Dehydrocurvularin

Dehydrocurvularin
Names
Preferred IUPAC name
(4S,8E)-11,13-Dihydroxy-4-methyl-4,5,6,7-tetrahydro-2H-3-benzoxacyclododecine-2,10(1H)-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C16H18O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h4,6-7,9-10,17,19H,2-3,5,8H2,1H3/b6-4+/t10-/m0/s1
    Key: AVIRMQMUBGNCKS-RWCYGVJQSA-N
  • InChI=1/C16H18O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h4,6-7,9-10,17,19H,2-3,5,8H2,1H3/b6-4+/t10-/m0/s1
    Key: AVIRMQMUBGNCKS-RWCYGVJQBB
  • C[C@H]1CCC/C=C/C(=O)c2c(cc(cc2O)O)CC(=O)O1
Properties
C16H18O5
Molar mass 290.315 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dehydrocurvularin also known as Curvularin is an antimicrobial made by Penicillium. It was first isolated in 1967. It has been shown to possess antifungal properties against Candida albicans and Candida auris, as well as nematicidal efficacy against Root-knot nematode and Root-lesion nematode.

References

  1. ↑ Chambers, Michael. "ChemIDplus - 0021178574 - AVIRMQMUBGNCKS-RWCYGVJQSA-N - Dehydrocurvularin - Similar structures search, synonyms, formulas, resource links, and other chemical information". chem.nlm.nih.gov.
  2. ↑ Savchuk, IaI; Zaĭchenko, A. M.; Tsyganenko, E. S. (2012). "Biological activity of Penicillium sp. 10-51 exometabolites". Mikrobiolohichnyi Zhurnal. 74 (4): 52–6. PMID 23088100.
  3. ↑ Munro, H. D.; Musgrave, O. C.; Templeton, Richard (1967). "Curvularin. Part V. The compound C 16 H 18 O 5 , αβ-dehydrocurvularin". J. Chem. Soc. C. 0: 947–948. doi:10.1039/J39670000947. ISSN 0022-4952.
  4. ↑ Kamauchi, Hitoshi; Furukawa, Miho; Kiba, Yuka; Kitamura, Masashi; Usui, Kanako; Katakura, Masanori; Takao, Koichi; Sugita, Yoshiaki (September 2022). "Antifungal activity of dehydrocurvularin for Candida spp. through the inhibition of adhesion to human adenocarcinoma cells". The Journal of Antibiotics. 75 (9): 530–533. doi:10.1038/s41429-022-00543-5. ISSN 1881-1469. PMID 35859164.
  5. ↑ Xiang, Chao; Liu, Ying; Liu, Shi-Ming; Huang, Ya-Fei; Kong, Ling-An; Peng, Huan; Liu, Mao-Yan; Liu, Jing; Peng, De-Liang; Huang, Wen-Kun (2020-03-04). "αβ-Dehydrocurvularin isolated from the fungus Aspergillus welwitschiae effectively inhibited the behaviour and development of the root-knot nematode Meloidogyne graminicola in rice roots". BMC Microbiology. 20 (1): 48. doi:10.1186/s12866-020-01738-2. ISSN 1471-2180. PMC 7055078. PMID 32126973.