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).
Infobox references

Dehydrocurvularin also known as Curvularin is an antimicrobial made by Penicillium.[2] It was first isolated in 1967.[3] It has been shown to possess antifungal properties against Candida albicans and Candida auris,[4] as well as nematicidal efficacy against Root-knot nematode and Root-lesion nematode.[5]

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.


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