126-17-0

Basic information

• Product Name: SOLASODINE
• Synonyms: (3beta,22alpha,25r)-spirosol-5-en-3-o;delta5-20betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol;Salasdine;Salasodine;Solanidine-S;Solasodin;Solasodine hydrochloride base;Sosasodine
• CAS NO: 126-17-0
• Molecular Formula: C₂₇H₄₃NO₂
• Molecular Weight: 413.64
• EINECS: 204-774-2
• Product Categories: Alkaloids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 126-17-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: 200-202°
• Boiling Point: 532.75°C (rough estimate)
• Flash Point: 279.1 °C
• Appearance: white to beige/
• Density: 1.0159 (rough estimate)
• Vapor Pressure: 8.21E-14mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble0.5mg/mL, clear (warmed)
• PKA: pKb 6.30(at 25℃)
• CAS DataBase Reference: SOLASODINE(CAS DataBase Reference)
• NIST Chemistry Reference: SOLASODINE(126-17-0)
• EPA Substance Registry System: SOLASODINE(126-17-0)

Safety Data

• Safety Statements: 22-24/25
• RTECS: WF1300000
• Hazardous Substances Data: 126-17-0(Hazardous Substances Data)

Usage

Description

There is still some doubt as to whether this base occurs as such in Solanum aviculare and S. xanthocarpum or whether it is an artifact formed from Sola_x0002_sonine (q.v.) during the extraction process. The base is laevorotatory having [α]20D - 92.4° (C6H6) and the following salts and derivatives have been prepared: hydrochloride, m.p. 314°C; hydriodide, m.p. 293°C; oxalate, m.p. 248°C; tartrate, m.p. 222°C; picrate, m.p. 1.4l-2°C; picrolonate, m.p. 234°C; acetyl derivative, m.p. 195°C; benzoyl compound, m.p. 2l6-7°C and the 3:5-dinitrobenzoyl derivative, m.p. 191.5-193°C. The alkaloid forms a sparingly soluble digitonide and yields Diels's hydrocarbon on selenium dehydrogenation.

Uses

Different sources of media describe the Uses of 126-17-0 differently. You can refer to the following data:
1. Solasodine is a potentially useful precursor for steroidal compounds and hormones, this is usually found in plants from the solanaceae family. It also has potent cytotoxic and anti-inflammatory effects.
2. antineoplastic, antiinflammatory
3. A potentially useful precursor.
4. Starting material for steroidal drugs.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Solasodine is a neuroprotective antioxidant glycoalkaloid of Solanum species. Solasodine increases superoxide dismutase (SOD), catalase (CAT),and glutathione (GSH) levels, while reducing lipid peroxidation (LPO) and nitric oxide (NO) levels in the brains of ischemia/reperfusion (I/R)-injury model in rats. Also, Solasonine displayed multiple activities including, anti-cancer and leishmanicidal activities.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Solasodine crystallises (as monohydrate) from MeOH as lustrous plates (on heating, the plates change to needles as they melt and resolidify in needles), or aqueous 80% EtOH, and sublimes at high vacuum. After recrystallisation from H2O, m 198-199o, then from Me2CO/H2O, m 199-201o, it has [] D 22 -109.3o (c 0.581, CHCl3). On TLC with silica gel G (*C6H6/absolute EtOH, 8:2) it has RF 0.45. IR (KBr): max at 10.3, 10.4, 11.2, 11.5 (azaoxaspirane bands). [Schreiber & Rnsch Tetrahedron 20 1939 1964, Uhle J Org Chem 27 656 1962, Kessar et al. Tetrahedron 27 2153 1971, Beilstein 27 III/IV 2000.]

References

Rochelmeyer, Chen., Arch. Pharm., 277,329 (1939) Briggs., J. Chem. Soc., 3, (1942) Briggs et al., ibid, 3013 (1950)Absolute configuration: Boll, Phillipsborn., Acta Chem. Scand., 19, 1365 (1965) Synthesis: Schreiber, Walther, Ronsch., Tetrahedron, 20, 1939 (1964) Adam, Schreiber., Experientia, 21,471 (1965) Adam, Schreiber., Tetrahedron, 22,3591 (1966)

InChI:InChI=1/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3/t16-,17+,19+,20?,21?,22+,23+,24?,25+,26+,27-/m1/s1

Synthetic route

solasodine-3β-acetate (1415-78-7, 6159-99-5) → solasodine (126-17-0)

Conditions	Yield
With water; sodium hydroxide In methanol; dichloromethane at 20℃; for 3h;	93%

C43H61NO2Si → solasodine (126-17-0)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 70℃; Inert atmosphere;	88%
With hydrogenchloride; water In ethanol for 2h; Reflux;

C27H41N3O2 (1000612-48-5) → solasodine (126-17-0)

Conditions	Yield
Stage #1: C27H41N3O2 With chloro-trimethyl-silane; sodium iodide In acetonitrile at 20℃; for 2h; Stage #2: With sodium thiosulfate In water; acetonitrile Stage #3: With sodium hydroxide In water; acetonitrile pH=9; diastereoselective reaction;	72%
Multi-step reaction with 2 steps 1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 20 °C 2: sodium thiosulfate; sodium hydroxide / water; acetonitrile View Scheme

(22S,25R)-22,26-epiminocholest-5-ene-3β,16β-diol (6785-55-3) → (25R)-22αN-spirosol-4-en-3-one (17094-86-9) + solasodine (126-17-0)

Conditions	Yield
With manganese(IV) oxide	A 12% B 68%
With manganese(IV) oxide In chloroform at 20℃; for 24h;	A 12% B 68%

C30H47NO5S → solasodine (126-17-0)

Conditions	Yield
Stage #1: C30H47NO5S With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.25h; Inert atmosphere; Stage #2: With oxygen In tetrahydrofuran; hexane at 20℃; for 3h;	44%

C27H43NO2 (514-32-9) → solasodine (126-17-0)

Conditions	Yield
With chloro-trimethyl-silane In dichloromethane for 12h; Inert atmosphere;	43%
Stage #1: C27H43NO2 With sodium thiosulfate; sodium hydroxide In water; acetonitrile Stage #2: In water; acetonitrile

N,O-diacetyl-22-episolasodine → solasodine (126-17-0)

Conditions	Yield
With sodium; butan-1-ol for 24h; Reflux;	40%

(22S,25R)-N-Chloro-22,26-epiminocholest-5-ene-3β,16α-diol (129850-55-1) → 25-Isoetioline (129938-55-2) + solasodine (126-17-0)

Conditions	Yield
With sodium ethanolate In ethanol for 2h;	A 27% B n/a

(25R)-3β-hydroxy-26-phthalimido-cholest-5-ene-16,22-dione (122387-24-0) → solasodine (126-17-0)

Conditions	Yield
Reaktion ueber mehrere Stufen;

solamargine (20311-51-7) → solasodine (126-17-0)

Conditions	Yield
With hydrogenchloride; ethanol
With hydrogenchloride
(acid hydrolysis);

solasonine (19121-58-5, 20318-30-3) → solasodine (126-17-0)

Conditions	Yield
With hydrogenchloride
With sulfuric acid
With hydrogen bromide
(acid hydrolysis);

solasonine (19121-58-5, 20318-30-3) → solasodine (126-17-0) + (25R)-22αN-spirosola-3,5-diene (3669-17-8)

Conditions	Yield
With hydrogenchloride

N-((25R)-3β,22-dihydroxy-(22ξH)-furost-5-en-26-yl)-phthalimide (107387-55-3) → solasodine (126-17-0)

Conditions	Yield
(i) N2H4, MeOH, CH2Cl2, (ii) aq. HCl; Multistep reaction;

N-((25R)-3β-hydroxy-furosta-5,20(22)-dien-26-yl)-phthalimide (7604-97-9) → solasodine (126-17-0)

Conditions	Yield
(i) (hydrazinolysis), (ii) aq. HCl, MeOH; Multistep reaction;

O4-(22R,25R)-spirosol-3-en-3β-yl-β-L-6-deoxy-mannopyranosyl β-D-glucopyranoside (54302-48-6) → solasodine (126-17-0)

Conditions	Yield
With hydrogenchloride In methanol Heating;

(25R)-22,26-epiminocholesta-5,22(N)-diene-3β,16β-diol diacetate (30040-85-8) → solasodine (126-17-0)

Conditions	Yield
With potassium hydroxide In methanol Heating;

(22S,25R)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one (129938-54-1) → 25-Isoetioline (129938-55-2) + solasodine (126-17-0)

Conditions	Yield
Yield given. Multistep reaction. Further byproducts given;

solanavione-3-acetate → solasodine (126-17-0)

Conditions	Yield
With hydrazine dihydrochloride Product distribution; Wolff-Kishner reduction;

solamargine → solasodine (126-17-0)

Conditions	Yield
With trifluoroacetic acid

di-O-acetyl-pseudosolasodine-B → solasodine (126-17-0)

Conditions	Yield
With potassium hydroxide

pseudosolasodine diacetate (36506-65-7) + methanol. KOH-solution → solasodine (126-17-0)

pseudodiosgenin → solasodine (126-17-0)

Conditions	Yield
Reaktion ueber mehrere Stufen;

(22S,25R)-22,26-Epiminocholest-5-ene-3β,16α-diol (36456-16-3) → solasodine (126-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / N-chlorosuccinimide / CHCl3 / 0.5 h / Ambient temperature 2: NaOEt / ethanol / 2 h View Scheme

(22S,25R)-N-Benzyloxycarbonyl-22,26-epiminocholest-5-ene-3β,16β-diol (129938-53-0) → solasodine (126-17-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 60 percent / CrO3, NaOAc*3H2O, AcOH / H2O / 20 h / Ambient temperature 2: Na, i-PrOH / toluene / 2 h 3: 96 percent / N-chlorosuccinimide / CHCl3 / 0.5 h / Ambient temperature 4: NaOEt / ethanol / 2 h View Scheme
Multi-step reaction with 2 steps 1: 60 percent / CrO3, NaOAc*3H2O, AcOH / H2O / 20 h / Ambient temperature View Scheme

(22S,25R)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one (129938-54-1) → solasodine (126-17-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: Na, i-PrOH / toluene / 2 h 2: 96 percent / N-chlorosuccinimide / CHCl3 / 0.5 h / Ambient temperature 3: NaOEt / ethanol / 2 h View Scheme

(25R)-26-iodo-3β-hydroxy-cholest-5-ene-16,22-dione (114696-99-0) → solasodine (126-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide 2: Reaktion ueber mehrere Stufen View Scheme

(25R)-3β-hydroxy-26-(toluene-4-sulfonyloxy)-cholest-5-ene-16,22-dione (115388-90-4) → solasodine (126-17-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: butanone; NaI 2: dimethylformamide 3: Reaktion ueber mehrere Stufen View Scheme

kryptogenin (468-99-5) → solasodine (126-17-0)

Conditions	Yield
Multi-step reaction with 4 steps 2: butanone; NaI 3: dimethylformamide 4: Reaktion ueber mehrere Stufen View Scheme

solasonine (19121-58-5, 20318-30-3) → solasodine (126-17-0)

Conditions	Yield
With hydrogenchloride; water In isopropyl alcohol at 20℃; Product distribution / selectivity; Heating / reflux;

acetic anhydride (108-24-7) + solasodine (126-17-0) → (25R)-22,26-epiminocholesta-5,22(N)-diene-3β,16β-diol diacetate (30040-85-8)

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid at 24.84℃; for 0.00555556h;	100%

18α-glycyrrhizic acid + solasodine (126-17-0) → C42H62O16*C27H43NO2

Conditions	Yield
In methanol Reflux;	99%

p-toluenesulfonyl chloride (98-59-9) + solasodine (126-17-0) → (25R)-N-(toluene-4-sulfonyl)-3β-(toluene-4-sulfonyloxy)-22αN-spirosol-5-ene (79659-49-7)

Conditions	Yield
With pyridine at 20℃;	95%

solasodine (126-17-0) → (22R,25R)-22,26-epiminocholest-5-ene-3β,16β-diol (68422-03-7)

Conditions	Yield
With sodium tetrahydroborate In methanol; dichloromethane at 0 - 20℃; for 1h;	87%

2-bromo-3,4,4-trichloro-3-butenoyl chloride (913966-90-2) + solasodine (126-17-0) → solasodinyl 2-bromo-3,4,4-trichlorobut-3-enoate

Conditions	Yield
With pyridine In benzene at 20 - 23℃;	84%

C61H64Cl3NO24 + solasodine (126-17-0) → C86H105NO25

Conditions	Yield
Stage #1: solasodine at -20℃; for 0.333333h; Molecular sieve; Sealed tube; Inert atmosphere; Stage #2: C61H64Cl3NO24 With hydrogen tetrakis(pentafluorophenyl)borate for 0.5h; Molecular sieve; Inert atmosphere; Sealed tube;	82%

1-Adamantanecarbonyl chloride (2094-72-6) + solasodine (126-17-0) → (25R)-solasod-5-en-3β-yl 1-adamantanecarboxylate

Conditions	Yield
With pyridine In benzene for 8h; Heating;	78%

solasodine (126-17-0) → (25R)-22αN-spirosol-4-en-3-one (17094-86-9)

Conditions	Yield
With cyclohexanone; aluminum tri-tert-butoxide In toluene for 11h; Heating;	68%
With aluminum tri-tert-butoxide; acetone
With copper
Multi-step reaction with 2 steps 1: 95 percent / anhyd. pyridine / 20 °C 2: 29 percent / anhyd. sodium acetate / dimethylsulfoxide / 4 h / 80 - 90 °C View Scheme

acetic acid (64-19-7) + solasodine (126-17-0) → 16-dehydropregnenolone acetate (979-02-2)

Conditions	Yield
Stage #1: solasodine With pyridine; ammonium chloride at 125 - 135℃; for 8 - 9h; Stage #2: acetic acid With chromium(VI) oxide In water; 1,2-dichloro-ethane at 0 - 20℃; for 1h; Product distribution / selectivity;	65%

C25H34O7S (1307870-93-4) + solasodine (126-17-0) → C49H69NO9 (1307870-88-7)

Conditions	Yield
With N-iodo-succinimide; silver trifluoromethanesulfonate at -50℃; for 2h;	65%

solasodine (126-17-0) → C27H42N2O3 (1370010-28-8)

Conditions	Yield
With boron trifluoride diethyl etherate; sodium nitrite In acetic acid at 20℃; for 1h;	56.2%

acetic anhydride (108-24-7) + solasodine (126-17-0) → N,O-diacetyl-22-episolasodine

Conditions	Yield
With pyridine at 20℃;	55%

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8, 3068-32-4, 4026-32-8, 6919-96-6, 13242-53-0, 14227-54-4, 14795-18-7, 19186-59-5, 19285-38-2, 21698-13-5, 29907-26-4, 53369-42-9, 60619-58-1, 61303-35-3, 67337-79-5, 69127-37-3, 70749-15-4, 72002-90-5, 75247-30-2, 75880-74-9, 78418-57-2, 102339-89-9, 102339-90-2, 103530-40-1, 114028-03-4, 114718-45-5, 138514-70-2, 138514-71-3) + solasodine (126-17-0) → solasodine tetra-O-acetyl-3β-D-glucopyranoside (14144-02-6, 14197-67-2)

Conditions	Yield
Stage #1: solasodine With silver(I) acetate In benzene Koenigs-Knorr Glycosidation; Reflux; Stage #2: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide In benzene for 14h; Koenigs-Knorr Glycosidation; Reflux;	51.83%

solasodine (126-17-0) → 3β,16β-dihydroxypregna-5-ene-20-carboxylic acid 22,16-lactone (33282-87-0)

Conditions	Yield
With boron trifluoride diethyl etherate; sodium nitrite In chloroform; acetic acid at 20℃; for 2h;	48.2%

acetic anhydride (108-24-7) + solasodine (126-17-0) → 16-dehydropregnenolone acetate (979-02-2)

Conditions	Yield
Stage #1: acetic anhydride; solasodine With pyridine for 1.5h; Heating / reflux; Stage #2: With acetic acid for 0.25h; Heating / reflux; Stage #3: With sodium sulphite; sodium dichromate Product distribution / selectivity; more than 3 stages;	48%
Stage #1: acetic anhydride; solasodine With pyridine; toluene-4-sulfonic acid at 160℃; for 6h; Heating / reflux; Stage #2: With acetic acid In water at 20 - 160℃; for 4h; Heating / reflux; Stage #3: With chromium(VI) oxide; sodium sulphite; acetic anhydride Product distribution / selectivity; more than 3 stages;	44.6%
Stage #1: acetic anhydride; solasodine With pyridine for 1h; Heating / reflux; Stage #2: With pyridine hydrochloride In pyridine for 2h; Heating / reflux; Stage #3: With sodium sulphite; sodium dichromate Product distribution / selectivity; more than 3 stages;	20%
Stage #1: acetic anhydride; solasodine; toluene-4-sulfonic acid In acetic acid at 20℃; for 7h; Heating / reflux; Stage #2: With sodium dichromate In acetic acid at 15 - 40℃; for 1h; Stage #3: With sodium sulphite In acetic acid for 2h; Product distribution / selectivity; Heating / reflux;	15%
Behandeln des Reaktionsprodukts mit CrO3 in wss. Essigsaeure und Erhitzen des danach erhaltenen Reaktionsprodukts mit Essigsaeure;

solasodine (126-17-0) → (25R)-22αN-spirosol-4-en-3-one (17094-86-9) + solasod-5-en-3β-ol salt with 6-methylsalicylic acid

Conditions	Yield
fungus penicillium patulum;	A 18% B 0.5%
fungus penicillium patulum;	A 18% B 0.5%

acetic anhydride (108-24-7) + solasodine (126-17-0) → (25R)-3β,N-diacetoxysolasod-5-ene (4860-15-5)

Conditions	Yield
With pyridine for 0.5h; Heating;	12.5%

solasodine (126-17-0) → N-Hydroxysolasodine (142182-57-8)

Conditions	Yield
With selenium(IV) oxide; dihydrogen peroxide In methanol for 264h;	11%

solasodine (126-17-0) → 3β-hydroxysolasod-5-en-7-one (103369-64-8) + solasod-5-ene-3β,7β-diol (107297-22-3) + solasod-5-ene-3β,7α-diol

Conditions	Yield
fungus Cunninghamella elegans;	A 0.04% B 8% C 5.8%
fungus Cunninghamella elegans;	A 0.04% B 8% C 5.8%

Upstream product

• 20311-51-7 solamargine 
• 36506-65-7 pseudosolasodine diacetate 
• 324740-29-6 3-O-(tert-butyldiphenylsilyl)diosgenin 
• 1415-78-7 solasodine-3β-acetate 
• 1240049-83-5 (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1->2)-[6-O-acetyl-β-D-glucopyranosyl-(1->4)]-β-D-glucopyranoside 
• 991-62-8 (3b,25R)-3-hydroxyfurosta-5,20⁽²²⁾-dien-26-yl 4-Methylbenzenesulfonate 
• 514-32-9 C₂₇H₄₃NO₂ 
• 1061-54-7 diosgenin acetate 
• 512-04-9 diosgenin 
• 109214-38-2 pseudodiosgenin 3β-acetate 
• 1000612-48-5 C₂₇H₄₁N₃O₂ 
• 21143-00-0 C₃₆H₅₀O₆S 
• 1000612-51-0 C₂₉H₄₃N₃O₃ 

Downstream Products

• 1307870-88-7 C₄₉H₆₉NO₉ 
• 68422-03-7 (22R,25R)-22,26-epiminocholest-5-ene-3β,16β-diol 
• 979-02-2 16-dehydropregnenolone acetate 
• 5672-30-0 pseudosolasodine diacetate 
• 6885-51-4 (25R)-3β-(toluene-4-sulfonyloxy)-22αN-spirosol-5-ene 
• 79659-50-0 (25R)-5α,22αN-spirosolane-3β,5,6β-triol 3-tosylate 
• 79659-58-8 (25R)-3β-(toluene-4-sulfonyloxy)-5,6α-epoxy-5α,22αN-spirosolane 
• 17094-86-9 (25R)-22αN-spirosol-4-en-3-one 
• 6785-55-3 (22S,25R)-22,26-epiminocholest-5-ene-3β,16β-diol 
• 79659-49-7 (25R)-N-(toluene-4-sulfonyl)-3β-(toluene-4-sulfonyloxy)-22αN-spirosol-5-ene 
• 36506-65-7 pseudosolasodine diacetate 
• 1415-78-7 solasodine-3β-acetate 
• 66934-60-9 (22R,25R)-3β-acetoxy-(5α)-spirosolane 
• 1162-53-4 3β-hydroxy-pregna-5,16-dien-20-one 

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Facile synthesis of SOLASODINE (cas 126-17-0) based on a mild halogenation-ring opening reaction of spiroketals in steroidal sapogenins09/30/2019

Herein we report a halogenation-ring opening reaction of spiroketals in steroidal sapogenins at room temperature to gain highly valuable ω-halo enol ethers in excellent yields. Boosted by this method, we have prepared solasodine, an antitumor steroidal alkaloid, from diosgenin acetate in three ...detailed

Methyl jasmonate elicits the SOLASODINE (cas 126-17-0) production and anti-oxidant activity in hairy root cultures of Solanum trilobatum L.09/29/2019

Hairy root cultures of Solanum trilobatum L. were established from leaf explants infected with Agrobacterium rhizogenes strains viz., MTCC 532, MTCC 2364 and ATCC A4. Initially 27 independent root clones were obtained and 5 clones (ST-02, ST-09, ST-11, ST-13 and ST-17) were scrutinized based on ...detailed

Regeneration, Repair, and Developmental NeuroscienceResearch PaperThe naturally occurring steroid SOLASODINE (cas 126-17-0) induces neurogenesis in vitro and in vivo09/28/2019

In this study, we explored the capacity of the naturally occurring compound solasodine to promote neurogenesis in vitro and in vivo. Mouse embryonic teratocarcinoma P19 cells exposed to solasodine for 2 days followed by a 5-day washout differentiated into cholinergic neurons that expressed speci...detailed

Development and validation a liquid chromatography mass spectrometry for determination of SOLASODINE (cas 126-17-0) in rat plasma and its application to a pharmacokinetic study10/01/2019

Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the Solanaceae family. A simple and selective liquid chromatography mass spectrometry method for determination of solasodine in rat plasma was developed and validated over the range of 3–1000 ng/mL. Chromatographic se...detailed

A facile and efficient method for the synthesis of SOLASODINE (cas 126-17-0) from diosgenin09/26/2019

A facile and high-yielding route for the synthesis of solasodine from diosgenin is devised. Ring opening of steroidal spiroketal under mild conditions with trifluoroacetyl trifluoromethanesulfonate (TFAT) provides an applicable protocol to prepare key intermediates 4 or 3-Ac-solasodine, which ca...detailed

SOLASODINE (cas 126-17-0) inhibits invasion of human lung cancer cell through downregulation of miR-21 and MMPs expression09/25/2019

Solasodine, a naturally occurring aglycone of glycoalkaloid in eggplant (Solanum melongena), was found to inhibit proliferation in various tumor cells. However, the effect of solasodine on cancer cell metastasis remains unclear. This study investigates the suppression mechanism of solasodine on ...detailed

Some observations on SOLASODINE (cas 126-17-0) reactivity09/24/2019

This article presents new transformations of solasodine – a representative steroid alkaloid sapogenin from the Solanum family. Oxidation of N,O-diacetylated solasodine with either NaNO2/BF3·Et2O or t-BuONO/BF3·Et2O resulted in partial degradation of the side chain to (20S)-3β-acetoxypregn-5-...detailed

SOLASODINE (cas 126-17-0)-3-O-β-d-glucopyranoside is hydrolyzed by a membrane glucosidase into active molecule SOLASODINE (cas 126-17-0) against Candida albicans09/10/2019

Antifungal activity of some natural molecules can be abated or blocked by efflux pumps in Candida albicans, which restricts the discovery of potential antifungal agents. Here we found that the steroidal alkaloid solasodine is active against C. albicans efflux pump-deficient strains but inert tow...detailed

SOLASODINE (cas 126-17-0) reverses stemness and epithelial-mesenchymal transition in human colorectal cancer09/09/2019

Adverse side effects of conventional chemotherapy, acquired resistance and fatal tumor metastasis of human colorectal cancer (CRC) are propelling the exploration for novel selective anticarcinogens. Solasodine is a main active component isolated from Solanum incanum L that exhibited a potent ste...detailed

Relevant articles and documents

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Revision of the Structure of N, O-Diacetylsolasodine. Unusual Epimerization at the Spiro Carbon Atom during Acetylation of Solasodine

The steroidal alkaloid solasodine (1) undergoes inversion of configuration at the C-22 spiro atom when treated with acetic anhydride-pyridine at ambient temperature. The basic solvolysis of the N,O-diacetyl derivative (2) reverses the reaction, yielding the starting solasodine (1). The mechanisms of both processes (acetylation and deacetylation) were studied in terms of possible reaction pathways.

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Facile synthesis of solasodine based on a mild halogenation-ring opening reaction of spiroketals in steroidal sapogenins

Herein we report a halogenation-ring opening reaction of spiroketals in steroidal sapogenins at room temperature to gain highly valuable ω-halo enol ethers in excellent yields. Boosted by this method, we have prepared solasodine, an antitumor steroidal alkaloid, from diosgenin acetate in three steps with an overall yield of 50%.