Helvolic acid

Helvolic acid

Names
IUPAC name (2Z)-2-[(4S,5S,6S,8S,9S,10R,13R,14S,16S)-6,16-diacetyloxy-4,8,10,14-tetramethyl-3,7-dioxo-5,6,9,11,12,13,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
Other names Fumigacin
Identifiers
CAS Number	29400-42-8  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:62460  Y
ChEMBL	ChEMBL505132
ChemSpider	2273343
PubChem CID	3002143
UNII	MZX54GS8AH  Y
InChI InChI=1S/C33H44O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(41-20(5)35)29(37)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,14-15,18,22,24-25,27-28H,9,11-13,16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,24+,25+,27-,28+,31-,32+,33-/m1/s1 N Key: MDFZYGLOIJNNRM-OAJDADRGSA-N Y
SMILES CC1C2C(C(=O)C3(C(C2(C=CC1=O)C)CCC4C3(CC(C4=C(CCC=C(C)C)C(=O)O)OC(=O)C)C)C)OC(=O)C
Properties
Chemical formula	C33H44O8
Molar mass	568.707 g·mol−1
Appearance	crystalline solid
Density	1.2 g/cm³ [1]
Boiling point	675.9
Solubility in water	slightly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N (what is  YN ?) Infobox references

Helvolic acid is a steroidal antibiotic compound classified as a fusidane-type nortriterpenoid. ^{[2] [3]} It is a tetracyclic steroid acid characterized by a 29-nordammarane skeleton, which is substituted with acetoxy groups at positions C-6 and C-16, oxo groups at C-3 and C-7, and double bonds at C-1, C-17(20), and C-24. Its molecular formula is C₃₃H₄₄O₈. ^[4]

Natural occurence

The acid is produced by various fungi, notably Aspergillus species such as Aspergillus fumigatus and Aspergillus terreus , as well as members of the genus Fusarium and Xylaria . The acid was originally isolated from Aspergillus fumigatus. ^[5]

Helvolic acid was isolated from the culture broth which was separated from the fungus mycelium by filtration. ^[6]

References

1. "Helvolic acid". chemsrc.com. Retrieved 24 July 2025.
2. Gupta, Vijai G.; Rodriguez-Couto, Susana (6 February 2018). New and Future Developments in Microbial Biotechnology and Bioengineering: Penicillium System Properties and Applications. Elsevier. p. 77. ISBN   978-0-444-63512-9 . Retrieved 24 July 2025.
3. Lv, Jian-Ming; Hu, Dan; Gao, Hao; Kushiro, Tetsuo; Awakawa, Takayoshi; Chen, Guo-Dong; Wang, Chuan-Xi; Abe, Ikuro; Yao, Xin-Sheng (21 November 2017). "Biosynthesis of helvolic acid and identification of an unusual C-4-demethylation process distinct from sterol biosynthesis". Nature Communications . 8 (1): 1644. Bibcode:2017NatCo...8.1644L. doi:10.1038/s41467-017-01813-9. ISSN   2041-1723. PMC   5696383 . PMID   29158519.
4. Genetics and Molecular Biology of Entomopathogenic Fungi. Academic Press. 27 April 2016. p. 377. ISBN   978-0-444-63723-9 . Retrieved 24 July 2025.
5. Ratnaweera, Pamoda B.; Williams, David E.; de Silva, E. Dilip; Wijesundera, Ravi L. C.; Dalisay, Doralyn S.; Andersen, Raymond J. (March 2014). "Helvolic acid, an antibacterial nortriterpenoid from a fungal endophyte, Xylaria sp. of orchid Anoectochilus setaceus endemic to Sri Lanka". Mycology. 5 (1): 23–28. doi:10.1080/21501203.2014.892905. ISSN   2150-1203. PMC   3979440 . PMID   24772371.
6. Ciegler, Alex; Kadis, Solomon; Ajl, Samuel J. (15 June 2016). Fungal Toxins: A Comprehensive Treatise. Elsevier. p. 266. ISBN   978-1-4832-1590-7 . Retrieved 24 July 2025.