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Papyracon Ⅴ

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Category Bioactive by-products
Catalog number BBF-02366
CAS
Molecular Weight 266.29
Molecular Formula C14H18O5

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Lachnum papyraceum. It has weak effect against nematodes and has inhibitory effect on L1210 and HL60 cells. It also has weak anti-gram-positive bacterial effect.

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Synonyms Lachnumlactone A
IUPAC Name 1-[1-hydroxy-2-(2-methyl-5-oxo-2H-furan-4-yl)ethyl]-4,4-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one
Canonical SMILES CC1C=C(C(=O)O1)CC(C23CC2C(OC3=O)(C)C)O
InChI InChI=1S/C14H18O5/c1-7-4-8(11(16)18-7)5-10(15)14-6-9(14)13(2,3)19-12(14)17/h4,7,9-10,15H,5-6H2,1-3H3
InChI Key UQOLUJIRDKSNLW-UHFFFAOYSA-N
Appearance Yellow Oily Matter
Antibiotic Activity Spectrum Gram-positive bacteria; Neoplastics (Tumor); Parasites
Solubility Soluble in Chloroform
1. New metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. VIII. Isolation, structure determination and biological activities of minor metabolites structurally related to mycorrhizin A
R Shan, M Stadler, O Sterner, H Anke J Antibiot (Tokyo). 1996 May;49(5):447-52. doi: 10.7164/antibiotics.49.447.
Five new minor metabolites, papyracon D (6), 6-O-methylpapyracon B (9), 6-O-methylpapyracon C (10), lachnumfuran A (11) and lachnumlactone A (12a), together with the known chloromycorrhizinol A (4), have been isolated from extracts of the culture fluids of the ascomycete Lachnum papyraceum. The compounds, which structures were determined by spectroscopic methods, are structurally related to the nematicidal and antibiotic mycorrhizin A (1), which also is produced by the fungus. The nematicidal, antibiotic and cytotoxic activities of the new compounds are weaker compared to those of mycorrhizin A (1). Papyracon D (6) possesses the highest antibiotic activities while lachnumlactone A (12a) is the most nematicidal and cytotoxic.
2. New metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. VI. Structure determination of non-halogenated metabolites structurally related to mycorrhizin A
M Stadler, H Anke, R Shan, O Sterner J Antibiot (Tokyo). 1995 Feb;48(2):154-7. doi: 10.7164/antibiotics.48.154.
The structure determination of four new biologically active non-halogenated metabolites isolated from submerged cultures of the ascomycete Lachnum papyraceum is described. The compounds are structurally related to the antibiotic mycorrhizin A: (l'Z)-Dechloromycorrhizin A (12), a stereoisomer of dechloromycorrhizin A (5) previously isolated from the same fungus, as well as papyracon A (13), papyracon B (14) and papyracon C (15) containing an exocyclic double bond. The amounts of the latter three increased significantly when CaBr2 was added to the culture medium. The structures were determined by spectroscopic methods.

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