Aureoverticillactam

Aureoverticillactam is an antifungal macrocyclic lactam with the molecular formula C28H39NO4 which is produced by the marine bacterium Streptomyces aureoverticillatus.[3][1][4][5][6] Aureoverticillactam has also cytotoxic activity.[7][8]

Aureoverticillactam
Names
IUPAC name
(3E,5E,7E,13Z,15E,17E,19E)-22-[(E)-Hex-2-enyl]-9,10,12-trihydroxy-17-methyl-1-azacyclodocosa-3,5,7,13,15,17,19-heptaen-2-one[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C28H39NO4/c1-3-4-5-8-17-24-18-13-11-15-23(2)16-12-14-19-25(30)22-27(32)26(31)20-9-6-7-10-21-28(33)29-24/h5-16,19-21,24-27,30-32H,3-4,17-18,22H2,1-2H3,(H,29,33)/b7-6+,8-5+,13-11+,16-12+,19-14-,20-9+,21-10+,23-15+
    Key: VMKRIAILWBEBLR-TWCCLTHVSA-N[2]
  • CCC/C=C/CC1C/C=C/C=C(/C=C/C=C\C(CC(C(/C=C/C=C/C=C/C(=O)N1)O)O)O)\C
Properties
C28H39NO4
Molar mass 453.623 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. "Aureoverticillactam". Pubchem.ncbi.NLM.nih.gov.
  2. "Natural Products Atlas | Compounds". www.npatlas.org.
  3. Blunt, John W.; Munro, Murray H. G. (19 September 2007). Dictionary of Marine Natural Products with CD-ROM. CRC Press. p. 157. ISBN 978-0-8493-8217-8.
  4. Mitchell, Scott S.; Nicholson, Benjamin; Teisan, Sy; Lam, Kin S.; Potts, Barbara C. M. (1 August 2004). "Aureoverticillactam, a Novel 22-Atom Macrocyclic Lactam from the Marine Actinomycete Streptomyces aureoverticillatus". Journal of Natural Products. 67 (8): 1400–1402. doi:10.1021/np049970g. PMID 15332863.
  5. Communications, EBCONT. "Aureoverticillactam". Roempp.thieme.de.
  6. Wang, Lan-Ying; Zhang, Yun-Fei; Yang, De-You; Zhang, Shu-Jing; Han, Dan-Dan; Luo, Yan-Ping (2021). "Aureoverticillactam, a Potent Antifungal Macrocyclic Lactam from Streptomyces aureoverticillatus HN6, Generates Calcium Dyshomeostasis-Induced Cell Apoptosis via the Phospholipase C Pathway in Fusarium oxysporum f. sp. cubense Race 4". Phytopathology. 111 (11): 2010–2022. doi:10.1094/PHYTO-12-20-0543-R. ISSN 0031-949X. PMID 33900117. S2CID 233398248.
  7. Kim, Se-Kwon (14 March 2012). Marine Medicinal Foods: Implications and Applications: Animals and Microbes. Academic Press. p. 398. ISBN 978-0-12-416003-3.
  8. Studies in Natural Products Chemistry. Elsevier. 24 July 2008. p. 240. ISBN 978-0-08-056984-0.

Further reading
  • Kim, Se-Kwon (27 November 2014). Handbook of Anticancer Drugs from Marine Origin. Springer. p. 245. ISBN 978-3-319-07145-9.
  • Patra, Jayanta Kumar; Shukla, Amritesh C.; Das, Gitishree (30 March 2020). Advances in Pharmaceutical Biotechnology: Recent Progress and Future Applications. Springer Nature. p. 343. ISBN 978-981-15-2195-9.
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