Piperolactam A

Chemical compound From Wikipedia, the free encyclopedia

Piperolactam A is a tetracyclic alkaloid found in many plants but first isolated from the roots of Piper longum (long pepper). As a group, such compounds are called aristolactams, and are related to the aristolochic acid found in European birthwort.

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Piperolactam A
Names
Preferred IUPAC name
1-Hydroxy-2-methoxydibenzo[cd,f]indol-4(5H)-one
Other names
Aristolactam FI
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C16H11NO3/c1-20-12-7-10-13-11(17-16(10)19)6-8-4-2-3-5-9(8)14(13)15(12)18/h2-7,18H,1H3,(H,17,19) checkY
    Key: KBGNBPGXVKPRQI-UHFFFAOYSA-N
  • COC1=CC2=C3C(NC2=O)=CC2=C(C=CC=C2)C3=C1O
Properties
C16H11NO3
Molar mass 265.268 g·mol−1
Melting point 313 °C (595 °F; 586 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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History

Piperolactam A was first reported in 1988 after isolation from an extract of Piper longum.[1] Many closely related natural product alkaloids are known including aristolochic acid and its lactam derivatives.[2][3] In some reports, piperolactam A is called aristolactam FI.[4]

Synthesis

Biosynthesis

Main article: Aristolochic_acid § Biosynthesis

It has been suggested that piperolactam A and related compounds are biosynthesised from aporphine class precursors.[5]

Chemical synthesis

Aristolactams including piperolactam A have been the subject of total synthesis studies,[4] which have been reviewed.[6]

Natural occurrence

Piperolactam A and related compounds are found in Aristolochiaceae (birthwort), Annonaceae (custard apple), Piperaceae (pepper), and Saururaceae plant families.[2][6]

References

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