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Solasodine

Names

[ CAS No. ]:
126-17-0

[ Name ]:
Solasodine

[Synonym ]:
(3b,22a,25R)-Spirosol-5-en-3-ol
Solanearpidine
Solasod-5-en-3β-ol
(3β,22α,25R)-Spirosol-5-en-3-ol
Solancarpidine
Solasod-5-en-3b-ol
Solasod-5-en-3β-ol (8CI)
Purapuridine
MFCD00037844
EINECS 204-774-2
Solasod-5-en-3-β-ol
Solanidine-S
Solasodine
Spirosol-5-en-3-ol, (3β,22α,25R)-
D5-20bF,22aF,25aF,28-azaspirosten-3b-ol

Biological Activity

[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 markers and displayed important axonal formation that continued growing even 30 days after treatment [2].in vivo: A 2-week infusion ofsolasodine into the left ventricle of the rat brain followed by a 3-week washout resulted in a significant increase in bromodeoxyuridine uptake by cells of the ependymal layer, subventricular zone, and cortex that co-localized with doublecortin immunostaining, demonstrating the proliferative and differentiating properties of solasodine on neuronal progenitors. Solasodine treatment in rats resulted in a dramatic increase in expression of the cholesterol- and drug-binding translocator protein in ependymal cells, suggesting a possible role played by neurosteroid production in solasodine-induced neurogenesis. In GAD65-GFP mice that express the green fluorescent protein under the control of the glutamic acid decarboxylase 65-kDa promoter, solasodine treatment increased the number of GABAergic progenitors and neuroblasts generated in the subventricular zone and present in the olfactory migratory tract [2]. intraperitoneal (i.p.) injection of solasodine (25 mg/kg) significantly delayed (p < 0.01) latency of hind limb tonic extensor (HLTE) phase in the PCT-induced convulsions. In the MES model, solasodine significantly reduced (p < 0.001) duration of HLTE at 25, 50, and 100 mg/kg, i.p. in a dose-dependent manner [3]. Oral administration (80 mg/kg body wt/day for 30 days) of solasodine (extracted and isolated from the berries of the Solanum xanthocarpum) to intact dogs significantly decreased the epithelial cell height of cauda epididymides [4].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> MDM-2/p53
Natural Products >> Alkaloid
Research Areas >> Cancer

[References]

[1]. Sarthak Bhattacharya, et al. Isolation of Solasodine from the Unripe Fruits of Solanum xanthocarpum Schrad and Wendl.(Solanaceae) and it's Anti Cancer Activity against Hela and U937 Cell Lines.

[2]. Lecanu L, et al. The naturally occurring steroid solasodine induces neurogenesis in vitro and in vivo. Neuroscience. 2011 Jun 2;183:251-64.

[3]. Chauhan K, et al. Anticonvulsant activity of solasodine isolated from Solanum sisymbriifolium fruits in rodents. Pharm Biol. 2011 Feb;49(2):194-9.

[4]. Gupta RS, et al. Effects of short-term treatment of solasodine on cauda epididymis in dogs. Indian J Exp Biol. 2002 Feb;40(2):169-73.

[5]. Akhtar S, et al. Evaluation and Elucidation Studies of Natural Aglycones for Anticancer Potential using Apoptosis-Related Markers: An In silico Study. Interdiscip Sci. 2018 Jun;10(2):297-310.


[Related Small Molecules]

Pifithrin-α hydrobromide | RG7388 | Nutlin-3a | AMG232 | Pifithrin-β (hydrobromide) | Stylomycin aminonucleoside | RG7112 | APR-246 | NVP-HDM201 | SAR 405838 | RITA (NSC 652287) | NVP-CGM097 | Tenovin-1 | SJ 172550

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
537.9±50.0 °C at 760 mmHg

[ Melting Point ]:
284 °C (dec.)(lit.)

[ Molecular Formula ]:
C27H43NO2

[ Molecular Weight ]:
413.636

[ Flash Point ]:
279.1±30.1 °C

[ Exact Mass ]:
413.329376

[ PSA ]:
41.49000

[ LogP ]:
5.78

[ Vapour Pressure ]:
0.0±3.2 mmHg at 25°C

[ Index of Refraction ]:
1.572

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
200 g/L (25 ºC)

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WF1300000
CHEMICAL NAME :
Solasod-5-en-3-beta-ol
CAS REGISTRY NUMBER :
126-17-0
BEILSTEIN REFERENCE NO. :
0094578
LAST UPDATED :
199612
DATA ITEMS CITED :
14
MOLECULAR FORMULA :
C27-H43-N-O2
MOLECULAR WEIGHT :
413.71
WISWESSER LINE NOTATION :
T F5 E5 B666 HXO OUTJ A1 E1 G1 RQ H-& BT6MXTJ E1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4978 mg/kg
TOXIC EFFECTS :
Autonomic Nervous System - other (direct) parasympathomimetic Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - urine volume increased
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
396 mg/kg
TOXIC EFFECTS :
Autonomic Nervous System - other (direct) parasympathomimetic Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - urine volume increased
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
27500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 24,469,1961
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
899 mg/kg
TOXIC EFFECTS :
Autonomic Nervous System - other (direct) parasympathomimetic Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - urine volume increased
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
103 mg/kg
TOXIC EFFECTS :
Autonomic Nervous System - other (direct) parasympathomimetic Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - urine volume increased
REFERENCE :
FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 37,719,1974
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
1200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 17,327,1978 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4250 mg/kg/4W-I
TOXIC EFFECTS :
Brain and Coverings - other degenerative changes Kidney, Ureter, Bladder - interstitial nephritis Related to Chronic Data - death
REFERENCE :
FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 37,719,1974
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3375 mg/kg/5W-I
TOXIC EFFECTS :
Liver - hepatitis (hepatocellular necrosis), zonal Liver - changes in liver weight Blood - changes in leukocyte (WBC) count
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,1095,1977
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
120 mg/kg/8D-I
TOXIC EFFECTS :
Related to Chronic Data - death
REFERENCE :
FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 24,469,1961 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
120 mg/kg
SEX/DURATION :
female 6-9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,1187,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
300 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
IJANDP International Journal of Andrology. (Scriptor Publisher ApS, 15 Gasvaerksvej, DK-1656 Copenhagen V, Denmark) V.1- 1978- Volume(issue)/page/year: 5,295,1982
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
15 gm/kg
SEX/DURATION :
male 150 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
REFERENCE :
ANDRDQ Andrologia. (Grosse Verlag GmbH, Kurfuerstenstr. 112-113, D-1000 Berlin 30, Fed. Rep. Ger.) V.6- 1974- Volume(issue)/page/year: 21,542,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1500 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
BECTA6 Bulletin of Environmental Contamination and Toxicology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1966- Volume(issue)/page/year: 15,522,1976
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1184 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System
REFERENCE :
RCOCB8 Research Communications in Chemical Pathology and Pharmacology. (PJD Pub. Ltd., P.O. Box 966, Westbury, NY 11590) V.1- 1970- Volume(issue)/page/year: 13,723,1976

Safety Information

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
WF1300000

Synthetic Route

Precursor & DownStream


Related Compounds

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