Panicudine Explained

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.

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

Notes and References

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