10-Norparvulenone
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02136 |
| CAS | 618104-32-8 |
| Molecular Weight | 238.24 |
| Molecular Formula | C12H14O5 |
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Description
It is originally isolated from Microsphaeropsis sp. FO-5050. 10-Norparvulenone inhibits viral Sialidase by IC50 of 21 μg/mL and inhibits influenza virus A/PR/8/34 replication in MDCK cells.
Specification
| Synonyms | MLS004711975; 3,4-dihydro-4,8-dihydroxy-7-(hydroxymethyl)-6-methoxy-1(2H)-naphthalenone |
| Storage | Store at -20°C |
| IUPAC Name | 4,8-dihydroxy-7-(hydroxymethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one |
| Canonical SMILES | COC1=C(C(=C2C(=O)CCC(C2=C1)O)O)CO |
| InChI | InChI=1S/C12H14O5/c1-17-10-4-6-8(14)2-3-9(15)11(6)12(16)7(10)5-13/h4,8,13-14,16H,2-3,5H2,1H3 |
| InChI Key | NXSUIALRPVXVTA-UHFFFAOYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | viruses |
| Solubility | Soluble in Ethanol, Methanol, Dichloromethane, DMSO |
Reference Reading
1. Pulvinulin A, graminin C, and cis-gregatin B--new natural furanones from Pulvinula sp. 11120, a fungal endophyte of Cupressus arizonica
E M Kithsiri Wijeratne, Yaming Xu, A Elizabeth Arnold, A A Leslie Gunatilaka Nat Prod Commun. 2015 Jan;10(1):107-11.
Three new natural furanones, pulvinulin A (1), graminin C (2), and cis-gregatin B (3), together with the known fungal metabolites, graminin B (4) and 10-norparvulenone (5), were isolated from Pulvinula sp. 11120, an endophytic fungal strain occurring in healthy foliage of Cupressus arizonica (Arizona cypress). The structures of 1 and 2 were elucidated by the analysis of their spectroscopic data and chemical interconversions, and that of 3 was determined by comparison with data for synthetic cis-gregatin B. Comparison of spectroscopic data of 4 and 5 with those reported identified them as graminin B and 10-norparvulenone, respectively. Metabolites 1-4 exhibited antibacterial activity against E. coli.
2. Total synthesis of 10-norparvulenone and of O-methylasparvenone using a xanthate-mediated free radical addition-cyclization sequence
Alejandro Cordero Vargas, Béatrice Quiclet-Sire, Samir Z Zard Org Lett. 2003 Oct 2;5(20):3717-9. doi: 10.1021/ol035394o.
[reaction: see text] A short synthesis of (+/-)-10-norparvulenone and (+/-)-O-methylasparvenone was developed starting from commercially available m-methoxyphenol, hinging on a xanthate-mediated addition-cyclization sequence for the construction of the alpha-tetralone subunit.
3. Mono- and Dimeric Naphthalenones from the Marine-Derived Fungus Leptosphaerulina chartarum 3608
Panpan Zhang, Chunxiu Jia, Jiajia Lang, Jing Li, Guangyuan Luo, Senhua Chen, Sujun Yan, Lan Liu Mar Drugs. 2018 May 21;16(5):173. doi: 10.3390/md16050173.
Five new naphthalenones, two enantiomers (-)-1 and (+)-1 leptothalenone A, (-)-4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one ((-)-2), (4S, 10R, 4'S)-leptotha-lenone B (5), (4R, 10S, 4'S)-leptothalenone B (6), and a new isocoumarine, 6-hydroxy-5,8-dimethoxy-3-methyl-1H-isochromen-1-one (4), along with two known compounds (+)-4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one ((+)-2) and (+)-10-norparvulenone (3) were isolated from the marine-derived fungus Leptosphaerulina chartarum 3608. The structures of new compounds were elucidated by HR-ESIMS, NMR, and ECD analysis. All compounds were evaluated for cytotoxicity and anti-inflammatory activity. Compound 6 showed moderate anti-inflammatory activity by inhibiting the production of nitric oxide (NO) in lipopolysaccharide-stimulated RAW264.7 cells, with an IC50 value of 44.5 μM.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
