Steroid potato

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. 

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. 

Stobiecki, M. et al.. Monitoring changes in anthocyanin and steroid alkaloid glycoside content in lines of transgenic potato plants using liquid chromatography/mass spectrometry. Phytochemistry, 62, 959, 2003. 

The synthesis of triterpenoid saponins from the skeletons shown in Fig. 2 involves a series of further modifications that may include a variety of different oxidation and substitution events [9]. Very little is known about the enzymes and genes involved in the elaboration of the triterpenoid skeleton, although genetic and biochemical analysis of saponin-deficient mutants of plants is likely to accelerate the dissection of these processes [16]. Progress has been made in the characterisation of saponin glucosyltransferases (primarily for steroidal and steroidal alkaloid saponins), and the first of these enzymes (StSGT from potato) has been cloned. Since glycosylation at the C-3 hydroxyl position confers am-... 

Krits, R, Fogelman, E., Ginzberg, I. (2007). Potato steroidal glycoalkaloid levels and the expression of key isoprenoid metabolic genes. Planta, 227, 143-150. 

McCue, K. F., Shepherd, L. V. T., Allen, P. V, Maccree, M. M., Rockhold, D. R., Corsini, D. L., Davies, H. V, Belknap, W. R. (2005). Metabolic compensation of steroidal glycoalkaloid biosynthesis in transgenic potato tubers using reverse genetics to confirm the in vivo enzyme function of a steroidal alkaloid galactosyltransferase. Plant science, 168, 267-273. 

A number of alkaloids (nitrogenous bases) are derived from steroids. An example is solanidine (Fig. 22-12), which is present in the skins and sprouts of potatoes, making both quite toxic. 

Bachem, C.W.B., Horvath, B., Trindale, L., Claassens, M., Davelaar, E., Jordi, W., and Visser, R.G.F., A potato tuber expressed mRNA with homology to steroid dehydrogenases affects gibberellin levels and plant development, Plant J., 25, 595-604, 2001. 

Dietary compounds are represented in a number of highly successful drugs such as lovastatin 31 and salicylic acid, the archetypal statin and non-steroid anti-inflammatory drugs, respectively. Lovastatin occurs in the red yeast of rice Monascus ruber),91 an ingredient of Eastern cuisine used to give a red colour to the Pekinese duck, while salicylic acid is ubiquitous in plants.92 Other important dietary drug candidates are curcumin 32 from turmeric and capsaicin from hot pepper 33,93 while traces of pharmaceutical benzodiazepines (including diazepam) occur in common edible plants such as potatoes and cherries.5... 

The potato beetle (Leptinotarsa decemlineata) lives on Solanum species containing steroid alkaloids, which are tolerated, but not stored, by this species. The bruchid beetle Callosobruchus fasciatus predates... 

A general survey of the scope of the reaction between alcohols and dihydropyran to form tetrahydropyranyl ethers may be of value in devising syntheses requiring the protecting of hydroxy-groups. The glycosylation of 3/ -hydroxy-steroids by potato-tuber slices has been systematically investigated. 

The use of gas-liquid chromatography for the identification and estimation of potato glycoalkaloids has been described. The glycosides were rendered sufficiently volatile by conversion into their permethyl ether derivatives. Solasodine and soladulcidine in admixture may be conveniently estimated by thin-layer chromatography after bromination of the former. The detection of steroidal alkaloids on t.l.c. plates and a colorimetric method for the estimation of solasodine have been discussed. 

Reversed-phase HPLC of potato steroid glycoalkaloids was reported by Bushway et al. . ... 

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