Meleagrin

Meleagrin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1
    Key: JTJJJLSLKZFEPJ-ZAYCRUKZSA-N
  • InChI=1/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1
    Key: JTJJJLSLKZFEPJ-ZAYCRUKZBE
  • CC(C)(C=C)[C@@]12C=C(C(=O)N\3[C@]1(NC(=O)/C3=C\c4c[nH]cn4)N(c5c2cccc5)OC)O
Properties
C23H23N5O4
Molar mass 433.468 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Meleagrin and its derivatives such as oxaline are bio-active benzylisoquinoline alkaloids made by various species of Penicillium fungi.[1] It is similar to other fungal alkaloids, such as Roquefortine C, which is made as an intermediate in the same biosynthetic pathway.

It was suggested to have inhibitory activity on fatty acid synthesis for the bacteria Staphylococcus aureus and Streptococcus pneumoniae.[2]

  1. ^ Du, L; Feng, T; Zhao, B; Li, D; Cai, S; Zhu, T; Wang, F; Xiao, X; Gu, Q (April 2010). "Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities". The Journal of Antibiotics. 63 (4): 165–70. doi:10.1038/ja.2010.11. PMID 20186171. S2CID 12744541.
  2. ^ Zheng, CJ; Sohn, MJ; Lee, S; Kim, WG (2013). "Meleagrin, a new FabI inhibitor from Penicillium chryosogenum with at least one additional mode of action". PLOS ONE. 8 (11): e78922. Bibcode:2013PLoSO...878922Z. doi:10.1371/journal.pone.0078922. PMC 3842914. PMID 24312171.