| Identification | Back Directory | [Name]
Isoacteoside | [CAS]
61303-13-7 | [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 | [Molecular Formula]
C29H36O15 | [MDL Number]
MFCD06798947 | [MOL File]
61303-13-7.mol | [Molecular Weight]
624.59 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [Description]
Isoverbascoside is a phenylethanoid glycoside that has been found in C. trichotomum and has diverse biological activities.1,2,3,4 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.1 Isoverbascoside (7.5-30 μM) induces apoptosis and production of reactive oxygen species (ROS) in, and reduces viability of, OVCAR-3 cells.2 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).3 It also decreases xylene-induced ear edema in mice and increases survival in a mouse model of LPS-induced endotoxic shock.4 | [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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