular carcinoma cells
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2018-09-01
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 EC50 values of 85.36 ± 4.36, 92.63 ± 1.41, and 29.18 ± 3.48 µg/mL against Hep3B cells, respectively.
topic Neonauclea reticulate
iridoid
neonanin
Hep3B
url http://www.mdpi.com/1420-3049/23/9/2297
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