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Afzelin

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-A1002

  • Specification : 98%

  • CAS number : 482-39-3

  • Formula : C21H20O10

  • Molecular Weight : 432.381

  • PUBCHEM ID : 5316673

  • Volume : 5mg

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Catalogue Number

BF-A1002

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

432.381

Appearance

Yellow powder

Botanical Source

Albizia julibrissin,Lindera aggregata,Houttuynia cordata,Ailanthus fordii,Bergenia scopulosa

Structure Type

Flavonoids

Category

SMILES

CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O

Synonyms

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

Density

1.7±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

272.4±26.4 °C

Boiling Point

765.6±60.0 °C at 760 mmHg

Melting Point

InChl

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

InChl Key

SOSLMHZOJATCCP-AEIZVZFYSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:482-39-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31017255

Abstract

Particulate matter (PM), a widespread airborne contaminant, is a complex mixture of solid and liquid particles suspended in the air. Recent studies have demonstrated that PM induces oxidative stress and inflammatory reactions, and may cause certain skin diseases. Afzelin is a flavonoid isolated from Thesium chinense Turcz, which has anti‑inflammatory, anticancer and antibacterial properties. Therefore, the present study aimed to investigate if afzelin affected inflammatory responses in human keratinocytes exposed to PM. HaCaT cells were treated with PM (25 µg/cm2) in the presence or absence of afzelin (200 µM). Here, standard reference material 1649b was used as PM. Cell viability was assessed using the water‑soluble tetrazolium salt‑1 assay. The generation of reactive oxygen species (ROS) was measured using the dichloro‑dihydro‑​fluorescein diacetate assay. Gene and protein expression were investigated using reverse transcription‑quantitative polymerase chain reaction and western blot analysis, respectively. Levels of secreted inflammatory cytokines were measured using ELISA. The results suggested that afzelin inhibited PM‑induced proinflammatory cytokine mRNA expression and protein secretion in HaCaT cells. In addition, afzelin suppressed PM‑induced intracellular ROS generation, and p38 mitogen‑activated protein kinase and transcription factor activator protein‑1 component c‑Fos and c‑Jun activation. The results indicated that afzelin exerts anti‑inflammatory and antioxidant effects in PM‑exposed HaCaT. Afzelin may have potential for preventing PM‑induced inflammatory skin diseases.

Title

Afzelin suppresses proinflammatory responses in particulate matter-exposed human keratinocytes

Author

Ju Hee Kim 1, Minjeong Kim 1, Jae Min Kim 1, Mi-Kyung Lee 2, Seong Jun Seo 1, Kui Young Park 1

Publish date

2019 Jun

PMID

30249997

Abstract

Cyclocarya paliurus has been widely used as an ingredient in functional foods in China. However, the antioxidant properties of phenolic compounds and the effect of the plant origin remain unclear. The present study evaluated the geographical variation of this plant in term of its phenolic composition and antioxidant activities based on leaf materials collected from five regions. high-performance liquid chromatography (HPLC) analysis showed that there are three major components, quercetin-3-O-glucuronide, kaempferol-3-O-glucuronide, and kaempferol-3-O-rhamnoside, and their contents varied significantly among sampling locations. The investigated phenolic compounds showed substantial antioxidant activities, both in vitro and in vivo, with the highest capacity observed from Wufeng and Jinzhongshan. Correlation analysis revealed that quercetin and kaempferol glycosides might be responsible for the antioxidant activities. Our results indicate the importance of geographic origin, with sunny hours and temperature as the main drivers affecting the accumulation of C. paliurus phenolics and their antioxidant properties.

KEYWORDS

Cyclocarya paliurus; HPLC; antioxidant; geographic origin; phenolics.

Title

Geographic Variation in the Chemical Composition and Antioxidant Properties of Phenolic Compounds from Cyclocarya paliurus (Batal) Iljinskaja Leaves

Author

Yang Liu 1 2, Pei Chen 3, Mingming Zhou 4, Tongli Wang 5, Shengzuo Fang 6 7, Xulan Shang 8 9, Xiangxiang Fu 10 11

Publish date

2018 Sep 24

PMID

30080245

Abstract

Quercitrin, hyperoside, rutin, and afzelin are the dominant flavonoids compounds from Zanthoxylum bungeanum leaves, and they play major roles in the antioxidant activity. Macroporous adsorption resin (MAR) treatment, a simple, low-cost and efficient method, was combined with ultrasound-assisted extraction (UAE) to enrich and purify these four flavonoids from Z. bungeanum leaves efficiently. The optimal conditions for UAE based on Response Surface Methodology (RSM) were determined to be an ethanol concentration of 60%, leaves size of 40 mesh, temperature of 50 °C and ultrasonic power of 400 W with four flavonoids contents of 120.84 mg/g. After the extraction process, five kinds of MARs (D4020, D-101, NKA-9, AB-8, and X-5) were tested through static adsorption/desorption to enrich and purify the ultrasonic-assisted extracts, and D-101 was selected as the most suitable resin. The optimal adsorption conditions were 5 bed volumes (BV) of sample solution with an initial concentration of 7.5 mg/mL and pH 5.0. Meanwhile, the optimal desorption parameters were 5 BV each of deionized water and 30% ethanol, then 10 BV 70% ethanol, and a flow rate of 2 BV/hr. Under the optimized conditions, the contents of quercitrin, hyperoside, rutin, and afzelin increased by 276.39%, 187.46%, 221.81%, and 288.45%, respectively, and the recovery yields were 85.47%, 73.53%, 81.35%, and 65.06%. In addition, laboratory preparative-scale separation indicated that the preparative separation of four flavonoids was feasible and easy. Moreover, the antioxidant activities of the purified products were significantly increased after enrichment. In conclusion, all of the results indicated that these methods are highly efficient, low cost, environmentally friendly and easy to scale up.

Practical application: This study provided an environmentally friendly, rapid, and highly productive method for the extraction and purification of four active compounds from Zanthoxylum bungeanum leaves. The results can be used for the utilization of Z. bungeanum leaves as a kind of food supplement in an industrial setting.

KEYWORDS

antioxidant activity; flavonoids; macroporous adsorption resins; ultrasound-assisted extraction, Zanthoxylum bungeanum leaves.

Title

Simultaneous Enrichment and Separation of Four Flavonoids from Zanthoxylum bungeanum Leaves by Ultrasound-Assisted Extraction and Macroporous Resins with Evaluation of Antioxidant Activities

Author

Zhaochen Wu 1, Wei Wang 1, Fengyuan He 1, Dengwu Li 1, Dongmei Wang 1

Publish date

2018 Aug


Description :

Antibacterial effects of afzelin isolated from Cornus macrophylla on Pseudomonas aeruginosa, a leading cause of illness in immunocompromised individuals. PUMID/DOI:24642906 Molecules. 2014 Mar 17;19(3):3173-80. Bioactivity-guided separation led to the isolation of kaempferol 3-O-α-L-rhamnopyranoside (Afzelin). The structure was determined based on evaluation of its spectroscopic (UV, MS, and NMR) data. The minimum inhibitory concentration (MIC) of Afzelin against Pseudomonas aeruginosa was found to be 31 µg/mL. In addition, the results indicated that a hydroxyl group at C3 of the C-ring of the flavone skeleton and the rhamnose group may act as a negative factor and an enhancing factor, respectively, in the antibacterial activities of Afzelin. Afzelin positively regulates melanogenesis through the p38 MAPK pathway. PUMID/DOI:27287415 Chem Biol Interact. 2016 Jul 25;254:167-72. Melanogenesis refers to synthesis of the skin pigment melanin, which plays a critical role in the protection of skin against ultraviolet irradiation and oxidative stressors. We investigated the effects of Afzelin on melanogenesis and its mechanisms of action in human epidermal melanocytes. In this study, we found that Afzelin increased both melanin content and tyrosinase activity in a concentration-dependent manner. While the mRNA levels of microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein (TRP)-1 increased following Afzelin treatment, the mRNA levels of TRP-2 were not affected by Afzelin. Likewise, Afzelin increased the protein levels of MITF, TRP-1, and tyrosinase but not TRP-2. Mechanistically, we found that Afzelin regulated melanogenesis by upregulating MITF through phosphorylation of p38 mitogen-activated protein kinase (MAPK), independent of cyclic adenosine monophosphate (cAMP)-protein kinase A (PKA) signaling. Taken together, these findings indicate that the promotion of melanogenesis by Afzelin occurs through increased MITF gene expression, which is mediated by activation of p38 MAPK, and suggest that Afzelin may be useful as a protective agent against ultraviolet irradiation. Afzelin exhibits anti-cancer activity against androgen-sensitive LNCaP and androgen-independent PC-3 prostate cancer cells through the inhibition of LIM domain kinase 1. PUMID/DOI:26622852 Oncol Lett. 2015 Oct;10(4):2359-2365. Prostate cancer presents high occurrence worldwide. Medicinal plants are a major source of novel and potentially therapeutic molecules; therefore, the aim of the present study was to investigate the possible anti-prostate cancer activity of Afzelin, a flavonol glycoside that was previously isolated from Nymphaea odorata. The effect of Afzelin on the proliferation of androgen-sensitive LNCaP and androgen-independent PC-3 cells was evaluated by performing a water soluble tetrazolium salt-1 assay. In addition, the effect of Afzelin on the cell cycle of the LNCaP and PC-3 prostate cancer cell lines was evaluated. Western blot analysis was performed to evaluate the effect of Afzelin on the kinases responsible for the regulation of actin organization. Afzelin was identified to inhibit the proliferation of LNCaP and PC3 cells, and block the cell cycle in the G0 phase. The anticancer activity of Afzelin in these cells was determined to be due to inhibition of LIM domain kinase 1 expression. Thus, the in vitro efficacy of Afzelin against prostate cancer is promising; however, additional studies on different animal models are required to substantiate its anticancer potential.