TY - JOUR
T1 - Two pyrolysate products from Omani frankincense smoke
T2 - First evidence of thermal aromatization of boswellic acids
AU - Al-Harrasi, Ahmed
AU - Hussain, Hidayat
AU - Hussain, Javid
AU - Al-Rawahi, Ahmed
AU - Hakkim, Farruck Lukmanul
AU - Khan, Husain Yar
AU - Rehman, Najeeb Ur
AU - Ali, Liaqat
AU - Al-Harrasi, Rashid
AU - Al-Hadrami, Sara
AU - Al-Hadrami, Iman
N1 - Publisher Copyright:
© 2014 Elsevier B.V. All rights reserved.
PY - 2014
Y1 - 2014
N2 - 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 smokesaturated 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.
AB - 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 smokesaturated 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.
KW - Anticancer activity
KW - Boswellic acids
KW - Frankincense
KW - NMR
KW - Pyrolysis
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U2 - 10.1016/j.jaap.2014.10.007
DO - 10.1016/j.jaap.2014.10.007
M3 - Article
AN - SCOPUS:84922726230
SN - 0165-2370
VL - 110
SP - 430
EP - 434
JO - Journal of Analytical and Applied Pyrolysis
JF - Journal of Analytical and Applied Pyrolysis
IS - 1
ER -