Solanum steroid alkaloids

Solanum alkaloids steroid alkaloids that occur in plants of the nightshade family (Solanaceae) of the genera Solanum, Lycopersicon, Cyphomandra and Cestrum. S. a. are structurally related to the parent hydrocarbon, cholestane (see Steroids). 

The structural features of the solanum alkaloids are based on two primary skeletal configurations solanidane, with or without glycoside functionalities, as featured by the toxic and teratogenic steroidal alkaloids a-chaconine and a-solanine with the indolizidine type E-F ring (Figure 2.7a) and the spirosolane... 

The solanum alkaloids are of interest as a starting material for the synthesis of steroid hormones, and show interesting pharmaceutical and fungicidal activity. 

Schreiber, K., Aurich, O., and Osske, G., Solanum alkaloids. XVBI. Thin-layer chromatography of Solanum steroid alkaloids and steroidal sapogenins, J. Chromatogr., 12, 63, 1963 Chem. Abs., 60, 4442h, 1964. 

The family Solanaceae is one of the important and interesting plant families. It may be classified into four groups based on their usefulness and chemical composition of alkaloids contained (1) Nicotiana spp. such as N. tabacum and N. rustica, which provide tobacco and contain nicotiana alkaloids such as nicotine and nomicotine (2) Hyoscyamus, Scopolia, Atropa, and Datura species, which are pharmacologically important and contain tropane alkaloids such as hyocyamine, scopolamine, and tropine (3) Solanum spp., which are sometimes the starting material for production of synthetic steroids for medical uses and which contain solanum alkaloids and (4) Capsicum, Solanum, and Lycoper-sicum species, which serve as foods and are alkaloid-free. 

Solanum. The steroid alkaloids of this genus are mostly produced in the sprouts but also in the roots (281a, 281b). 

SoLANUM. The steroid alkaloids in this genus arise mainly in the aerial portion, but the roots seem to be important as weU (282). Young organs seem to have a greater facility for generating alkaloids, and the alkaloid content of tomatoes and potatoes continually increases (231, 313, 370, 371). In the ripening plant alkaloid disappears from the roots, and the absolute content decreases partly in consequence of its translocation into the flowers, which in turn lose alkaloid as the seeds develop. When the plants are deprived of fruits there is an increase in alkaloid content in consequence of the loss of these organs of alkaloid breakdown (282). 

Solasodine (1) and related Solanum alkaloids are useful starting materials for the commercial preparation of steroid hormones." In particular the pregnane derivative (6) was prepared from solasodine in 65% overall yield via the intermediates (2), (3), and (4). The oxidative cleavage of the 20(22) double bond of pseudosolasodine diacetate (3), which is the least efficient step in this synthesis, has been investigated in more detail With sodium dichromate in acetic acid compound (3) gave the hydroxyester (5) and the hydroxylactone (7), in addition to the ester (4). Results of a kinetic study of this reaction were interpreted in terms of formation of hydroxyester (5) via allylic oxidation of pseudosolasodine diacetate prior to cleavage of the 20(22) double bond. ... 

There is no uniform classification for the A. In the literature divisions according to origin (examples Aconitum, Amaryllidaceae, Aspidosperma, cactus, Catharanthus, Cephalotaxus, Cinchona, coca, Corydalis, curare, Dendrobates, ergot, Erythrina, Iboga, Lycopodium, Maytenus, opium, Rauvol-fia, Senecio, Strychnos, tobacco, Vinca alkaloids, salamander, Solanum, Veratrum steroid alkaloids) in addition to divisions according to chemical structure (examples aporphine, benzylisoquinoline, bis-benzylisoquinoline, berberine, carboline, diterpene, inudazole, indole, indolizidine, isoquinoline, lupinane, macrocyclic, morphine, peptide, / -phenyl-ethylamine, piperidine, purine, pyridine, pyrrolidine, pyrrolizidine, quinoline, quinolizidine, quinucli-dine, spermine, spermidine, steroid, terpene, tro-pane, tropolone alkaloids) are used. 

Steroid and Triterpenoid Alkaloids Solanum Alkaloids Biosynthesis... 

The above-mentioned types of Solanum alkaloids are derived from the same pathways as most other steroids in plants. For more information on the formation of the various precursors involved, see Chapters 23 and 24. The biosynthesis and metabolism of the C27 sapogenins and alkaloids are closely related (Ripperger and Schreiber, 1981 Gross et al, 1985). Acetate and mevalonate are incorporated into all types of steroid alkaloids. 

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

The nomenclature used in this review is the same as that used in the former chapter on Solanum alkaloids (i) and follows the lUPAC-IUB recommendations for steroid nomenclature (50), with the exception of the "-anine designation of steroid alkaloids. 

The alkamines isolated directly from plant material or obtained by acid or enzymatic hydrolysis of naturally occurring glycosides between 1967 and 1979 are summarized in Table III. Physical me ods are of increasing importance in structure elucidation. Recent papers have dealt with IR spectra (173), H NMR (174,175), NMR (176-178,357,358), EPR (179), ORD (180-183), and MS (184,351,352) of Solanum alkamines. Some X-ray analyses have been carried out since 1967 (58, 81, 149, 185-189, 359). Tables rV-VI survey the characteristic features of H NMR, NMR, and MS of Solanum alkaloids. Silver nitrate-containing adsorption layers were shown to be useful in TLC separation of 5a-saturated and S-unsaturated alkamines (194,195). High-pressure liquid chromatography has been applied successfully for the separation of steroidal Solanum and Veratrum alkamines (373). 

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). 

The solanum alkaloids occurring in species of Solarium, including potatoes, Dead Sea Apple, and poro-poro, also contain the steroid nucleus... 

The chemistry of the Solanum alkaloids up to the year 1952 has been reviewed fully by V. Prelog and 0. Jeger in Chapter 21 of Volume III of The Alkaloids. More recent work, until about 1957, has been discussed briefly by the same authors in Chapter 16 of Volume VII of this series. The present chapter will deal with work reported since that time results of earlier investigations will be mentioned briefly only if necessary. But the present review will include a tabulated survey of the general occurrence of Solanum alkaloids so far known in the plant kingdom (Table I) and two additional surveys of the well-characterized steroid... 

The fruit of a number of solanaceous plants, including tomato Lycopersicon esculentum), potato Solanum tuberosum) and eggplant Solarium melongena esculentum), have cholinesterase-inhibiting effects (Krasowski et al. 1997). They contain solanaceous glycoalkaloids o-solanine and o-chaconine, which are triglycosides of solanidine, a steroidal alkaloid derived from cholesterol. They are the only plant chemicals known to inhibit both acetlycholinesterase and butyrylcholinesterase, both in vitro and in vivo. 

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

Figure 2.7 Two steroidal alkaloids from Solanum spp. (a) a-chaconine, with teratogenic activity, and (b) tomatidine, non-teratogenic alkaloid.

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

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. 

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