Semisynthesis and Cytotoxic Activities of Novel Oxime Ester Derivatives of the Diterpene Stemodin

被引：0
|
作者：
de Oliveira, Jose Augusto C. [1 ]
Filho, Carlos Jose Alves [1 ]
Lima, Antonio Marcelo A. [1 ]
Pessoa, Claudia do O. [2 ]
de Oliveira, Fatima de Cassia E. [2 ]
Miranda, Fatima N. [1 ]
de Mattos, Marcos Carlos [1 ]
Oliveira, Maria Conceicao F. [1 ]
Mafezoli, Jair [1 ]
Barbosa, Francisco Geraldo [1 ]
机构：
[1] Univ Fed Ceara, Ctr Ciencias, Dept Quim Organ & Inorgan, Campus Pici, BR-60440900 Fortaleza, CE, Brazil
[2] Univ Fed Ceara, Dept Fisiol & Farmacol, BR-60430270 Fortaleza, CE, Brazil
来源：
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2024年 / 35卷 / 06期
关键词：
Stemodia maritima; stemodin; chemical derivatives; cytotoxicity; BIOTRANSFORMATION; METABOLITES; ANALOGS;
D O I：
10.21577/0103-5053.20230193
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Stemodin (1) is a diterpene produced by Stemodia maritima L. (Scrophulariaceae) and shows antiviral and tumor cell proliferation inhibitory activities. Chemical modifications of 1 were performed to produce the known stemodinone (2), two new stemodinone oximes, Z (3) and E (4), and seven new oxime esters derivatives (5, 6, 7, 8, 9, 10, and 11). All derivatives were evaluated for their cytotoxic activity in HL60 (promyelocytic leukemia), SNB-19 (astrocytoma), HCT-116 (colon carcinoma), and PC3 (prostate) human cancer cell lines, and L929 (healthy murine cells). Oximes 3 and 4 showed lower cytotoxic values than 1 against all cancer cell lines tested. However, esters 9 and 10 exhibited cell growth inhibition percentages higher than 1 against PC3, SNB-19, and HCT-116 cancer cell lines, ranging from 62.96 to 94.27%. Many of these values exceed that presented by doxorubicin (66.05-86.87%). All compounds showed no cytotoxic effect on healthy cells at the tested concentration of 25 mu g mL-1.
引用
收藏
页数：8
相关论文
共 50 条
  • [21] Synthesis and Biological Activities of Hydroxytyrosol Ester Derivatives
    Zang, Hao
    Xu, Qian
    Zhang, Luyun
    Xia, Guangqing
    Sun, Jiaming
    Zhu, Junyi
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2020, 42 (01): : 109 - 119
  • [22] Cytotoxic and trypanocidal activities of cinchona alkaloid derivatives
    Kacprzak, Karol
    Ruszkowski, Piotr
    Valentini, Luisa
    Huczynski, Adam
    Steverding, Dietmar
    CHEMICAL BIOLOGY & DRUG DESIGN, 2018, 92 (04) : 1778 - 1787
  • [23] Semisynthesis, Cytotoxic Activity, and Oral Availability of New Lipophilic 9-Substituted Camptothecin Derivatives
    Rodriguez-Berna, Guillermo
    Diaz Cabanas, Maria Jose
    Mangas-Sanjuan, Victor
    Gonzalez-Alvarez, Marta
    Gonzalez-Alvarez, Isabel
    Abasolo, Ibane
    Schwartz, Simo, Jr.
    Bermejo, Marival
    Corma, Avelino
    ACS MEDICINAL CHEMISTRY LETTERS, 2013, 4 (07): : 86 - 90
  • [24] Synthesis and cytotoxic activities of β-carboline amino acid ester conjugates
    Zhao, Ming
    Bi, Lanrong
    Wang, Wei
    Wang, Chao
    Baudy-Floc'h, Michele
    Ju, Jingfang
    Peng, Shiqi
    BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (20) : 6998 - 7010
  • [25] NATURAL-PRODUCT-BASED INSECTICIDAL AGENTS 16. SEMISYNTHESIS OF C7-OXIME SULFONATE ESTER DERIVATIVES OF OBACUNONE AS INSECTICIDAL AGENTS AGAINST MYTHIMNA SEPARATA WALKER
    Yu, Xiang
    Ding, Guodong
    Gao, Zhinan
    Zha, Jing
    Xu, Hui
    HETEROCYCLES, 2015, 90 (02) : 1367 - 1374
  • [26] Discovery of novel NO-releasing celastrol derivatives with Hsp90 inhibition and cytotoxic activities
    Li, Na
    Xu, Manyi
    Bao, Na
    Shi, Wei
    Li, Qixing
    Zhang, Xiaowei
    Sun, Jianbo
    Chen, Li
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 160 : 1 - 8
  • [27] A review on biological activities of Schiff base, hydrazone, and oxime derivatives of curcumin
    Omidi, Sakineh
    Kakanejadifard, Ali
    RSC ADVANCES, 2020, 10 (50) : 30186 - 30202
  • [28] INVITRO ANTIMALARIAL AND CYTOTOXIC ACTIVITIES OF SEMISYNTHETIC DERIVATIVES OF BRUSATOL
    ALLEN, D
    TOTH, I
    WRIGHT, CW
    KIRBY, GC
    WARHURST, DC
    PHILLIPSON, JD
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (03) : 265 - 269
  • [29] α-Santalol derivatives from Santalum album and their cytotoxic activities
    Matsuo, Yukiko
    Mimaki, Yoshihiro
    PHYTOCHEMISTRY, 2012, 77 : 304 - 311
  • [30] In vitro antiplasmodial and cytotoxic activities of asymmetrical pyridinium derivatives
    Rubio-Ruiz, Belen
    Castillo-Acosta, Victor M.
    Perez-Moreno, Guiomar
    Espinosa, Antonio
    Gonzalez-Pacanowska, Dolores
    Ruiz-Perez, Luis M.
    Entrena, Antonio
    Conejo-Garcia, Ana
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 85 : 289 - 292
12345