ChemicalBook CAS DataBase List 61303-13-7

61303-13-7

Name	Isoacteoside
CAS	61303-13-7
Molecular Formula	C29H36O15
MDL Number	MFCD06798947
Molecular Weight	624.59
MOL File	61303-13-7.mol

Synonyms

Isoacteosid Isokusaginin ISOACTEOSIDE ISOVERBASCOSIDE Isoacteoside, >=98% Isoacteoside，HPLC≥98% Isoacteoside (Isoverbascoside) 3,4-Dihydroxyphenethyl 3-O-α-L-rhamnopyranosyl-6-O-(3,4-dihydroxycinnamoyl)-β-D-glucopyranoside 2-(3,4-Dihydroxyphenyl)ethyl 3-O-α-L-rhamnopyranosyl-6-O-(3,4-dihydroxycinnamoyl)-β-D-glucopyranoside 2-(3,4-Dihydroxyphenyl)ethyl 3-O-(α-L-rhamnopyranosyl)-6-O-[(E)-3-(3,4-dihydroxyphenyl)acryloyl]-β-D-glucopyranoside 2-(3,4-Dihydroxyphenyl)ethyl 3-O-(α-L-rhamnopyranosyl)-6-O-[(E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]-β-D-glucopyranoside β-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-, 6-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate] [(2R,3R,4S,5R,6R)-5-(3,4-Dihydroxyphenyl)-6-ethoxy-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate [(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Chemical Properties

Melting point	220～230℃
Boiling point	942.9±65.0 °C(Predicted)
density	1.60±0.1 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
solubility	DMSO : ≥ 48 mg/mL (76.85 mM)
form	Powder
pka	9.32±0.10(Predicted)
color	White to yellow
biological source	plant
Major Application	metabolomics vitamins, nutraceuticals, and natural products
InChIKey	FNMHEHXNBNCPCI-RRYJURSWNA-N
SMILES	O1[C@H]([C@@H]([C@@H]([C@H]([C@@H]1C)O)O)O)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2O)COC(=O)\C=C\c4cc(c(cc4)O)O)OCCc3cc(c(cc3)O)O)O

Safety Data

WGK Germany	WGK 3
HS Code	29389090
Storage Class	11 - Combustible Solids

Hazard Information

Description

Isoverbascoside is a phenylethanoid glycoside that has been found in C. trichotomum and has diverse biological activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay and inhibits hydrogen peroxide-induced lipid peroxidation in V79-4 cells when used at a concentration of 10 μg/ml. Isoverbascoside (7.5-30 μM) induces apoptosis and production of reactive oxygen species (ROS) in, and reduces viability of, OVCAR-3 cells. It inhibits tumor growth in an OVCAR-3 mouse xenograft model when administered at a dose of 30 mg/kg. Isoverbascoside (2.5 and 5 mg/kg) decreases brain amyloid deposition and increases exploratory behavior in rats when infused into the cerebral ventricles with amyloid-β (1-42) (Aβ42; Item No. 20574). It also decreases xylene-induced ear edema in mice and increases survival in a mouse model of LPS-induced endotoxic shock.

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Cistanche deserticola and Rehmannia glutinosa.

Uses

Isoacteoside is a possible food antioxidant.

Definition

ChEBI: Isoacteoside is a hydroxycinnamic acid.

in vivo

Isoacteoside (25-100 mg/kg, ip, single dose) exhibits anti-inflammatory efficacy in mouse xylene-induced ear edema models, LPS (HY-D1056)-induced endotoxin shock models, and LPS (HY-D1056)-induced acute kidney injury (AKI) models^[2].
Isoacteoside (30 mg/kg, ip, three times a week for 5 weeks) exhibits antitumor efficacy in mouse OVCAR-3 xenograft models^[3].
Isoacteoside (2.5-5 mg/kg, icv for 15 days) exhibits neuroprotective effect against Aβ 1-42-induced neurotoxicity and cognitive impairment in SD rats models^[5].

Animal Model:	Acute kidney injury (AKI) model^[2]
Dosage:	25-100 mg/kg
Administration:	ip, single dose
Result:	Ameliorated LPS induced acute kidney injury.

Animal Model:	Mouse OVCAR-3 xenograft model^[3]
Dosage:	30 mg/kg
Administration:	ip, three times a week for 5 weeks
Result:	Reduced the tumor weight and volume.

Animal Model:	Aβ 1-42 induced neurotoxicity in Sprague-Dawley rats models^[5]
Dosage:	2.5-5 mg/kg
Administration:	icv for 15 days
Result:	Increased the exploratory behavior, shortened the escape latency.

References

[1] SUNGWOOK CHAE. Antioxidant activity of isoacteoside from Clerodendron trichotomum.[J]. Journal of Toxicology and Environmental Health-Part A-Current Issues, 2005, 68 5: 389-400. DOI: 10.1080/15287390590900750
[2] XILI YANG. Suppression of in vitro and in vivo human ovarian cancer growth by isoacteoside is mediated via sub-G1 cell cycle arrest, ROS generation, and modulation of AKT/PI3K/m-TOR signalling pathway.[J]. Journal of Buon, 2019, 24 1: 285-290.
[3] YOUNG-JI SHIAO. Acteoside and Isoacteoside Protect Amyloid β Peptide Induced Cytotoxicity, Cognitive Deficit and Neurochemical Disturbances In Vitro and In Vivo.[J]. International Journal of Molecular Sciences, 2017, 18 4. DOI: 10.3390/ijms18040895
[4] HONGWEI GAO. Isoacteoside, a dihydroxyphenylethyl glycoside, exhibits anti-inflammatory effects through blocking toll-like receptor 4 dimerization[J]. British Journal of Pharmacology, 2017, 174 17: 2880-2896. DOI: 10.1111/bph.13912

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