Chemistry:Nebularine
| File:Nebularine.svg Molecular structure of nebularine
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| IUPAC name
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-purin-9-yloxolane-3,4-diol
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| Properties | |
| C10H12N4O4 | |
| Molar mass | 252.230 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Nebularine is an organic compound with the chemical formula C10H12N4O4, belonging to the purine family. In biochemical nomenclature, the short abbreviation symbol for nebularine is P. It is a ribonucleoside, with adenosine as its precursor.[1][2][3]
Origins
In 1953, Swedish chemists Nils Löfgren and Björn Lüning, alongside veterinary bacteriologist Harry Hedström[4] isolated nebularine from a secondary metabolite of the fungus Clitocybe nebularis, from which nebularine gets its name.[4] Subsequently, it was also found in the bacterium Streptomyces yokosukanensis and certain mesophilic bacteria of the Microbispora genus.[5] Since the amount of nebularine in the fungus is too low to allow for sufficient extraction via mycelial culture, the compound is produced biotechnologically from the bacterium S. yokosukanensis[1] or by chemical synthesis.[5]
Properties
Nebularine exhibits antiviral activity against influenza B; antibiotic activity against bacteria of the genera Mycobacterium and Brucella melitensis; antiparasitic activity against Entamoeba histolytica and Schistosoma mansoni; and oncoststic activity.[5] It also has moderate antifungal activity.[6]
Nebularine also has a very strong inhibitory effect on the growth of wheat, lettuce, spinach, and carrot seedlings. It is a potent antagonist of cytokinin activity, as demonstrated by biological assays on Amaranthus and leaf senescence. It has also been shown to be a noncompetitive inhibitor of xanthine oxidase.[1]
References
- ↑ 1.0 1.1 1.2 Konuk, M. (1993). "Studies of the biosynthesis and properties of nebularine" (in en). University College of Swansea. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.637822.
- ↑ PubChem. "Nebularine" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/68368.
- ↑ Rahman, M. S.; Humayun, M. Z. (1997-07-03). "Nebularine (9-2'-deoxy-beta-D-ribofuranosylpurine) has the template characteristics of adenine in vivo and in vitro". Mutation Research 377 (2): 263–268. doi:10.1016/s0027-5107(97)00084-5. ISSN 0027-5107. PMID 9247623. https://pubmed.ncbi.nlm.nih.gov/9247623.
- ↑ 4.0 4.1 N Löfgren; B Lüning; H Hedström (1954). "The isolation of nebularine and the determination of its structure" (in en). Acta Chemical Scandinavia 8: 670–680. doi:10.3891/acta.chem.scand.08-0670. http://actachemscand.org/pdf/acta_vol_08_p0670-0680.pdf.
- ↑ 5.0 5.1 5.2 Florence Cherqui; Sylvie Rapior; Pierre Cuq (1999). "Les activités biologiques de Lepista nebularis (Batsch:Fr) Harm." (in fr). Société d'Horticulture et d'Histoire Naturelle de l'Hérault 139: 75-86. https://s2hnh.org/wp-content/uploads/2017/02/2-Cherqui1999_SHHNH_LepistaClitocybenebularis_F2600930d01.pdf.
- ↑ Young-Sook (2008). "Chemical Constituents of the Fruiting Bodies of Clitocybe nebularis and Their Antifungal Activity" (in en). Mycobiology 36 (2): 110–113. doi:10.4489/MYCO.2008.36.2.110. PMID 23990744. PMC 3755233. Bibcode: 2008Mycob..36..110K. https://www.tandfonline.com/doi/pdf/10.4489/MYCO.2008.36.2.110. Retrieved 2020-10-26.
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