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Planta Med 2000; 66(8): 781-782
DOI: 10.1055/s-2000-9614
DOI: 10.1055/s-2000-9614
Letter
© Georg Thieme Verlag Stuttgart · New York
3-Acetoxy Group of Genuine AKBA (Acetyl-11-keto-β-boswellic Acid) is α-Configurated
Further Information
Publication History
Publication Date:
31 December 2000 (online)
Abstract
The pentacyclic triterpenoid 3-acetyl-11-keto-β-boswellic acid (AKBA) from the resin of Boswellia spec. is a potent inhibitor of 5-lipoxygenase (5-LO). We noticed discrepancies in the nomenclature and stereochemistry of the 3-acetoxy group of boswellic acids. Isolation of AKBA under mild conditions and the data from the first X-ray crystallography study evidence the 3α-orientation of AKBA's acetoxy function.
References
- 1 Safayhi H,, Mack T,, Sabieraj J,, Anazodo M J,, Subramanian L R,, Ammon H PT.. Boswellic acids: novel, specific, nonredox inhibitors of 5-lipoxygenase. J. Pharmacol. Exp. Ther.. 1992;; 261 1143-6
- 2 Safayhi H,, Sailer E-R,, Ammon H PT.. Mechanism of 5-lipoxygenase inhibition by acetyl-11-keto-β-boswellic acid. Mol. Pharmacol.. 1995;; 47 1212-6
- 3 Sailer E-R,, Subramanian L R,, Rall B,, Hoernlein R F,, Ammon H PT,, Safayhi H.. Acetyl-11-keto-β-boswellic acid (AKBA): structure requirements for binding and 5-lipoxygenase inhibitory activity. Br. J. Pharmacol.. 1996;; 117 615-8
- 4 Samuelsson B,, Dahlen S E,, Lindgren J A,, Rouzer C E,, Serhan C N.. Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science. 1987;; 237 1171-6
- 5 Steele V E,, Holmes C A,, Hawk E T,, Kopelovich L,, Lubet R A,, Crowell J A,, Sigman C C,, Kelloff G J.. Lipoxygenase inhibitors as potential cancer chemopreventives. Cancer Epidemiol. Biomar. Prevent. 1999;; 8 467-83
- 6 Ghosh J,, Myers C E.. Inhibition of arachidonate 5-lipoxygenase triggers massive apoptosis in human prostata cancer cells. Proc. Natl. Acad. Sci.. USA 1998;; 95 13182-7
- 7 Böker D-K,, Winking M.. Die Rolle von Boswellia-Säuren in der Therapie maligner Gliome. Deutsches Ärzteblatt. 1997;; 94 A1197-9
- 8 Gupta I,, Parihar A,, Malhotra P,, Singh G B,, Lüdtke R,, Safayhi H,, Ammon H PT.. Effects of Boswellia serrata gum resin in patients with ulcerative colitis. Eur. J. Med. Res.. 1997;; 2 37-43
- 9 Gupta I,, Gupta V,, Parihar A,, Gupta S, Lüdtke R,, Safayhi H,, Ammon H PT.. 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.. 1998;; 3 511-4
- 10 Winterstein A,, Stein G.. Untersuchungen in der Spaponinreihe. Zur Kenntnis der Mono-oxy-triterpensäuren. Hoppe-S. Z. Physiol. Chem.. 1932;; 208 9-25
- 11 Pardhy R S,, Bhattacharyya S C.. β-Boswellic acid, acetyl-β-boswellic acid, acetyl-11-keto-β-boswellic adid & 11-keto-β-boswellic acid, four pentacyclic triterpene acids from the resin of Boswellia serrata . Roxb. Ind. J. Chem.. 1978;; 16B 176-8
- 12 Ruzicka L,, Rey E,, Spillmann M,, Baumgartner H.. Zur Kenntnis der Triterpene. Über die Beziehung zwischen der α-Elomolsäure und der sogen. β-Elomonsäure. Helv. Chim. Acta. 1943;; 26 1638-58
Dr. Hasan Safayhi
Institute of Pharmaceutical Sciences Department of Pharmacology
Auf der Morgense 8
72076 Tübingen
Germany
Email: hasan.safayhi@uni-tuebingen.de