Meleagrin

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.

Meleagrin

Identifiers
CAS Number	71751-77-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:70399
ChemSpider	23510990
PubChem CID	115080
UNII	5780K492K3 Y
CompTox Dashboard (EPA)	DTXSID80891812
InChI 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
SMILES 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
Chemical formula	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). Infobox references

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

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.
3. Ali, Hazrat; Ries, Marco I.; Nijland, Jeroen G.; Lankhorst, Peter P.; Hankemeier, Thomas; Bovenberg, Roel A. L.; Vreeken, Rob J.; Driessen, Arnold J. M. (12 June 2013). "A Branched Biosynthetic Pathway Is Involved in Production of Roquefortine and Related Compounds in Penicillium chrysogenum". PLOS ONE. 8 (6): e65328. Bibcode:2013PLoSO...865328A. doi:10.1371/journal.pone.0065328. PMC 3680398. PMID 23776469.
4. García-Estrada, Carlos; Ullán, Ricardo V.; Albillos, Silvia M.; Fernández-Bodega, María Ángeles; Durek, Pawel; von Döhren, Hans; Martín, Juan F. (23 November 2011). "A Single Cluster of Coregulated Genes Encodes the Biosynthesis of the Mycotoxins Roquefortine C and Meleagrin in Penicillium chrysogenum". Chemistry & Biology. 18 (11): 1499–1512. doi:10.1016/j.chembiol.2011.08.012. PMID 22118684.