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

doi:10.1016/j.jaap.2014.10.007

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 journal › Article › peer-review

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Abstract

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 language	English (US)
Pages (from-to)	430-434
Number of pages	5
Journal	Journal of Analytical and Applied Pyrolysis
Volume	110
Issue number	1
DOIs	https://doi.org/10.1016/j.jaap.2014.10.007
State	Published - 2014
Externally published	Yes

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.

Keywords

Anticancer activity
Boswellic acids
Frankincense
NMR
Pyrolysis

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Publisher link

10.1016/j.jaap.2014.10.007

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Al-Harrasi, A., Hussain, H., Hussain, J., Al-Rawahi, A., Hakkim, F. L., Khan, H. Y., Rehman, N. U., Ali, L., Al-Harrasi, R., Al-Hadrami, S., & Al-Hadrami, I. (2014). Two pyrolysate products from Omani frankincense smoke: First evidence of thermal aromatization of boswellic acids. Journal of Analytical and Applied Pyrolysis, 110(1), 430-434. https://doi.org/10.1016/j.jaap.2014.10.007

Al-Harrasi, A, Hussain, H, Hussain, J, Al-Rawahi, A, Hakkim, FL, Khan, HY, Rehman, NU, Ali, L, Al-Harrasi, R, Al-Hadrami, S & Al-Hadrami, I 2014, 'Two pyrolysate products from Omani frankincense smoke: First evidence of thermal aromatization of boswellic acids', Journal of Analytical and Applied Pyrolysis, vol. 110, no. 1, pp. 430-434. https://doi.org/10.1016/j.jaap.2014.10.007

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abstract = "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.",

keywords = "Anticancer activity, Boswellic acids, Frankincense, NMR, Pyrolysis",

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

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: {\textcopyright} 2014 Elsevier B.V. All rights reserved.",

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doi = "10.1016/j.jaap.2014.10.007",

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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 - 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.

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.

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KW - Anticancer activity

KW - Boswellic acids

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KW - Pyrolysis

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

Abstract

Bibliographical note

Keywords

UN SDGs

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