Fusarium proliferatum, an endophytic fungus from Dysoxylum binectariferum Hook.f, produces rohitukine, a chromane alkaloid possessing anti-cancer activity

Antonie van Leeuwenhoek, International Journal of General and Molecular Microbiology

Volumn 101, Issue 2, 2012, Pages 323-329

  Mohana Kumara, Patel ^a   Zuehlke, Sebastian ^b   Priti, Vaidyanathan ^a   Ramesha, Bheemanahally Thimmappa ^a   Shweta, Singh ^a   Ravikanth, Gudasalamani ^a,c   Vasudeva, Ramesh ^d   Santhoshkumar, Thankayyan Retnabai ^e   Spiteller, Michael ^b   Uma Shaanker, Ramanan ^a,c  

^a UNIVERSITY OF AGRICULTURAL SCIENCES   (India)

^b TU DORTMUND UNIVERSITY   (Germany)

^c ASHOKA TRUST FOR RESEARCH IN ECOLOGY AND THE ENVIRONMENT   (India)

^d College of Forestry   (India)

^e RAJIV GANDHI CENTRE FOR BIOTECHNOLOGY   (India)

Author keywords

Dysoxylum binectariferum; Endophytic fungus; Flavopiridol; Fusarium proliferatum; LC HRMS MS; Rohitukine

Indexed keywords

GLUCOSE; METHANOL; MICROBIAL PRODUCTS NOT CLASSIFIED ELSEWHERE; ROHITUKINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BARK; CELL STRAIN HCT116; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; DRY WEIGHT; DYSOXYLUM BINECTARIFERUM; ENDOPHYTE; FUNGUS CULTURE; FUNGUS ISOLATION; FUSARIUM PROLIFERATUM; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MELIACEAE; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL;

ALKALOIDS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; ENDOPHYTES; FUSARIUM; HUMANS; MELIACEAE; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PLANT BARK;

AMOORA ROHITUKA; DYSOXYLUM; FUNGI; FUSARIUM PROLIFERATUM; MELIACEAE; RUBIACEAE; SCHUMANNIOPHYTON; SOLANUM TUBEROSUM;

EID: 84857997769     PISSN: 00036072     EISSN: 15729699     Source Type: Journal    
DOI: 10.1007/s10482-011-9638-2     Document Type: Article

References (38)

1. Aly AH, Debbab A, Kjer J, Proksch P (2010) Fungal endophytes from higher plants: a prolific source of phytochemicals and other bioactive natural products. Fungal Divers 41:1-16
2. Aly AH, Debbab A, Proksch P (2011) Fungal endophytes: unique plant inhabitants with great promises. Appl Microbiol Biotechnol 90(6):1829-1845
3. Amna T, Puri SC, Verma V, Sharma JP, Khajuria RK, Musarrat J, Spiteller M, Qazi GN (2006) Bioreactor studies on the endophytic fungus Entrophospora infrequens for the production of an anti-cancer alkaloid camptothecin. Can J Microbiol 52(3):189-196 (Pubitemid 43873021)
4. Biglione S, Byers SA, Price JP, Nguyen VT, Bensaude O, Price DH, Maury W (2007) Inhibition of HIV-1 replication by P-TEFb inhibitors DRB, seliciclib and flavopiridol correlates with release of free P-TEFb from the large, inactive form of the complex. Retrovirology 4:47
5. Byrd JC, Lin TS, Dalton JT, Phelps M, Fischer B, Moran M, Blum K, Rovin B, Colevas AD, Grever MR (2006) Pharmacologically derived schedule of flavopiridol has significant efficacy in refractory, genetically high risk chronic lymphocytic leukemia (CLL). J Clin Oncol 24:6516
6. Cragg GM, Newman DJ (2005) International collaboration in drug discovery and development from natural sources. Pure Appl Chem 77:1923-1942 (Pubitemid 41746295)
7. Dancey J, Sausville EA (2003) Issues and progress with protein kinase inhibitors for cancer treatment. Nat Rev Drug Discov 2:296-313 (Pubitemid 37361688)
8. De Souza NJ (1993) Rohitukine and forskol. In: Kinghorn DA, Balandrin MF (eds) Human medicinal agents from plants. American Chemical Society, Washington, DC, pp 331-334
9. Guo LD, Hyde KD, Liew ECY (2001) Detection and taxonomic placement of endophytic fungi within frond tissues of Livistona chinensis based on rDNA sequences. Mol Phylogenet Evol 20:1-13 (Pubitemid 32656898)
10. Gurudatt PS, Priti V, Shweta S, Ramesha BT, Ravikanth G, Vasudeva R, Amna T, Deepika S, Ganeshaiah KN, Uma Shaanker R, Puri SC, Qazi NG (2010) Attenuation of camptothecin production and negative relation between hyphal biomass and camptothecin content in endophytic fungal strains isolated from Nothapodytes nimmoniana Graham (Icacinaceae). Curr Sci 98:1006-1010
11. Harmon AD, Weiss U, Silverton JV (1979) The structure of rohitukine, the main alkaloid of Amoora rohituka (syn. Aphanamixis polystachya) (Meliaceae). Tetrahedron Lett 8:721-724 (Pubitemid 9089392)
12. Houghton PJ, Hairong Y (1987) Further chromane alkaloids from Schumanniophyton magnificum. Planta Med 53:262-264 (Pubitemid 17094898)
13. Houghton PJ, Woldemariam TZ (1993) High performance liquid chromatographic analysis of chromane alkaloids from Schumanniophyton species. Phytochem Anal 4:9-13 (Pubitemid 23064502)
14. Ismail IS, Nagakura Y, Hirasawa Y, Hosoya T, Lazim MI, Lajis NH, Shiro M, Morita HJ (2009) Chrotacumines A-D, chromone alkaloids from Dysoxylum acutangulum. J Nat Prod 72:1879-1883
15. Karp JE, Douglas SB, Levis MJ, Gore SD, Greer J, Hattenburg C, Briel J, Jones RJ, Wright JJ, Dimitri CA (2007) Sequential flavopiridol, cytosine arabinoside, and mitoxantrone: a phase II trial in adults with poor-risk acute myelogenous leukemia. Clin Cancer Res 13:4467-4473 (Pubitemid 47219715)
16. Keshri G, Oberoi RM, Lakshmi V, Pandey K, Singh MM (2007) Contraceptive and hormonal properties of the stem bark of Dysoxylum binectariferum in rat and docking analysis of rohitukine, the alkaloid isolated from active chloroform soluble fraction. Contraception 76:400-407 (Pubitemid 47600131)
17. Kusari S, Lamshoft M, Zuehlke S, Spiteller M (2008) An endophytic fungus from Hypericum perforatum that produces hypericin. J Nat Prod 71:159-162 (Pubitemid 351362970)
18. Kusari S, Zuehlke S, Spiteller M (2009) An endophytic fungus from Camptotheca acuminata that produces camptothecin and analogues. J Nat Prod 72(1):2-7
19. Leslie JF, Summerell BA, Bullock S (2006) The Fusarium laboratory manual. Wiley-Blackwell, Hoboken, NJ, p 224
20. Manske FRH, Brossi (1987) The alkaloids: chemistry and pharmacology, vol 31, chap 3. Academic; San Diego, CA, pp 123-155
21. Mohana Kumara P, Sreejayan N, Priti V, Ramesha BT, Ravikanth G, Ganeshaiah KN, Vasudeva R, John Santhoshkumar TR, Dutt MP, Viswakarma R, Uma Shaanker R (2010) Dysoxylum binectariferum Hook.f (Meliaceae), a rich source of rohitukine. Fitoterapia 81:145-148
22. Myers N, Mittermeier RA, Mittermeier CG, daFonseca GAB, Kent J (2000) Biodiversity hotspots for conservation priorities. Nature 403:853-858 (Pubitemid 30130979)
23. Naik R, Ramachandra G, Kattige SL, Bhat SV, Alreja B, De Souza NJ, Rupp RH (1988) An anti-inflammatory and immune modulatory piperidinylbenzopyranone from Dysoxylum binectariferum: isolation, structure and total synthesis. Tetrahedron 44:2081-2086
24. Perkins KJ, Lusic M, Mitar I, Giacca M, Proudfoot NJ (2008) Transcription-dependent gene looping of the HIV-1 provirus is dictated by recognition of pre-mRNA processing signals. Mol Cell 29:56
25. Priti V, Ramesha BT, Shweta S, Ravikanth G, Ganeshaiah KN, Suryanarayanan TS, Uma Shaanker R (2009) How promising are endophytic fungi as alternative sources of plant secondary metabolites? Curr Sci 97(4):477-478
26. Puri SC, Verma V, Amna T, Qazi GN, Spiteller M (2005) An endophytic fungus from Nothapodytes foetida that produces camptothecin. J Nat Prod 68(12):1717-1719 (Pubitemid 43082640)
27. Sedlacek HH, Czech J, Naik R, Kaur G, Worland P, Losiewicz M, Parker B, Carlson B, Smith A, Senderowicz A, Sausville E (1996) Flavopiridol (L86 8275; NSC 649890): a new kinase inhibitor for tumor therapy. Int J Oncol 9:1143-1168 (Pubitemid 26393307)
28. Senderowicz AM, Sausville EA (2000) Preclinical and clinical development of cyclin-dependent kinase modulators. J Natl Cancer Inst 92:376-387 (Pubitemid 30154819)
29. Shweta S, Zuehlke S, Ramesha BT, Priti V, Mohana Kumar P, Ravikanth G, Spiteller M, Vasudeva R, Uma Shaanker R (2010) Endophytic fungal strains of Fusarium solani, from Apodytes dimidiata E. Mey. ex Arn (Icacinaceae) produce camptothecin, 10-hydroxycamptothecin and 9-methoxycamptothecin. Phytochemistry 71:117-122
30. Stadler WM, Vogelzang NJ, Amato R, Sosman J, Taber D, Liebowitz VokesE (2000) Flavopiridol, a novel cyclin-dependent kinase inhibitor, in metastatic renal cancer: a University of Chicago phase II consortium study. J Clin Oncol 18:371-375 (Pubitemid 30056427)
31. Stierle A, Strobel G, Stierle D (1993) Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of pacific yew. Science 260:214-216 (Pubitemid 23140886)
32. Strobel G, Daisy B (2003) Bioprospecting for microbial endophytes and their natural products. Microbiol Mol Biol Rev 67:491-502 (Pubitemid 37549769)
33. Suryanarayanan TS, Kumaresan V, Johnson JA (1998) Foliar endophytes from two species of the mangrove Rhizophora. Can J Microbiol 44:1003-1006
34. Vainio EJ, Korhonen K, Hantula J (1998) Genetic variation in Phlebiopsis gigantea as detected with random amplified microsatellite (RAMS) markers. Mycol Res 102:187-192
35. White TJ, Bruns T, Lee S, Taylor JW (1990) Amplification and direct sequencing of fungal ribosomal RNA genes for phylogenetics. In: PCR protocols: a guide to methods and applications. Academic, San Diego, CA, pp 315-322
36. Yang DH, Cai SQ, Yu YZ, Hong L (2003) Determination of the absolute configuration of rohitukine. Chin Chem Lett 14(7):720-723 (Pubitemid 37088360)
37. Yang DY, Cai SQ, Zhao YY, Liang H (2004) A new alkaloid from Dysoxylum binectariferum. J Asian Nat Prod Res 6(3):233-236
38. Zhao J, Shan T, Mou Y, Zhou L (2011) Plant-derived bioactive compounds produced by endophytic fungi. Mini Rev Med Chem 11:159-168