Helvolic acid

ID 2: 508

Toxin: y

Trivial name:

Helvolic acid (6CI,​7CI); (Z)​-​6β,​16β-​Dihydroxy-​3,​7-​dioxo-​29-​nor-​8α,​9β,​13α,​14β-​dammara-​1,​17(20)​,​24-​trien-​21-​oic acid diacetate; Fumigacin; NSC 319943

Systematic name:

29-Nordammara-1,17(20),24-trien-21-oic acid, 6,16-bis(acetyloxy)-3,7-dioxo-, (4a,6b,8a,9b,13a,14b,16b,17Z)- (9CI)

Molecular formulae: 

C₃₃H₄₄O₈

Molecular weight: 568.70

Chemical abstract number: 29400-42-8

Literature reference:

• Production of two antibacterial substances, fumigacin and clavacin. Waksman, Selman A.; Horning, Elizabeth S.; Spencer, Ernest L. Science (Washington, DC, United States) (1942), 96, 202-3.
  WILLIAMS TI.Biochem J. 1952 Jul;51(4):538-42. Some chemical properties of helvolic acid.
  OKUDA S, IWASAKI S, TSUDA K, SANO Y, HATA T, UDAGAWA S, NAKAYAMA Y, YAMAGUCHI H. THE STRUCTURE OF HELVOLIC ACID.Chem Pharm Bull (Tokyo). 1964 Jan;12:121-4.
  
  Amitani R, Taylor G, Elezis EN, Llewellyn-Jones C, Mitchell J, Kuze F, Cole PJ, Wilson R. Purification and characterization of factors produced by Aspergillus fumigatus which affect human ciliated respiratory epithelium.
  Infect Immun. 1995 Sep;63(9):3266-71.
  Metabolites of Aspergillus sp. HT-​2. Zhang, Limin; Li, Zhanlin; Bai, Jiao; Wu, Xin; Wang, Yu; Hua, Huiming. Zhongguo Yaoxue Zazhi (Beijing, China) (2011), 46(15), 1154-1158
  Secondary metabolites of Aspergillus sp. CM9a, an endophytic fungus of Cephalotaxus mannii. Xue, Heng; Lu, Chunhua; Liang, Lanying; Shen, Yuemao. Records of Natural Products (2012), 6(1), 28-34.
  Bioactive meroditerpenes and indole alkaloids from the soil fungus Neosartorya fischeri (KUFC 6344)​, and the marine-​derived fungi Neosartorya laciniosa (KUFC 7896) and Neosartorya tsunodae (KUFC 9213). Eamvijarn, Amnat; Gomes, Nelson M.; Dethoup, Tida; Buaruang, Jamrearn; Manoch, Leka; Silva, Artur; Pedro, Madalena; Marini, Ioulia; Roussis, Vasilios; Kijjoa, Anake. Tetrahedron (2013), 69(40), 8583-8591.
  

References URL: 

• http://pubchem.ncbi.nlm.nih.gov/compound/3002143
• http://www.sciencemag.org/search?volume=96&submit=yes&firstpage=202
• http://www.acgpubs.org/RNP/2012/Volume%206/Abstracts%206.1/3-RNP-1101_459.htm
• http://www.sciencedirect.com/science/article/pii/S0040402013011976

Aspergillus Species known to produce this metabolite:

• /species/a-fumigatus
• /species/aspergillus-sp-ht-2
• /species/aspergillus-sp-cm9a
• /species/neosartorya-fischeri
• /species/neosartorya-tsunodae

Toxicity:

mouse LD50 intraperitoneal 400mg/kg (400mg/kg) “Antibiotics: Origin, Nature, and Properties,” Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 3, Pg. 1837, 1978.

mouse LDLo intravenous 500mg/kg (500mg/kg) “Antibiotics: Origin, Nature, and Properties,” Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 3, Pg. 1837, 1978.

Date uploaded: 2008-01-25 00:53:58

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