meleagrin
{{Chembox
| ImageFile = Meleagrin.png
| ImageSize = 150px
| ImageAlt =
| IUPACName =
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 71751-77-4
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5780K492K3
| PubChem = 115080
| ChEBI = 70399
| ChemSpiderID = 23510990
| 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
| 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
| InChIKey = JTJJJLSLKZFEPJ-ZAYCRUKZBE
| StdInChI = 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
| StdInChIKey = JTJJJLSLKZFEPJ-ZAYCRUKZSA-N}}
|Section2={{Chembox Properties
| C=23 | H=23 | N=5 | O=4
| Formula =
| MolarMass =
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
Meleagrin and its derivatives such as oxaline are bio-active benzylisoquinoline alkaloids made by various species of Penicillium fungi.{{cite journal |last1=Du |first1=L |last2=Feng |first2=T |last3=Zhao |first3=B |last4=Li |first4=D |last5=Cai |first5=S |last6=Zhu |first6=T |last7=Wang |first7=F |last8=Xiao |first8=X |last9=Gu |first9=Q |title=Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities. |journal=The Journal of Antibiotics |date=April 2010 |volume=63 |issue=4 |pages=165–70 |doi=10.1038/ja.2010.11 |pmid=20186171|s2cid=12744541 |doi-access=free }} 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.{{cite journal |last1=Zheng |first1=CJ |last2=Sohn |first2=MJ |last3=Lee |first3=S |last4=Kim |first4=WG |title=Meleagrin, a new FabI inhibitor from Penicillium chryosogenum with at least one additional mode of action. |journal=PLOS ONE |date=2013 |volume=8 |issue=11 |pages=e78922 |doi=10.1371/journal.pone.0078922 |pmid=24312171 |pmc=3842914 |bibcode=2013PLoSO...878922Z |doi-access=free }}
Biosynthesis
The biosynthetic pathway was determined to contain several genes, including a non-ribosomal peptide synthetase.{{cite journal |last1=Ali |first1=Hazrat |last2=Ries |first2=Marco I. |last3=Nijland |first3=Jeroen G. |last4=Lankhorst |first4=Peter P. |last5=Hankemeier |first5=Thomas |last6=Bovenberg |first6=Roel A. L. |last7=Vreeken |first7=Rob J. |last8=Driessen |first8=Arnold J. M. |title=A Branched Biosynthetic Pathway Is Involved in Production of Roquefortine and Related Compounds in Penicillium chrysogenum |journal=PLOS ONE |date=12 June 2013 |volume=8 |issue=6 |pages=e65328 |doi=10.1371/journal.pone.0065328 |pmid=23776469 |pmc=3680398 |bibcode=2013PLoSO...865328A |doi-access=free }} 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.{{cite journal |last1=García-Estrada |first1=Carlos |last2=Ullán |first2=Ricardo V. |last3=Albillos |first3=Silvia M. |last4=Fernández-Bodega |first4=María Ángeles |last5=Durek |first5=Pawel |last6=von Döhren |first6=Hans |last7=Martín |first7=Juan F. |title=A Single Cluster of Coregulated Genes Encodes the Biosynthesis of the Mycotoxins Roquefortine C and Meleagrin in Penicillium chrysogenum |journal=Chemistry & Biology |date=23 November 2011 |volume=18 |issue=11 |pages=1499–1512 |doi=10.1016/j.chembiol.2011.08.012 |pmid=22118684 }}