Boswellic acids are a series of pentacyclic terpenoid molecules that are produced by plants in the genus Boswellia. Like many other terpenes, boswellic acids appear in the resin of the plant that exudes them; it is estimated that they make up 30% of the resin of Boswellia serrata.[1] While boswellic acids are a major component of the resin, the steam or hydro distilled frankincense essential oil does not contain any boswellic acid as these components are non-volatile and too large to come over in the steam distillation process (the essential oil is composed mainly of the much lighter monoterpene and sesquiterpene molecules with small amounts of diterpenoid components being the upper limit in terms of molecular weight).[2][3][4]
Structure of α-boswellic acid3D model of α-boswellic acidStructure of β-boswellic acid3D model of β-boswellic acidStructure of 11-keto-β-boswellic acid3D model of 11-keto-β-boswellic acid
The boswellic acids are organic acids, consisting of a pentacyclic triterpene, a carboxyl group and at least one other functional group. Alpha-boswellic acid and beta-boswellic acid, C30H48O3 both have an additional hydroxyl group; they differ only in their triterpene structure. Acetyl-alpha-boswellic acid and acetyl-beta-boswellic acid, C32H50O4, replace the hydroxyl group with an acetyl group.
Other boswellic acids include the keto-boswellic acids and their acetyl counterparts.
Usesedit
Beta-boswellic acid, keto-beta-boswellic acid, and acetyl-keto-beta-boswellic acid (AKBA) have been indicated in apoptosis of cancer cells, in particular brain tumors and cells affected by leukemia or colon cancer.[5]
Acetyl-boswellic acids also exhibit anti-inflammatory behaviour by inhibiting leukotriene synthesis.[6] It inhibits the activity of the enzyme 5-lipoxygenase through a non-redox reaction. Specifically the 3-acetyl-11-keto-beta-boswellic acid binds as an allosteric partial inhibitor, initiating a shift in regioselectivity of the catalyzed reaction.[7] Clinical trials[8][9] have investigated the effectiveness of boswellic acids in treating ulcerative colitis, but a study on chemically induced colitis in mouse models[10] showed little effectiveness. A later study showed that low doses of Boswellia serrata extract may have hepatoprotective effects. The higher dose was found to have a milder hepatoprotective effect than the lower dose.[11]
Boswellic acids are also thought to decrease the symptoms of asthma; a small 1998 placebo-controlled trial of Boswellia extract for the treatment of asthma showed good results.[12]Boswellia extracts are sold in tablet, capsule and tincture form, but no dosage guidelines have been developed. The risk of hepatotoxicity due to Boswellia administration has not been assessed. A meta-study of Indian Frankincense (Boswellia serrata) as a complementary therapy for arthritis found it had positive effect in all four trials reviewed.[13]
^Verghese, J.; Joy, M. T.; Retamar, J. A.; et al. (1987). "A Fresh Look at the Constituents of Indian Olibanum Oil". Flavour Fragr. J. 2 (3): 99–102. doi:10.1002/ffj.2730020304.
^Hayashi, S.; Amemori, H.; Kameoka, H.; et al. (1998). "Comparison of Volatile Compounds from Olibanum from Various Countries". J. Essent. Oil Res. 10 (1): 25–30. doi:10.1080/10412905.1998.9700833.
^Baser, S.; Koch, A.; König, W. A. (2001). "A Verticillane-type Diterpene from Boswellia carterii Essential Oil". Flavour Fragr. J. 16 (5): 315–8. doi:10.1002/ffj.992.
^Liu, J.-J.; Nilsson, A.; Oredsson, S.; et al. (2002). "Boswellic acids trigger apoptosis via a pathway dependent on caspase-8 activation but independent on Fas/Fas ligand interaction in colon cancer HT-29 cells". Carcinogenesis. 23 (12): 2087–93. doi:10.1093/carcin/23.12.2087. PMID 12507932.
^Ammon, H. P.; Safayi, H.; Mack, T.; Sabieraj, J. (1993). "Mechanism of antiinflammatory actions of curcumine and boswellic acids". Journal of Ethnopharmacology. 38 (2–3): 113–9. doi:10.1016/0378-8741(93)90005-p. PMID 8510458.
^Gilbert, Nathaniel C.; Gerstmeier, Jana; Schexnaydre, Erin E.; et al. (2020-05-11). "Structural and mechanistic insights into 5-lipoxygenase inhibition by natural products". Nature Chemical Biology. 16 (7): 783–790. doi:10.1038/s41589-020-0544-7. ISSN 1552-4450. PMC7747934. PMID 32393899.
^Ammon, H. P. (2002). "Boswelliasäuren (Inhaltsstoffe des Weihrauchs) als wirksame Prinzipien zur Behandlung chronisch entzündlicher Erkrankungen" [Boswellic acids (components of frankincense) as the active principle in treatment of chronic inflammatory diseases]. Wiener Medizinische Wochenschrift (in German). 152 (15–16): 373–8. doi:10.1046/j.1563-258X.2002.02056.x. PMID 12244881.
^Anthoni, C.; Laukoetter, M. G.; Rijcken, E.; et al. (2006). "Mechanisms underlying the anti-inflammatory actions of boswellic acid derivatives in experimental colitis". American Journal of Physiology. Gastrointestinal and Liver Physiology. 290 (6): G1131–7. doi:10.1152/ajpgi.00562.2005. PMID 16423918.
^Kiela, P. R.; Midura, A. J.; Kuscuoglu, N.; et al. (2005). "Effects of Boswellia serrata in mouse models of chemically induced colitis". American Journal of Physiology. Gastrointestinal and Liver Physiology. 288 (4): G798–808. doi:10.1152/ajpgi.00433.2004. PMID 15539433.
^Jyothi, Y.; Kamath, J. V.; Asad, M. (2006). "Effect of hexane extract of Boswellia serrata oleo-gum resin on chemically induced liver damage". Pak J Pharm Sci. 19 (2): 129–33. PMID 16751123.
^Gupta, I.; Gupta, V.; Parihar, A.; et al. (1998). "Effects of Boswellia serrata gum resin in patients with bronchial asthma: results of a double-blind, placebo-controlled, 6-week clinical study". Eur J Med Res. 3 (11): 511–4. PMID 9810030.
Paul, M. (2012). "Chemotaxonomic Investigations on Resins of the Frankincense Species Boswellia papyrifera, Boswellia serrata and Boswellia sacra, respectively, Boswellia carterii: A Qualitative and Quantitative Approach by Chromatographic and Spectroscopic Methodology" (PDF). Dissertation. Saarland University. doi:10.22028/D291-22839.
January 01, 1970
boswellic, acid, series, pentacyclic, terpenoid, molecules, that, produced, plants, genus, boswellia, like, many, other, terpenes, boswellic, acids, appear, resin, plant, that, exudes, them, estimated, that, they, make, resin, boswellia, serrata, while, boswel. Boswellic acids are a series of pentacyclic terpenoid molecules that are produced by plants in the genus Boswellia Like many other terpenes boswellic acids appear in the resin of the plant that exudes them it is estimated that they make up 30 of the resin of Boswellia serrata 1 While boswellic acids are a major component of the resin the steam or hydro distilled frankincense essential oil does not contain any boswellic acid as these components are non volatile and too large to come over in the steam distillation process the essential oil is composed mainly of the much lighter monoterpene and sesquiterpene molecules with small amounts of diterpenoid components being the upper limit in terms of molecular weight 2 3 4 Structure of a boswellic acid 3D model of a boswellic acid Structure of b boswellic acid 3D model of b boswellic acid Structure of 11 keto b boswellic acid 3D model of 11 keto b boswellic acid Contents 1 Structure 2 Uses 3 References 4 External linksStructure editThe boswellic acids are organic acids consisting of a pentacyclic triterpene a carboxyl group and at least one other functional group Alpha boswellic acid and beta boswellic acid C30H48O3 both have an additional hydroxyl group they differ only in their triterpene structure Acetyl alpha boswellic acid and acetyl beta boswellic acid C32H50O4 replace the hydroxyl group with an acetyl group Other boswellic acids include the keto boswellic acids and their acetyl counterparts Uses editBeta boswellic acid keto beta boswellic acid and acetyl keto beta boswellic acid AKBA have been indicated in apoptosis of cancer cells in particular brain tumors and cells affected by leukemia or colon cancer 5 Acetyl boswellic acids also exhibit anti inflammatory behaviour by inhibiting leukotriene synthesis 6 It inhibits the activity of the enzyme 5 lipoxygenase through a non redox reaction Specifically the 3 acetyl 11 keto beta boswellic acid binds as an allosteric partial inhibitor initiating a shift in regioselectivity of the catalyzed reaction 7 Clinical trials 8 9 have investigated the effectiveness of boswellic acids in treating ulcerative colitis but a study on chemically induced colitis in mouse models 10 showed little effectiveness A later study showed that low doses of Boswellia serrata extract may have hepatoprotective effects The higher dose was found to have a milder hepatoprotective effect than the lower dose 11 Boswellic acids are also thought to decrease the symptoms of asthma a small 1998 placebo controlled trial of Boswellia extract for the treatment of asthma showed good results 12 Boswellia extracts are sold in tablet capsule and tincture form but no dosage guidelines have been developed The risk of hepatotoxicity due to Boswellia administration has not been assessed A meta study of Indian Frankincense Boswellia serrata as a complementary therapy for arthritis found it had positive effect in all four trials reviewed 13 References edit SaluGenecists Inc Boswellia information Verghese J Joy M T Retamar J A et al 1987 A Fresh Look at the Constituents of Indian Olibanum Oil Flavour Fragr J 2 3 99 102 doi 10 1002 ffj 2730020304 Hayashi S Amemori H Kameoka H et al 1998 Comparison of Volatile Compounds from Olibanum from Various Countries J Essent Oil Res 10 1 25 30 doi 10 1080 10412905 1998 9700833 Baser S Koch A Konig W A 2001 A Verticillane type Diterpene from Boswellia carterii Essential Oil Flavour Fragr J 16 5 315 8 doi 10 1002 ffj 992 Liu J J Nilsson A Oredsson S et al 2002 Boswellic acids trigger apoptosis via a pathway dependent on caspase 8 activation but independent on Fas Fas ligand interaction in colon cancer HT 29 cells Carcinogenesis 23 12 2087 93 doi 10 1093 carcin 23 12 2087 PMID 12507932 Ammon H P Safayi H Mack T Sabieraj J 1993 Mechanism of antiinflammatory actions of curcumine and boswellic acids Journal of Ethnopharmacology 38 2 3 113 9 doi 10 1016 0378 8741 93 90005 p PMID 8510458 Gilbert Nathaniel C Gerstmeier Jana Schexnaydre Erin E et al 2020 05 11 Structural and mechanistic insights into 5 lipoxygenase inhibition by natural products Nature Chemical Biology 16 7 783 790 doi 10 1038 s41589 020 0544 7 ISSN 1552 4450 PMC 7747934 PMID 32393899 Ammon H P 2002 Boswelliasauren Inhaltsstoffe des Weihrauchs als wirksame Prinzipien zur Behandlung chronisch entzundlicher Erkrankungen Boswellic acids components of frankincense as the active principle in treatment of chronic inflammatory diseases Wiener Medizinische Wochenschrift in German 152 15 16 373 8 doi 10 1046 j 1563 258X 2002 02056 x PMID 12244881 Anthoni C Laukoetter M G Rijcken E et al 2006 Mechanisms underlying the anti inflammatory actions of boswellic acid derivatives in experimental colitis American Journal of Physiology Gastrointestinal and Liver Physiology 290 6 G1131 7 doi 10 1152 ajpgi 00562 2005 PMID 16423918 Kiela P R Midura A J Kuscuoglu N et al 2005 Effects of Boswellia serrata in mouse models of chemically induced colitis American Journal of Physiology Gastrointestinal and Liver Physiology 288 4 G798 808 doi 10 1152 ajpgi 00433 2004 PMID 15539433 Jyothi Y Kamath J V Asad M 2006 Effect of hexane extract of Boswellia serrata oleo gum resin on chemically induced liver damage Pak J Pharm Sci 19 2 129 33 PMID 16751123 Gupta I Gupta V Parihar A et al 1998 Effects of Boswellia serrata gum resin in patients with bronchial asthma results of a double blind placebo controlled 6 week clinical study Eur J Med Res 3 11 511 4 PMID 9810030 Indian frankincense External links editLipid Molecular Structure Database Paul M 2012 Chemotaxonomic Investigations on Resins of the Frankincense Species Boswellia papyrifera Boswellia serrata and Boswellia sacra respectively Boswellia carterii A Qualitative and Quantitative Approach by Chromatographic and Spectroscopic Methodology PDF Dissertation Saarland University doi 10 22028 D291 22839 Retrieved from https en wikipedia org w index php title Boswellic acid amp oldid 1176210433, wikipedia, wiki, 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