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]
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.
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]
In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on naturally occurring resins.
Acetoacetic acid is the organic compound with the formula CH3COCH2COOH. It is the simplest beta-keto acid, and like other members of this class, it is unstable. The methyl and ethyl esters, which are quite stable, are produced on a large scale industrially as precursors to dyes. Acetoacetic acid is a weak acid.
Frankincense is an aromatic resin used in incense and perfumes, obtained from trees of the genus Boswellia in the family Burseraceae. The word is from Old French franc encens.
Histamine is an organic nitrogenous compound involved in local immune responses, as well as regulating physiological functions in the gut and acting as a neurotransmitter for the brain, spinal cord, and uterus. Since histamine was discovered in 1910, it has been considered a local hormone (autocoid) because it lacks the classic endocrine glands to secrete it; however, in recent years, histamine has been recognized as a central neurotransmitter. Histamine is involved in the inflammatory response and has a central role as a mediator of itching. As part of an immune response to foreign pathogens, histamine is produced by basophils and by mast cells found in nearby connective tissues. Histamine increases the permeability of the capillaries to white blood cells and some proteins, to allow them to engage pathogens in the infected tissues. It consists of an imidazole ring attached to an ethylamine chain; under physiological conditions, the amino group of the side-chain is protonated.
Cromoglicic acid (INN)—also referred to as cromolyn (USAN), cromoglycate, or cromoglicate—is traditionally described as a mast cell stabilizer, and is commonly marketed as the sodium salt sodium cromoglicate or cromolyn sodium. This drug prevents the release of inflammatory chemicals such as histamine from mast cells.
Boswellia is a genus of trees in the order Sapindales, known for its fragrant resin. The biblical incense frankincense is an extract from the resin of the tree Boswellia sacra, and is now produced also from B. frereana.
The Burseraceae are a moderate-sized family of 17-19 genera and about 540 species of flowering plants. The actual numbers differ according to the time period in which a given source is written describing this family. The Burseraceae are also known as the torchwood family, the frankincense and myrrh family, or simply the incense tree family. The family includes both trees and shrubs, and is native to tropical regions of Africa, Asia. Australasia, and the Americas.
Collagenous colitis is an inflammatory bowel disease affecting the colon specifically with peak incidence in the 5th decade of life, affecting women more than men. Its clinical presentation involves watery diarrhea in the absence of rectal bleeding. It is often classified under the umbrella entity microscopic colitis, that it shares with a related condition, lymphocytic colitis.
In biochemistry, fatty acid synthesis is the creation of fatty acids from acetyl-CoA and NADPH through the action of enzymes called fatty acid synthases. This process takes place in the cytoplasm of the cell. Most of the acetyl-CoA which is converted into fatty acids is derived from carbohydrates via the glycolytic pathway. The glycolytic pathway also provides the glycerol with which three fatty acids can combine to form triglycerides, the final product of the lipogenic process. When only two fatty acids combine with glycerol and the third alcohol group is phosphorylated with a group such as phosphatidylcholine, a phospholipid is formed. Phospholipids form the bulk of the lipid bilayers that make up cell membranes and surrounds the organelles within the cells.
Arachidonate 5-lipoxygenase, also known as ALOX5, 5-lipoxygenase, 5-LOX, or 5-LO, is a non-heme iron-containing enzyme that in humans is encoded by the ALOX5 gene. Arachidonate 5-lipoxygenase is a member of the lipoxygenase family of enzymes. It transforms essential fatty acids (EFA) substrates into leukotrienes as well as a wide range of other biologically active products. ALOX5 is a current target for pharmaceutical intervention in a number of diseases.
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).
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.
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.
Arachidonate 5-lipoxygenase inhibitors are compounds that slow or stop the action of the arachidonate 5-lipoxygenase enzyme, which is responsible for the production of inflammatory leukotrienes. The overproduction of leukotrienes is a major cause of inflammation in asthma, allergic rhinitis, and osteoarthritis.
2-Oxoisovalerate dehydrogenase subunit beta, mitochondrial is an enzyme that in humans is encoded by the BCKDHB gene.
Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.
12-Hydroxyeicosatetraenoic acid (12-HETE) is a derivative of the 20 carbon polyunsaturated fatty acid, arachidonic acid, containing a hydroxyl residue at carbon 12 and a 5Z,8Z,10E,14Z Cis–trans isomerism configuration in its four double bonds. It was first found as a product of arachidonic acid metabolism made by human and bovine platelets through their 12S-lipoxygenase enzyme(s). However, the term 12-HETE is ambiguous in that it has been used to indicate not only the initially detected "S" stereoisomer, 12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid, made by platelets, but also the later detected "R" stereoisomer, 12(R)-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid made by other tissues through their 12R-lipoxygenase enzyme, ALOX12B. The two isomers, either directly or after being further metabolized, have been suggested to be involved in a variety of human physiological and pathological reactions. Unlike hormones which are secreted by cells, travel in the circulation to alter the behavior of distant cells, and thereby act as Endocrine signalling agents, these arachidonic acid metabolites act locally as Autocrine signalling and/or Paracrine signaling agents to regulate the behavior of their cells of origin or of nearby cells, respectively. In these roles, they may amplify or dampen, expand or contract cellular and tissue responses to disturbances.
Eoxins are proposed to be a family of proinflammatory eicosanoids. They are produced by human eosinophils, mast cells, the L1236 Reed–Sternberg cell line derived from Hodgkin's lymphoma, and certain other tissues. These cells produce the eoxins by initially metabolizing arachidonic acid, an omega-6 (ω-6) fatty acid, via any enzyme possessing 15-lipoxygenase activity. The product of this initial metabolic step, 15(S)-hydroperoxyeicosatetraenoic acid, is then converted to a series of eoxins by the same enzymes that metabolize the 5-lipoxygenase product of arachidonic acid metabolism, i.e. 5-Hydroperoxy-eicosatetraenoic acid to a series of leukotrienes. That is, the eoxins are 14,15-disubstituted analogs of the 5,6-disubstituted leukotrienes.
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.