Nebularine
 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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| DrugBank | |
| ECHA InfoCard | 100.008.166 |
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PubChem CID |
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CompTox Dashboard (EPA) |
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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 C
10H
12N
4O
4, 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
[edit]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
[edit]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
[edit]- 1 2 3 Konuk, M. (1993). "Studies of the biosynthesis and properties of nebularine". University College of Swansea.
- ↑ PubChem. "Nebularine". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-08-23.
- ↑ 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.
- 1 2 N Löfgren; B Lüning; H Hedström (1954). "The isolation of nebularine and the determination of its structure" (PDF). Acta Chemical Scandinavia. 8: 670–680. doi:10.3891/acta.chem.scand.08-0670.
- 1 2 3 Florence Cherqui; Sylvie Rapior; Pierre Cuq (1999). "Les activités biologiques de Lepista nebularis (Batsch:Fr) Harm" (PDF). Société d'Horticulture et d'Histoire Naturelle de l'Hérault (in French). 139: 75-86.
- ↑ Young-Sook; et al. (2008). "Chemical Constituents of the Fruiting Bodies of Clitocybe nebularis and Their Antifungal Activity". Mycobiology. 36 (2): 110–113. Bibcode:2008Mycob..36..110K. doi:10.4489/MYCO.2008.36.2.110. PMC 3755233. PMID 23990744. Retrieved 2020-10-26.