Chemistry:Helvolic acid
From HandWiki
| |
| 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 | |
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C33H44O8 | |
| Molar mass | 568.707 g·mol−1 |
| Appearance | crystalline solid |
| Density | 1.2 g/cm³[1] |
| Boiling point | 675.9 |
| 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 | |
Tracking categories (test):
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 C
33H
44O
8.[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" (in en). chemsrc.com. https://www.chemsrc.com/en/cas/29400-42-8_34671.html.
- ↑ Gupta, Vijai G.; Rodriguez-Couto, Susana (6 February 2018) (in en). New and Future Developments in Microbial Biotechnology and Bioengineering: Penicillium System Properties and Applications. Elsevier. p. 77. ISBN 978-0-444-63512-9. https://books.google.com/books?id=QAVKCgAAQBAJ&dq=Helvolic+acid&pg=PA77. Retrieved 24 July 2025.
- ↑ Lv, Jian-Ming; Hu, Dan; Gao, Hao; Kushiro, Tetsuo; Awakawa, Takayoshi; Chen, Guo-Dong; Wang, Chuan-Xi; Abe, Ikuro et al. (21 November 2017). "Biosynthesis of helvolic acid and identification of an unusual C-4-demethylation process distinct from sterol biosynthesis" (in en). Nature Communications 8 (1): 1644. doi:10.1038/s41467-017-01813-9. ISSN 2041-1723. PMID 29158519. Bibcode: 2017NatCo...8.1644L.
- ↑ (in en) Genetics and Molecular Biology of Entomopathogenic Fungi. Academic Press. 27 April 2016. p. 377. ISBN 978-0-444-63723-9. https://books.google.com/books?id=RpF4CgAAQBAJ&dq=Helvolic+acid&pg=PA377. 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. PMID 24772371.
- ↑ Ciegler, Alex; Kadis, Solomon; Ajl, Samuel J. (15 June 2016) (in en). Fungal Toxins: A Comprehensive Treatise. Elsevier. p. 266. ISBN 978-1-4832-1590-7. https://books.google.com/books?id=36FmDAAAQBAJ&dq=Helvolic+acid&pg=PA266. Retrieved 24 July 2025.
 |  |
