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

Ahmed Al-Harrasi, Hidayat Hussain, Javid Hussain, Ahmed Al-Rawahi, Farruck Lukmanul Hakkim, Husain Yar Khan, Najeeb Ur Rehman, Liaqat Ali, Rashid Al-Harrasi, Sara Al-Hadrami, Iman Al-Hadrami

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)430-434
Number of pages5
JournalJournal of Analytical and Applied Pyrolysis
Issue number1
StatePublished - 2014
Externally publishedYes

Bibliographical note

Funding Information:
The authors would like to thank The Oman Research Council (TRC) for the generous support through the project ORG/CBS/10/002, and the University of Nizwa through the project (A109-10-UON/28/A & S/IF). We thank Mr Imtiaz Hussain for his experimental help.

Publisher Copyright:
© 2014 Elsevier B.V. All rights reserved.


  • Anticancer activity
  • Boswellic acids
  • Frankincense
  • NMR
  • Pyrolysis


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