Consolida

D. consolida, L. From this species Keller isolated three alkaloids of which one (Base A ) was well defined. Markwood obtained three crystalline alkaloids of which delcosine was probably Keller s base A, and Cionga and Iliescu have added to Markwood s observations, but failed to obtain his third base. This work has recently been critically revised by Marion and Edwards, ( > who have isolated from the seeds six alkaloids of which two, delcosine and delsoline, were already known another, consolidine, may be Markwood s third base, and the remaining three are new records for this species, viz. delsonine, lycoctonine and anthranoyllycoctonine. They have also altered the empirical formulas of the alkaloids delcosine and delsoline. 

The genera of Aconitum (commonly known as Monkshood) and Delphinium, and to a lesser extent Rumex, Consolida, and Spiraea, have long been recognized as a rich source of alkaloid natural products [1], The diterpenoid alkaloids are generally classified into two major groups the Ci9-diterpenoid alkaloids (sometimes referred to as the Cig-norditerpenoid alkaloids) and the C2o-diterpenoid alkaloids. Within the C2o-diterpenoid alkaloids, at least 11 separate classes have been isolated, including the hetisine alkaloids (Chart 1.1). 

There is a long history of the use of Aconitum, Delphinium and Consolida species as the source of poisons and medicinals [1]. These three genera in Ranunculaceae family yield diterpenoid and norditerpenoid alkaloids. The name Delphinium derived from dolphine-delphine due to the shape of their flower buds [2]. Aconitum has an evil reputation from the antiquity [3]. The plant was used as poison in old Greece, also in north-west Pacific the natives used it to poison the whales and also as arrow poison. In England in the ancient times the plant was used against wolves, boars, tigers as well as against rodents, and it was also a homicide material [4]. 

In Turkey there are about 31 Delphinium, 8 Consolida and only 4 Aconitum species. So far we had studied 17 Delphinium, 7 Consolida and 3 Aconitum species. From these studies we have obtained more than 100 alkaloids, about 50 of them were new compounds [17]. 

Among the new anthocyanins, which have been reported after 1992, 47, 22, and 36 contain sophorose, rutinose, and sambubiose, respectively (Figure 10.5). Most of the anthocyanins containing sophorose were first isolated from species belonging to Convolvulaceae (22) and Cruciferae (13) (Table 10.2). This disaccharide has also been identified in new anthocyanins isolated from AJuga (Labiatae), " "" Consolida (Ranunculaceae)," Begonia (Begonia-ceae)," and in the flavonol unit of two covalent anthocyanin-flavonol complexes from Allium (Alliaceae)."... 

Most of the 16 anthocyanins that are acylated with p-hydroxybenzoic acid (Appendix A) have been isolated from flowers of Deiphinium hybridum, Aconitum chinense, Consolida armeniaca (Ranunculaceae), Campanula species (Campanulaceae)," or roots of Ipomoea batatas (Convolvulaceae). In the examined species from Ranunculacea and Campanula, one to as many as four -hydroxybenzoyl moieties belong to the anthocyanidin... 

Nearly 35 different anthocyanins have been reported to occur in one or more species in the family Ranunculaceae (Figure 10.15), and 24 of these have been reported after 1992 as novel compounds. Flowers of species in the genera Delphinium (blue), ° Consolida (blue-violet), and Aconitum (purplish-blue) " contain similar anthocyanins with polyacyl substitution based on -hydroxybenzoylglucose residues at the 7-hydroxyl of delphinidin, in addition to a more simple glycosyl moiety at the 3-position. Red flowers of Delphinium hybridum share a similar 3,7-disubstitution pattern based on pelargonidin instead of delphinidin. 

Saito, N. et al., Acylated delphinidin glycosides in the blue-violet flowers of Consolida armeniaca. Phytochemistry, 41, 1599, 1996. 

Adonis spp. (Ranunculaceae) cccc 52,804 87 Annona cherimolia (Annonaceae) jnp 48,151 85 Ayuilegia spp. (Ranunculaceae) cccc 52, 804 87 Aristolochia clematitis (Aristolochiaceae) cccc 52,804 87 Caltha palustris (Ranunculaceae) cccc 52, 804 87 Chelidonium majus (Papaveraceae) pm 60, 380 94 Cissampelos pareira (Menispermaceae) fit 63, 282 92 Clematis recta (Ranunculaceae) cccc 52, 804 87 Consolida regalis (Ranunculaceae) cccc 52, 804 87 Corydalis dasyptera (Papaveraceae) tcyyk 9,37 97 Corydalis gortschakovii (Papaveraceae) cnc 13,702 77 Corydalis nobilis (Papaveraceae) cccc 54,2009 89... 

Diterpenoid alkaloids have been isolated from the genera of the families Ranunculaceae (Aconitum, Consolida, Delphinium, Thalictrum), Garryaceae (Garraya), Rosaceae (Spiraea), and Compositae (Inula). These alkaloids can be divided into two broad categories norditerpenoid alkaloids (based on a C -skeleton) and the diterpenoid alkaloids (based on a Cft-skeleton).1 The chemistry of the diterpenoid alkaloids has been reviewed in earlier literature. ... 

Aconitetta stenocarpa (Hossain and P. H. Davis) Sojak. Syn. Consolida Slenocarpa Hossain and PH Davis... 

Consolida glandulosa (Boiss. et Huet.) Bomm. (Syn. Delphinium glandularum Boiss et Huett)... 

Consolida stenocarpa Hussain and P.H. Davis Stenocarpine Delphinium ajacis Ajaconine Dihydroajaconine Delphinium albiflorum DC... 

Consolida glandulosa(Boiss. et Huet) Bomm., syn. Delphinium glandulosum Boiss. syn. et Huet. 

Consolida hellespontica (Boiss) Chater syn., Delphinium hellespontica (Boiss) and D. tomentosum (Boiss)1. 

Consolida glandulosa (Boiss. e I Huct) Bormn, Syn. Delphinium ghmdulosum Boiss. el Hiil I. 

Consolida ambigua (Delphinium ajacis)1 Prepared from 7a-hydroxyisoatisine2... 

Surveys of recent developments in the chemistry of C2o diterpenoid alkaloids,4 of the alkaloids of Consolida ambigua,5 and of the synthesis of diterpenoid alkaloids by thermolysis6 have appeared. 

Ajaconine, the major alkaloid of the seeds of Delphinium ajacis syn. Consolida ambigua (garden larkspur) and D. consolida, has been known since 1913 (S3). Recently, ajaconine has been isolated from the whole plants of D. virescens Nutt (84) and D. carolinianum (85), two relatively rare plants native to the southeastern United States. In 1961, Dvornik and Edwards (86) reported a full account of the structure elucidation of ajaconine as 80. 

C22H33N03 MW 359 mp 167° [ ]D -122° (EtOH) Delphinium ajacis D. consolida Consolida ambigua D. virescens D. carolinianum... 

The genus Consolida, Aconitum, and Delphinium (Ranunculaceae) are well-known to be rich in diterpene alkaloids, which possess a diverse range of biological activities. These plants have also been the cause of poisonings, which primarily occur in cattle as well as human beings, due to toxicity of their alkaloids. In one of our recent studies, five diterpenoid-derivative alkaloids, lycoctonine (9), 18-O-methyllycoctonine (10), delcosine (11), 14-acetyldelcosine (12), and 14-acetylbrowniine (13) (as shown in Fig. 3) were screened for their antibacterial, antifungal, and antiviral activities [39]. 

Even though much is already known about the toxicity of diterpene alkaloids that contribute to the toxicity of Consolida, Delphinium, and Aconitium species, no antiviral study has been so far reported on this type of alkaloids. Therefore, no SAR studies have been encountered by us on the antiviral or antimicrobial activities of these alkaloids. However, a quantitative SAR analysis performed on a number of diterpene alkaloids isolated from an Aconitum sp. indicated that biological activity of these alkaloids may be related to their toxicity rather than to a specific pharmacological action [40]. In a current study on 43 norditerpenoid alkaloids from Consolida, Delphinium, and Aconitum species against several tumor cell lines, lycoctonine and browniine were... 

DIBOA-GIc H H Secale cereale (Poaceae)34 Triticum aestivum (Poaceae)41 Consolida orientaiis (Ranunculaceae)60 Acanthus mollis (Acanthaceae)84 Acanthus ebracteatus (Acanthaceae)43... 

Aphelandra tetragona (Acanthaceae)77 Consolida oriental is60... 

High-moderate Consolida orientalis BOA-6-O-glucoside (major product) glucoside carbamate Ranunculaceae Amarantho- Chenopodion... 

Ozden, S., Ozden T., Attila, J., Kucukislamoglu, M., and Okatan, A. 1992. Isolation and identification via high performance liquid chromatography and thin layer chromatography of benzoxazolinone precursors from Consolida orientalis flowers. J. Chromatogr. 609, 402-406... 

Delsoline (= Aconomine Aconitum monticola, Consolida nACh-R antagonist (19) (a 7... 

Methyldelcosine) (norditerpene alkaloid) ajacis, Delphinium consolida, (Ranunculaceae) [root] aBgTX site) [hypotensive]... 

---