Citation: Wu Zheng-Feng, Bao Han, Zhou Fa-Yang, Liu Jing-Xin, Meng Fan-Cheng, Lu Feng, Lu Jin-Jian, Zhang Qing-Wen, Ye Yang, Lin Li-Gen. Cytotoxic cassane diterpenoids from the seeds of Caesalpinia sappan[J]. Chinese Chemical Letters, ;2017, 28(8): 1711-1715. doi: 10.1016/j.cclet.2017.04.023 shu

Cytotoxic cassane diterpenoids from the seeds of Caesalpinia sappan

a.
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao 999078, China
b.
State Key Laboratory of Drug Research, and Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhangjiang Hi-Tech Park, Shanghai 201203, China

Corresponding author: Lin Li-Gen, ligenl@umac.mo
Received Date: 20 January 2017
Revised Date: 28 March 2017
Accepted Date: 17 April 2017
Available Online: 21 August 2017

Figures(3)

Phytochemical investigation on the seeds of Caesalpinia sappan led to the isolation of five new cassanetype diterpenoids, named 11-oxo-phanginin A (1), caesalsappanins O-Q (2-4) and phanginin U (5), together with five known compounds. The structures of the new compounds were elucidated by extensive analysis of mass spectrometric and 1D and 2D NMR spectroscopic data. All the new compounds showed moderate cytotoxic effects on human breast cancer MCF-7 and human colon cancer HCT116 cell lines.
- Caesalpinia sappan,
- Cassane diterpenoid,
- Phanginin,
- Caesalsappanin,
- Cytotoxicity
1. [1]
  Editorial Board of Flora of China, vol. 39, Science Press, Beijing, 1988 pp.105.
2. [2]
  Badami S., Rai S.R., Moorkoth S., Rajan S., Suresh B.. Pharmacognostical evaluation of Caesalpinia sappan heartwood[J]. Anc. Sci. Life, 2003,23:100-107.
3. [3]
  Wang D., Chen C., Zhou Y.. The research progress of clinical pharmacology and chemical constituents from Caesalpinia sappan L[J]. Inf. Tradit. Chin. Med., 2003,20:15-16.
4. [4]
  Gómez-Hurtado M.A., Álvarez-Esquivel F.E., Rodríguez-García G.. Cassane diterpenes from Caesalpinia platyloba[J]. Phytochemistry, 2013,96:397-403. doi: 10.1016/j.phytochem.2013.09.028
5. [5]
  Pranithanchai W., Karalai C., Ponglimanont C., Subhadhirasakul S., Chantrapromma K.. Cassane diterpenoids from the stem of Caesalpinia pulcherrima[J]. Phytochemistry, 2009,70:300-304. doi: 10.1016/j.phytochem.2008.12.006
6. [6]
  Yodsaoue O., Karalai C., Ponglimanont C., Tewtrakul S., Chantrapromma S.. Potential anti-inflammatory diterpenoids from the roots of Caesalpinia mimosoides Lamk[J]. Phytochemistry, 2010,71:1756-1764. doi: 10.1016/j.phytochem.2010.06.016
7. [7]
  Zanin J.L.B., De Carvalho B.A., Salles Martineli P.. The genus Caesalpinia L. (Caesalpiniaceae):phytochemical and pharmacological characteristics[J]. Molecules, 2012,17:7887-7902.
8. [8]
  Bao H., Zhang L.L., Liu Q.Y.. Cytotoxic and pro-apoptotic effects of cassane diterpenoids from the seeds of Caesalpinia sappan in cancer cells[J]. Molecules, 2016,21791.
9. [9]
  Xu Y.J., Zhang J., Tang C.P., Ye Y.. A new diterpenoid from the seeds of Caesalpinia sappan Linn[J]. Rec. Nat. Prod., 2013,7:124-128.
10. [10]
  Xiao F., Tang C.P., Ke C.Q., Yao S., Ye Y.. Rearranged diterpenoids from the seeds of Caesalpinia sappan[J]. Chin. Chem. Lett., 2016,27:1751-1754. doi: 10.1016/j.cclet.2016.04.022
11. [11]
  Bao H., Zhang Q.W., Ye Y., Lin L.. Naturally occurring furanoditerpenoids:distribution, chemistry and their pharmacological activities[J]. Phytochem. Rev., 2016,16:235-270.
12. [12]
  Yodsaoue O., Cheenpracha S., Karalai C.. Phanginin A-K, diterpenoids from the seeds of Caesalpinia sappan Linn[J]. Phytochemistry, 2008,69:1242-1249. doi: 10.1016/j.phytochem.2007.11.013
13. [13]
  Ma G.X., Wu H.F., Chen D.L.. Antimalarial and antiproliferative cassane diterpenes of Caesalpinia sappan[J]. J. Nat. Prod., 2015,78:2364-2371. doi: 10.1021/acs.jnatprod.5b00317
14. [14]
  Zheng Y., Zhang S.W., Cong H.J., Huang Y.J., Xuan L.J.. Caesalminaxins A-L, cassane diterpenoids from the seeds of Caesalpinia minax[J]. J. Nat. Prod., 2013,76:2210-2218. doi: 10.1021/np400545v
15. [15]
  Nguyen H.X., Nguyen N.T., Dang P.H.. Cassane diterpenes from the seed kernels of Caesalpinia sappan[J]. Phytochemistry, 2016,122:286-293. doi: 10.1016/j.phytochem.2015.12.018
16. [16]
  Deng Z.T., Su J., Ding L.F.. Six new cassane diterpenoids from the seeds of Caesalpinia sappan[J]. Phytochem. Lett., 2016,16:207-212. doi: 10.1016/j.phytol.2016.04.014
1. [1]
  Jin Wang , Xiaoyan Pan , Junyu Zhang , Qingqing Zhang , Yanchen Li , Weiwei Guo , Jie Zhang . Active molecule-based theranostic agents for tumor vasculature normalization and antitumor efficacy. Chinese Chemical Letters, 2024, 35(8): 109187-. doi: 10.1016/j.cclet.2023.109187
2. [2]
  Chuan Li , Yangyang Han , Yanan Zhai , Ke Li , Xingzhong Liu , Zhuan Zhang , Cai Jia , Yongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019
3. [3]
  Jing JIN , Zhuming GUO , Zhiyin XIAO , Xiujuan JIANG , Yi HE , Xiaoming LIU . Tuning the stability and cytotoxicity of fac-[Fe(CO)₃I₃]^- anion by its counter ions: From aminiums to inorganic cations. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 991-1004. doi: 10.11862/CJIC.20230458

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(734)
HTML views(11)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return