Meleagrin

Chemical compound From Wikipedia, the free encyclopedia

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.

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

Biosynthesis

The biosynthetic pathway was determined to contain several genes, including a non-ribosomal peptide synthetase.[3] The biosynthesis begins by cyclizing the two amino acids histidine and tryptophan, and is the followed by the addition of an isoprene, and several ring rearrangement steps.[4]

References

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