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Agnuside

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Agnuside Basic information

Product Name:
Agnuside
Synonyms:
  • chasteberry oil
  • [(1r,2s,6s,7s)-7-hydroxy-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,8-dien-9-yl]methyl 4-hydroxybenzoate
  • AGNUSIDE
  • AGNUSIDE WITH HPLC
  • AGNUSIDE(P)
  • Agnuside (25 mg)
  • Vitex negundo oil，Agnuside
  • OLEUMVITICISNEGUNDO Oil
CAS:
11027-63-7
MF:
C22H26O11
MW:
466.44
Product Categories:
  • Aromatic Phenols
Mol File:
11027-63-7.mol
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Agnuside Chemical Properties

Melting point:
146℃
Boiling point:
785.5±60.0 °C(Predicted)
Density 
1.59±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO, Methanol
pka
8.14±0.15(Predicted)
form 
Solid
color 
Yellow
optical activity
[α]/D -98.0±5°, c = 0.1 in ethanol
BRN 
4925795
InChI
InChI=1/C22H26O11/c23-8-15-17(26)18(27)19(28)22(32-15)33-21-16-11(7-14(25)13(16)5-6-30-21)9-31-20(29)10-1-3-12(24)4-2-10/h1-7,13-19,21-28H,8-9H2/t13-,14+,15-,16+,17-,18+,19-,21-,22+/s3
InChIKey
GLACGTLACKLUJX-QNAXTHAFSA-N
SMILES
[C@]12([H])C(COC(=O)C3=CC=C(O)C=C3)=C[C@H](O)[C@@]1([H])C=CO[C@@H]2O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O |&1:0,15,17,22,24,25,27,28,30,r|
LogP
-1.240 (est)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36
Safety Statements 
26
WGK Germany 
3
HS Code 
29329990
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Agnuside Usage And Synthesis

Chemical Properties

Yellow Oil

Uses

Agnuside is an known iridoid glycoside found in Vitex herbs or plants. Agnuside have been used in various applications including in the treatment of premenstrual syndrome and regulation of menopause s ymptoms. This is mainly due to the fact that Agnuside exhibits estrogen-like activities as it interacts with estrogen receptors (ER-alpha) and estrogen receptor-regulated pregesterone receptors. Recen t studies have also evaluated Agnuside for the probable mechanism of anti-arthritic activity, which suggested the possible development of Agnuside as a therapeutic agent in the treatment of arthritis by the modulation of the host immune response.

Definition

ChEBI: Agnuside is a benzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with the primary hydroxy group of aucubin. It is an iridoid glycoside found in several Vitex plants including Vitex agnus-castus. It has a role as a plant metabolite, an anti-inflammatory agent, a pro-angiogenic agent and a cyclooxygenase 2 inhibitor. It is a terpene glycoside, an iridoid monoterpenoid, a benzoate ester, a member of phenols, a beta-D-glucoside, a cyclopentapyran and a monosaccharide derivative. It is functionally related to an aucubin.

benefits

Agnuside is one of the most significant active ingredients in chasteberry and is described chemically as an ester of p-hydroxybenzoic acid and aucubin. Agnuside’s greatest areas of benefit involve female reproductive cycles, which researchers believe is due to its effect on the pituitary gland. One study has also shown that extracts of chasteberry fruit bind to the opiate receptors in the brain, which would explain its use in relieving discomfort.

in vivo

Agnuside (6.25 mg/kg; Oral administration; Single dose) reduces the levels of allergic inflammatory mediators in a dose-dependent manner and can inhibit allergic inflammation in Balb/C mice[1]. Agnuside (6.25 mg/kg; Oral administration; Single dose) can inhibit autophagy in allergic asthma in Balb/C mice [1]. Agnuside (6.25 mg/kg; Oral administration; single dose) can reduce synovitis and fibrosis in knee osteoarthritis (KOA) in MIA-induced KOA mice[4].

Animal Model:Balb/C female mice model [1]
Dosage:30 mg/kg, 60 mg/kg
Administration:Oral gavage (p.o.); Single dose;
Result:Decreased the expression of LC3B and increased the expression of Beclin1/p62 (LC3B and Beclin1/p62 are autophagy markers).
Decreased the levels of IgE and IL-4/ IL-10 in a dose-dependent manner.( IgE and IL-4/ IL-10 are allergic inflammatory mediators)
Animal Model:KAO rat model[4]
Dosage:6.25 mg Monosodium iodoacetate (MIA): 1 mg
Administration:Oral gavage (p.o.); Single dose
Result:Alleviated the degree of local hypoxia in the synovial tissue of rats and significantly reduced the level of pro-fibrotic substances in the synovial tissue.
Inhibited the accumulation of HIF-1α and activation of NLRP3 inflammasome.

IC 50

EP

AgnusideSupplier

Chengdu Biopurify Ltd. Gold
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Chemsky（shanghai）International Co.,Ltd.
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Shandong Xiya Chemical Co., Ltd
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4009903999 13355009207
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3007715519@qq.com
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