Boswellic acids

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The boswellic acids (also boswellic acids ) are a group of chemical compounds that occur naturally in the resin of the frankincense trees ( boswellia ), the frankincense . The two basic structures represent the α-boswellic acid ( oleanane type) and the β-boswellic acid ( ursan type), depending on the arrangement of the two methyl groups on the ring E. Chemically, the substances belonging to the resin acids have a pentacyclic triterpene structure with a cis - Position of rings D and E is based.

Boswellic acids
Surname α-boswellic acid β-boswellic acid
Structural formula Alpha-boswellic acid.svg Beta-boswellic acid.svg
CAS number 471-66-9 631-69-6
PubChem 17750984 168928
Molecular formula C 30 H 48 O 3
Molar mass 456.70 g mol −1
Physical state firmly
GHS
labeling
no GHS pictograms
no GHS pictograms
H and P phrases no H-phrases no H-phrases
no EUH phrases no EUH phrases
no P-phrases no P-phrases

Derivatives

Some derivatives of the boswellic acids are also known, in particular compounds which carry a keto group in position 11 and / or are acetylated in position 3 .

Derivatives of boswellic acids
Surname structure CAS number PubChem Molecular formula
  • 3- O -acetyl-α-boswellic acid
 89913-60-0 C 32 H 50 O 4
  • 3- O -acetyl-11-keto-α-boswellic acid
 C 32 H 48 O 5
  • 3- O -acetyl-β-boswellic acid (AcBA)
 5968-70-7 C 32 H 50 O 4
  • 11-keto-β-boswellic acid (KBA)
 11-keto-beta-boswellic acid.svg 17019-92-0 6918114 C 30 H 46 O 4
  • 3- O -acetyl-11-keto-β-boswellic acid (AKBA)
 67416-61-9 6918115 C 32 H 48 O 5

properties

Boswellic acids are the main pharmacologically active components of frankincense and are also considered to be the ingredients that determine the effectiveness of preparations made from dry frankincense extracts. However, not every boswellic acid has a pharmacological effect at the usual dosage and oral intake.

In particular, the 3- O- acetyl-11-keto-β-boswellic acid (AKBA) and 11-keto-β-boswellic acid (KBA) contained in frankincense resin have anti-inflammatory effects by non-competitively inhibiting 5-lipoxygenase and thus leukotriene synthesis reduce.

At high concentrations, the inflammation cascade, starting from arachidonic acid , is inhibited. The role of leukotrienes in metabolism is related to inflammatory reactions in the body (including allergies ). When ingested orally, no pharmacologically effective concentrations are reached in the blood for these two boswellic acids due to the low bioavailability . For β-boswellic acid, on the other hand, concentrations 100 times higher were found, which inhibit prostaglandin E synthase 1 in microsomes and the serine protease cathepsin G.

Boswellic acids show cytotoxic and anti- tumor effects and are being studied for the treatment of tumors. Induced apoptosis and its effect as a topoisomerase inhibitor also play a role here. Frankincense extracts are also being investigated for the treatment of inflammatory bowel diseases .

literature

  • Michael Paul, Johann Jauch: 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 . Saarbrücken 2012, DNB  1052551505 , urn : nbn: de: bsz: 291-scidok-49998 (dissertation).

Individual evidence

  1. ↑ Data sheet α-Boswellic acid, analytical standard from Sigma-Aldrich , accessed on May 16, 2020 ( PDF ).
  2. ↑ Data sheet β-Boswellic acid, analytical standard from Sigma-Aldrich , accessed on May 16, 2020 ( PDF ).
  3. ↑ Data sheet 3-O-Acetyl-α-boswellic acid from Sigma-Aldrich , accessed on May 16, 2020 ( PDF ).
  4. ↑ Data sheet 3-O-Acetyl-β-boswellic acid from Sigma-Aldrich , accessed on May 16, 2020 ( PDF ).
  5. ↑ Stange, Eduard F .: Inflammatory bowel disease. Schattauer Verlag, 2015, ISBN 978-3-794-53081-6 , p. 274.
  6. ↑ Z. Du, Z. Liu, Z. Ning, Y. Liu, Z. Song, C. Wang, A. Lu: Prospects of boswellic acids as potential pharmaceutics. In: Planta medica. Volume 81, Number 4, March 2015, pp. 259-271, doi : 10.1055 / s-0034-1396313 , PMID 25714728 .
  7. ↑ a b c M. Abdel-Tawab, O. Werz, M. Schubert-Zsilavecz: Boswellia serrata: an overall assessment of in vitro, preclinical, pharmacokinetic and clinical data. In: Clinical Pharmacokinetics . Volume 50, number 6, June 2011, pp. 349-369, doi : 10.2165 / 11586800-000000000-00000 , PMID 21553931 .
  8. ↑ K. Hardtke et al. (Ed.): Commentary on the European Pharmacopoeia Ph. Eur. 5.7, Indian incense. Loose-leaf collection, 28th delivery 2007, Wissenschaftliche Verlagsgesellschaft Stuttgart.
  9. ↑ Nathaniel C. Gilbert, Jana Gerstmeier, Erin E. Schexnaydre, Friedemann Börner, Ulrike Garscha, David B. Neau, Oliver Werz & Marcia E. Newcomer (2020) Structural and mechanistic insights into 5-lipoxygenase inhibition by natural products. Nature Chemical Biology, doi : 10.1038 / s41589-020-0544-7 (May 11, 2020)
  10. ^ MA Khan, R. Ali, R. Parveen, AK Najmi, S. Ahmad: Pharmacological evidences for cytotoxic and antitumor properties of Boswellic acids from Boswellia serrata. In: Journal of ethnopharmacology. Volume 191, September 2016, pp. 315–323, doi : 10.1016 / j.jep.2016.06.053 , PMID 27346540 .
  11. ↑ [1]
  12. ↑ [2]
  13. ↑ SC Ng, YT Lam, KK Tsoi, FK Chan, JJ Sung, JC Wu: Systematic review: the efficacy of herbal therapy in inflammatory bowel disease. In: Alimentary pharmacology & therapeutics. Volume 38, Number 8, October 2013, pp. 854-863, doi : 10.1111 / apt.12464 , PMID 23981095 .