Illudin C2

Illudin C2

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Category Antibiotics
Catalog number BBF-01498
CAS
Molecular Weight 248.32
Molecular Formula C15H20O3

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Description

Illudin C2 is produced by the strain of Coprinus atramentarius ASI 20013. It has the effect of resisting bacterium and fungus, and the antibacterial activity is weak.

Specification

IUPAC Name 7-hydroxy-2-(hydroxymethyl)-2,7-dimethyl-5-methylidenespiro[1,3-dihydroindene-6,1'-cyclopropane]-4-one
Canonical SMILES CC1(CC2=C(C1)C(C3(CC3)C(=C)C2=O)(C)O)CO
InChI InChI=1S/C15H20O3/c1-9-12(17)10-6-13(2,8-16)7-11(10)14(3,18)15(9)4-5-15/h16,18H,1,4-8H2,2-3H3
InChI Key QZJXMQBEUMDWAU-UHFFFAOYSA-N

Properties

Appearance Oily Matter
Antibiotic Activity Spectrum fungi

Reference Reading

1. Illudins C2 and C3 stimulate lipolysis in 3T3-L1 adipocytes and suppress adipogenesis in 3T3-L1 preadipocytes
Sun-Ok Kim, Krisada Sakchaisri, Yukihiro Asami, In-Ja Ryoo, Soo-Jin Choo, Ick-Dong Yoo, Nak-Kyun Soung, Young Sang Kim, Jae-Hyuk Jang, Bo Yeon Kim, Jong Seog Ahn J Nat Prod. 2014 Apr 25;77(4):744-50. doi: 10.1021/np400520a. Epub 2014 Mar 5.
The secondary metabolites illudins C2 (1) and C3 (2), obtained from the culture broth of Coprinus atramentarius, have been shown to possess antimicrobial activity. In the present study, we discovered novel biological activities of 1 and 2 in lipolysis of differentiated 3T3-L1 adipocytes and adipogenesis of 3T3-L1 preadipocytes. Compounds 1 and 2 exhibit a dose-dependent increase in glycerol release and thereby reduce intracellular lipid accumulation. The stimulatory effects of 1 and 2 on lipolysis are prevented by cAMP-dependent protein kinase (PKA) and extracellular signal-regulated kinase (ERK) inhibitors. Compounds 1 and 2 down-regulated perilipin and also affected the mRNA and protein levels of adipose triglyceride lipase (ATGL) and hormone-sensitive lipase (HSL). However, 1 and 2 treatment leads to a significant increase in PKA-mediated phosphorylation of HSL at S563 and S660. In addition, 1 and 2 treatment in 3T3-L1 preadipocytes induces down-regulation of the critical transcription factors, CCAAT/enhancer binding protein α and β (C/EBPα and C/EBPβ), and peroxisome proliferator activated receptor γ (PPARγ), which are required for adipogenesis, and accordingly inhibits adipogenesis. These results suggest that 1 and 2 might be useful for treating obesity due to their modulatory effects on fat by affecting adipocyte differentiation and fat mobilization.

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* 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

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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