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Merck
CN

SMB00515

Afzelin

≥90% (LC/MS-UV)

Synonym(s):

3,4′,5,7-Tetrahydroxyflavone 3-rhamnoside, Afzeloside, Kaempferin, Kaempferol 3-O-alpha-L-rhamnoside, Kaempferol 3-rhamnoside

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About This Item

Empirical Formula (Hill Notation):
C21H20O10
CAS Number:
482-39-3
Molecular Weight:
432.38
NACRES:
NA.25
PubChem Substance ID:
329825042
UNSPSC Code:
12352205
MDL number:
MFCD00210589

Key Documents

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InChI key

SOSLMHZOJATCCP-AEIZVZFYSA-N

SMILES string

OC1=CC(O)=C(C(C(O[C@H]2[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O2)=C(C3=CC=C(O)C=C3)O4)=O)C4=C1

InChI

1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21-/m0/s1

assay

≥90% (LC/MS-UV)

form

solid

solubility

DMSO: 1 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

Related Categories

General description

Afzelin is a natural product derived from a plant source. Ficus palmata and Nymphaea odoratam are the major sources of afzelin, a flavonol glycoside.

Application

DNA-protective, antioxidant, anti-inflammatory, UV-absorbing and anti-bacterial activities. Afzelin has been used in HPLC (high performance liquid chromomatography) analysis of Comarum palustre L. extract to detect its major compounds.

Biochem/physiol Actions

NOS inhibitor, NADPH oxidase inhibitor, Afzelin is known to possess antibacterial, anti-inflammatory, anti-apoptotic and anti-tumor activities. Afzelin might serve as an effective treatment against P. aeruginosa related diseases. Afzelin also promotes apoptosis to inhibit cell proliferation in breast cancer. It exhibits anti-asthmatic effects in a mouse model.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
122228350V
AD122228251V
122228251V

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Seoung Woo Shin et al.
PloS one, 8(4), e61971-e61971 (2013-04-30)
Ultraviolet (UV) radiation induces DNA damage, oxidative stress, and inflammatory processes in human keratinocytes, resulting in skin inflammation, photoaging, and photocarcinogenesis. Adequate protection of skin against the harmful effects of UV irradiation is essential. Therefore, in this study, we investigated
Agrimoniin, an active ellagitannin from Comarum palustre herb with anti-α-glucosidase and antidiabetic potential in streptozotocin-induced diabetic rats
Kashchenko N, et al.
Molecules (Basel), 22(1), 73-73 (2017)
Sang Yeol Lee et al.
Molecules (Basel, Switzerland), 19(3), 3173-3180 (2014-03-20)
The crude ethyl acetate extract of the leaves of Cornus macrophylla showed antibacterial activity against Pseudomonas aeruginosa, a leading cause of illness in immunocompromised individuals. Bioactivity-guided separation led to the isolation of kaempferol 3-O-α-L-rhamnopyranoside (afzelin). The structure was determined based
Afzelin attenuates asthma phenotypes by downregulation of GATA3 in a murine model of asthma
Zhou Wenbo and Nie Xiuhong
Molecular Medicine Reports, 12(1) (2015)
Parham Taslimi
Journal of biochemical and molecular toxicology, 34(11), e22566-e22566 (2020-07-03)
Tyrosinase enzyme is a functional oxidase that is extensively divided in nature. It is the main enzyme in melanin synthesis and is also involved in designating the color of mammalian hair and skin. Additionally, it is accountable for the unfavorable

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