Staphisagria

Delphinium Staphisagria L. From the seeds of this species, the oil of which is used as a pediculicide, Brandes isolated delphinine in 1819, and this and other alkaloidal components were subsequently examined by various workers including Marquis, Kara-Stojanov, Ahrens, Keller, Walz and most recently by Jacobs and Craig. ... 

The history of Delphinium is more peaceful, although, due to its poisinous property it was used against mammals. Crushed seeds of Delphinium staphisagria L. was used against body lice [5]. British army used the plant for this aim in Waterloo war as well as in the Great War. Medicinal use of Aconitum and Delphinium spans... 

The alkaloids of Delphinium staphisagria have been reviewed. Delphidine has been shown to possess the structure (106) whilst delphirine (107) possesses the unusual C-1 hydroxy-group. Staphigine and staphirine are bisditerpenoid alkaloids which have been obtained " from D. staphisagria. Examination of D. tricorne afforded " a new alkaloid tricornine (108) which was shown to be 18-acetyl-... 

Delphinium peregrinum var. elongatum Boiss 13-0-Acetylhetisine-2-one Delphinium staphisagria Staphidine Staphigine Staphimine Staphinine Staphirine Staphisagnine... 

Carrot, bird s nest, bee s nest, Queen Anne s lace) Delphinium staphisagria (Delphinium, stavesacre, lousewort)... 

Recently, a new class of diterpenoid alkaloids, known as bisditerpenoid alkaloids, has been isolated from the seeds of Delphinium staphisagria (2). The bisditerpenoid alkaloids (e.g., staphisine, iv) may be formally derived by... 

Besides the two bisditerpenoid alkaloids discussed earlier, two new imine-containing alkaloids designated as staphinine and staphimine have been isolated (148) from the seeds of D. staphisagria. The structures of staphinine (188) and staphimine (189) were also assigned on the basis of 13C- and H-NMR spectral analysis. 

The authors were unable to carry out any transformation of staphinine and staphimine to staphisine and staphidine, respectively, because of the instability of these alkaloids toward various mild reducing agents (e.g., sodium borohydride, sodium cyanoborohydride). Staphimine and staphinine occur in extremely small amounts in the seeds of D. staphisagria. It has been suggested that the imine-containing alkaloids may be biogenetic precursors of staphisine and staphidine. 

Staphigine and staphirine have been isolated (149) in extremely small amounts from the seeds of D. staphisagria. Staphigine and staphirine are the C-19 lactam derivatives of staphisine and staphidine, respectively. The structures of staphigine (190) and staphirine (191) were determined on the basis of their 13C- and H-NMR spectra. 

Staphisagnine (193) and staphisagrine (194) were also isolated (150) in extremely small amounts from the mother liquors accumulated during the isolation of delphinine from the seeds of D. staphisagria. These alkaloids are unusual in containing an oxazolidine ring of the atisine and veat-chine type in addition to many of the uncommon features of the staphisine skeleton. 

It is interesting to note that these two bisditerpenoid alkaloids did not contain the conjugated diene system, which is present in the other six bisditerpenoid alkaloids. Biogenetically, it is worth noting that all these bisditerpenoid alkaloids occur as methoxyl and desmethoxyl pairs in the seeds of D. staphisagria. 

The power of the 13C-NMR spectroscopic technique was demonstrated (148-150) in the elucidation of the structures of some very complex natural products, the bisditerpenoid alkaloids, isolated from D. staphisagria. On the basis of l3C-NMR data of the known alkaloid, staphisine (185), the structures of seven new related alkaloids, staphidine (187), staphinine (188), staphimine (189), staphigine (190), staphirine (191), staphisagnine (193),... 

C43H60N2O2 MW 636 mp 211-213 [a]D -148.4° (C6H6) Delphinium staphisagria Chemical, spectral, and X-ray analysis Refs. 144-148... 

Five new diterpenoid alkaloids have been isolated from Aconitum species (Ranunculaceae) and five from Delphinium species (Ranunculaceae). Four new Anopterus (Escalloniaceae) bases have been identified. The most significant synthetic achievement has been the total synthesis of racemic chasmanine. A detailed review of the alkaloids of Delphinium staphisagria has appeared.1... 

Alkaloids of Delphinium staphisagria Delphidine31 and Delphirine.32—These new bases were isolated from the mother liquors accumulated from the large-scale separation of delphinine (40) from the seeds of D. staphisagria L. 

The Follicle or pod is a dry, simple capsular fruit formed of a single carpel which dehisces by one suture. This is usually the ventral suture as in Aconite, Staphisagria, Larkspur and some other Ranuncidacea, but may be the dorsal suture as in Magnolia, Fig. 99 (i). 

Diterpenoid Alkaloids.— The alkaloids of Delphinium staphisagria include some bisditerpenoid alkaloids such as staphidine, staphinine, and staphimine. The full paper has appeared on the structure and stereochemistry of delphisine, neoline, chasmanine, and homochasmanine. The application of n.m.r. measurements to these alkaloids has led to the revision of the structure of the alkaloid A from D. bicolor... 

Used by Moors in Europe in the 15th Century and earlier in India and China. Used by elephant hunters in India and said to have been tested in small arms ammunition at Buchenwald. Aconitine and delphinine alkaloids from the root of Aconitine napellus (aconite, monkshood, wolfsbane) and from the seeds of Delphinium staphisagria (starvesacre seeds). Delays repolarization due to impaired closure to Na channels. Weak diaphoretic was used in fevers. Local... 

Delphonine (OCXVII) is the parent amino alcohol of the diester delphinine (CCXVIII). The latter is the main alkaloid of Delphinium staphisagria L. which was first isolated in 1819 and became the subject of... 

Delphisine.—A new alkaloid, delphisine, C28H43NO8, m.p. 121—122 °C, has been isolated from the seeds of Delphinium staphisagria, by a combination of pH extractions and chromatographic techniques. Chemical and spectral studies indicated it to be a member of the aconitine-type alkaloids. 

Staphisagria. Stavesacre. Ripe seed of Delphinium staphisagria L., Ranunculaceae. Habit Mediterranean basin cultivated in France, Italy. Constit. Delphinine, delphinoidine. delphisine, staphisagrine, staphisagroine, malic acid, fixed oil. 

Early in 1800 the seeds of Delphinium staphisagria L., commonly known as stavesacre, were extracted to furnish the oil and alkaloids in pure form in order to determine their insecticidal activity. The seeds of D. staphisagria have been found on extraction with ligroin to yield an appreciable amount of an alkaloid fraction, which consists mainly of the alkaloid delphinine. The latter was first isolated in 1819 by Lassaigne and Feneulle (47). Walz (48) revised the formula reported for delphinine by earlier workers to C34H47NO9 on the basis of the analysis of the free base and its oxalate. This formula was also supported by Keller (49) and later by Markwood (50). 

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