Veratrum alkaloids steroids

In addition to the alkaloids such as cyclobuxiae-D (129) and solanidine (130) where the stmctural similarities to steroids are clear (although it must be remembered that detailed evidence actually linkiag the compounds is lacking) there are the less obvious (but nonetheless also clearly related) Veratrum alkaloids. These compounds, of which protoverattine A [143-57-7] (131), obtained from the rhizome of Veratrum album L. (LiUaceae), is a... 

Alkaloids are active bioagents in animal tissues. There is clear scientific evidence of this. Crawford and Kocan" " have tested the toxicity of steroidal alkaloids from the potato Solanum tuberosum), such as a-chaconine, a-solanine, solanidine and solasodine, and Veratrum alkaloid, jervine on fish. The results of Crawford and Kocan s research proved that rainbow trout exhibited a toxic response to chaconine, solasidine and solanine, while medaka only did so to chaconine and solanine. Embryo mortality was observed as an effect of toxicity in both species. Many other alkaloids are known to disturb or cause disorder in animal reproductive systems. For example, gossypol from cotton-seed oil is known as a clear reducer of spermatogenesis and premature abortion of the embryo. 

Figure 26 shows the formula, conformation, and absolute configuration of veratridine (52). The structure and conformation of the C27-steroidal base is very similar to that determined for zygacine (C32H49N08) another Veratrum alkaloid (53). Variations in the pharmacological effects of Veratrum alkaloids appear to be dependent on the substituents attached to the essentially rigid molecular framework. The numerous intramolecular hydrogen bonds that enhance the molecular rigidity are indicated in Fig. 26. The positions of all the hydrogen atoms have been located for the veratridine molecule and the intramolecular donors and acceptors are identified as...

Interest continues in the preparation of c-nor-D-homo-steroids from readily available Veratrum alkaloids. In this connection the jervine-derived enamine (14) gave the ketone (15) (40%) on sensitized photo-oxygenation. Similarly, enamine (16) gave the expected ketone (17) and the ring-contracted product (18). ... 

Solanum and veratrum alkaloids Separation steroidal alka-loids(Fig.10.1 and 10.2) Zorbax Sil 6 Mm 250x4.6 n-Hexane-Me0H-Me,C0(18 1 1) n-Hexane-EtOH-Me CO(18 1 1) 4... 

Occasionally, plant alkaloids of terpenoid origin are sequestered by insects. For example, larvae of many species of sawfly are chemically protected by toxic metabolites they sequester from their host plants. This includes iridoid glycosides (see Section 2.04.3) and a group of steroidal alkaloids produced by plants of the genus Veratrum, such as zygadenine (149). In some cases, sawfly larvae have been shown to further metabolize sequestered Veratrum alkaloids for example, zygadenine is derived from hydrolysis of the ester functionalities in sequestered protoveratrine A (150). ... 

Jervine, one of the most readily available Veratrum alkaloids, was the starting material for the synthesis of C-nor-D-homo steroid hormone analogs. Kupchan and Abu El-Haj (31) degraded jervine to the 3 8-hydroxy-14(1312 8-H)-a6eo-androst-5-ene-ll,17-dione (28) and prepared 17a-hydroxy-14(13 12)3H)-a6eo-pregn-4-ene-3,ll,20-trione (29) and its 17(8-isomer (30). 

Steroidal Alkaloids.—Further study on the biosynthesis of Veratrum alkaloids has been published (for earlier work see refs. 224 and 225). The results obtained with dormant rhizome slices of V. grandiflorum were that (a) labelled verazine (207) gave rise to radioactive rubijervine (211) and hakurirodine (210), a new alkaloid isolated from dormant tuber slices, and (b) labelled etioline (208), a probable progenitor of solanidine (209), was not incorporated into either alkaloid. It was concluded that the biosynthetic pathway to solanidine (209) branches from that to rubijervine (211) at verazine (207) (see Scheme 25). 

The Solanum and Veratrum alkaloids form part of the material of two reviews on biochemical aspects of plant steroids. ... 

Solarium and Veratrum Steroidal Alkaloids 2 Veratrum Alkaloids... 

Triterpene (Steroid) Solanum alkaloids Veratrum alkaloids Funtumia alkaloids Holarrhena alkaloids Buxus alkaloids Salamander alkaloids... 

TricMoroacetic acid for steroids, digitalis glycosides and Veratrum alkaloids. 

Examination of over a dozen Veratrum alkaloids showed that three were capable of inducing monkey face lamb disease jervine (1), cyclopamine (11-deoxojervine) (2) and cycloposine (3-gluco-syl-ll-deoxojervine) (3) all of which project the amino nitrogen a or below the plane of the steroid (Keeler and Binns, 1968). 

This chapter presents a survey of newly isolated Veratrum and Solanum alkaloids between 1974 and 2014. These alkaloids generally possess a C27 cholestane carbon skeleton with five or six carbocyclic or heterocyclic rings they occur as glycosides, aglycones, or esters with various acids. Following lUPAC recommendations, these alkaloids are organized on the basis of their carbon framework into isosteroidal alkaloids and steroidal alkaloids. The former—sometimes designated as Veratrum alkaloids—are... 

C-nor-D-homo- or [14(13 2)-abeo] systems. The latter, also referred to as Solanum alkaloids, share a common ABCD steroid skeleton, i.e., six-membered C-rings and five-membered D-rings. The Veratrum alkaloids are further divided into three subgroups (see Figure 1) the jervanine, the veratramine, and the cevanine. The Solanum alkaloids on the other hand, are further divided into the solanidine and verazine subgroups (see Figure 1). 

Steroidal alkaloids found in Veratrum spp. and Solanum spp. with their relative teratogenic potency, as determined in a hamster bioassay. 

Steroidal alkaloids found in the Filiaceae family, primarily Veratrum and Zygadenus, have been responsible for large losses in livestock. Fluman and livestock deaths have occurred from accidental ingestion of death camas (Panter et al., 1987). Thousands of lambs have died or been destroyed because of Veratrum-indvLCQd malformations, most notably a craniofacial defect called cyclopia (Binns et al., 1965 James, 1999 Figure 2.8). Tracheal stenosis, skeletal malformations and early embryonic death are also common (Keeler and... 

Figure 2.8 Congenital cyclopia induced by maternal ingestion of Veratrum californicwn (or the steroidal alkaloid cyclopamine) on day 14 of gestation.

Figure 2.9 (a) Cyclopamine, steroidal alkaloid teratogen from Veratrum spp., and (b) zygacine, non-teratogenic alkaloid from Zygadenus spp. 

Steroidal alkaloids can cause malformations of fetuses during development. Domestic sheep feeding on Veratrum californicum often give birth to lambs with grotesquely shaped one-eyed heads. This cyclopia is caused by the steroidal alkaloids jervine, cyclopamine, and cycloposine (reviewed by Keeler, 1986). 

Steroid alkaloids Solanaceae Liliaceae Solanum tuberosum Lycopersicon esculentum Veratrum album Solanidine Tomatine Jervine Cyclop amine Cycloposine Protoveratrine A Protoveratrine B... 

Even (R)-2-methylbutanoic acid of high enantiomeric purity (more than 99%) has been reported as a natural compound in the extract of the steroid alkaloid containing drug Veratrum album L. [40]. 

N.A. Veratrum viride Ait. Steroidal, alkaloids, chelidonic acid.99 Lower blood pressure, dilate the peripheral blood vessels. 

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