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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:62460 ;
ChEMBL	ChEMBL505132;
ChemSpider	2273343;
PubChem CID	3002143;
UNII	MZX54GS8AH ;
CompTox Dashboard (EPA)	DTXSID201017874;
	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 Key: MDFZYGLOIJNNRM-OAJDADRGSA-N ;
	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
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). (what is ?) 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 occurrence

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

^ "Helvolic acid". chemsrc.com. Retrieved 24 July 2025.
^ 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.
^ 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.
^ Genetics and Molecular Biology of Entomopathogenic Fungi. Academic Press. 27 April 2016. p. 377. ISBN 978-0-444-63723-9. Retrieved 24 July 2025.
^ 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.
^ 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.

[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.

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v t e Tetracyclics
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