Article · Wikipedia archive · Last revised Jul 16, 2026

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.

Last revised
Jul 16, 2026
Read time
≈ 2 min
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Citations
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Source
Wikipedia ↗
Panicudine
source ↗
Names
Other names
6-Hydroxy-11-deoxy-13-dehydrohetisane; (2α)-2,6-Dihydroxyhetisan-13-one
Identifiers
3D model (JSmol)
  • 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
  • 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
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).

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.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 the herb Rumex pictus.3

Panicutine is the acetate ester of panicudine.

Chemical structure of panicutine source ↗

A variety of related alkaloids have been isolated from other natural sources.45

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. 31 (6): 705–707. Bibcode:1995CNatC..31..705B. 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. Bibcode:2010SJBS...17...57S. 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. Bibcode:2007CNatC..43..581D. 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. Bibcode:2007JNAtP..70.1808W. doi:10.1021/np070266k. PMID 17966986.