Favolon

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Category Antibiotics
Catalog number BBF-00904
CAS
Molecular Weight 590.74
Molecular Formula C33H50O9

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Description

Favolon is a triterpene antifungal antibiotic produced by Favolaschia sp. 87129. It has anti-fungal activities such as Ascomycetes, Basidiomycetes, Oomycetes and Combinative Fungi.

Specification

IUPAC Name [(1R,2S,5S,7R,9R,11R,12S,15R,16R,18R)-15-[(2S)-4-hydroxy-5,6-dimethyl-3-oxoheptan-2-yl]-2,16-dimethyl-10-oxo-8,19-dioxahexacyclo[9.8.0.01,18.02,7.07,9.012,16]nonadecan-5-yl] 2,3-dihydroxy-3-methylbutanoate
Canonical SMILES CC(C)C(C)C(C(=O)C(C)C1CCC2C1(CC3C4(C2C(=O)C5C6(C4(CCC(C6)OC(=O)C(C(C)(C)O)O)C)O5)O3)C)O
InChI InChI=1S/C33H50O9/c1-15(2)16(3)23(34)24(35)17(4)19-9-10-20-22-25(36)27-32(42-27)13-18(40-28(38)26(37)29(5,6)39)11-12-31(32,8)33(22)21(41-33)14-30(19,20)7/h15-23,26-27,34,37,39H,9-14H2,1-8H3/t16?,17-,18-,19+,20-,21+,22-,23?,26?,27-,30+,31-,32-,33+/m0/s1
InChI Key SDVHFMSSWIIGCL-HSOJFHCCSA-N

Properties

Appearance White Needle Crystal
Antibiotic Activity Spectrum fungi
Melting Point 188-190°C

Reference Reading

1. Favolon B, a new triterpenoid isolated from the Chilean Mycena sp. strain 96180
Pedro Aqueveque, Timm Anke, Heidrun Anke, Olov Sterner, José Becerra, Mario Silva J Antibiot (Tokyo). 2005 Jan;58(1):61-4. doi: 10.1038/ja.2005.7.
A new biologically active triterpenoid, favolon B (1), was isolated from fermentation broths of Mycena sp. strain 96180. Favolon B showed antifungal activities towards Botrytis cinerea, Mucor miehei, Paecilomyces variotii and Penicillium notatum. No activities were observed against bacteria and yeasts. The structure of favolon B was elucidated by spectroscopic techniques.
2. Monochlorinated calocerins A-D and 9-oxostrobilurin derivatives from the basidiomycete Favolaschia calocera
Clara Chepkirui, Christian Richter, Josphat Clement Matasyoh, Marc Stadler Phytochemistry. 2016 Dec;132:95-101. doi: 10.1016/j.phytochem.2016.10.001. Epub 2016 Oct 13.
Eight previously undescribed compounds were isolated and characterised from the supernatant and mycelium of a culture of the basidiomycete Favolaschia calocera originating from Kakamega equatorial rainforest in Kenya. These were: 9- oxostrobilurins A, G, K and I and the four monochlorinated calocerins A, B, C and D. The calocerins extend our knowledge of halogenated compounds obtained from natural sources. Four further known compounds were also identified: strobilurin G, favolon, pterulinic acid and 2,3 -dihydro-1-benzoxepin derivative. The four oxostrobilurins exhibited prominent antifungal and cytotoxic activities while the four calocerins only showed cytotoxic activity.

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