Isolation and characterization of an anticancer catechol compound from Semecarpus anacardium.
BACKGROUND
The fruits and seeds of Semecarpus anacardium are used widely for the treatment of human cancers and other diseases in the Ayurvedic and Sidda systems of medicine in India.


OBJECTIVE
The principal aim of this investigation was to isolate and characterize the anticancer compound from the kernel of Semecarpus anacardium nut.


METHODS
The bioactivity-tailored isolation and detailed chemical characterization were used to identify the active compound. Cytotoxicity, apoptosis, cell cycle arrest as well as synergism between the identified anticancer compound and doxorubicin in human tumor cell lines were analyzed.


RESULTS
GC/MS, IR, proton NMR, carbon NMR and collisionally induced dissociation (CID) spectra analysis showed that the isolated active compound is 3-(8'(Z),11'(Z)-pentadecadienyl) catechol (SA-3C). SA-3C is cytotoxic to tumor cell lines with IC(50) values lower than doxorubicin and even multidrug resistant tumor cell lines were equally sensitive to SA-3C. SA-3C induced apoptosis in human leukemia cell lines in a dose-dependent manner and showed synergistic cytotoxicity with doxorubicin. The cell cycle arrest induced by SA-3C at S- and G(2)/M-phases correlated with inhibition of checkpoint kinases.


CONCLUSIONS
SA-3C isolated from the kernel of Semecarpus anacardium can be developed as an important anticancer agent for single agent and/or multiagent cancer therapy.
Nair
P K Raveedran
PK
Devaswom Board College, Mahatma Gandhi University, Kerala, India.
Melnick
Steven J
SJ
Wnuk
Stanislaw F
SF
Rapp
Magdalena
M
Escalon
Enrique
E
Ramachandran
Cheppail
C
D000903:Antibiotics, Antineoplastic / Q000494:pharmacology* / Q000627:therapeutic use; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects*; D002396:Catechols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002453:Cell Cycle / Q000187:drug effects; D045744:Cell Line, Tumor; D004317:Doxorubicin / Q000494:pharmacology* / Q000627:therapeutic use; D004357:Drug Synergism; D006801:Humans; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D011494:Protein Kinases / Q000378:metabolism; D012639:Seeds; D031023:Semecarpus / Q000737:chemistry*
C542488:3-(8',11'-pentadecadienyl)catechol; D000903:Antibiotics, Antineoplastic; D000972:Antineoplastic Agents, Phytogenic; D002396:Catechols; D010936:Plant Extracts; D004317:Doxorubicin; D011494:Protein Kinases