Cunninghamella elegans

Cunninghamella elegans is a species of fungus in the genus Cunninghamella found in soil.[3]

Cunninghamella elegans
Scientific classification
Kingdom:
Fungi
Subdivision:
Mucoromycotina
Order:
Mucorales
Family:
Cunninghamellaceae
Genus:
Cunninghamella
Species:
C. elegans
Binomial name
Cunninghamella elegans
Lendner (1907)[1]
Synonyms
  • Cunninghamella echinulata var. elegans (Lendner) Lunn & Shipton[2]
  • Cunninghamella elegans var. elegans Lendn. 1905

It can be grown in Sabouraud dextrose broth, a liquid medium used for cultivation of yeasts and molds from liquid which are normally sterile.

As opposed to C. bertholletiae, it is not a human pathogen,[4] with the exception of two documented patients.[5]

Description

C. elegans is a filamentous fungus that produces purely gray colonies.[6]

Electron microscopy studies show that the conidia are covered with spines.[7]

Use as a fungal organism capable of xenobiotics metabolism

Cunninghamella elegans is able to degrade xenobiotics.[8] It has a variety of enzymes of phases I (modification enzymes acting to introduce reactive and polar groups into their substrates) and II (conjugation enzymes) of the xenobiotic metabolism, as do mammals. Cytochrome P450 monooxygenase, aryl sulfotransferase, glutathione S-transferase, UDP-glucuronosyltransferase, UDP-glucosyltransferase activities have been detected in cytosolic or microsomal fractions.[9]

Cytochrome P-450 and cytochrome P-450 reductase in C. elegans are part of the phase I enzymes. They are induced by the corticosteroid cortexolone and by phenanthrene.[10] C. elegans also possesses a lanosterol 14-alpha demethylase, another enzyme in the cytochrome P450 family.[11]

C. elegans also possesses a glutathione S-transferase.[12]

Use as a fungal model organism of mammalian drug metabolism

Cunninghamella elegans is a microbial model of mammalian drug metabolism.[13][14][15][16] The use of this fungus could reduce the over-all need for laboratory animals.[17]

C. elegans is able to transform the tricyclic antidepressants amitriptyline[18] and doxepin,[19] the tetracyclic antidepressant mirtazapine,[20] the muscle relaxant cyclobenzaprine,[21] the typical antipsychotic chlorpromazine as well as the antihistamine and anticholinergic methdilazine[22] and azatadine. It is also able to transform the antihistamines brompheniramine, chlorpheniramine and pheniramine.[23]

It forms a glucoside with the diuretic furosemide.[16]

The transformation of oral contraceptive mestranol by C. elegans yields two hydroxylated metabolites, 6beta-hydroxymestranol and 6beta,12beta-dihydroxymestranol.[24]

Metabolism of polycyclic aromatic hydrocarbons

The phase I cytochrome P450 enzyme systems of C. elegans has been implicated in the neutralization of numerous polycyclic aromatic hydrocarbons (PAH).[6]

It can degrade molecules such as anthracene, 7-methylbenz[a]anthracene and 7-hydroxymethylbenz[a]anthracene,[25] phenanthrene,[26] acenaphthene,[27] 1- and 2-methylnaphthalene,[28] naphthalene,[29] fluorene[30] or benzo(a)pyrene.[31]

In the case of phenanthrene, C. elegans produces a glucoside conjugate of 1-hydroxyphenanthrene (phenanthrene 1-O-beta-glucose).[32]

Metabolism of pesticides

C. elegans is also able to degrade the herbicides alachlor,[33] metolachlor[34] and isoproturon[35] as well as the fungicide mepanipyrim.[3]

Metabolism of phenolics

Cunninghamella elegans can be used to study the metabolism of phenols. This type of molecules already have reactive and polar groups comprised within their structure therefore phases I enzymes are less active than phase II (conjugation) enzymes.

Metabolism of flavonoids
Flavonols

In flavonols, an hydroxyl group is available in the 3- position allowing the glycosylation at that position. The biotransformation of quercetin yields three metabolites, including quercetin 3-O-β-D-glucopyranoside, kaempferol 3-O-β-D-glucopyranoside and isorhamnetin 3-O-β-D-glucopyranoside. Glucosylation and O-methylation are involved in the process.[36]

Flavones

In flavones, there is no hydroxyl group available at the 3- position. Conjugation, in the form of sulfation occurs at the 7- or 4'- positions. Apigenin and chrysin are also transformed by C. elegans and produce apigenin 7-sulfate, apigenin 7,4′-disulfate, chrysin 7-sulfate.[37]
Sulfation also occurs on naringenin and produces naringenin-7-sulfate.[38]

Glucosylation may nevertheless occur but in 3'- position, as happens during the microbial transformation of psiadiarabin and its 6-desmethoxy analogue, 5,3′ dihydroxy-7,2′,4′,5′-tetramethoxyflavone, by Cunninghamella elegans NRRL 1392 that gives the 3′-glucoside conjugates of the two flavones.[39]

flavanones

As in flavones, there is no hydroxyl groups available at the 3- position for glycosylation in flavanones. Therefore, sulfation occurs at the 7- position. In compounds like 7-methoxylated flavanones like 7-O-methylnaringenin (sakuranetin), demethylation followed by sulfation occur.[40]

Metabolism of synthetic phenolics

It is also able to degrade synthetic phenolic compounds like bisphenol A.[41]

Metabolism of heterocyclic organic compounds

C. elegans can transform the nitrogen containing compound phthalazine[42] It is also able to oxidize the organosulfur compound dibenzothiophene.[43]

Uses in biotechnology

Methods for efficient C. elegans genomic DNA isolation and transformation have been developed.[44]

The cytochrome P450 of C. elegans has been cloned in Escherichia coli[45] as well as an enolase.[46]

Use in bioconversion

Techniques employed

Cunninghamella elegans can be grown in stirred tank batch bioreactor.[47] Protoplasts cultures have been used.[48]

Examples of uses

C. elegans can be used for phenanthrene bioconversion[47] or for steroid transformation.[48] It has been used to produce isoapocodeine from 10,11-dimethoxyaporphine,[49] triptoquinone from the synthetic abietane diterpene triptophenolide[50] or for the rational and economical bioconversion of antimalarial drug artemisinin to 7beta-hydroxyartemisinin.[51]

Environmental biotechnology

Cunninghamella elegans has been used in environmental biotechnology for the treatment of textile wastewaters,[52] for instance those discoloured by azo dyes[53] or malachite green.[54]

Chitin[55] and chitosan isolated from C. elegans can be used for heavy metal biosorption.[56] Production can be made on yam bean (Pachyrhizus erosus L. Urban) medium.[57]

Strains

Cunninghamella elegans ATCC 9245[36]
Cunninghamella elegans ATCC 36112[6]
Cunninghamella elegans ATCC 26269[6]
Cunninghamella elegans NRRL 1393[6]
Cunninghamella elegans IFM 46109[56]
Cunninghamella elegans UCP 542[53]

gollark: If someone had accidentally made unaligned AGI, we would have bigger problems.
gollark: I see.
gollark: About what?
gollark: This doesn't say anything about *how* they're using it or how much, but it's pretty clear that it is not actually declining in users overall.
gollark: > But yeah i think 'normal' people have left the hype-train of the social media decade.Not according to this random graph of exactly one social media site!

References
  1. Lendner A. (1907). "Sur quelques Mucorinées". Bulletin de l'Herbier Boissier (in French). 7 (3): 249–51.
  2. Weitzmann I. (1984). "The case for Cunninghamella elegans, C. bertholletiae and C. echinulata as separate species". Transactions of the British Mycological Society. 83 (3): 527–529. doi:10.1016/S0007-1536(84)80056-X.
  3. Zhu, Y. Z.; Keum, Y. S.; Yang, L.; Lee, H.; Park, H.; Kim, J. H. (2010). "Metabolism of a Fungicide Mepanipyrim by Soil FungusCunninghamella elegansATCC36112". Journal of Agricultural and Food Chemistry. 58 (23): 12379–12384. doi:10.1021/jf102980y. PMID 21047134.
  4. Weitzman, I.; Crist, M. Y. (1979). "Studies with clinical isolates of Cunninghamella. I. Mating behavior". Mycologia. 71 (5): 1024–1033. doi:10.2307/3759290. JSTOR 3759290. PMID 545137.
  5. Kwon-Chung, K. J.; Young, R. C.; Orlando, M. (1975). "Pulmonary mucormycosis caused by Cunninghamella elegans in a patient with chronic myelogenous leukemia". American Journal of Clinical Pathology. 64 (4): 544–548. doi:10.1093/ajcp/64.4.544. PMID 1060379.
  6. Asha S, Vidyavathi M (2009). "Cunninghamella - a microbial model for drug metabolism studies - a review". Biotechnol. Adv. 27 (1): 16–29. doi:10.1016/j.biotechadv.2008.07.005. PMID 18775773.
  7. Hawker, L. E.; Thomas, B.; Beckett, A. (1970). "An Electron Microscope Study of Structure and Germination of Conidia of Cunninghamella elegans Lendner". Microbiology. 60 (2): 181–189. doi:10.1099/00221287-60-2-181.
  8. Wackett, L. P.; Gibson, D. T. (1982). "Metabolism of xenobiotic compounds by enzymes in cell extracts of the fungus Cunninghamella elegans". The Biochemical Journal. 205 (1): 117–122. doi:10.1042/bj2050117. PMC 1158453. PMID 6812568.
  9. Zhang, D.; Yang, Y.; Leakey, J. E. A.; Cerniglia, C. E. (1996). "Phase I and phase II enzymes produced byCunninghamella elegansfor the metabolism of xenobiotics". FEMS Microbiology Letters. 138 (2–3): 221–226. doi:10.1111/j.1574-6968.1996.tb08161.x. PMID 9026450.
  10. Lisowska, K.; Szemraj, J.; Rózalska, S.; Długoński, J. (2006). "The expression of cytochrome P-450 and cytochrome P-450 reductase genes in the simultaneous transformation of corticosteroids and phenanthrene byCunninghamella elegans". FEMS Microbiology Letters. 261 (2): 175–180. doi:10.1111/j.1574-6968.2006.00339.x. PMID 16907717.
  11. Lanosterol 14-alpha demethylase from Cunninghamella elegans on www.uniprot.org
  12. Cha, C. J.; Kim, S. J.; Kim, Y. H.; Stingley, R.; Cerniglia, C. E. (2002). "Molecular cloning, expression and characterization of a novel class glutathione S-transferase from the fungus Cunninghamella elegans". Biochemical Journal. 368 (2): 589–95. doi:10.1042/BJ20020400. PMC 1223007. PMID 12196209.
  13. Kristian Björnstad; Anders Helander; Peter Hultén; Olof Beck (2009). "Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications". Journal of Analytical Toxicology. 33 (9): 604–609. doi:10.1093/jat/33.9.604. PMID 20040135.
  14. Joanna D. Moody; Donglu Zhang; Thomas M. Heinze; Carl E. Cerniglia (2000). "Transformation of amoxapine by Cunninghamella elegans". Applied and Environmental Microbiology. 66 (8): 3646–3649. doi:10.1128/AEM.66.8.3646-3649.2000. PMC 92200. PMID 10919836.
  15. A. Jaworski; L. Sedlaczek; J. Dlugoński; Ewa Zajaczkowska (1985). "Inducible nature of the steroid 11-hydroxylases in spores of Cunninghamella elegans (Lendner)". Journal of Basic Microbiology. 25 (7): 423–427. doi:10.1002/jobm.3620250703.
  16. Hezari, M.; Davis, P. J. (1993). "Microbial models of mammalian metabolism. Furosemide glucoside formation using the fungus Cunninghamella elegans". Drug Metabolism and Disposition. 21 (2): 259–267. PMID 8097695.
  17. Sharma, KK; Mehta, T; Joshi, V; Mehta, N; Rathor, AK; Mediratta, KD; Sharma, PK (2011). "Substitute of animals in drug research: An approach towards fulfillment of 4R′s". Indian Journal of Pharmaceutical Sciences. 73 (1): 1–6. doi:10.4103/0250-474X.89750. PMC 3224398. PMID 22131615.
  18. Zhang, D.; Evans, F. E.; Freeman, J. P.; Duhart Jr, B.; Cerniglia, C. E. (1995). "Biotransformation of amitriptyline by Cunninghamella elegans". Drug Metabolism and Disposition. 23 (12): 1417–1425. PMID 8689954.
  19. Moody, J. D.; Freeman, J. P.; Cerniglia, C. E. (1999). "Biotransformation of doxepin by Cunninghamella elegans". Drug Metabolism and Disposition. 27 (10): 1157–1164. PMID 10497142.
  20. Moody, J. D.; Freeman, J. P.; Fu, P. P.; Cerniglia, C. E. (2002). "Biotransformation of Mirtazapine by Cunninghamella Elegans". Drug Metabolism and Disposition. 30 (11): 1274–1279. doi:10.1124/dmd.30.11.1274. PMID 12386135.
  21. Zhang, D.; Evans, F. E.; Freeman, J. P.; Yang, Y.; Deck, J.; Cerniglia, C. E. (1996). "Formation of mammalian metabolites of cyclobenzaprine by the fungus, Cunninghamella elegans". Chemico-Biological Interactions. 102 (2): 79–92. doi:10.1016/S0009-2797(96)03736-2. PMID 8950223.
  22. Zhang, D.; Freeman, J. P.; Sutherland, J. B.; Walker, A. E.; Yang, Y.; Cerniglia, C. E. (1996). "Biotransformation of chlorpromazine and methdilazine by Cunninghamella elegans". Applied and Environmental Microbiology. 62 (3): 798–803. PMC 167846. PMID 8975609.
  23. Hansen, E. B.; Cho, B. P.; Korfmacher, W. A.; Cerniglia, C. E. (1995). "Fungal transformations of antihistamines: Metabolism of brompheniramine, chlorpheniramine, and pheniramine toN-oxide andN-demethylated metabolites by the fungusCunninghamella elegans". Xenobiotica. 25 (10): 1081–1092. doi:10.3109/00498259509061908. PMID 8578764.
  24. Choudhary, M. I.; Musharraf, S. G.; Siddiqui, Z. A.; Khan, N. T.; Ali, R. A.; Ur-Rahman, A. (2005). "Microbial transformation of mestranol by Cunninghamella elegans". Chemical & Pharmaceutical Bulletin. 53 (8): 1011–1013. doi:10.1248/cpb.53.1011. PMID 16079537.
  25. Cerniglia, C. E.; Fu, P. P.; Yang, S. K. (1982). "Metabolism of 7-methylbenzaanthracene and 7-hydroxymethylbenzaanthracene by Cunninghamella elegans". Applied and Environmental Microbiology. 44 (3): 682–689. PMC 242076. PMID 7138006.
  26. Cerniglia, C. E.; Yang, S. K. (1984). "Stereoselective metabolism of anthracene and phenanthrene by the fungus Cunninghamella elegans". Applied and Environmental Microbiology. 47 (1): 119–124. PMC 239622. PMID 6696409.
  27. Pothuluri, J. V.; Freeman, J. P.; Evans, F. E.; Cerniglia, C. E. (1992). "Fungal metabolism of acenaphthene by Cunninghamella elegans". Applied and Environmental Microbiology. 58 (11): 3654–3659. PMC 183157. PMID 1482186.
  28. Cerniglia, C. E.; Lambert, K. J.; Miller, D. W.; Freeman, J. P. (1984). "Transformation of 1- and 2-methylnaphthalene by Cunninghamella elegans". Applied and Environmental Microbiology. 47 (1): 111–118. PMC 239621. PMID 6696408.
  29. Cerniglia, C. E.; Gibson, D. T. (1977). "Metabolism of naphthalene by Cunninghamella elegans". Applied and Environmental Microbiology. 34 (4): 363–370. PMC 242664. PMID 921262.
  30. Pothuluri, J. V.; Freeman, J. P.; Evans, F. E.; Cerniglia, C. E. (1993). "Biotransformation of fluorene by the fungus Cunninghamella elegans". Applied and Environmental Microbiology. 59 (6): 1977–1980. PMC 182201. PMID 8328814.
  31. Cerniglia, C. E.; Mahaffey, W.; Gibson, D. T. (1980). "Fungal oxidation of benzo\a]pyrene: Formation of (−)-trans-7,8-dihydroxy-7,8-dihydrobenzo\a]pyrene by Cunninghamella elegans". Biochemical and Biophysical Research Communications. 94 (1): 226–232. doi:10.1016/S0006-291X(80)80210-5. PMID 7190014.
  32. Cerniglia, C. E.; Campbell, W. L.; Freeman, J. P.; Evans, F. E. (1989). "Identification of a novel metabolite in phenanthrene metabolism by the fungus Cunninghamella elegans". Applied and Environmental Microbiology. 55 (9): 2275–2279. PMC 203068. PMID 2802607.
  33. Pothuluri, J. V.; Freeman, J. P.; Evans, F. E.; Moorman, T. B.; Cerniglia, C. E. (1993). "Metabolism of alachlor by the fungus Cunninghamella elegans". Journal of Agricultural and Food Chemistry. 41 (3): 483–488. doi:10.1021/jf00027a026.
  34. Jairaj V. Pothuluri, Frederick E. Evans; Doerge, D.R.; Churchwell, M.I. & Carl E. Cerniglia (1997). "Metabolism of metolachlor by the fungus Cunninghamella elegans". Arch. Environ. Contam. Toxicol. 32 (2): 117–125. doi:10.1007/s002449900163. PMID 9069185.
  35. Hangler, M.; Jensen, B.; Rønhede, S.; Sørensen, S. R. (2007). "Inducible hydroxylation and demethylation of the herbicide isoproturon by Cunninghamella elegans". FEMS Microbiology Letters. 268 (2): 254–260. doi:10.1111/j.1574-6968.2006.00599.x. PMID 17328751.
  36. Zi, J.; Valiente, J.; Zeng, J.; Zhan, J. (2011). "Metabolism of quercetin by Cunninghamella elegans ATCC 9245". Journal of Bioscience and Bioengineering. 112 (4): 360–362. doi:10.1016/j.jbiosc.2011.06.006. PMID 21742550.
  37. Ibrahim, A. R. S. (2005). "Biotransformation of Chrysin and Apigenin by Cunninghamella elegans". Chemical & Pharmaceutical Bulletin. 53 (6): 671–672. doi:10.1248/cpb.53.671. PMID 15930780.
  38. Abdel-Rahim S. Ibrahim (2000). "Sulfation of naringenin by Cunninghamella elegans". Phytochemistry. 53 (2): 209–212. doi:10.1016/S0031-9422(99)00487-2. PMID 10680173.
  39. Ibrahim, A. R.; Galal, A. M.; Mossa, J. S.; El-Feraly, F. S. (1997). "Glucose-conjugation of the flavones of Psiadia arabica by Cunninghamella elegans". Phytochemistry. 46 (7): 1193–1195. doi:10.1016/s0031-9422(97)00421-4. PMID 9423290.
  40. Ibrahim, A. R.; Galal, A. M.; Ahmed, M. S.; Mossa, G. S. (2003). "O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans". Chemical & Pharmaceutical Bulletin. 51 (2): 203–206. doi:10.1248/cpb.51.203. PMID 12576658. INIST:14569933.
  41. Keum, Y. S.; Lee, H. R.; Park, H. W.; Kim, J. H. (2010). "Biodegradation of bisphenol a and its halogenated analogues by Cunninghamella elegans ATCC36112". Biodegradation. 21 (6): 989–997. doi:10.1007/s10532-010-9358-8. PMID 20455075.
  42. Sutherland, John B.; Freeman, James P.; Williams, Anna J.; Deck, Joanna (1999). "Biotransformation of Phthalazine by Fusarium moniliforme and Cunninghamela elegans". Mycologia. 91 (1): 114–116. doi:10.2307/3761198. JSTOR 3761198.
  43. Crawford, D. L.; Gupta, R. K. (1990). "Oxidation of dibenzothiophene byCunninghamella elegans". Current Microbiology. 21 (4): 229–231. doi:10.1007/BF02092161.
  44. Zhang, D.; Yang, Y.; Castlebury, L. A.; Cerniglia, C. E. (1996). "A method for the large scale isolation of high transformation efficiency fungal genomic DNA". FEMS Microbiology Letters. 145 (2): 261–265. doi:10.1111/j.1574-6968.1996.tb08587.x. PMID 8961565.
  45. Wang, R. F.; Cao, W. W.; Khan, A. A.; Cerniglia, C. E. (2000). "Cloning, sequencing, and expression inEscherichia coliof a cytochrome P450 gene fromCunninghamella elegans". FEMS Microbiology Letters. 188 (1): 55–61. doi:10.1111/j.1574-6968.2000.tb09168.x. PMID 10867234.
  46. Wang, R. F.; Khan, A. A.; Cao, W. W.; Cerniglia, C. E. (2000). "Cloning, sequencing, and expression of the gene encoding enolase from Cunninghamella elegans". Mycological Research. 104 (2): 175–179. doi:10.1017/S0953756299001112.
  47. Lisowska, K.; Bizukojc, M.; Długoński, J. (2006). "An unstructured model for studies on phenanthrene bioconversion by filamentous fungus Cunninghamella elegans". Enzyme and Microbial Technology. 39 (7): 1464–1470. doi:10.1016/j.enzmictec.2006.03.039.
  48. Długoński, J.; Sedlaczek, L.; Jaworski, A. (1984). "Protoplast release from fungi capable of steroid transformation". Canadian Journal of Microbiology. 30 (1): 57–62. doi:10.1139/m84-010. PMID 6713303. (French)
  49. Smith, R. V.; Davis, P. J. (1978). "Regiospecific synthesis of isoapocodeine from 10,11-dimethoxyaporphine by using Cunninghamella elegans". Applied and Environmental Microbiology. 35 (4): 738–742. PMC 242915. PMID 25623.
  50. TMilanova, R.; Stoynov, N.; Moore, M. (1996). "The optimization of triptoquinone production by Cunninghamella elegans using factorial design". Enzyme and Microbial Technology. 19 (2): 86–93. doi:10.1016/0141-0229(95)00184-0.
  51. Parshikov, I. A.; Muraleedharan, K. M.; Avery, M. A.; Williamson, J. S. (2004). "Transformation of artemisinin by Cunninghamella elegans". Applied Microbiology and Biotechnology. 64 (6): 782–786. doi:10.1007/s00253-003-1524-z. PMID 14735322.
  52. Tigini, V.; Prigione, V.; Donelli, I.; Anastasi, A.; Freddi, G.; Giansanti, P.; Mangiavillano, A.; Varese, G. C. (2010). "Cunninghamella elegans biomass optimisation for textile wastewater biosorption treatment: An analytical and ecotoxicological approach". Applied Microbiology and Biotechnology. 90 (1): 343–352. doi:10.1007/s00253-010-3010-8. PMID 21127858.
  53. Ambrósio, S.; Campos-Takaki, G. M. (2004). "Decolorization of reactive azo dyes by Cunninghamella elegans UCP 542 under co-metabolic conditions". Bioresource Technology. 91 (1): 69–75. doi:10.1016/S0960-8524(03)00153-6. PMID 14585623.
  54. Cha, C. -J.; Doerge, D. R.; Cerniglia, C. E. (2001). "Biotransformation of Malachite Green by the Fungus Cunninghamella elegans". Applied and Environmental Microbiology. 67 (9): 4358–4360. doi:10.1128/AEM.67.9.4358-4360.2001. PMC 93171. PMID 11526047.
  55. Andrade, V. S.; Neto, B. B.; Souza, W.; Campos-Takaki, G. M. (2000). "A factorial design analysis of chitin production byCunninghamella elegans". Canadian Journal of Microbiology. 46 (11): 1042–1045. doi:10.1139/w00-086. PMID 11109493.
  56. Franco, L. D. O.; Maia, R. D. C. S. C.; Porto, A. L. C. F.; Messias, A. S.; Fukushima, K.; Campos-Takaki, G. M. D. (2004). "Heavy metal biosorption by chitin and chitosan isolated from Cunninghamella elegans (IFM 46109)". Brazilian Journal of Microbiology. 35 (3): 243–247. doi:10.1590/S1517-83822004000200013.
  57. Montenegro Stamford, T. C.; Montenegro Stamford, T. L.; Pereira Stamford, N.; De Barros Neto, B.; De Campos-Takaki, G. M. (2007). "Growth of Cunninghamella elegans UCP 542 and production of chitin and chitosan using yam bean medium". Electronic Journal of Biotechnology. 10: 0. doi:10.2225/vol10-issue1-fulltext-1.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.