Abstract
Solanum glaucophyllum Desf. is a calcinogenic plant growing wild mainly in South America, where its ingestion causes intoxication of grazing animals. Early work suggested that glycosides of various vitamin D3 sterols occur in minute concentrations in the plant leaves and are responsible for a calcinotic disease of cattle prevalent in Argentina and Brazil, with symptoms resembling vitamin-D intoxication. The vast literature on this topic describing chemical, toxicological, and physiological aspects has been extensively reviewed in the last decade (Wasserman and Nobel 1980; Morris 1982; Boland 1986; Weissenberg 1989). A few communications reporting the occurrence of small amounts of other steroids such as β- sitosterol, diosgenin and solasodine, and also of phenolic derivatives (vide infra), have already been summarized (Weissenberg 1989). Since this chapter is concerned with the in vitro production of metabolites in S. glaucophyllum, the naturally occurring steroidal derivatives which have been found to occur also in vitro will be treated preferentially in the following survey.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Birner J (1969) Determination of total steroid bases in Solanum species. J Pharm Sci 58: 258–260
Boland RL (1986) Plants as a source of vitamin D3 metabolites. Nutr Rev 44: 1–8
Cabrera AL (1965) Solanaceae in Flora de la Provincia de Buenos Aires. In: Colección Científica del INT A, vol 4, part 5a. Instituto Nacional de Tecnología Agropecuaria, Buenos Aires, pp 190–250
Coppen JJW (1979) Steroids: from plants to pills - the changing picture. Trop Sci 21: 125–141
Corradino RA, Ebel JG, Craig PH, Taylor AN, Wasserman RH (1971) Calcium absorption and the vitamin D3-dependent calcium-binding protein. Calcif Tissues Res 7: 81–92
Das AK, Banerjee AB (1980) A rapid method for quantification of sterols after thin-layer chromatography. Indian J Exp Biol 18: 969–971
Deb DB (1979) Solanaceae in India. In: Hawkes JG, Lester RN (eds) The biology and taxonomy of the Solanaceae. Linnean Soc Symp Ser 7. Academic Press, London, pp 87–112
Djerassi C (1976) The manufacture of steroidal contraceptives: technical versus political aspects. Proc R Soc Lond Sect B 195: 175–186
Ellis BE (1988) Natural products from plant tissue culture. Nat Prod Rep 5: 581–612
Esparza MS, Vega M, Boland RL (1982) Synthesis and composition of vitamin D3 metabolites in Solanum malacoxylon,. Biochim Biophys Acta 719: 633–640
Furmanowa M, Guzewska J (1989) Dioscorea: in vitro culture and the mieropropagation of diosgenin- containing species. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 7. Medicinal and aromatic plants II. Springer, Berlin Heidelberg New York, pp 162–184
Fürst A, Labler L, Meier W (1983) Synthese von ß-D-glucopyranosiden einiger hydroxylierter Vitamin D-Verbindungen. Helv Chim Acta 66: 2093–2102
Gröger D (1988) Terpenoids and steroid alkaloids. In: Constabel F, Vasil IK (eds) Cell culture and somatic cell genetics of plants, vol 5. Academic Press, New York, pp 435–448
Haussler MR (1986) Vitamin D receptors: nature and function. Annu Rev Nutr 6: 527–562
Haussler MR, Cordy PE (1982) Metabolites and analogues of vitamin D. J Am Med Assoc 247:841–844
Haussler MR, Wasserman RH, McCain TA, Peterlik M, Bursak KM, Hughes MR (1976) 1,25- Dihydroxyvitamin D3-glycoside: identification of a calcinogenic principle of Solanum malacoxylon. Life Sci 18: 1049–1056
Heble MR, Narayanaswamy S, Chadha MS (1971) Hormonal control of steroid synthesis is Solanum xanthocarpum tissue cultures. Phytochemistry 10: 2393–2394
Heftmann E (1983) Biogenesis of steroids in Solanaceae. Phytochemistry 22: 1843–1860
Holick MF, Adams JS, Clemens TL, MacLaughlin J, Horiuchi N, Smith E, Holick SA, Nolan J, Hannifan N (1982) Photoendocrinology of vitamin D: the past, present and future. In: Norman AW, Schaefer K, von Herrath D, Grigoleit HG (eds) Proc 5th Workshop Vitamin D (Vitamin D, Chemical, Biochemical and Clinical Endocrinology of Calcium Metabolism). Walter de Gruyter, Berlin, pp 1151–1156
Horst RL, Reinhardt TA, Russell JR, Napoli JL (1984) The isolation and identification of vitamin D2 and vitamin D3 from Medicago sativa (alfalfa plant). Arch Biochem Biophys 231: 67–71
INTA-FAO (1970) Estudio de las enfermedades y deficiencias nutricionales del ganado vacuno en la Argentina. Final Report, UN Special Fund Project, FAO, Rome
Jain SC, Sahoo S (1986) Isolation of steroids and glycoalkaloids from Solanum glaucophyllum Desf. Pharmazie 41: 820–821
Londowski JM, Kost SB, Meier W, Labler L, Kumar R (1986) Biological activity of the C-l, C-3, C-25, ß-D-glucopyranosides of 1,25-dihydroxyvitamin D3. J Pharmacol Exp Ther 237: 837–840
Macek TE (1989) Solanum aviculare Forst.,Solanum laciniatum Ait. (Poroporo): in vitro culture and the production of solasodine. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 7. Medicinal and aromatic plants II. Springer, Berlin Heidelberg New York, pp 443–467
Mann JD (1978) Production of solasodine for the pharmaceutical industry. In: Brady NC (ed) Advances in agronomy, vol 30. Academic Press, New York, pp 207–243
Martin KA (1984) Sterols. In: Rehm H-J, Reed G (eds) Biotechnology, vol 6a. Verlag Chemie, Weinheim, pp 80–95
Meier W (1981) Die chemische Entwicklung von Rocaltrol. Nieren Hochdruckkrankh 10: 175–179
Morris KML (1982) Plant induced calcinosis: a review. Vet Hum Toxicol 24: 34–48
Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiol Plant 15: 473–497
Okada KA, Carrillo BJ, Tilley M (1977)Solanum malacoxylon Sendtner: a toxic plant in Argentina. Econ Bot 31: 225–236
Omdahl JL, DeLuca HF (1972) Rachitogenic activity of dietary strontium: inhibition of intestinal calcium absorption and 1,25 dihydroxycholecalciferol synthesis. J Biol Chem 247: 5520–5526
Pardo R, Santelli M (1985) Synthèse des métabolites de la vitamine D. Bull Soc Chim Fr (II): 98–114
Pike JW (1987) Emerging concepts of the biologie role and mechanism of action of 1,25-dihyd- roxyvitamin D3. Steroids 49: 3–27
Puri RK, Bhatnagar JK (1974) Studies on the genus Solanum- a review. Pharmacos 19: 7–24
Rambeck WA, Kreutzerg O, Bruns-Droste C, Zucker H (1981) Vitamin D3in the grass Trisetum flavescens.Z Pflanzenphysiol 104: 9–16
Rambeck WA, Weiser H, Zucker H (1986) Antirachitische Aktivität von Glukosiden des 1,25- Dihydroxyvitamin D3und des la-Hydroxyvitamin D3beim Hühnerküken. Wien Tieraerztl Monatsschr 73: 169–171
Rappaportt I, Giacopello D, Seldes AM, Blanco MC, Deulofeu V (1977) Phenolic glycosides from Solanum glaucophyllum:a new quercetin triglycoside containing D-apiose. Phytochemistry 16: 1115–1116
Ripperger H, Schreiber K (1981) Solanumsteroid alkaloids. In: Manske RHF, Rodrigo RGA (eds) The alkaloids: chemistry and physiology, vol 19. Academic Press, New York, pp 81–192
Roddick JG (1986) Steroidal alkaloids of the Solanaceae. In: D’Arcy WG (ed) Solanaceae: biology and systematics, chapter 16. Columbia Univ Press, New York, pp 201–222
Sahoo SL, Jain SC (1987) Isolation of steroids and glycoalkaloid from seeds and seedling callus of Solanum glaucophyllum Desf. tissue culture. Cell Chromosome Res 10: 104–109
Sanchez GL, Medina Acevedo JC, Soto RR (1972) Spectrophotometric determination of diosgenin in Dioscorea composita following thin-layer chromatography Analyst 97: 973–978
Schreiber K (1968) Steroid alkaloids: the Solanum group. In: Manske RHF (ed) THE alkaloids: chemistry and physiology, vol 10. Academic Press, New York, pp 1–192
Simpson RV, Wishaar R (1986) Newly discovered activities for calcitriol (1,25-dihydroxyvitamin D3): implications for future pharmacological use. Bio Assays 4: 65–70
Vidal MC, Lescano W, Avdolov R, Puche RC (1985) Partial structure elucidation of the carbohydrate moiety of 1,25-dihydroxycholeealciferol glycoside isolated from Solanum glaucophyllum leaves. Turrialba 35: 65–70
Wasserman RH, Nobel TA (1980) Vitamin D-related compounds as the toxic principle in calcinogenic plants. In: Norman AW (ed) Basic clinical nutrition, vol 2. Vitamin D: molecular biology and clinical nutrition. Marcel Dekker, New York, pp 455–487
Wasserman RH, Henion JD, Haussier MR, McCain TA (1976) Calcinogenic factor in Solanum malacoxylon: evidence that it is 1,25-dihydroxyvitamin D3-glycoside. Science 194: 853–855
Weiler EW, Kruger H, Zenk MH (1980) Radioimmunoassay for the determination of the steroidal alkaloid solasodine and related compounds in living plants and herbarium specimens. Planta Med 39: 112–124
Weissenberg M (1979) Isolation of alkaloidal steroids from plants. Israeli Patent 58227, 30 July 1982; appl. 11 Sept 1979. Chem Abstr 99: 28002, 1983
Weissenberg M (1989) Calcinogenic glycosides. In: Cheeke PR (ed) Toxicants of plant origin, vol 2. Glycosides. CRC Press, Boca Raton, pp 201–238
Weissenberg M, Levy A, Wasserman RH (1987) Studies on calcinogenic Solanaceae plants of potential value as source of active vitamin D-like derivatives. Report 1–389-81, United States-Israel Binational Agricultural Research and Development Fund (BARD), Bet Dagan, Israel
Weissenberg M, Maoz A, Levy A, Wasserman RH (1988) Radioimmunoassay for rapid estimation of vitamin D derivatives in calcinogenic plants. Planta Med 54: 63–65
Weissenberg M, Levy A, Wasserman RH (1989) Distribution of calcitriol activity in Solanum glaucophyllum plants and cell cultures. Phytochemistry 28: 795–798
Weissenberg M, Schaeffler I, Maoz A, Levy A, Wasserman RH (1990) The fractionation of Solanum glaucophyllum extracts with lead acetate revisited. Fitoterapia 61: 258–262
Worker NA, Carrillo BJ (1967) “Enteque seco”, calcification and wasting in grazing animals in the 370 Argentine. Nature 215; 72–74
Zenk MH (1978) The impact of plant cell culture on industry. In: Thorpe TA (ed) Frontiers of plant tissue culture, Proc 4th Int Congr Plant tissue and cell culture, Univ Calgary. Offset Printing Service, Calgary, Alberta, pp 1–13
Zucker H, Stark H, Rambeck WA (1980) Light-dependent synthesis of cholecalciferol in a green plant. Nature 283: 68–69
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1993 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Weissenberg, M., Levy, A., Wasserman, R.H. (1993). Solatium glaucophyllum Desf. (Duraznillo Blanco): In Vitro Culture and the Production of Steroidal Secondary Metabolites. In: Bajaj, Y.P.S. (eds) Medicinal and Aromatic Plants IV. Biotechnology in Agriculture and Forestry, vol 21. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-77004-3_24
Download citation
DOI: https://doi.org/10.1007/978-3-642-77004-3_24
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-77006-7
Online ISBN: 978-3-642-77004-3
eBook Packages: Springer Book Archive