Cunninghamella elegans

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Cunninghamella elegans
Scientific classification
Kingdom: Fungi
Subphylum: 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 is a species of fungus in the genus Cunninghamella found in soil.[3]

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[edit]

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[edit]

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[edit]

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[edit]

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[edit]

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[edit]

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[edit]

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[edit]

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

Metabolism of heterocyclic organic compounds[edit]

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

Uses in biotechnology[edit]

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[edit]

Techniques employed[edit]

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

Examples of uses[edit]

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[edit]

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[edit]

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]

References[edit]

  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". The Transactions of the British Mycological Society. 83 (3): 527–529. doi:10.1016/S0007-1536(84)80056-X. 
  3. ^ a b 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. 
  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. PMID 545137. JSTOR 3759290. 
  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. PMID 1060379. 
  6. ^ a b c d e 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. Retrieved 2009-03-17. 
  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. 
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  11. ^ Lanosterol 14-alpha demethylase from Cunninghamella elegans on www.uniprot.org
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External links[edit]