Screening of filamentous fungi to identify biocatalysts for lupeol biotransformation

Molecules

Volumn 15, Issue 9, 2010, Pages 6140-6151

  De Carvalho, Tatiane C ^a   Polizeli, Aline M ^a   Turatti, Izabel C C ^a   Severiano, Marcela E ^b   De Carvalho, Carlos E ^b   Ambrósio, Sérgio R ^b   Crotti, Antônio E M ^b   De Figueiredo, Uir S ^c   Vieira, Paulo C ^d   Furtado, Niege A J C ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSIDADE DE FRANCA   (Brazil)

^c Universidade Federal   (Brazil)

^d Universidade Federal de S Carlos   (Brazil)

Author keywords

Biocatalysts; Biotransformation; Filamentous fungi; Lupeol; Mass spectrometry

Indexed keywords

ANTIINFLAMMATORY AGENT; LUPEOL; PENTACYCLIC TRITERPENE; TRITERPENE;

ARTICLE; ASPERGILLUS OCHRACEUS; BIOTRANSFORMATION; CATALYSIS; CHEMISTRY; FUNGUS; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; MUCOR;

ANTI-INFLAMMATORY AGENTS; ASPERGILLUS OCHRACEUS; BIOTRANSFORMATION; CATALYSIS; FUNGI; MASS SPECTROMETRY; MUCOR; PENTACYCLIC TRITERPENES; TRITERPENES;

EID: 77957299897     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15096140     Document Type: Article

References (41)

1. Shibuya, M.; Xiang, T.; Katsube, Y.; Otsuka, M.; Zhang, H.; Ebizuka, Y. Origin of structural diversity in natural triterpenes: direct synthesis of seco-triterpene skeletons by oxidosqualene cyclase. J. Am. Chem. Soc. 2007, 129, 1450-1455.
2. Barroso-González, J.; Jaber-Vazdekis, N. E.; García- Expósito, L.; Machado, J. D.; Zárate, R.; Ravelo, A. G.; Estévez-Braun, A.; Valenzuela-Fernández, A. The Lupane-type triterpene 30-oxo-calenduladiol is a CCR5 antagonist with anti-HIV-1 and anti-chemotactic activities. J. Biol. Chem. 2009, 284, 16609-16620.
3. Qian, K.; Yu, D.; Chen, C.; Huang, L.; Morris-Natschke, S. L.; Nitz, T. J.; Salzwedel, K.; Reddick, M.; Allaway, G. P.; Lee, K.; Anti-AIDS agents 78. Design, synthesis, metabolic stability assessment, and antiviral evaluation of novel betulinic acid derivatives as potent anti-human immunodeficiency virus (HIV) agents. J. Med. Chem. 2009, 52, 3248-3258.
4. Badria, F. A.; Abu-Karam, M.; Mikhaeil, B. R.; Maatooq, G. T.; Amer, M. M. Anti-herpes activity of isolated compounds from frankincense. Biosci. Biotechnol. Res. Asia 2003, 1, 1-10.
5. Nakagawa-Goto, K.; Yamada, K.; Taniguchi, M.; Tokuda, H.; Lee, K.; Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents. Bioorg. Med. Chem. Lett. 2009, 19, 3378-3381.
6. Nguemfo, E. L.; Dimol, T.; Dongmo, A. B.; Azebaze, A. G. B.; Alaoui, K.; Asongalem, A. E.; Cherrah, Y.; Kamtchouingl, P. Anti-oxidative and anti-inflammatory activities of some isolated constituents from the stem bark of Allanblackia monticola Staner L. C (Guttiferae). Inflammopharmacology 2009, 17, 37-41.
7. Fulda, S.; Kroemer, G. Targeting mitochondrial apoptosis by betulinic acid in human cancers. Drug Discov. Today 2009, 14, 885-890.
8. Saleem, M.; Murtaza, I.; Tarapore, R. S.; Suh, Y.; Adhami, V. M.; Johnson, J. J.; Siddiqui, I. A.; Khan, N.; Asim, M.; Hafeez, B. B.; Shekhani, M. T.; Li, B.; Mukhtar, H. Lupeol inhibits proliferation of human prostate cancer cells by targeting beta-catenin signaling. Carcinogenesis 2009, 30, 808-817.
9. Xu, R.; Fazio, G. C.; Matsuda, S. P. T. On the origins of triterpenoid skeletal diversity. Phytochemistry 2004, 65, 261-291.
10. Reddy, K. P.; Singh, A. B.; Puri, A.; Srivastava, A. K.; Narender, T. Synthesis of novel triterpenoid (lupeol) derivatives and their in vivo antihyperglycemic and antidyslipidemic activity. Bioorg. Med. Chem. Lett. 2009, 19, 4463-4466.
11. Huang, L.; Yub, D.; Hoa, P.; Leeb, K.; Chen, C. Synthesis and anti-HIV activity of bi-functional triterpene derivatives. Lett. Drug Des. Discov. 2007, 4, 471-478.
12. Petronelli, A.; Pannitteri, G.; Testa, U. Triterpenoids as new promising anticancer drugs. Anticancer Drugs 2009, 20, 880-892.
13. Martin, D. E.; Blum, R.; Wilton, J.; Doto, J.; Galbraith, H.; Burgess, G. L.; Smith, P. C.; Ballow, C. Safety and pharmacokinetics of Bevirimat (PA-457), a novel inhibitor of human immunodeficiency virus maturation, in healthy volunteers. Antimicrob. Agents Chemother. 2007, 51, 3063-3066.
14. Smith, P. F.; Ogundele, A.; Forrest, A.; Wilton, J.; Salzwedel, K.; Doto, J.; Allaway, G. P.; Martin, D. E. Phase I and II study of the safety, virologic effect, and pharmacokinetics/pharmacodynamics of single-dose 3-O-(3′, 3′-Dimethylsuccinyl) betulinic acid (Bevirimat) against human immunodeficiency virus infection. Antimicrob. Agents Chemother. 2007, 51, 3574-3581.
15. Willmann, M.; Wacheck, V.; Buckley, J.; Nagy, K.; Thalhammer, J.; Paschke, R.; Triche, T.; Jansen, B.; Selzer E. Characterization of NVX-207, a novel betulinic acid-derived anti-cancer compound. Eur. J. Clin. Invest. 2009, 39, 384-394.
16. Akihisa, T.; Takamine, Y.; Yoshizumi, K.; Tokuda, H.; Kimura, Y.; Ukiya, M.; Nakahara, T.; Yokochi, T.; Ichiishi, E.; Nishino, H. Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products. J. Nat. Prod. 2002, 65, 278-282.
17. Bastos, D. Z. L.; Pimentel, I. C.; Jesus, D. A.; Oliveira, B. H. Biotransformation of betulinic and betulonic acids by fungi. Phytochemistry 2007, 68, 834-839.
18. Tolstikova, T. G.; Sorokina, I. V.; Tolstikov, G. A.; Tolstikov, A. G.; Flekhter, O. B. Biological activity and pharmacological prospects of Lupane terpenoids: I. Natural Lupane derivatives. Russ. J. Bioorganic Chem. 2006, 32, 37-49.
19. Hudlicky, T.; Reed, J. W. Applications of biotransformations and biocatalysis to complexity generation in organic synthesis. Chem. Soc. Rev. 2009, 38, 3117-3132.
20. Thomason, M. J.; Rhys-Williams, W.; Lloyd A. W.; Hanlon, G. W. The stereo inversion of 2-arylpropionic acid non-steroidal anti-inflammatory drugs and structurally related compounds by Verticillium lecanii. J. Appl. Microbiol. 1998, 85, 155-163.
21. Faramarzi, M. A.; Badiee, M.; Yazdi, M. T.; Amini, M.; Torshabi, M. Formation of hydroxysteroid derivatives from androst-4-en-3, 17-dione by the filamentous fungus Mucor racemosus. J. Mol. Catal., B Enzym. 2008, 50, 7-12.
22. Pekala, E.; Kochan, M.; Carnell, A. J. Microbial transformation of hydroxy metabolites of 1-oxohexyl derivatives of theobromine by Cunninghamella echinulata NRRL 1384. Lett. Appl. Microbiol. 2009, 48, 19-24.
23. Thiericke, R.; Rohr, J. Biological variation of microbial metabolites by precursor-directed biosynthesis. Nat. Prod. Rep. 1993, 10, 265-289.
24. Branco, A.; Pinto, A. C.; Braz-Filho, R. Chemical constituents of Vellozia graminifolia (Velloziaceae). Ann. Braz. Acad. Sci. 2004, 76, 505-518.
25. Sutherland, J. B.; Freeman, J. P.; Heinze, T. M.; Moody, J. D.; Parshikov, I. A.; Williams, A. J.; Zhang, D. Oxidation of phenothiazine and phenoxazine by Cunninghamella elegans. Xenobiotica 2001, 31, 799-809.
26. Duhart, B. T.; Zhang, D.; Deck, J.; Freeman, J. P.; Cerniglia, C. E. Biotransformation of protriptyline by filamentous fungi and yeasts. Xenobiotica 1999, 29, 733-746.
27. Pohl, C. H.; Botha, A.; Kock, J. L. F.; Coetzee, D. J.; Botes, P. J.; Schewe, T.; Nigam, S. Oxylipin formation in fungi: biotransformation of arachidonic acid to 3-hydroxy-5, 8-tetradecadienoic acid by Mucor genevensis. Biochem. Biophys. Res. Commun. 1998, 253, 703-706.
28. Demyttenaere, J.; De Kimpe, N. Biotransformation of terpenes by fungi. Study of the pathways involved. J. Mol. Catal., B Enzym. 2001, 11, 265-270.
29. Tomer, K. B. Separations combined with mass spectrometry. Chem. Rev. 2001, 101, 297-328.
30. Budzikiewicz, H.; Wilson, J. M.; Djerassi, C. Mass spectrometry in structural and stereochemical problems. XXXII. Pentacyclic triterpenes. J. Am. Chem. Soc. 1963, 85, 3688-3699.
31. Ogunkoya, L. Application of mass spectrometry in structural problems in triterpenes. Phytochemistry 1981, 20, 121-126.
32. Heizen, H.; De Vries, J. X.; Moyna, P.; Remberg, G.; Martinez, R.; Tietze, L. F. Mass spectrometry of labelled triterpenoids: thermospray and electron impact ionization analysis. Phytochem. Anal. 1996, 7, 237-244.
33. Assimopoulou, A. N.; Papageorgiou, V. P. GC-MS analysis of penta- and tetra-cyclic triterpenes from resins of Pistacia species. Biomed. Chromatogr. 2005, 19, 586-605.
34. Aguiar, G. P.; Wakabayashi, K. A. L.; Luz, G. F.; Oliveira, V. B.; Mathias, L.; Vieira, I. J. C.; Braz-Filho, R. B.; Crotti, A. E. M. Fragmentation of plumeran índole alkaloids from Aspidosperma spruceanum by electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2010, 24, 295-308.
35. Saratale, G. D.; Humnabadkar, R. P.; Govindwar, S. P. Study of mixed function oxidase system in Aspergillus ochraceus (NCIM 1146). Indian J. Microbiol. 2007, 47, 304-309.
36. Faramarzi, M. A.; Zolfaghary, N.; Yazdi, M. T.; Adrangi, S.; Rastegar, H.; Amini, M.; Badiee, M. Microbial conversion of androst-1, 4-dien-3, 17-dione by Mucor racemosus to hydroxysteroid-1, 4-dien-3-one derivatives. J. Chem. Technol. Biotechnol. 2009, 84, 1021-1025.
37. 4,9(10)-19-norsteroid drug. Bioorg. Med. Chem. 1999, 7, 2329-2341.
38. Velayos, A.; Fuentes-Vicente, M.; Aguilar-Elena, R.; Eslava, A. P.; Iturriaga, E. A. A novel fungal prenyl diphosphate synthase in the dimorphic zygomycete Mucor circinelloides. Curr. Genet. 2004, 45, 371-377.
39. Rocha, R. F.; Lapa, A. J.; Vale, J. R.; Braz-Filho, R.; Silva, S. B. Pharmacological activity of crude and purified extracts from Acosmium dasycarpum (Vog) Yakvol. Cienc. Cult. 1980, 33, 158-162.
40. 13C spectra and investigation of hindered side-chain rotation in lupeol derivatives. Magn. Reson. Chem. 2000, 38, 488-493.
41. Jackson, M.; Karwoswski, J. P.; Humphrey, P. E.; Kohl, W. L.; Barlow, G. J.; Tanaka, S. K. Calbistrins, novel antifungal agents produced by Penicillium restrictum. J. Antibiot. 1993, 46, 34-38.