Staphidine is a bis-diterpene alkaloid of the atisane type, found in the tissues of Delphinium staphisagria in the larkspur family (Ranunculaceae)[1] along with staphimine and staphinine. Similar alkaloids are found in the genus Aconitum in that family, as well as Spiraea in the Rosaceae family.

Staphidine
Names
IUPAC name
5,5',7,7'-tetramethylspiro[20-oxa-7-azaheptacyclo[13.6.1.15,9.01,12.04,11.014,16.016,21]tricosa-4(11),12-diene-19,12'-7-azahexacyclo[9.6.2.01,8.05,17.09,14.014,18]nonadecane]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C42H58N2O/c1-36-8-5-9-42-32(36)7-11-39-21-40(25(16-33(39)42)15-30(39)34(42)44(4)23-36)12-13-41-29-17-28-26-14-24-18-37(2,22-43(3)20-24)27(26)6-10-38(28,19-31(29)41)35(41)45-40/h17,24-25,29-35H,5-16,18-23H2,1-4H3
    Key: MIQIFBIWUBAPTB-UHFFFAOYSA-N
  • CC12CCCC34C1CCC56C3CC(CC5C4N(C2)C)C7(C6)CCC89C1C8C=C2C3=C(CCC2(C1)C9O7)C1(CC(C3)CN(C1)C)C
Properties
C42H58N2O
Molar mass 606.939 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

References

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  1. ^ Pelletier, S.W.; Mody, N.V.; Djarmati, Z.; Mićović, I.V.; Thakkar, J.K. (April 1976). "The structures of staphidine, staphinine, and staphimine, three novel bis-diterpene alkaloids from delphinium staphisagria". Tetrahedron Letters. 17 (14): 1055–1058. doi:10.1016/S0040-4039(00)93749-3.