Derivatization of cassane diterpenoids from Caesalpinia puicherrima (L) Sw. and evaluation of their cytotoxic and leishmanicidal activities

被引:10
|
作者
Erharuyi, Osayemwenre [1 ,2 ]
Adhikari, Achyut [2 ]
Falodun, Abiodun [1 ]
Imad, Rehan [3 ]
Choudhary, M. Iqbal [2 ,4 ]
机构
[1] Univ Benin, Fac Pharm, Dept Pharmaceut Chem, Benin, Nigeria
[2] Univ Karachi, Int Ctr Chem & Biol Sci, HEJ Res Inst Chem, Karachi 75270, Pakistan
[3] Univ Karachi, Int Ctr Chem & Biol Sci, Dr Panjwani Ctr Mol Med & Drug Res, Karachi 75270, Pakistan
[4] King Abdulaziz Univ, Fac Sci, Dept Biochem, Jeddah 21412, Saudi Arabia
关键词
Caesalpinia pulcherrima; Cassane diterpenoids; Oxidation; Cancer cell lines; Cytotoxicity; Leishmanicidal activity; PULCHERRIMA;
D O I
10.1016/j.tetlet.2016.04.030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidation of the cassane diterpenoids 6 beta-cinnamoyl-7 alpha-hydroxyvouacapen-5 alpha-ol (1) and pulcherrimin A (2), which were isolated from the roots of Caesalpinia pulcherrima, yielded four new derivatives 3-6. The structures of the new compounds were confirmed on the basis of 1D and 2D NMR spectroscopy as well as mass spectrometry. The derivatives were tested for their cytotoxic activity against three cancer cell lines (MCF-7, HeLa, and PC-3) and their leishmanicidal activity against Leishmania major. Compound 4 showed cytotoxic activity against all cell lines (IC50 = 5.67 +/- 0.07, 3.16 +/- 0.16, and 7.90 +/- 1.60 mu M against MCF-7, HeLa, and PC-3, respectively), and was 2-3 times more active than the parent compound 1. Compound 6 showed significant leishmanicidal activity (IC50 = 9.18 +/- 0.48 mu g/mL), whereas the parent compound 2 was inactive.
引用
收藏
页码:2201 / 2206
页数:6
相关论文
共 31 条
  • [1] Cytotoxic cassane diterpenoids from the seeds of Caesalpinia sappan
    Zheng-Feng Wu
    Han Bao
    Fa-Yang Zhou
    Jing-Xin Liu
    Fan-Cheng Meng
    Lu Feng
    Jin-Jian Lu
    Qing-Wen Zhang
    Yang Ye
    Li-Gen Lin
    ChineseChemicalLetters, 2017, 28 (08) : 1711 - 1715
  • [2] Cytotoxic cassane diterpenoids from the seeds of Caesalpinia sappan
    Wu, Zheng-Feng
    Bao, Han
    Zhou, Fa-Yang
    Liu, Jing-Xin
    Meng, Fan-Cheng
    Feng, Lu
    Lu, Jin-Jian
    Zhang, Qing-Wen
    Ye, Yang
    Lin, Li-Gen
    CHINESE CHEMICAL LETTERS, 2017, 28 (08) : 1711 - 1715
  • [3] Guided Isolation of New Cytotoxic Cassane Diterpenoids from Caesalpinia sappan
    Jin, Yue
    Tong, Zi-Wei
    Gao, Hui-Yuan
    Wu, Zhao-Hua
    CHEMISTRY & BIODIVERSITY, 2023, 20 (05)
  • [4] Bridged cassane derivatives from the seeds of Caesalpinia sappan L. and their cytotoxic activities
    Jin, Yue
    Wang, Miao
    Yan, Yan-Fang
    Zhang, Xin-Xin
    Li, Xian-Zhe
    Gao, Hui-Yuan
    PHYTOCHEMISTRY, 2022, 197
  • [5] Caesalminaxins A-L, Cassane Diterpenoids from the Seeds of Caesalpinia minax
    Zheng, Yong
    Zhang, Shu-Wei
    Cong, Hai-Jian
    Huang, Yu-Jie
    Xuan, Li-Jiang
    JOURNAL OF NATURAL PRODUCTS, 2013, 76 (12): : 2210 - 2218
  • [6] Cassane diterpenoids from Caesalpinia pulcherrima and their anti-inflammatory and α-glycosidase inhibitory activities
    Yun, Xin
    Chen, Xiu-Mei
    Wang, Jia-Yun
    Lu, Wang
    Zhang, Zi-Han
    Kim, Young Ho
    Zong, Shi-Chun
    Li, Chun-Huan
    Gao, Jin-Ming
    NATURAL PRODUCT RESEARCH, 2022, 36 (18) : 4636 - 4644
  • [7] 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, 2016, 21 (06)
  • [8] Cassane diterpenoids from the seeds of Caesalpinia bonduc and their nitric oxide production and α-glucosidase inhibitory activities
    Tu, Wen-Chao
    Ding, Lin-Fen
    Peng, Li-Yan
    Song, Liu-Dong
    Wu, Xing-De
    Zhao, Qin-Shi
    PHYTOCHEMISTRY, 2022, 193
  • [9] Cassane-Type Diterpenoids from the Seeds of Caesalpinia bonduc (L.) Roxb.
    Cao, Jun
    Xu, Yunshao
    Lou, Ruohan
    Shi, Wei
    Chen, Jiali
    Gan, Lishe
    Lu, Jinjian
    Lin, Ligen
    CHEMISTRY & BIODIVERSITY, 2021, 18 (09)
  • [10] Cassane-type diterpenoids from Caesalpinia echinata (Leguminosae) and their NF-κB signaling inhibition activities
    Mitsui, Taichi
    Ishihara, Risa
    Hayashi, Ken-ichiro
    Matsuura, Nobuyasu
    Akashi, Haruo
    Nozaki, Hiroshi
    PHYTOCHEMISTRY, 2015, 116 : 349 - 358