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Phytochemical and Cytotoxic Evaluation of Peganum Harmala: Structure Activity Relationship Studies of Harmine
Author(s) -
Ayoob Iram,
Hazari Younis M.,
Lone Shabir H.,
Khuroo Mohammad A.,
Fazili Khalid M.,
Bhat Khursheed A.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700232
Subject(s) - harmine , peganum harmala , hela , cytotoxicity , cytotoxic t cell , chemistry , ic50 , alkaloid , phytochemical , stereochemistry , cell , pharmacology , biology , traditional medicine , biochemistry , in vitro , medicine
Four alkaloid constituents: harmine, vasicine, vasicinone and harmaline were isolated and characterized from Peganum harmala roots. Harmine showed the best cytotoxicity with IC 50 of 32, 106, 45, 33 and 61 μM against breast (HBL‐100), lung (A549), colon (HT‐29 & HCT‐116) and cervical (HELA) cells respectively. The harmine analogs, synthesized via click chemistry, revealed that few derivatives possess potent cytotoxic effects. m‐Fluoro phenyl‐1, 2,3‐triazolyl harmine was found to be selectively cytotoxic against human breast cancer cell lines only displaying an IC 50 of 16μM. p‐Fluoro phenyl‐1,2,3‐triazolyl harmine and p‐methoxy phenyl‐1,2,3‐triazolyl harmine displayed improved cytotoxicity. p‐Fluorophenyl‐1,2,3‐triazolyl harmine displayed broad spectrum cytotoxic effects against all the tested cancer‐cell lines with IC 50 of 17, 19, 29 and 17μM against lung (A‐549), Colon (HT‐29), Cervic (HELA) and Colon (HCT‐116) cell lines respectively while as p‐methoxy phenyl‐1,2,3‐triazolyl harmine showed selectivity towards lung and colon cancer cell lines with IC 50 of 27, 18 and 17μM against A549, HT‐29 and HCT‐116 respectively.