Biotransformation of 11-keto-β-boswellic acid by Cunninghamella blakesleana

Phytochemistry

Volumn 96, Issue , 2013, Pages 330-336

  Wang, Yue ^a   Sun, Yan ^b   Wang, Chao ^b   Huo, Xiaokui ^b   Liu, Pinduan ^a   Wang, Changyuan ^b   Zhang, Baojing ^b   Zhan, Libin ^b   Zhang, Houli ^b   Deng, Sa ^b   Zhao, Yanyan ^b   Ma, Xiaochi ^a,b  

^a JINZHOU MEDICAL UNIVERSITY   (China)

^b DALIAN MEDICAL UNIVERSITY   (China)

Author keywords

11 Keto boswellic acid; Biotransformation; Boswellia serrata; Burseraceae; Cunninghamella blakesleana AS 3.970; NO inhibition

Indexed keywords

BOSWELLIA SERRATA; BURSERACEAE; CUNNINGHAMELLA; CUNNINGHAMELLA BLAKESLEEANA;

11 KETO BOSWELLIC ACID; 11-KETO-BOSWELLIC ACID; ANTIINFLAMMATORY AGENT; IMMUNOLOGIC FACTOR; LIPOPOLYSACCHARIDE; NITRIC OXIDE; PLANT RESIN; TRITERPENE;

11-KETO-Β-BOSWELLIC ACID; ANIMAL; ARTICLE; BIOSYNTHESIS; BIOTRANSFORMATION; BOSWELLIA; BOSWELLIA SERRATA; BURSERACEAE; CHEMICAL STRUCTURE; CHEMISTRY; CUNNINGHAMELLA; CUNNINGHAMELLA BLAKESLEANA AS 3.970; DRUG ANTAGONISM; DRUG EFFECT; ISOLATION AND PURIFICATION; MACROPHAGE; METABOLISM; MOUSE; NO INHIBITION; OXIDATION REDUCTION REACTION; STRUCTURE ACTIVITY RELATION;

11-KETO-Β-BOSWELLIC ACID; BIOTRANSFORMATION; BOSWELLIA SERRATA; BURSERACEAE; CUNNINGHAMELLA BLAKESLEANA AS 3.970; NO INHIBITION;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BIOTRANSFORMATION; BOSWELLIA; CUNNINGHAMELLA; IMMUNOLOGIC FACTORS; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; MOLECULAR STRUCTURE; NITRIC OXIDE; OXIDATION-REDUCTION; RESINS, PLANT; STRUCTURE-ACTIVITY RELATIONSHIP; TRITERPENES;

EID: 84888356157     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.07.018     Document Type: Article

References (35)

1. E.A. Abourashed, A.M. Clark, and C.D. Hufford Microbial models of mammalian metabolism of xenobiotics: an updated review Curr. Med. Chem. 6 1999 359 374 (Pubitemid 29230819)
2. S.S. Agrawal, S. Saraswati, R. Mathur, and M. Pandey Antitumor properties of Boswellic acid against Ehrlich ascites cells bearing mouse Food Chem. Toxicol. 49 2011 1924 1934
3. H.P.T. Ammon Boswellic acids in chronic inflammatory diseases Planta Med. 72 2006 1100 1116 (Pubitemid 44638909)
4. S. Asha, and M. Vidyavathi Cunninghamella - a microbial model for drug metabolism studies - a review Biotechnol. Adv. 27 2009 16 29
5. R. Azerad Microbial models for drug metabolism Adv. Biochem. Eng. Biotechnol. 63 1999 169 218
6. Carla C.C.R. de Carvalho, and M. Manuela R. da Fonseca Biotransformation of terpenes Biotechnol. Adv. 24 2006 134 142 (Pubitemid 43172050)
7. S. Deng, B.J. Zhang, C.Y. Wang, Y. Tian, J.H. Yao, L. An, S.S. Huang, J.Y. Peng, K.X. Liu, and X.C. Ma Microbial transformation of deoxyandrographolide and their inhibitory activity on LPS-induced NO production in RAW 264.7 macrophages Bioorg. Med. Chem. Lett. 22 2012 1615 1618
8. I. Gupta, A. Parihar, P. Malhotra, G.B. Singh, R. Lüdtke, H. Safayhi, and H.P. Ammon Effects of Boswellia serrata gum resin in patients with ulcerative colitis Eur. J. Med. Res. 2 1997 37 43
9. I. Gupta, V. Gupta, A. Parihar, S. Gupta, R. Lüdtke, H. Safayhi, and H.P. Ammon 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 1998 511 514
10. R. Han Highlight on the studies of anticancer drugs derived from plants in China Stem Cells 12 1994 53 63 (Pubitemid 24045786)
11. B.H. Han, K.M. Kim, J.H. Park, M.H. Park, T.H. Kim, and Y.N. Han Studies on triterpenoid corticomimetics (III) determination of acetyl-11-keto-β- boswellic acid and 11-keto-β-boswellic acid in Olibanum Arch. Pharm. Res. 8 1985 213 220
12. S. Khan, R. Chib, B.A. Shah, Z.A. Wani, N. Dhar, D.M. Mondhe, S. Lattoo, S.K. Jain, S.C. Taneja, and J. Singh A cyano analogue of boswellic acid induces crosstalk between p53/PUMA/Bax and telomerase that stages the human papillomavirus type 18 positive HeLa cells to apoptotic death Eur. J. Pharmacol. 660 2011 241 248
13. D. Khanna, G. Sethi, K.S. Ahn, M.K. Pandey, A.B. Kunnumakkara, B. Sung, A. Aggarwal, and B.B. Aggarwal Natural products as a gold mine for arthritis treatment Curr. Opin. Pharmacol. 7 2007 344 351 (Pubitemid 46731200)
14. P. Krüger, R. Daneshfar, G.P. Eckert, J. Klein, D.A. Volmer, U. Bahr, W.E. Müller, M. Karas, M. Schubert-Zsilavecz, and M. Abdel-Tawab Metabolism of boswellic acids in vitro and in vivo Drug Metab. Dispos. 36 2008 1135 1142 (Pubitemid 351717472)
15. H. Li, M. Ye, H. Guo, Y. Tian, J. Zhang, J. Zhou, Y. Hu, and D. Guo Biotransformation of 20(S)-protopanaxadiol by Mucor spinosus Phytochemistry 70 2009 1416 1420
16. F.Y. Li, P.R. Chang, S.S. Huang, B.J. Zhang, X.L. Xin, J.H. Yao, Q. Zhou, Y. Tian, S. Deng, and X.C. Ma Microbial transformation of deoxyandrographolide by Cunninghamella echinulata J. Mol. Cata. B: Enzymatic 68 2011 187 191
17. W.A. Loughlin Biotransformations in organic synthesis Bioresour. Technol. 74 2000 49 62 (Pubitemid 30190277)
18. X.C. Ma, X. Xin, K.X. Liu, J. Han, and D.A. Guo Microbial transformation of cinobufagin by Syncephalastrum racemosum J. Nat. Prod. 71 2008 1268 1270
19. X.C. Ma, X. Xin, B.J. Zhang, S. Deng, J.H. Yao, C.Y. Wang, J. Cui, Y. Tian, and K.X. Liu Efficient isolation and purification of five products from microbial biotransformation of cinobufagin by high-speed counter-current chromatography J. Sep. Sci. 33 2010 2272 2277
20. D. Poeckel, and O. Werz Boswellic acids: biological actions and molecular targets Curr. Med. Chem. 13 2006 3359 3369 (Pubitemid 44873750)
21. M.Y. Rather, S. Mishra, V. Verma, and S. Chand Biotransformation of methyl-β-d-glucopyranoside to higher chain alkyl glucosides by cell bound β-glucosidase of Pichia etchellsii Bioresour. Technol. 107 2012 287 294
22. H. Safayhi, T. Mack, and H.P. Ammon Protection by boswellic acids against galactosamine/endotoxin-induced hepatitis in mice Biochem. Pharmacol. 41 1991 1536 1537
23. H. Safayhi, T. Mack, J. Sabieraj, M.I. Anazodo, L.R. Subramanian, and H.P. Ammon Boswellic acids: novel, specific, nonredox inhibitors of 5-lipoxygenase J. Pharmacol. Exp. Ther. 261 1992 1143 1146
24. H. Safayhi, B. Rall, E.R. Sailer, and H.P. Ammon Inhibition by boswellic acids of human leukocyte elastase J. Pharmacol. Exp. Ther. 281 1997 460 463 (Pubitemid 27203102)
25. B.A. Shah, G.N. Qazi, and S.C. Taneja Boswellic acids: a group of medicinally important compounds Nat. Prod. Rep. 26 2009 72 89
26. S. Sharma, V. Thawani, L. Hingorani, M. Shrivastava, V.R. Bhate, and R. Khiyani Pharmacokinetic study of 11-keto-β-boswellic acid Phytomedicine 11 2004 255 260
27. U. Siemoneit, A. Koeberle, A. Rossi, F. Dehm, M. Verhoff, S. Reckel, T.J. Maier, J. Jauch, H. Northoff, F. Bernhard, V. Doetsch, L. Sautebin, and O. Werz Inhibition of microsomal prostaglandin E2 synthase-1 as a molecular basis for the anti-inflammatory actions of boswellic acids from frankincense Br. J. Pharmacol. 162 2011 147 162
28. S. Singh, A. Khajuria, S.C. Taneja, R.K. Johri, J. Singh, and G.N. Qazi Boswellic acids: a leukotriene inhibitor also effective through topical application in inflammatory disorders Phytomedicine 15 2008 400 407
29. S. Singh, A. Khajuria, S.C. Taneja, R.K. Khajuria, J. Singh, R.K. Johri, and G.N. Qazi The gastric ulcer protective effect of boswellic acids, a leukotriene inhibitor from Boswellia serrata in rats Phytomedicine 15 2008 408 415
30. T. Syrovets, B. Büchele, C. Krauss, Y. Laumonnier, and T. Simmet Acetyl-boswellic acids inhibit lipopolysaccharide-mediated TNF-alpha induction in monocytes by direct interaction with IkappaB kinases J. Immunol. 174 2005 498 506 (Pubitemid 40007440)
31. J. Wu, X. Yang, J. Ge, Y. Zhang, L. Wu, J. Liu, and X. Zhang Biotransformation of sophoricoside in Fructus sophorae by the fungus Schizophyllum commune Bioresour. Technol. 111 2012 496 499
32. X.L. Xin, G. Yang, Z.P. Gou, J.H. Yao, R. Lan, and X.C. Ma Structural determination of two new triterpenoids biotransformed from glycyrrhetinic acid by Mucor polymorphosporus Magn. Reson. Chem. 48 2010 164 167
33. X.L. Xin, X. Cui, C. Wang, B.J. Zhang, X.C. Ma, S.S. Huang, S. Deng, Y. Tian, H.L. Zhang, and M.H. Yang Microbial transformation of deoxyandrographolide by Fusarium graminearum AS 3.4598 J. Asian Nat. Prod. Res. 13 2011 350 355
34. X.L. Xin, D.H. Su, D. Sa, Y. Tian, B.J. Zhang, X.C. Ma, L. An, S.S. Huang, J.H. Yao, and X. Cui Novel microbial transformation of resibufogenin by Fusarium solani J. Asian Nat. Prod. Res. 13 2011 831 837
35. M. Ye, J. Han, G.Z. Tu, D.G. An, and D.A. Guo Microbial hydroxylation of bufalin by Cunninghamella blakesleana andMocor spinosus J. Nat. Prod. 68 2005 626 628 (Pubitemid 40586336)