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Hirsutanonol
Hirsutanonol
ChemFaces products have been cited in many studies from excellent and top scientific journals
Product Name Hirsutanonol
Price:
CAS No.: 41137-86-4
Catalog No.: CFN98645
Molecular Formula: C19H22O6
Molecular Weight: 346.4 g/mol
Purity: >=98%
Type of Compound: Phenols
Physical Desc.: Powder
Source: The stem barks of Alnus hirsuta.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download: COA    MSDS    SDF    Manual
Similar structural: Comparison (Web)  (SDF)
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Size /Price /Stock 10 mM * 1 mL in DMSO / Inquiry
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Related Screening Libraries
Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
10 mM * 1 mL in DMSO / Inquiry / In-stock
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Biological Activity
Description: Hirsutanonol has potent antioxidant activity, it shows significant free radical scavenging activity and exhibits inhibition effect on the mitochondrial lipid peroxidation. Hirsutanonol shows potent cytotoxic activities against murine B16 melanoma cells and human SNU-C1 gastric cancer cells, it also has chemoprotective effect on human lymphocytes DNA. Hirsutanonol or oregonin as an active ingredient composition for treating atopic dermatitis, hirsutanonol shows significant inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced cyclooxygenase-2 (COX-2) expression in immortalized human breast epithelial MCF10A cells. Hirustenone and hirsutanonol show promising anti-filarial activity both in vitro and in vivo studies.
Targets: COX | Antifection
In vitro:
Planta Med. 2013 Apr;79(6):499-505.
Diarylheptanoids from Alnus glutinosa bark and their chemoprotective effect on human lymphocytes DNA.[Pubmed: 23512500]

METHODS AND RESULTS:
A study of secondary metabolites from the bark of Alnus glutinosa led to the isolation of fourteen diarylheptanoids: oregonin (1), platyphylloside (2), rubranoside A (3), rubranoside B (4), Hirsutanonol (5), hirsutenone (6), Hirsutanonol-5-O-β-D-glucopyranoside (7), platyphyllonol-5-O-β-D-xylopyranoside (8), aceroside VII (9), alnuside A (10), alnuside B (11), 1,7-bis-(3,4-dihydoxyphenyl)-5-hydroxy-heptane-3-O-β-D-xylopyranoside (12), (5S)-1-(4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)-5-O-β-D-glucopyranosyl-heptan-3-one (13), and (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-O-β-D-[6-(3,4-dimethoxycinnamoylglucopyranosyl)]-heptan-3-one (14). All of the diarylheptanoids, except 1 and 5, were found in A. glutinosa for the first time, while 13 and 14 were new compounds. The structures were determined by spectroscopic techniques: 1D and 2D NMR, HR-ESI-MS, FTIR, UV, and CD. All isolated compounds were analyzed for an in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using the cytokinesis-block micronucleus assay.
CONCLUSIONS:
The majority of them, including the new compounds 13 and 14, exerted a pronounced effect in decreasing DNA damage in human lymphocytes. Diarylheptanoids 1, 2, 5, 13, and 14 at a concentration of 1 µg/mL decreased the frequency of micronuclei by 52.8 %, 43.8 %, 63.6 %, 44.4 %, and 56.0 %, respectively, exerting a much stronger effect than the synthetic protector amifostine (17.2 %, c = 1 µg/mL).
Arch Pharm Res. 2008 Oct;31(10):1287-9.
Cytotoxic activities of diarylheptanoids from Alnus japonica.[Pubmed: 18958419]

METHODS AND RESULTS:
The diarylheptanoids (1-10) 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranoside (1), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-beta-D-apiofuranosyl(1-->6)-beta-D-glucopyranoside (2), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-beta-D-glucopyranoside (3), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane (4), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-beta-D-glucopyranoside (5), oregonin (6), Hirsutanonol (7), hirsutenone (8), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-O-beta-D-xylopyranoside (9), and platyphylloside (10), isolated from the bark of Alnus japonica, were analyzed for their cytotoxic activities on various human and mouse cancer cell lines. The cytotoxic activities of these ten compounds were evaluated against murine B16 melanoma, human SNU-1 gastric cancer, human SNU-354 hepatoma cancer and human SNU-C4 colorectal cell lines.
CONCLUSIONS:
The diarylheptanoids showed potent cytotoxic activities against murine B16 melanoma cells and human SNU-C1 gastric cancer cell when the cell viability was analyzed by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide) assay.
Korean J. Medicinal Crop Sci.,2005,13(2):85-90.
Constituents and their DPPH Scavenging Activities from the Leaves of Alnus hirsuta (Spach) Rupr.[Reference: WebLink]

METHODS AND RESULTS:
Phytochemical study on the EtOAc fraction from a MeOH extract of the leaves of Alnus hirsuta Rupr. led to the isolation of nine compounds betulin (1), betulinic acid (2), Hirsutanonol (3), hirsutenone (4), quercetin (5), avicularin (6), gallic acid (7), hyperin (8), and daucosterol (9). Among them, six compounds 1, 2, 57, and 9 are report from this plant for the first time. All isolated compounds were evaluated for their antioxidant activity using DPPH radical scavenging capacity and inhibition effect on mitochondrial lipid peroxidation.
CONCLUSIONS:
Six phenolic compounds 3-8 were found to have potent antioxidant activity. Of which, compounds 3, 4 and 5 showed significant free radical scavenging activity with the values of , respectively. In addition, the compounds 3-8 exhibited inhibition effect on the mitochondrial lipid peroxidation with the values of , respectively.
Hirsutanonol Description
Source: The stem barks of Alnus hirsuta.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

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Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8868 mL 14.4342 mL 28.8684 mL 57.7367 mL 72.1709 mL
5 mM 0.5774 mL 2.8868 mL 5.7737 mL 11.5473 mL 14.4342 mL
10 mM 0.2887 mL 1.4434 mL 2.8868 mL 5.7737 mL 7.2171 mL
50 mM 0.0577 mL 0.2887 mL 0.5774 mL 1.1547 mL 1.4434 mL
100 mM 0.0289 mL 0.1443 mL 0.2887 mL 0.5774 mL 0.7217 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Structure Identification:
Zhongguo Zhong Yao Za Zhi. 2014 Mar;39(6):1040-2.
Chemical constituents from roots of Chirita longgangensis var. hongyao.[Pubmed: 24956847]

METHODS AND RESULTS:
To study the chemical constituents from the roots of Chirita longgangensis var. hongyao. The methanol extract was isolated and purified by silica gel, Sephadex LH-20 and preparative HPLC. Their structures were elucidated by MS and spectral data (1H, 13C-NMR). Seven compounds were isolated and identified as plantainoside A (1), plantainoside B (2), calcedarioside C (3), calcedarioside D (4), platyphylloside (5), Hirsutanonol (6), and Hirsutanonol-5-O-beta-D-glucopyranoside (7).
CONCLUSIONS:
Compounds 5-7 were isolated for the first time from the family Gesneriaceae.
Phytomedicine. 2013 Jan 15;20(2):124-32.
Antifilarial diarylheptanoids from Alnus nepalensis leaves growing in high altitude areas of Uttarakhand, India.[Pubmed: 23219341]
Lymphatic filariasis continues to be a major health problem in tropical and subtropical countries. A macrofilaricidal agent capable of eliminating adult filarial parasites is urgently needed. Platyphyllenone (A), alusenone (B), hirustenone (C) and Hirsutanonol (D) are important biologically active diarylheptanoids present in Alnus nepalensis. In the present study, we report the antifilarial activity in diarylheptanoids isolated from the leaves of A. nepalensis.
METHODS AND RESULTS:
Out of four compounds (A-D) tested in vitro one has shown promising anti-filarial activity both in vitro and in vivo studies. This is the first ever report on antifilarial efficacy of a compound of the plant and warrants further studies around this scaffold. In addition, a sensitive, selective and robust densitometric high-performance thin-layer chromatographic method was developed and validated for the above four biomarker compounds. The separation was performed on silica gel 60F(254) high-performance thin layer chromatography plates using chloroform:methanol (9:1, v/v) as mobile phase.
CONCLUSIONS:
The quantitation of marker compounds was carried out using densitometric reflection/absorption mode at 600 nm after post-chromatographic derivatization using vanillin-sulfuric acid reagent. The method was validated for peak purity, precision, robustness, limit of detection (LOD) and quantitation (LOQ) etc., as per the International Conference on Harmonization (ICH) guidelines.
Biol Pharm Bull. 2000 Apr;23(4):517-8.
Inhibition of cyclooxygenase-2 expression by diarylheptanoids from the bark of Alnus hirsuta var. sibirica.[Pubmed: 10784440]

METHODS AND RESULTS:
Two known diarylheptanoids, oregonin (1), (5S)-1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-beta-D-xylopyranosi de and Hirsutanonol (2), (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-one isolated from the bark of Alnus hirsuta var. sibirica, showed significant inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced cyclooxygenase-2 (COX-2) expression in immortalized human breast epithelial MCF10A cells.
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