Piperolactam A

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).

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

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 precursors.[5]

Chemical synthesis

Aristolactams including piperolactam A have been the subject of chemical 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

  1. ^ Desai, Sanjay J.; Prabhu, Bharathi R.; Mulchandani, Newand B. (1988). "Aristolactams and 4,5-dioxoaporphines from Piper longum". Phytochemistry. 27 (5): 1511–1515. doi:10.1016/0031-9422(88)80226-7.
  2. ^ a b Kumar, Vineet; Poonam; Prasad, Ashok K.; Parmar, Virinder S. (2003). "Naturally occurring aristolactams, aristolochic acids and dioxoaporphines and their biological activities". Natural Product Reports. 20 (6): 565–83. doi:10.1039/B303648K. PMID 14700200.
  3. ^ Michl, Johanna; Ingrouille, Martin J.; Simmonds, Monique S. J.; Heinrich, Michael (2014). "Naturally occurring aristolochic acid analogues and their toxicities". Natural Product Reports. 31 (5): 676–93. doi:10.1039/c3np70114j. PMID 24691743.
  4. ^ a b Kim, Joa Kyum; Kim, Young Ha; Nam, Ho Tae; Kim, Bum Tae; Heo, Jung-Nyoung (2008). "Total Synthesis of Aristolactams via a One-Pot Suzuki−Miyaura Coupling/Aldol Condensation Cascade Reaction". Organic Letters. 10 (16): 3543–3546. doi:10.1021/ol801291k. PMID 18642834.
  5. ^ Dos Santos, Anderson R.; Vaz, Nelissa P. (2019). "Isoquinoline Alkaloids and Chemotaxonomy". Biodiversity and Chemotaxonomy. Sustainable Development and Biodiversity. Vol. 24. pp. 167–193. doi:10.1007/978-3-030-30746-2_8. ISBN 978-3-030-30745-5. S2CID 209712699.
  6. ^ a b Reddy, Mallu Chenna; Jeganmohan, Masilamani (2017). "Total synthesis of aristolactam alkaloids via synergistic C–H bond activation and dehydro-Diels–Alder reactions". Chemical Science. 8 (5): 4130–4135. doi:10.1039/c7sc00161d. PMC 6100235. PMID 30155216.