Panicudine

Panicudine
Names
	Other names 6-Hydroxy-11-deoxy-13-dehydrohetisane; (2α)-2,6-Dihydroxyhetisan-13-one
Identifiers
CAS Number	178451-93-9;
3D model (JSmol)	Interactive image;
	InChI InChI=1S/C20H25NO3/c1-9-4-18-7-20(24)16-17(2)5-10(22)6-19(16)12(18)3-11(9)14(23)13(18)15(19)21(20)8-17/h10-13,15-16,22,24H,1,3-8H2,2H3/t10-,11-,12+,13+,15?,16+,17-,18?,19-,20+/m0/s1 Key: UWHXIZAUFGDTMN-RPHVCTJRSA-N;
	SMILES O[C@@]12[C@]3([C@]45C([C@@]6(C7([C@]4(C[C@](C6=O)(C(=C)C7)[H])[H])C1)[H])[N@@]2C[C@]3(C)C[C@H](O)C5)[H];
Properties
Chemical formula	C20H25NO3
Molar mass	327.424 g·mol−1
Melting point	249–250 °C (480–482 °F; 522–523 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Panicudine (6-hydroxy-11-deoxy-13-dehydrohetisane) is a C₂₀-diterpene alkaloid of the hetisine type, first isolated from Aconitum paniculatum. It has empirical formula C₂₀H₂₅NO₃ and a melting point of 249–250 °C. The structure was determined to be a hetisine type diterpene by noting infrared spectrum absorption bands of 3405 cm⁻¹ (OH), 1718 (C=O), and 1650 (C=C), a proton magnetic resonance spectrum with "secondary hydroxy (4.02 ppm, m, 1H, W_1/2 = 10 Hz), exomethylene (4.87 and 4.76 ppm, br.s, 1H each), and tertiary methyl (1.29 ppm, s, 3H) groups and the absence of N-methyl, N-ethyl, and methoxy groups." Additional ultraviolet spectrum and carbon-13 NMR data, confirmed by high resolution mass spectrometry, completed the determination of the structure.^[1]

Panicudine was identified as an active antimicrobial substance in the chloroform extract of Polygonum aviculare, a traditional herbal medicine of the Mediterranean coastal region.^[2] It has also been isolated from epigeal parts of Rumex pictus.^[3]

Related compounds

Panicutine is the acetate ester of panicudine.

Chemical structure of panicutine

A variety of related alkaloids have been isolated from other natural sources.^[4]^[5]

References

^ I. A. Bessonova, Sh. A. Saidkhodzhaeva and M. F. Faskhutdinov (1995). "Panicudine — A new alkaloid from Aconitum paniculatum". Chemistry of Natural Compounds. 31 (6): 705–707. doi:10.1007/BF01386184. S2CID 30615425.
^ Hediat M.H. Salama; Najat Marraiki (January 2010). "Antimicrobial activity and phytochemical analyses of Polygonum aviculare L. (Polygonaceae), naturally growing in Egypt". Saudi Journal of Biological Sciences. 17 (1): 57–63. doi:10.1016/j.sjbs.2009.12.009. PMC 3730555. PMID 23961059.
^ Feng-Peng Wang (2002). C₂₀-diterpenoid alkaloids. Vol. 59. pp. 1–280. doi:10.1016/S0099-9598(02)59008-8. ISBN 9780124695597. PMID 12561418. {{cite book}}: |journal= ignored (help)
^ F. N. Dzhakhangirov; K. R. Kasymova; M. N. Sultankhodzhaev; B. T. Salimov; S. K. Usmanova; et al. (2007). "Toxicity and local anesthetic activity of diterpenoid alkaloids". Chemistry of Natural Compounds. 43 (5): 581–589. doi:10.1007/s10600-007-0197-8. S2CID 7975638.
^ Phurpa Wangchuk, John B. Bremner and Siritron Samosorn (2007). "Hetisine-Type Diterpenoid Alkaloids from the Bhutanese Medicinal Plant Aconitum orochryseum". J. Nat. Prod. 70 (11): 1808–1811. doi:10.1021/np070266k. PMID 17966986.

[1] I. A. Bessonova, Sh. A. Saidkhodzhaeva and M. F. Faskhutdinov (1995). "Panicudine — A new alkaloid from Aconitum paniculatum". Chemistry of Natural Compounds. 31 (6): 705–707. doi:10.1007/BF01386184. S2CID 30615425.

[2] Hediat M.H. Salama; Najat Marraiki (January 2010). "Antimicrobial activity and phytochemical analyses of Polygonum aviculare L. (Polygonaceae), naturally growing in Egypt". Saudi Journal of Biological Sciences. 17 (1): 57–63. doi:10.1016/j.sjbs.2009.12.009. PMC 3730555. PMID 23961059.

[3] Feng-Peng Wang (2002). C₂₀-diterpenoid alkaloids. Vol. 59. pp. 1–280. doi:10.1016/S0099-9598(02)59008-8. ISBN 9780124695597. PMID 12561418. {{cite book}}: |journal= ignored (help)

[4] F. N. Dzhakhangirov; K. R. Kasymova; M. N. Sultankhodzhaev; B. T. Salimov; S. K. Usmanova; et al. (2007). "Toxicity and local anesthetic activity of diterpenoid alkaloids". Chemistry of Natural Compounds. 43 (5): 581–589. doi:10.1007/s10600-007-0197-8. S2CID 7975638.

[5] Phurpa Wangchuk, John B. Bremner and Siritron Samosorn (2007). "Hetisine-Type Diterpenoid Alkaloids from the Bhutanese Medicinal Plant Aconitum orochryseum". J. Nat. Prod. 70 (11): 1808–1811. doi:10.1021/np070266k. PMID 17966986.

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