Panicudine

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, 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
Names
IUPAC name
[(1R,3S,5R,8R,9S,11S,14R,17R,18R)-5,7-dimethyl-12-methylidene-10,16-dioxo-7-azahexacyclo[9.6.2.01,8.05,17.09,14.014,18]nonadecan-3-yl] acetate
Systematic IUPAC name
6-Hydroxy-11-deoxy-13-dehydrohetisane
Other names
Panicutine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
  • InChI=1S/C23H29NO4/c1-11-6-22-9-15(26)19-21(3)7-13(28-12(2)25)8-23(19)16(22)5-14(11)18(27)17(22)20(23)24(4)10-21/h13-14,16-17,19-20H,1,5-10H2,2-4H3/t13-,14-,16+,17+,19+,20+,21-,22+,23+/m0/s1
    Key: CKNLFSFBGRRFCB-OETVPYRWSA-N
  • CC(=O)O[C@H]1C[C@]2(CN([C@@H]3[C@H]4C(=O)[C@H]5C[C@H]6[C@]3(C1)[C@@H]2C(=O)C[C@]64CC5=C)C)C
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).
Infobox references

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

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. 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. The Alkaloids: Chemistry and Biology. Vol. 59. pp. 1–280. doi:10.1016/S0099-9598(02)59008-8. ISBN 9780124695597. PMID 12561418.
  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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