Acteoside

Names

[ Name ]:
Acteoside

[Synonym ]:
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

Biological Activity

[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]:

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

Natural Products >> Phenols

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ 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

MSDS

Click to get detail MSDS

Toxicological Information

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

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
LZ5786000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Modulation of human keratinocyte responses to solar UV by plant polyphenols as a basis for chemoprevention of non-melanoma skin cancers.

Curr. Med. Chem. 20(7) , 869-79, (2013)

Excessive exposure to solar UVA and UVB radiation is widely considered to cause skin cancers such as squamous cell carcinoma and basalioma. Direct UVB damage to skin cell DNA as well as UV-induced chr...

A metabolite-profiling approach to assess the uptake and metabolism of phenolic compounds from olive leaves in SKBR3 cells by HPLC-ESI-QTOF-MS.

J. Pharm. Biomed. Anal. 72 , 121-6, (2013)

Olive leaves, an easily available natural low-cost material, constitute a source of extracts with significant antitumor activity that inhibits cell proliferation in several breast-cancer-cell models. ...

Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice.

J. Nat. Med. 68(3) , 561-6, (2014)

Acylated phenylethanoid glycosides, echinacoside (1) and acteoside (2), principal constituents in stems of Cistanche tubulosa (Orobanchaceae), inhibited the increase in postprandial blood glucose leve...