Semi-synthetic modification of nimbolide to 6-homodesacetylnimbin and 6-desacetylnimbin and their cytotoxic studies.
A new C-seco tetranortriterpenoid named as 6-homodesacetylnimbin 2, has been synthesised for the first time through semi-synthetic modification of nimbolide 1, a potent molecule with anticancer activity. Attempts were made to transesterify the -COOMe moiety in nimbolide using titanium (IV) isopropoxide and ethanol so as to obtain a molecule with -COOEt moiety. However, a novel product was envisaged during the course of the reaction, which was identified as 6-homodesacetylnimbin, a higher homologue of 6-desacetylnimbin 3 through spectroscopic and crystallographic methods. Also, 6-desacetylnimbin has been synthesised through acid hydrolysis of nimbolide. The compounds were screened for their cytotoxic properties through brine shrimp lethality bioassay method using Artemia salina.
Anitha
G
G
Asthagiri Herbal Research Foundation, 7/1 Thirumazhisai Street, Sundaram Colony, East Tambaram, Chennai, Tamil Nadu, India.
Raj
J Josepha Lourdu
JJ
Krishnan
V Radha
VR
Narasimhan
S
S
Solomon
K Anand
KA
Rajan
S S
SS
D000818:Animals; D001156:Artemia / Q000254:growth & development; D031601:Azadirachta / Q000737:chemistry*; D018360:Crystallography, X-Ray; D036701:Limonins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D036701:Limonins; C042198:nimbolide