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61276-17-3 61303-13-7

61276-17-3

61276-17-3 structure
61276-17-3 structure
  • Name: Acteoside
  • Chemical Name: Verbascoside
  • CAS Number: 61276-17-3
  • Molecular Formula: C29H36O15
  • Molecular Weight: 624.587
  • Catalog: Biochemical Natural product
  • Create Date: 2018-06-18 12:14:22
  • Modify Date: 2024-01-02 18:41:04
  • Verbascoside is isolated from Lantana camara, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 µM, and has antitumor, anti-inflammatory and antineuropathic pain activity.
Name Verbascoside
Synonyms Acteoside
β-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-4-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-
(2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-3-yl-(2E)-3-(3,4-dihydroxyphenyl)acrylat
2-(3,4-Dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-4-O-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-β-D-glucopyranoside
β-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-4-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]-
T6OTJ B1 CQ DQ EQ FO- DT6OTJ BO2R CQ DQ& CQ EOV1U1R CQ DQ& F1Q &&Stereoisomer
verbascoside
2-(3,4-Dihydroxyphenyl)ethyl-3-O-(6-deoxy-α-L-mannopyranosyl)-4-O-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-β-D-glucopyranoside
(2E)-3-(3,4-Dihydroxyphényl)acrylate de (2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphényl)éthoxy]-5-hydroxy-2-(hydroxyméthyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-méthyltétrahydro-2H-pyran-2-yl]oxy}tétrahydro-2H-pyran-3-yle
(2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-3-yl (2E)-3-(3,4-dihydroxyphenyl)acrylate
MFCD06798947
3-O-(6-Désoxy-α-L-mannopyranosyl)-4-O-[(2E)-3-(3,4-dihydroxyphényl)-2-propènan-1-oyl]-β-D-glucopyranoside de 2-(3,4-dihydroxyphényl)éthyle
2-(3,4-Dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-4-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-β-D-glucopyranoside
Description Verbascoside is isolated from Lantana camara, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 µM, and has antitumor, anti-inflammatory and antineuropathic pain activity.
Related Catalog
Target

PKC:25 μM (IC50)

In Vitro Verbascoside acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 µM. Verbascoside shows Kis of 22 and 28 µM with respect to ATP and histone, respectively. Verbascoside has potent antitumor activity against L-1210 cells, with an IC50 of 13 µM[1]. Verbascoside (5, 10 µM) suppresses 2,4-dinitrochlorobenzene (DNCB)-induced T cell costimulatory factors CD86 and CD54, proinflammatory cytokines, and NFκB pathway activation in THP-1 cells[2].
In Vivo Verbascoside (1%) reduces the overall scratching behavior incidence as well as the severity of the skin lesions in 2,4-dinitrochlorobenzene (DNCB)-induced atopic dermatitis (AD) mice model. Verbascoside also blocks DNCB-induced expression of proinflammatory cytokine TNF-α, IL-6, and IL-4 mRNA in skin lesions[2]. Verbascoside (50, 100 mg/kg, i.p.) does not modify chronic constriction injury (CCI)-induced cold allodynia. Verbascoside (200 mg/kg, i.p.) decreases hyper-sensitivity to cold stimulus, acetone, on day 3 in rats. Verbascoside also significantly reduces behavioral changes associated with neuropathy. Moreover, Verbascoside decreases Bax and increases Bcl-2 on day 3[3].
Cell Assay The lymphocytic mouse leukemia L1210 cells (ATCC, CCL 219) are plated sparsely at 104 cells per well in 24-well cluster plates in Dulbecco’s modified Eagle medium containing 10% fetal calf serum, 4 mM glutamine, 100 U/mL penicillin, 100 µg/mL streptomycin sulfate, and Verbascoside (solubilized in DMSO). After a 2-day incubation period at 37°C in a humidified atmosphere (5% CO2 in air), growth is monitored by counting cell numbers in a Coulter-counter. IC50 values are calculated on the basis of the linear regression lines established for each compound tested[1].
Animal Admin Rats[2] To induce atopic dermatitis (AD)-like symptoms, 2,4-dinitrochlorobenzene (DNCB) is used. Briefly, the dorsal hair of the mice is removed using an electronic clipper 2 days before DNCB treatment. An application of 200 µL of 1% DNCB (in acetone:olive oil = 4:1) is made to the shaved dorsal skin for sensitization. The repeated challenge is performed on the same site with 0.2% DNCB once every 3 days for about 2 weeks. The mice are divided into 4 groups (n = 6 per group): (1) vehicle-treated controls, (2) DNCB-treated only, (3) 1% Verbascoside (in acetone:olive oil 4:1)-treated only, and (4) DNCB + 1% Verbascoside-treated group[2].
References

[1]. Herbert JM, et al. Verbascoside isolated from Lantana camara, an inhibitor of protein kinase C. J Nat Prod. 1991 Nov-Dec;54(6):1595-600.

[2]. Li Y, et al. Verbascoside Alleviates Atopic Dermatitis-Like Symptoms in Mice via Its Potent Anti-Inflammatory Effect. Int Arch Allergy Immunol. 2018;175(4):220-230.

[3]. Amin B, et al. The Effect of Verbascoside in Neuropathic Pain Induced by Chronic Constriction Injury in Rats. Phytother Res. 2016 Jan;30(1):128-35.
Density 1.6±0.1 g/cm3
Boiling Point 908.8±65.0 °C at 760 mmHg
Molecular Formula C29H36O15
Molecular Weight 624.587
Flash Point 294.7±27.8 °C
Exact Mass 624.205444
PSA 245.29000
LogP 2.44
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.689
Storage condition room temp

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LZ5786000
CHEMICAL NAME :
Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-alpha-L-mannopyranosyl)-, 4-(3-(3,4-dihydroxyphenyl)-2-propenoate), (E)-beta-D-
CAS REGISTRY NUMBER :
61276-17-3
LAST UPDATED :
199206
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C29-H36-O15
MOLECULAR WEIGHT :
624.65

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 :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 35,3,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 35,3,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 35,3,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 35,3,1980 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
140 mg/kg
SEX/DURATION :
male 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - other effects on male
REFERENCE :
YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 105,1131,1985
Hazard Codes Xi
RIDADR NONH for all modes of transport
RTECS LZ5786000

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