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Panicudine

Panicudine (6-hydroxy-11-deoxy-13-dehydrohetisane) is a C20-diterpene alkaloid of the hetisine type, first isolated from monkshood. 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, W1/2 = 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.

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

References

References

  1. I. A. Bessonova, Sh. A. Saidkhodzhaeva and M. F. Faskhutdinov. (1995). "Panicudine — A new alkaloid from Aconitum paniculatum". Chemistry of Natural Compounds.
  2. (January 2010). "Antimicrobial activity and phytochemical analyses of Polygonum aviculare L. (Polygonaceae), naturally growing in Egypt". Saudi Journal of Biological Sciences.
  3. Feng-Peng Wang. (2002). "C20-diterpenoid alkaloids". The Alkaloids: Chemistry and Biology.
  4. (2007). "Toxicity and local anesthetic activity of diterpenoid alkaloids". Chemistry of Natural Compounds.
  5. Phurpa Wangchuk, John B. Bremner and Siritron Samosorn. (2007). "Hetisine-Type Diterpenoid Alkaloids from the Bhutanese Medicinal Plant Aconitum orochryseum". J. Nat. Prod..
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diterpene-alkaloids amines ketones heterocyclic-compounds-with-7-or-more-rings vinylidene-compounds nitrogen-heterocycles diols acetate-esters
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