Three new cembranoid-type diterpenes from Red Sea soft coral Sarcophyton glaucum: Isolation and antiproliferative activity against HepG2 cells

被引:36
作者
Al-Lihaibi, Sultan S. [1 ]
Alarif, Walled M. [1 ]
Abdel-Lateff, Ahmed [2 ,3 ]
Ayyad, Seif-Eldin N. [4 ]
Abdel-Naim, Ashraf B. [5 ]
El-Senduny, Fardous F. [6 ]
Badria, Farid A. [7 ]
机构
[1] King Abdulaziz Univ, Fac Marine Sci, Dept Marine Chem, Jeddah 21589, Saudi Arabia
[2] King Abdulaziz Univ, Fac Pharm, Dept Nat Prod & Alternat Med, Jeddah 21589, Saudi Arabia
[3] Menia Univ, Fac Pharm, Dept Pharmacognosy, Al Minya 61519, Egypt
[4] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia
[5] King Abdulaziz Univ, Fac Pharm, Dept Pharmacol & Toxicol, Jeddah 21589, Saudi Arabia
[6] Mansoura Univ, Fac Sci, Dept Chem, Mansoura 35516, Egypt
[7] Mansoura Univ, Fac Pharm, Dept Pharmacognosy, Mansoura 35516, Egypt
关键词
Sarcophyton; Cembranes; Antiproliferative; HepG2; PC-3; MARINE NATURAL-PRODUCTS; SINULARIA-QUERCIFORMIS; CRASSOCAULE; EHRENBERGI; GRANOSA; DRUGS;
D O I
10.1016/j.ejmech.2014.05.016
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Three new cembranoids: sarcophytolol (1), sarcophytolide B (2), and sarcophytolide C (3), along with three known metabolites: 10(14)aromadendrene (4), deoxosarcophine (5), and sarcophine (6) were obtained from the soft bodied coral Sarcophyton glaucum. The structures were determined based on spectroscopic measurements (NMR, UV, IR and MS). Compounds I, 3, and 4 had similar significant cytotoxic effects towards HepG2 (Human hepatocellular liver carcinoma; IC50 = 20 mu M). 2 and 3 showed activity against MCF-7 (Human breast adenocarcinoma; IC50 25 +/- 0.0164 and 29 +/- 0.030 mu M, respectively). Finally, 4 showed potent activity towards PC-3 (Prostate cancer; IC50 9.3 +/- 0.164 mu M). The antiproliferative activity of 1, 3 and 4, can be attributed, at least partly, to their ability to induce cellular apoptosis. (C) 2014 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:314 / 322
页数:9
相关论文
共 24 条
[1]   Selective cytotoxic effects on human breast carcinoma of new methoxylated flavonoids from Euryops arabicus grown in Saudi Arabia [J].
Alarif, Walied M. ;
Abdel-Lateff, Ahmed ;
Al-Abd, Ahmed M. ;
Basaif, Salim A. ;
Badria, Farid A. ;
Shams, Maher ;
Ayyad, Seif-Eldin N. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 66 :204-210
[2]   Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Hu, Wan-Ping ;
Munro, Murray H. G. ;
Northcote, Peter T. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2008, 25 (01) :35-94
[3]   New and emerging analytical techniques for marine biotechnology [J].
Burgess, J. Grant .
CURRENT OPINION IN BIOTECHNOLOGY, 2012, 23 (01) :29-33
[4]   A novel symmetric sulfur-containing biscembranoid from the Formosan soft coral Sinularia flexibilis [J].
Chen, Bo-Wei ;
Chao, Chih-Hua ;
Su, Jui-Hsin ;
Huang, Chiung-Yao ;
Dai, Chang-Feng ;
Wen, Zhi-Hong ;
Sheu, Jyh-Horng .
TETRAHEDRON LETTERS, 2010, 51 (44) :5764-5766
[5]   Bioactive norditerpenoids from the soft coral Sinularia gyrosa [J].
Cheng, Shi-Yie ;
Chuang, Cheng-Ta ;
Wen, Zhi-Hong ;
Wang, Shang-Kwei ;
Chiou, Shu-Fen ;
Hsu, Chi-Hsin ;
Dai, Chang-Feng ;
Duh, Chang-Yih .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (10) :3379-3386
[6]   Cembranoids from the Octocoral Sarcophyton ehrenbergi [J].
Cheng, Shi-Yie ;
Wang, Shang-Kwei ;
Chiou, Shu-Fen ;
Hsu, Chi-Hsin ;
Dai, Chang-Feng ;
Chiang, Michael Y. ;
Duh, Chang-Yih .
JOURNAL OF NATURAL PRODUCTS, 2010, 73 (02) :197-203
[7]   Cembrane diterpenoids from the Taiwanese soft coral Sarcophyton stolidotum [J].
Cheng, Yuan-Bin ;
Shen, Ya-Ching ;
Kuo, Yao-Haur ;
Khalil, Ashraf Taha .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (07) :1141-1145
[8]   Discovery of anticancer drugs from antimalarial natural products: a MEDLINE literature review [J].
Duffy, Robert ;
Wade, Christine ;
Chang, Raymond .
DRUG DISCOVERY TODAY, 2012, 17 (17-18) :942-953
[9]  
Edwards A. J., 1987, KEY ENV RED SEA, P440
[10]   Drugs from the deep: marine natural products as drug candidates [J].
Haefner, B .
DRUG DISCOVERY TODAY, 2003, 8 (12) :536-544