Cunninghamella elegans

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Cunninghamella elegans
Scientific classification OOjs UI icon edit-ltr.svg
Domain: Eukaryota
Kingdom: Fungi
Division: Mucoromycota
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

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

Contents

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

Cunninghamella 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]

Cunninghamella 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]

Cunninghamella 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

Cunninghamella 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

Cunninghamella 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

Cunninghamella 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]

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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. 1 2 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.
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  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. Bibcode:2000ApEnM..66.3646M. 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. S2CID   85744435.
  16. 1 2 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.
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  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.
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  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. doi:10.1128/AEM.44.3.682-689.1982. PMC   242076 . PMID   7138006.
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  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. Bibcode:1993ApEnM..59.1977P. doi:10.1128/AEM.59.6.1977-1980.1993. 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. Bibcode:1989ApEnM..55.2275C. doi:10.1128/AEM.55.9.2275-2279.1989. 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. S2CID   20614148.
  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. 1 2 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.
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