In recent years, the steroidal glycoalkaloids have emerged as an important class of bioactive compounds. Their occurrence in a number of foods and their diverse biological activities has encouraged the development of more efficient procedures for their isolation, purification and analysis, and more sensitive methods of detection and structure determination. This review is mainly concerned with new approaches for the characterization of these metabolites. The formation of artifacts of isolation and purification is discussed. The limited information on their biosynthesis is summarized.
FriedmanM., McDonaldGM. (1997) Steroidal glycoalkaloids. In Naturally Occurring Glycosides. IkanR (Ed), Wiley, New York, 311–343.
2.
RoddickJG. (1991) The importance of the Solanaceae in medicine and drug therapy. In Solanaceae III; Taxonomy, Chemistry, Evolution.HawkesJ. G, LesterRN, NeeM, EstradaN. (Eds). Royal Botanic Gardens, Kew.7–23.
3.
PrelogV, JegerO. (1953) The chemistry of Solanum and Veratrum alkaloids. In The Alkaloids. Vol. III, ManskeRHF, HolmesHL. (Eds). Academic Press, New York, 247–312.
4.
FieserLF, FieserM. (1959) Alkaloids. In Steroids. Chapter 22. Reinhold Publishing Company, New York. 847–857.
5.
PrelogV, JegerO. (1960) Steroid alkaloids: the Solanum group. In The Alkaloids. Vol. VII, ManskeRHF. (Ed). Academic Press, New York, 343–361.
6.
SchreiberK. (1968) Steroid alkaloids, the Solanum group. In The Alkaloids. Vol. X, ManskeRHF, HolmesHL. (Eds). Academic Press, New York, 1–192.
7.
RippergerH, SchreiberK. (1981) Solanum sterol alkaloids. In The Alkaloids. Vol. XIX, RodrigoRGA. (Ed). Academic Press, New York, 81–192.
8.
OsmanSF. (1983) Glycoalkaloids in potatoes. Food Chemistry, 11, 235–247.
9.
Van GelderWMJ. (1991) Steroidal glycoalkaloids in Solanum: Consequences for potato breeding and for food safety. In Toxicology of Plant and Fungal Compounds; Handbook of Natural Toxins. Vol. 6. KeelerRF, TuAT. (Eds). Marcel Dekker, Inc., New York, 101–134.
10.
JadhavSJ, LutzSE, MazzaG, SalunkheDK. (1997) Potato glycoalkaloids: chemical, analytical and biochemical perspectives, in “Antinutrients and phytochemicals in food” ACS Symposium Series 662, ShahidiF. (ed.). American Chemical Society, Washington D. C., 94–114.
11.
RippergerH. (1998) Solanum steroid alkaloids- an update. In Alkaloids: Chemical and Biological Perspectives. Vol. 12, PelletierSW. (Ed). Elsevier, Amsterdam, 103–185.
12.
FriedmanM, McDonaldGM. (1997) Potato glycoalkaloids: chemistry, analysis, safety and plant physiology. Critical Reviews in Plant Sciences, 16, 55–132.
13.
FriedmanM. (2002) Tomato glycoalkaloids: Role in the plant and in the diet. Journal of Agricultural and Food Chemistry, 50, 5751–5780.
14.
DesfossesM. (1820) Extrait d'une lettre de M. Desfosses, pharmacien, á Besançon, á M. Robriquet. Journal de Pharmacie, 6, 374–376.
15.
BaupM. (1826) Extrait d'une lettre de M. Baup aux redacteurs sur plusierss nouvelle substances. Annalen der Chemie und Physiologie, 31, 108–109.
16.
ZwengerC, KindA. (1861) On solanine and its cleavage products. Annalen der Chemie und Pharmacie, 118, 129–151.
17.
BellRC, BriggsLH. (1942) Solanum alkaloids. Part 1. The alkaloid from the fruit of Solanum aviculare. Journal of the Chemical Society, 1–2.
18.
BriggsLH, NewboldRP, StaceNE. (1942) Solanum alkaloids. Part II. Solasonine. Journal of the Chemical Society, 3–12.
19.
BriggsLH, BrookerEG, HarveyWE, OdellAL. (1952) Solanum alkaloids. Part VIII. Solarmargine, a new alkaloid from Solanum marginatum. Journal of the Chemical Society, 3587–3591.
20.
KuhnR, LöwI. (1954) Die konstitution des solanins. Angewandte Chemie, 66, 639–640.
21.
IrvingGW, FontaineTD, DoolittleSP. (1945) Lycopersicon, a fungistatic agent from the tomato plant. Science, 102, 9–11.
22.
YoshimitsuH, NishidaM, NomaraT. (2003) Steroidal glycosides from fruits of Solanum abutiloides. Phytochemistry, 64, 1361–1366.
23.
SindenS, SanfordLL, DeahlKL. (1986) Segregation of leptine glycoalkaloids in Solanum chacoense Bitter. Journal of Agriculture and Food Chemistry, 34, 372–377.
24.
RippergerH, PorzelA. (1993) (23R)-23-Hydroxysoladulcidine and related compounds from Solanum panduraeforme. Phytochemistry, 32, 1607–1609.
MimakiY, SashidaY. (1990) Steroidal saponins and alkaloids from the bulbs of Lilium brownii var. colchesteri. Chemical and Pharmaceutical Bulletin, 38, 3055–3059.
MurakamiK, EzimaH, TakaishiY, TakedasY, FujitaT, SatoA, NagayamaY, NoharaT. (1985) Studies on the constituents of Solanum plants. V. The constituents of S. lyratum Thunb. II. Chemical and Pharmaceutical Bulletin, 33, 67–73.
34.
OhmuraE, NakamuraT, Tian, RuiH, YaharaS, YoshimitsuH, NoharaT. (1995) 26-Aminocholestanol derivative, a novel key intermediate of steroidal alkaloids, from Solanum abutiloides. Tetrahedron Letters, 36, 8443–8444.
35.
TianR-H, OhmuraE, YoshimitsuH, NoharaT, MatsuiM. (1996) Solanaceous plants. XXXIV. Cholestane glycosides from Solanum abutiloides. Chemical and Pharmaceutical Bulletin, 44, 1119–1121.
36.
RippergerH, HimmelreichU. (1994) Anguivine and isoanguivine, steroid alkaloid glycosides from Solanum anguivi. Phytochemistry, 37, 1725–1727.
YamashitaT, FujimuraN, YaharaS, NoharaT, KawanobuS, FujiedaK. (1990) Constituents of solanaceous plants. Part XVII. Structures of three new steroidal alkaloid glycosides, solaverines I, II and III from Solanum toxicarium and S. verbascifolium. Chemical and Pharmaceutical Bulletin, 38, 827–829.
39.
YoshitaK, YaharaS, SaijoR, MurakamiK, TomimatsuT, NoharaT. (1987) Studies on the constituents of Solanum plants. Part 8. Changes caused by included enzymes in the constituents of Solanum nigrum berries. Chemical and Pharmaceutical Bulletin, 35, 1645–1648.
40.
LeeYY, HashimotoF, YaharaS, NoharaT, YoshidaN. (1994) Solanaceous plants. 29. Steroidal glycosides from Solanum dulcamara. Chemical and Pharmaceutical Bulletin, 42, 707–709.
41.
PuriR, WongTC, PuriRK. (1994) 1H- and 13C-nmr assignments and structural determination of a novel glycoalkaloid from Solanum platanifolium. Journal of Natural Products, 57, 587–96.
NezsmelyiA, MachytkaD, Marruan ShabanaM. (1988) 13C NMR spectroscopy of solasodine glycosides from Solanum laciniatum. Phytochemistry, 27, 603–605.
44.
XuW, XueZ. (1986) Chemical investigation of glycosidal steroidal alkaloids of Northoliron hyacinthenum. Yaoxue Xuebao, 21, 177–182. (Chemical Abstracts, 105, 21663, 1986).
45.
OsmanSF, SindenSL. (1982) The glycoalkaloids of Solanum demissum. Phytochemistry, 21, 2763–2764.
46.
OsmanSF, JohnsTA, PriceKR. (1986) Sisusine, a glycoalkaloid found in hybrids between Solanum acaule and Solanum X ajanhuiri. Phytochemistry, 25, 967–968.
47.
WanyonyiAW, ChhabraS. C., MkojiG., EilertU. and NbjueW. M. (2002) Bioactive steroidal alkaloid glycoside from Solanum aculeastrum. Phytochemistry, 59, 79–84.
48.
FukuharaK, ShimizuK, KuboI. (2004) Arudonine, an allelopathic steroidal glycoalkaloid from the root bark of Solanum arundo Mattei. Phytochemistry, 65, 1283–1286.
49.
XuWH, XueZ. (1988) The chemical structure of neohyacinthoside. Yaoxue Xuebao, 23, 61–63. (Chemical Abstracts, 109, 51701, 1988).
50.
CarmanAS, KuanSS, FrancisOJ, KirschenheuterGP. (1986) HPLC dermination of the potato glycoalkaloids alpha-solanine and alpha chaconine. Journal of Agricultural and Food Chemistry, 34, 279–282.
51.
EdwardEJ, CobbA. (1996) Improved high-performance liquid chromatographic method for the analysis of potato (Solanum tuberosum) glycoalkaloids. Journal of Agricultural and Food Chemistry, 44, 2705–2709.
52.
CarterS, MurrayPE, ParkinJE, DalwadiG. (2004) Method for the extraction, separation, and purification of triglycoalkaloids from eggplant fruit. PCT Int. Appl.38 pp. WO 2004002998 A1 20040108. (Chemical Abstracts, 140, 76030, 2004).
53.
FriedmanM, McDonaldGM. (1995) Acid-catalyzed partial hydrolysis of carbohydrate groups of the potato glycoalkaloid α-chaconine in alcoholic solution. Journal of Agricultural and Food Chemistry, 43, 1501–1508.
54.
LawsonC. (2002) Extraction of glycoalkaloids from Solanum sodomeum. WO 2002-EP10946 20020930. (Chemical Abstracts, 138, 292702, 2002)
55.
BushwayRJ, BardenES, BushwayAW, BushwayAA. (1980) The mass extraction of potato alkaloids from blossoms. American Potato Journal, 57, 175–180.
56.
VronenPJE, KovalN, de GrootA. (2004) The synthesis of 6-dehydropregnenolone from potato alkaloids. ARKIVOC, 24–50.
57.
GregoryP, SindenSL, OsmanSF, TingeyWM, ChessinWM. (1981) Glycoalkaloids of wild, tuber-bearing Solanum species. Journal of Agricultural and Food Chemistry, 29, 1212–1215.
58.
RoddickJG. (1974) The steroidal glycoalkaloid α-tomatine. Phytochemistry, 13, 9–25.
59.
RoddickJG. (1979) Complex formation between solanaceous steroidal glycoalkaloids and free sterols in vitro. Phytochemistry, 18, 1467–1470.
60.
RoddickJG. (1980) A steroid binding assay for potato glycoalkaloids. Phytochemistry, 19, 2455–2457.
61.
KeukensEAJ, de VrijeT, van den BoomC, de WaardP, PlasmaanHH, ThielF, ChupinV, JongenWMF, de KruijffB. (1995) Molecular basis of glycoalkaloid induced membrane disruption. Biochemica Biophysica Acta, 1240, 216–228.
62.
KeukensEAJ, de VrijeT, JansenLAM., de BoerH, JanssenM, de KroonAIP M, JongenWMF, de KruijfB. (1996) Glycoalkaloid selectively permeabilize cholesterol containing biomembranes. Biochemica Biophysica Acta, 1279, 243–250.
63.
DaoL, FriedmanM. (1996) Comparison of glycoalkaloid content of fresh and freeze-dried potato leaves determined by HPLC and colorimetry. Journal of Agricultural and Food Chemistry, 44, 2287–2291.
64.
VäänänenT, KuronenP, PehuE. (2000) Comparison of commercial solid-phase extraction sorbents for the sample preparation of potato glycoalkaloids. Journal of Chromatography A, 869, 301–305.
65.
KvasnickaF, PriceKR, NgK, FenwickGR. (1994) Determination of potato alkaloids using isotachophoresis and comparison with a HPLC method. Journal of Liquid Chromatography, 17, 1941–1951.
66.
FukuharaK, KuboI. (1991) Isolation of steroidal glycoalkaloids from Solanum incanum by two countercurrent chromatographic methods. Phytochemistry, 30, 685–687.
67.
FerreiraC, MoynaF, SouleS, VazquezA. (1993) Rapid determination of solanum glycoalkaloids by thin-layer chromatographic scanning. Journal of Chromatography, 53, 380–384.
68.
LawsonD. R., ErbW. A. and MillarA. R. (1992) Analysis of Solanum alkaloids using internal standardization and capillary gas chromatography. Journal of Agricultural and Food Chemistry, 40, 2186–2191.
69.
PlhakLC, SpornsP. (1992) Enzyme immunoassay for potato glycoalkaloidsJournal of Agricultural and Food Chemistry, 40, 2533–2540.
70.
SimonovskaB, VovkI. (2000) High-performance thin-layer chromatographic determination of potato glycoalkaloids. Journal of Chromatography A, 903, 219–225.
71.
HunterR, WaldenMK, WagnerJR, HeftmannE. (1976) Thin-layer chromatography of steroidal alkaloids. Journal of Chromatography A, 118, 259–262.
72.
BaerheimSvendsen A, VerpoorteR. (1983) Chromatography of alkaloids. Part A: Thin-Layer Chromatography, Elsevier, Amsterdam.
73.
FriedmanM. (2004) Analysis of biologically active compounds in potatoes (Solanum tuberosum), tomatoes (Lycopersicon esculentum), and jimson weed (Datura stramonium). Journal of Chromatography A, 1054, 143–155.
74.
ChamiLA, MendezR, ChataingR, O'CallaghanJ, UsubillagaA, LaCruzL. (2003) Toxicological effects of α-solarmargine in experimental animals. Phytotherapy Research, 17, 254–258.
75.
FiladelfiMA, ZitnakA. (1983) A simple TLC standard for identification of potato glycoalkaloids. Canadian Institute of Food Science and Technology Journal, 16, 151–153.
76.
McCollumGD, SindenSL. (1979) Inheritance study of tuber glycoalkaloids in a wild potato. American Potato Journal, 56, 95–113.
77.
NagaokaT, YoshiharaT, OhraJ, SakamuraS. (1993) Steroidal alkaloids from roots of tomato stock. Phytochemistry, 34, 1153–1157.
78.
MahatoSB, SahuNP, GangulyAN, KasaiR, TanakaO. (1980) Steroidal alkaloids from Solanum khasianum: application of 13C NMR spectroscopy to their structural elucidation. Phytochemistry, 19, 2017–2020.
79.
FriedmanM, KozukueN, HardenLA. (1997) Structure of the tomato glycoalkaloid tomatidenol 3-β-lycotetraose (dehydrotomatine). Journal of Agricultural and Food Chemistry, 41, 1541–1547.
80.
BudzikiewiczH. (1964) Zum massenspectroskopischen fragmentierungsverhalten von steroidalkaloiden. Tetrahedron, 20, 2267–2288.
81.
KanekoK, WatanabeM, KawakoshiY, MitsuhashiH. (1971) Etioline as important precursor in solanidine biosynthesis in Veratrum grandiflorum: (25S) 22, 26-iminocholesta-5, 22 (N)-diene-3β, 16α-diol. Tetrahedron Letters, 4251–4254.
82.
SatoY, SatoY, KanekoH, BianchiE, KataokaH. (1969) Alkaloids from Solanum congestiflorum. Journal of Organic Chemistry, 34, 1577–1582.
83.
AliE, ChakravartyAK, PakrashiSC, BiemannK, HigniteCE. (1977) Studies on Indian medicinal plants. Tetrahedron, 33, 1371–1377.
84.
RippergerH, BudzikiewiczH, SchreiberK. (1967) Jurubin, ein stickstoffhaltiges steroidensaponin neuartigen strukturtyps aus Solanum paniculatum L.; über die struktur von paniculidin. Chemiche Berichte, 100, 1725–1740.
85.
KuronenP, VäänänenT, PehuE. (1999) Reversed-phase liquid chromatographic separation and simulataneous profiling of steroidal glycoalkaloids and their aglycones. Journal of Chromatography A, 863, 25–35.
86.
FriedmanM, RoitmanJN, KozukueN. (2003) Glycoalkaloid and calystegine contents of eight potato cultivars. Journal of Agricultural and Food Chemistry, 51, 2964–2973.
ZywickiB, CatchpoleG, DraperJ, FiehnO. (2005) Comparison of rapid liquid chromatography-electrospray ionisation-tandem mass spectrometry methods for determination of glycoalkaloids in transgenic field-grown potatoes. Analytical Biochemistry, 336, 178–186.
89.
KozukueN, HaeJS, LeeKR, FriedmanM. (2004) Dehydrotomatine and α-tomatine content in tomato fruits and vegetative plant tissues. Journal of Agricultural and Food Chemistry, 52, 2079–2083.
90.
CataldiTRI, LelarioF, BufoSA. (2005) Analysis of tomato glycoalkaloids by liquid chromatography coupled with electronspray ionization tandem mass spectrometry. Rapid Communications in Mass Spectrometry, 19, 3103–3110.
91.
WantEJ, CravattBF, SiuzdakG. (2005) The expanding role of mass spectrometry in metabolite profiling and characterization. ChemBioChem., 6, 1941–1951.
WeissenbergM. (2001) Isolation of solasodine and other steroidal alkaloids and sapogenins by direct hydrolysis-extraction of Solanum plants or glycosides therefrom. Phytochemistry, 58, 501–508.
94.
RippergerH. (1995) 22, 26-epiminocholestane alkaloids with unusual (20R)-configurations from Solanum species Phytochemistry, 39, 1629–16731.
95.
OnoH, KozukaD, ChibaY, HoriganaA, IsshikiK. (1997) Structure and cytotoxicity of dehydrotomatine, a minor component of tomato glycoalkaloids. Journal of Agricultural and Food Chemistry, 45, 3743–3746.
96.
Atta-ur-Rahman (1990) Handbook of Natural Products Data, Vol. 1, Diterpenoid and Steroidal Alkaloids, Elsevier, Amsterdam, 1–482.
97.
AgrawalPK, SrivastavaSK, GaffieldW. (1991) in Alkaloids: Chemical and Biological Perspectives. Vol. 7. PelletierSW. (Ed). Springer-Verlag, New York, 43–295.
98.
SwainAP, FitzpatrickTJ, TalleyEA, HerbFS, OsmanSF. (1978) Enzymatic hydrolysis of α-chaconine and α-solanine. Phytochemistry, 17, 800–801.
99.
Ruiz-RubioM, Perez-EspinosaA, Roldan-ArjonaT, LairiniK. (2001) α-Tomatine hydrolyzing enzymes in fungi. Recent Research Developments in Phytochemistry, 5, 11–17.
100.
WoodsK, HamiltonCJ, FieldRA. (2004) Enzymatic liberation of lycotetraose from the Solanum glycoalkaloid α-tomatine. Carbohydrate Research, 339, 2325–2328.
101.
MarkerRE, RohrmannE. (1939) Sterols LIII. The structure of the side chain of sarsasapogenin. Journal of the American Chemical Society, 61, 846–851.
102.
WallME, SerotaS, WitnauerLP. (1955) Steroidal sapogenins. XXIV. The hydrochloric acid catalyzed equilibration of 22ξ,25D-and 22ξ-25L-spirostans. Journal of the American Chemical Society, 77, 3086–3089.
103.
WoodwardRB, SondheimerF, MazurY. (1958) Mechanism of the isomerization of steroidal sapogenins at C-25. Journal of the American Chemical Society, 80, 6693–6694.
104.
ZieglerJB, RosenWE, ShabicaAC. (1955) The stereochemistry of steroidal sapogenins. Journal of the American Chemical Society, 77, 1223–1229.
105.
TobariA, TeshimaM, KoyanagiJ, KawaseM, MiyamaeH, YozaK, TakasakiA, NagamuraY, SatoS. (2000) Spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides. European Journal of Medicinal Chemistry, 5, 511–527.
106.
KozukueN, TsuchidaH, FriedmanM. (2001) Tracer studies on the incorporation of [2-14C]-DL-mevalonate into chlorophylls a and b, α-chaconine, and α–solanine of potato sprouts. Journal of Agricultural and Food Chemistry, 49, 92–97.
107.
RonchettiF, RussoG. (1974) Stereochemistry of the hydrogen introduction at C-25 in the biosynthesis of tomatidine. Journal of the Chemical Society Chemical Communications, 785–786.
108.
RonchettiF, RussoG, FerraraG, VecchioG. (1975) The role of (25S)-5α-cholestan-3β, 26-diol and (25S)-5α-furostan-3β, 26-diol in the biosynthesis of tomatidine and neotigogenin. Phytochemistry, 14, 2423–2425.
KanekoK, TanakaMK, MitsuhashiH. (1977) Dormantinol, a possible precursor in solanidine bioynthesis, from budding Veratrum grandiflorum. Phytochemistry, 16, 1247–1251.
111.
CanonicaL.RonchettiF, RussoG, SportolettiG. (1977) Fate of the 16β-hydrogen atom of cholesterol in the biosynthesis of tomatidine and solanidine. Journal of the Chemical Society Chemical Communications, 286–287.
112.
KalinowskaM, ZimowskiJ, PaczkowskiC, ZdzislawA. (2005) The formation of sugar chains in triterpenoid saponins and glycoalkaloids. Phytochemistry Reviews, 4, 237–257.
113.
ChenZ, MillerAR. (2001) Steroidal alkaloids in solanaceous vegetable crops. In Horticultural Reviews. Vol. 25. JanickJ. (Ed). John Wiley & Sons, 171–196.
114.
KeelerRF, BakerDC, GaffieldW. (1991) Teratogenic Solanum species and the responsible teratogens. In Toxicology of Plant and Fungal Compounds; Handbook of Natural Toxins. Vol. 6, KeelerRF, TuAT. (Eds). Marcel Dekker, New York, 83–99.
115.
GaffieldW, KeelerRF, BakerDC. (1991) Solanum glycoalkaloids: Plant toxins possessing disparate physiologically active structural entities. In Toxicology of Plant and Fungal Compounds; Handbook of Natural Toxins. Vol. 6, KeelerRF, TuAT. (Eds). Marcel Dekker, New York, 135–138.
116.
BakerDC, KeelerF, GaffieldW. (1991) Toxicosis from steroid alkaloids of Solanum species. In Toxicology of Plant and Fungal Compounds; Handbook of Natural Toxins. Vol. 6, KeelerRF, TuAT. (Eds). Marcel Dekker, Inc., New York, 71–82.
117.
PlhakLC, SpornsP. (1997) Biological activities of potato glycoalkaloids. In Antinutrients and phytochemicals in food. ACS Symposium Series 662, ShahidiF. (Ed). American Chemical Society, Washington D. C., 115–126.
118.
MarstonA, HostettmannK. (2006) Developments in the application of counter-current chromatography to plant analysis. Journal of Chromatography A, 1112, 181–194.