Two pyrolysate products from Omani frankincense smoke: First evidence of thermal aromatization of boswellic acids

•First two isolated pyrolysate products from smoke of resin of Boswellia sacra.•First evidence of thermal aromatization of boswellic acids.•Structural elucidation of two isolated compounds was performed by NMR, MS, UV, and IR.•Two isolated compounds were capable of inhibiting breast cancer cell grow...

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Published in:Journal of analytical and applied pyrolysis 2014-11, Vol.110, p.430-434
Main Authors: Al-Harrasi, Ahmed, Hussain, Hidayat, Hussain, Javid, Al-Rawahi, Ahmed, Hakkim, Farruck Lukmanul, Khan, Husain Yar, Rehman, Najeeb Ur, Ali, Liaqat, Al-Harrasi, Rashid, Al-Hadrami, Sara, Al-Hadrami, Iman
Format: Article
Language:English
Subjects:
Anticancer activity
Boswellic acids
Frankincense
NMR
Pyrolysis
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Summary:•First two isolated pyrolysate products from smoke of resin of Boswellia sacra.•First evidence of thermal aromatization of boswellic acids.•Structural elucidation of two isolated compounds was performed by NMR, MS, UV, and IR.•Two isolated compounds were capable of inhibiting breast cancer cell growth. The frankincense resin of botanically-certified Boswellia sacra was pyrolyzed and the smoke was trapped into water using self-developed assembly. Two compounds, namely 1,2,4a,9-tetramethyl-1,2,3,4,4a,5, 6,14b-octahydropicene (1) and 2,9-dimethylpicene (2) were isolated from n-hexane extract of the smoke-saturated water. Their structures were determined by means of spectroscopic data including ESIMS, 1H NMR, 13C NMR, and 2D NMR (COSY, HSQC, HMBC, and NOESY). Dehydration of C-3 alcohols in boswellic acids (BAs) lead to aromatization of ring A followed by dehydrogenation and demethylation to afford triaromatic derivative viz., 1,2,4a,9-tetramethyl-1,2,3,4,4a,5, 6,14b-octahydropicene (1) and finally penta-aromatic derivative viz., 2,9-dimethylpicene (2). Compounds 1 and 2 were screened for their antiproliferative effects on MDA-MB-231 breast cancer cells. It was found that these pyrolysate products were capable of inhibiting cancer cell growth. However, this growth inhibitory effect was less when compared to their precursor AKBA (3-acetyl-11-keto-β-boswellic acid). The antiproliferative activity is inversely proportional to loss of functional groups.
ISSN:0165-2370
1873-250X
DOI:10.1016/j.jaap.2014.10.007