The C8 side chain is one of the key functional group of Garcinol for its anti-cancer effects.
Garcinol from the fruit rind of Garcinia indica shows anti-carcinogenic and anti-inflammatory properties, but its mechanism and key functional groups were still need to be identified. Our previous computer modeling suggested that the C8 side chain of Garcinol is so large that it may influence the bioactivity of the compound. 8-Me Garcinol, a derivative of Garcinol in which the bulky side chain at the C8 position of Garcinol is replaced with a much smaller methyl group, was synthesized through a 12-step procedure starting from 1,3-cyclohexanedione. The antitumor activity of Garcinol and 8-Me Garcinol was evaluated in vitro by MTT, cell cycle and cell apoptosis assays. The results showed that 8-Me Garcinol had weaker inhibitory activity on cells proliferation, and little effects on cell cycle and apoptosis in oral cancer cell line SCC15 cells when compared with Garcinol. All of the results indicated 8-Me Garcinol exerts weaker antitumor activity than Garcinol, and the C8 side chain might be an important active site in Garcinol. Changing the C8 side chain will affect the inhibitory effect of Garcinol.
Beijing Institute of Dental Research, Beijing Stomatological Hospital, Capital Medical University, Beijing 100050, PR China.
Xin-Ying
XY
Zhou
School of Pharmaceutical Engineering and Life Sciences, Changzhou University, Jiangsu 213164, PR China.
Jing
J
Cao
School of Pharmaceutical Engineering and Life Sciences, Changzhou University, Jiangsu 213164, PR China.
Chao-Ming
CM
Han
Hua Lookeng Honors College, Changzhou University, Jiangsu 213164, PR China.
Shu-Wen
SW
Li
Hua Lookeng Honors College, Changzhou University, Jiangsu 213164, PR China.
Chen
C
Zhang
School of Pharmaceutical Engineering and Life Sciences, Changzhou University, Jiangsu 213164, PR China.
Yin-Duan
YD
Du
School of Pharmaceutical Engineering and Life Sciences, Changzhou University, Jiangsu 213164, PR China.
Qian-Qian
QQ
Zhou
Beijing Institute of Dental Research, Beijing Stomatological Hospital, Capital Medical University, Beijing 100050, PR China. Electronic address: xinyanzhangzh@126.com.
Xin-Yan
XY
Zhang
School of Pharmaceutical Engineering and Life Sciences, Changzhou University, Jiangsu 213164, PR China. Electronic address: xinchen@cczu.edu.cn.
Xin
X
Chen
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D002453:Cell Cycle / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003512:Cyclohexanones / Q000737:chemistry; D005638:Fruit / Q000737:chemistry; D029760:Garcinia / Q000737:chemistry*; D006801:Humans; D008745:Methylation; D009062:Mouth Neoplasms / Q000188:drug therapy*; D013729:Terpenes / Q000737:chemistry* / Q000494:pharmacology*
D000972:Antineoplastic Agents, Phytogenic; D003512:Cyclohexanones; D013729:Terpenes; C004636:1,3-cyclohexanedione; C054597:garcinol
8-Me Garcinol; Garcinol; Oral squamous cell carcinoma cell; Synthesis