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Home > Encyclopedia > Solasodine

Solasodine

pharmaceutical raw materials
Solasodine structure

Solasodine 

structure
  • CAS No:

    126-17-0

  • Formula:

    C27H43NO2

  • Chemical Name:

    Solasodine

  • Synonyms:

    Spirosol-5-en-3-ol,(3β,22α,25R)-;Solasod-5-en-3β-ol;Spiro[8H-naphth[2′,1′:4,5]indeno[2,1-b]furan-8,2′-piperidine],spirosol-5-en-3-ol deriv.;(3β,22α,25R)-Spirosol-5-en-3-ol;Purapuridine;Solancarpidine;Solasodin;Solasodine;NSC 178260;NSC 179187;(-)-Solasodine

  • Categories:

    Natural Products  >  Steroids

Description

Solasodine(Purapuridine) is a poisonous alkaloid chemical compound that occurs in plants of the Solanaceae family. Solasodine showed selective cytotoxicity against cervical cancer cell line (HeLa) and human myeloid leukemia cell line (U937).IC50 Value: 12.17 ± 3.3 uM (Hela cell line)[1]Target: Anticancerin vitro: Mouse embryonic teratocarcinoma P19 cells exposed to solasodine for 2 days followed by a 5-day washout differentiated into cholinergic neurons that expressed specific neuronal m


Solid

Solasodine Basic Attributes

413.64

413.64

204-774-2

179187|178260

HEXAGONAL PLATES FROM METHANOL OR BY SUBLIMATION IN HIGH VACUUM

Characteristics

41.49000

5.78

white to beige

1.0159 (rough estimate)

200-202 °C

532.75°C (rough estimate)

279.1±30.1 °C

1.6400 (estimate)

DMSO: soluble0.5mg/mL, clear (warmed)

2-8°C

8.21E-14mmHg at 25°C

D25 -98° (c = 0.14 in methanol); D -113° (CHCl3)

PKB: 6.3

ALKALINE REACTION TO LITMUS IN ALCOHOLIC SOLN

Safety Information

NONH for all modes of transport

22-24/25

WF1300000

A REVIEW ON THE UTILIZATION OF SOLASODINE AS A POTENTIAL ECDYSONE ANTAGONIST.[CAMBIE RC, POTTER GJ; UTILIZATION OF SOLASODINE AS A POTENTIAL ECDYSONE ANTAGONIST; CHEM NZ 43 (3): 91-4 (1979)]|A REVIEW AND DISCUSSION CONCERNING THE SOURCES, CHEMISTRY, BIOCHEMISTRY, ISOLATION AND DETERMINATION OF SOLASODINE.[MANN JD; PRODUCTION OF SOLASODINE FOR THE PHARMACEUTICAL INDUSTRY; ADV AGRON 30 207-45 (1978)]

Toxicity

SOLASODINE WAS ISOLATED FROM THE DRIED ROOTS AND LEAVES OF SOLANUM SURATTENSE.|DEVELOPING BERRIES AND LEAVES OF SOLANUM SISYMBRIFOLIUM WERE SCREENED FOR SOLASODINE CONTENT. THE CONTENT INCR WITH THE AGE OF THE BERRIES REACHING ITS MAX VALUE (7.2% OF DRY WT) 45 DAYS AFTER ANTHESIS WHEN THE COLOR WAS SCARLET. IN LEAVES THE CONTENT VARIED FROM 6.4 TO 7.2%.|THE SOLASODINE CONTENT IN THE FRUITS OF SOLANUM MARGINATUM DURING 3 STAGES OF MATURITY WAS INVESTIGATED. THE GREEN FRUIT CONTAINED 2.3% AND THE DEEP YELLOW FRUITS CONTAINED 1.4%.

Drug Information

LABELED SOLASODINE WAS INJECTED INTO 2 NORMAL MEN AND INTO SYRIAN HAMSTERS. IN BOTH MEN, BLOOD (3)H WAS LARGELY ASSOCIATED WITH ERYTHROCYTES WHICH AFTER 8 DAYS STILL ACCOUNTED FOR 3.3% OF THE DOSE; PLASMA CONTAINED 1.6%, URINE 7% AND FECES 20% OF THE DOSE. EXCRETION OF (3)H BY HAMSTERS HAD DECLINED TO A VERY LOW LEVEL AFTER 8 DAYS WHEN 22-30% OF THE DOSE HAD BEEN EXCRETED. UNCHANGED SOLASODINE WAS STILL DETECTABLE IN LIVER 22 DAYS AFTER ADMIN.

solasodine

Solasodine Use and Manufacturing

Methods of Manufacturing

STEROIDAL ALKALOID ISOLATED FROM VARIOUS SOLANUM SPECIES. BY HYDROLYSIS OF SOLASONINE: ROCHELMEYER, ARCH PHARM 277, 329 (1939).|THE ISOLATION AND IDENTIFICATION OF SOLASODINE IN CALLUS CULTURE OF SOLANUM JASMINOIDES ARE DESCRIBED.

Uses

Starting material for steroidal drugs. A neuroprotective antioxidant glycoalkaloid that can increase brain tissue superoxide dismutase (SOD), catalase (CAT) and gluten in the rat brain ischemia-reperfusion (I/R) injury model. Glutathione (GSH) levels reduce lipid peroxidation (LPO) and nitric oxide (NO) levels.

A RADIOIMMUNOASSAY FOR THE DIRECT QUANTITATION OF NANOGRAM AMT OF SOLASODINE IN PLANTS WAS STUDIED.|AN EXTRACT OF SOLANUM KHASIANUM FRUITS WAS FRACTIONATED WITH CHROMATOFUGE. THE FRACTION CONTAINING SOLASODINE WAS APPLIED TO A HIGH-PERFORMANCE LIQ CHROMATOGRAPHY COLUMN AND THE EFFLUENT WAS MONITORED BY UV SPECTROSCOPY.|SOLASODINE WAS DETERMINED BY GAS LIQUID CHROMATOGRAPHY FROM EXTRACTS OF SOLANUM ALATUM AND S ATRIPLICIFOLIUM.

Computed Properties

Molecular Weight:413.6
XLogP3:5.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:413.329379614
Monoisotopic Mass:413.329379614
Topological Polar Surface Area:41.5
Heavy Atom Count:30
Complexity:749
Undefined Atom Stereocenter Count:11
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product has a certain inhibitory effect on mouse transplanted tumors and human liver cancer cell xenografts. When rats were given it for 90 consecutive days, some animals had reversible SGPT elevation.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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