Piperolactam A

Piperolactam A
Names
	Preferred IUPAC name 1-Hydroxy-2-methoxydibenzo[cd,f]indol-4(5H)-one
	Other names Aristolactam FI
Identifiers
CAS Number	112501-42-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:387864 ;
ChEMBL	ChEMBL387864;
ChemSpider	2338707 ;
PubChem CID	3081016;
UNII	CXQ3T84KLC ;
CompTox Dashboard (EPA)	DTXSID90150083 ;
	InChI 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) Key: KBGNBPGXVKPRQI-UHFFFAOYSA-N;
	SMILES COC1=CC2=C3C(NC2=O)=CC2=C(C=CC=C2)C3=C1O;
Properties
Chemical formula	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). Infobox references

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.

History

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

Synthesis

Biosynthesis

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

Chemical synthesis

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

Natural occurrence

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

References

↑ Desai, Sanjay J.; Prabhu, Bharathi R.; Mulchandani, Newand B. (1988). "Aristolactams and 4,5-dioxoaporphines from Piper longum". Phytochemistry. 27 (5): 1511–1515. Bibcode:1988PChem..27.1511D. doi:10.1016/0031-9422(88)80226-7.
1 2 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.
↑ 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.
1 2 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.
↑ 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.
1 2 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.

[1] Desai, Sanjay J.; Prabhu, Bharathi R.; Mulchandani, Newand B. (1988). "Aristolactams and 4,5-dioxoaporphines from Piper longum". Phytochemistry. 27 (5): 1511–1515. Bibcode:1988PChem..27.1511D. doi:10.1016/0031-9422(88)80226-7.

[Parmar-2] 1 2 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.

[Lactamfi-4] 1 2 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.

[Synthesis-6] 1 2 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.