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Cytotoxic and Pro-Apoptotic Effects of Cassane Diterpenoids from the Seeds of Caesalpinia sappan in Cancer Cells
The chemical study on the seeds of Caesalpinia sappan led to the isolation of five new cassane diterpenoids, phanginins R‒T (1–3) and caesalsappanins M and N (4 and 5), together with seven known compounds 6–12. Their structures were elucidated on the basis of NMR and HRESIMS analyses. The absolute c...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2016
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274183/ https://www.ncbi.nlm.nih.gov/pubmed/27322234 http://dx.doi.org/10.3390/molecules21060791 |
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author | Bao, Han Zhang, Le-Le Liu, Qian-Yu Feng, Lu Ye, Yang Lu, Jin-Jian Lin, Li-Gen |
author_facet | Bao, Han Zhang, Le-Le Liu, Qian-Yu Feng, Lu Ye, Yang Lu, Jin-Jian Lin, Li-Gen |
author_sort | Bao, Han |
collection | PubMed |
description | The chemical study on the seeds of Caesalpinia sappan led to the isolation of five new cassane diterpenoids, phanginins R‒T (1–3) and caesalsappanins M and N (4 and 5), together with seven known compounds 6–12. Their structures were elucidated on the basis of NMR and HRESIMS analyses. The absolute configurations of compounds 1 and 4 were determined by the corresponding CD spectra. All the isolated compounds were tested for their cytotoxicity against ovarian cancer A2780 and HEY, gastric cancer AGS, and non-small cell lung cancer A549 cells. Compound 1 displayed significant toxicity against the four cell lines with the IC(50) values of 9.9 ± 1.6 µM, 12.2 ± 6.5 µM, 5.3 ± 1.9 µM, and 12.3 ± 3.1 µM, respectively. Compound 1 induced G1 phase cell cycle arrest in A2780 cells. Furthermore, compound 1 dose-dependently induced A2780 cells apoptosis as evidenced by Hoechst 33342 staining, Annexin V positive cells, the up-regulated cleaved-PARP and the enhanced Bax/Bcl-2 ratio. What’s more, compound 1 also promoted the expression of the tumor suppressor p53 protein. These findings indicate that cassane diterpenoids might have potential as anti-cancer agents, and further in vivo animal studies and structural modification investigation are needed. |
format | Online Article Text |
id | pubmed-6274183 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62741832018-12-28 Cytotoxic and Pro-Apoptotic Effects of Cassane Diterpenoids from the Seeds of Caesalpinia sappan in Cancer Cells Bao, Han Zhang, Le-Le Liu, Qian-Yu Feng, Lu Ye, Yang Lu, Jin-Jian Lin, Li-Gen Molecules Article The chemical study on the seeds of Caesalpinia sappan led to the isolation of five new cassane diterpenoids, phanginins R‒T (1–3) and caesalsappanins M and N (4 and 5), together with seven known compounds 6–12. Their structures were elucidated on the basis of NMR and HRESIMS analyses. The absolute configurations of compounds 1 and 4 were determined by the corresponding CD spectra. All the isolated compounds were tested for their cytotoxicity against ovarian cancer A2780 and HEY, gastric cancer AGS, and non-small cell lung cancer A549 cells. Compound 1 displayed significant toxicity against the four cell lines with the IC(50) values of 9.9 ± 1.6 µM, 12.2 ± 6.5 µM, 5.3 ± 1.9 µM, and 12.3 ± 3.1 µM, respectively. Compound 1 induced G1 phase cell cycle arrest in A2780 cells. Furthermore, compound 1 dose-dependently induced A2780 cells apoptosis as evidenced by Hoechst 33342 staining, Annexin V positive cells, the up-regulated cleaved-PARP and the enhanced Bax/Bcl-2 ratio. What’s more, compound 1 also promoted the expression of the tumor suppressor p53 protein. These findings indicate that cassane diterpenoids might have potential as anti-cancer agents, and further in vivo animal studies and structural modification investigation are needed. MDPI 2016-06-18 /pmc/articles/PMC6274183/ /pubmed/27322234 http://dx.doi.org/10.3390/molecules21060791 Text en © 2016 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 Bao, Han Zhang, Le-Le Liu, Qian-Yu Feng, Lu Ye, Yang Lu, Jin-Jian Lin, Li-Gen Cytotoxic and Pro-Apoptotic Effects of Cassane Diterpenoids from the Seeds of Caesalpinia sappan in Cancer Cells |
title | Cytotoxic and Pro-Apoptotic Effects of Cassane Diterpenoids from the Seeds of Caesalpinia sappan in Cancer Cells |
title_full | Cytotoxic and Pro-Apoptotic Effects of Cassane Diterpenoids from the Seeds of Caesalpinia sappan in Cancer Cells |
title_fullStr | Cytotoxic and Pro-Apoptotic Effects of Cassane Diterpenoids from the Seeds of Caesalpinia sappan in Cancer Cells |
title_full_unstemmed | Cytotoxic and Pro-Apoptotic Effects of Cassane Diterpenoids from the Seeds of Caesalpinia sappan in Cancer Cells |
title_short | Cytotoxic and Pro-Apoptotic Effects of Cassane Diterpenoids from the Seeds of Caesalpinia sappan in Cancer Cells |
title_sort | cytotoxic and pro-apoptotic effects of cassane diterpenoids from the seeds of caesalpinia sappan in cancer cells |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274183/ https://www.ncbi.nlm.nih.gov/pubmed/27322234 http://dx.doi.org/10.3390/molecules21060791 |
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