Boswellic acid

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Structure of a-boswellic acid Alpha-boswellic acid.svg
Structure of α-boswellic acid
3D model of a-boswellic acid Alpha-BoswellicAcid3D.png
3D model of α-boswellic acid
Structure of b-boswellic acid Beta-boswellic acid.svg
Structure of β-boswellic acid
3D model of b-boswellic acid Beta-Boswellic Acid.png
3D model of β-boswellic acid
Structure of 11-keto-b-boswellic acid 11-keto-beta-boswellic acid.svg
Structure of 11-keto-β-boswellic acid
3D model of 11-keto-b-boswellic acid 11-keto-beta-BoswellicAcid3D.png
3D model of 11-keto-β-boswellic acid

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]

Contents

Structure

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.

Uses

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 latter 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]

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Boswellia sacra is a tree in the Burseraceae family. It is the primary tree in the genus Boswellia from which frankincense, a resinous dried sap, is harvested. It is native to the Arabian Peninsula, and horn of Africa (Somalia).

<i>Boswellia serrata</i> Species of plant

Boswellia serrata is a plant that produces Indian frankincense. The plant is native to much of India and the Punjab region that extends into Pakistan.

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Boswellia papyrifera, also known as the Sudanese frankincense, is a species of flowering plant and frankincense that is native to Ethiopia, Eritrea and Sudan. The tree is cultivated in Ethiopia because of its valuable resin. The incense smoke is characterized by a fresh lemon-pine scent, and is therefore highly esteemed. In Ethiopia where it is called itan zaf, it comes in semi-translucent yellow tears. The gum resin of Boswellia papyrifera coming from Ethiopia, Sudan and E. Africa is believed to be the main source of frankincense of antiquity.

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<span class="mw-page-title-main">12-Hydroxyeicosatetraenoic acid</span> Chemical compound

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<span class="mw-page-title-main">13-Hydroxyoctadecadienoic acid</span> Chemical compound

13-Hydroxyoctadecadienoic acid (13-HODE) is the commonly used term for 13(S)-hydroxy-9Z,11E-octadecadienoic acid. The production of 13(S)-HODE is often accompanied by the production of its stereoisomer, 13(R)-hydroxy-9Z,11E-octadecadienoic acid. The adjacent figure gives the structure for the (S) stereoisomer of 13-HODE. Two other naturally occurring 13-HODEs that may accompany the production of 13(S)-HODE are its cis-trans isomers viz., 13(S)-hydroxy-9E,11E-octadecadienoic acid and 13(R)-hydroxy-9E,11E-octadecadienoic acid. Studies credit 13(S)-HODE with a range of clinically relevant bioactivities; recent studies have assigned activities to 13(R)-HODE that differ from those of 13(S)-HODE; and other studies have proposed that one or more of these HODEs mediate physiological and pathological responses, are markers of various human diseases, and/or contribute to the progression of certain diseases in humans. Since, however, many studies on the identification, quantification, and actions of 13(S)-HODE in cells and tissues have employed methods that did not distinguish between these isomers, 13-HODE is used here when the actual isomer studied is unclear.

Ahmed Sulaiman Al-Harrasi is an Omani scientist and a professor of organic chemistry at the University of Nizwa, Nizwa, Sultanate of Oman.

References

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  5. 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.
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  13. "Indian frankincense".