ALEXIS Biochemicals: 8-Isopentenylnaringenin

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ALX-350-147

Revised 03-Oct-07

Bavachin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Antioxidants

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-147-MC05		0.5 mg	120.00 USD

Product Specification

FORMULA:	C₂₀H₂₀O₄
MW:	324.4
CAS NUMBER:	19879-32-4
SOURCE/HOST:	Isolated from plant Psoralea corylifolia.
PURITY:	≥97% (HPLC)
APPEARANCE:	Yellow solid.
SOLUBILITY:	Soluble in DMSO or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.
IDENTITY:	Determined by ¹H-NMR, ¹³C-NMR and MS.

Product Description

Weak antioxidant. Antimutagenic. Stimulates bone formation and has potential activity against osteoporosis. Shows inhibitory activities against the antigen-induced degranulation and weak estrogen-like activity.

Product Specific Literature References

Antiplatelet flavonoids from seeds of Psoralea corylifolia: W.J. Tsai, et al.; J. Nat. Prod. 59, 671 (1996) Abstract
Osteoblastic proliferation stimulating activity of Psoralea corylifolia extracts and two of its flavonoids: D. Wang, et al.; Planta Med. 67, 748 (2001) Abstract
Antioxidative components of Psoralea corylifolia (Leguminosae): H. Haraguchi, et al.; Phytother. Res. 16, 539 (2002) Abstract
Bioactive constituents from Chinese natural medicines. XX. Inhibitors of antigen-induced degranulation in RBL-2H3 cells from the seeds of Psoralea corylifolia: H. Matsuda, et al.; Chem. Pharm. Bull. (Tokyo) 55, 106 (2007) Abstract
Synthesis of four natural prenylflavonoids and their estrogen-like activities: X. Dong, et al.; Arch. Pharm. (Weinheim) 340, 372 (2007) Abstract

Further Categories Containing This Product:

Natural Products - Immunomodulators • Estrogen & Estrogen Receptors / Related Products • Flavanones • Bone Metabolism Other Products

ALX-350-279

Revised 02-Jun-08

Isoxanthohumol
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Natural Products - DNA Regulation / Transcription

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-279-M001		1 mg	60.00 USD

Product Specification

FORMULA:	C₂₁H₂₂O₅
MW:	354.4
SOURCE/HOST:	Synthetic.
PURITY:	≥98%
APPEARANCE:	White powder.
SOLUBILITY:	Soluble in DMSO (50mg/ml) or methanol (50mg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C

Product Description

Prenylated flavonoid. Phytoestrogen. Induces apoptosis in mature adipocytes.

Product Specific Literature References

Xanthohumol and related prenylflavonoids from hops and beer: to your good health!: J.F. Stevens & J.E. Page; Phytochemistry 65, 1317 (2004), (Review) Abstract
Inhibition of endothelial cell functions by novel potential cancer chemopreventive agents: E. Bertl, et al.; BBRC 325, 287 (2004) Abstract
Metabolism of xanthohumol and isoxanthohumol, prenylated flavonoids from hops (Humulus lupulus L.), by human liver microsomes: D. Nikolic, et al.; J. Mass Spectrom. 40, 289 (2005) Abstract
The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine: S. Possemiers, et al.; J. Nutr. 136, 1862 (2006) Abstract
Identification of human hepatic cytochrome P450 enzymes involved in the metabolism of 8-prenylnaringenin and isoxanthohumol from hops (Humulus lupulus L.): J. Guo, et al.; Drug Metab. Dispos. 34, 1152 (2006)
Effect of xanthohumol and isoxanthohumol on 3T3-L1 cell apoptosis and adipogenesis: J.Y. Yang, et al.; Apoptosis 12, 1953 (2007) Abstract

Further Categories Containing This Product:

Flavanones • Estrogen & Estrogen Receptors / Related Products • Natural Products - Apoptosis Inducers & Inhibitors • Active Substances from Fruit and Vegetables • Natural Products - Other Signal Transduction Pathway Modulators • Lipid Metabolism Other Products

ALX-350-346

Revised 12-Sep-08

Silybin
SYNONYMS	Silibinin 2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-6-(3,5,7-trihydroxy-4-oxobenzopyran-2-yl)benzodioxin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Chemopreventive Agents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-346-G001		1 g	10.00 USD
ALX-350-346-G005		5 g	35.00 USD

Product Specification

FORMULA:	C₂₅H₂₂O₁₀
MW:	482.4
CAS NUMBER:	22888-70-6; 65666-07-1
MERCK INDEX:	14: 8532
RTECS:	DJ2981770
SOURCE/HOST:	Originally isolated from Silybum marianum.
PURITY:	≥98%
APPEARANCE:	White to light yellow solid.
SOLUBILITY:	Soluble in 100% ethanol (0.1mg/ml), DMSO (10mg/ml), dimethyl formamide (20mg/ml), acetone or methanol; 0.5mg/ml soluble in a 1:9 solution of dimethyl formamide:PBS (pH 7.2) (dilute the dimethyl formamide solution with PBS).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	We do not recommend storing aqueous solutions for more than one day.
HAZARD:	IRRITANT.

Product Description

Mixture of silybin A and silybin B. Major active constituent of silymarin. Anti-inflammatory, cytoprotective and anti-cancer compound. Shows chemopreventive effect against skin cancer. Inhibits mitogen-activated protein kinase (MAPK). Inhibits P-glycoprotein (Pgp)-mediated cellular efflux. Inhibits cytochrome P450 enzymes. Apoptosis inducer. Blocks the production of superoxide in Kupffer cells (EC₅₀=100µM). Antioxidant. Free radical scavenger.

Product Specific Literature References

[On the chemistry of silymarin (silybin), the active principle of the fruits from Silybum marianum (L.) Gaertn. (Carduus marianus L.)]: H. Wagner, et al.; Arzneimittelforschung 18, 688 (1968) Abstract
Inhibition of Kupffer cell functions as an explanation for the hepatoprotective properties of silibinin: C. Dehmlow, et al.; Hepatology 23, 749 (1996) Abstract; Full Text
Silibinin decreases prostate-specific antigen with cell growth inhibition via G1 arrest, leading to differentiation of prostate carcinoma cells: implications for prostate cancer intervention: X. Zi & R. Agarwal; PNAS 96, 7490 (1999) Abstract; Full Text
The flavanolignan silybin and its hemisynthetic derivatives, a novel series of potential modulators of P-glycoprotein: M. Maitrejean, et al.; Bioorg. Med. Chem. Lett. 10, 157 (2000) Abstract
Silibinin inhibits constitutive and TNFalpha-induced activation of NF-kappaB and sensitizes human prostate carcinoma DU145 cells to TNFalpha-induced apoptosis: S. Dhanalakshmi, et al.; Oncogene 21, 1759 (2002) Abstract; Full Text
Silibinin upregulates the expression of cyclin-dependent kinase inhibitors and causes cell cycle arrest and apoptosis in human colon carcinoma HT-29 cells: C. Agarwal, et al.; Oncogene 22, 8271 (2003) Abstract; Full Text
Epidermal growth factor receptor mediates silibinin-induced cytotoxicity in a rat glioma cell line: L. Qi, et al.; Cancer Biol. Ther. 2, 526 (2003) Abstract; Full Text
Silibinin down-regulates survivin protein and mRNA expression and causes caspases activation and apoptosis in human bladder transitional-cell papilloma RT4 cells: A.K. Tyagi, et al.; BBRC 312, 1178 (2003) Abstract
Silibinin causes cell cycle arrest and apoptosis in human bladder transitional cell carcinoma cells by regulating CDKI-CDK-cyclin cascade, and caspase 3 and PARP cleavages: A. Tyagi, et al.; Carcinogenesis 25, 1711 (2004) Abstract; Full Text
Silibinin protects against photocarcinogenesis via modulation of cell cycle regulators, mitogen-activated protein kinases, and Akt signaling: G. Mallikarjuna, et al.; Cancer Res. 64, 6349 (2004) Abstract; Full Text
Silibinin up-regulates DNA-protein kinase-dependent p53 activation to enhance UVB-induced apoptosis in mouse epithelial JB6 cells: S. Dhanalakshmi, et al.; J. Biol. Chem. 280, 20375 (2005) Abstract; Full Text
Silibinin inhibits invasion of oral cancer cells by suppressing the MAPK pathway: P.N. Chen, et al.; J. Dent. Res. 85, 220 (2006) Abstract; Full Text
Pilot study of oral silibinin, a putative chemopreventive agent, in colorectal cancer patients: silibinin levels in plasma, colorectum, and liver and their pharmacodynamic consequences: C. Hoh, et al.; Clin. Cancer Res. 12, 2944 (2006) Abstract; Full Text
Silibinin prevents UV-induced HaCaT cell apoptosis partly through inhibition of caspase-8 pathway: L.H. Li, et al.; Biol. Pharm. Bull. 29, 1096 (2006) Abstract; Full Text
Silibinin inhibits UVB- and epidermal growth factor-induced mitogenic and cell survival signaling involving activator protein-1 and nuclear factor-kappaB in mouse epidermal JB6 cells: R.P. Singh, et al.; Mol. Cancer Ther. 5, 1145 (2006) Abstract; Full Text
Silibinin activates p53-caspase 2 pathway and causes caspase-mediated cleavage of Cip1/p21 in apoptosis induction in bladder transitional-cell papilloma RT4 cells: evidence for a regulatory loop between p53 and caspase 2: A. Tyagi, et al.; Carcinogenesis 27, 2269 (2006) Abstract; Full Text
Silibinin inhibits constitutive activation of Stat3, and causes caspase activation and apoptotic death of human prostate carcinoma DU145 cells: C. Agarwal, et al.; Carcinogenesis 28, 1463 (2007) Abstract
Effects and mechanisms of silibinin on human hepatoma cell lines: J.J. Lah, et al.; World J. Gastroenterol. 13, 5299 (2007) Abstract; Full Text
Silibinin suppresses PMA-induced MMP-9 expression by blocking the AP-1 activation via MAPK signaling pathways in MCF-7 human breast carcinoma cells: S.O. Lee, et al.; BBRC 354, 165 (2007) Abstract
Immunosuppressive effect of silibinin in experimental autoimmune encephalomyelitis: K. Min, et al.; Arch. Pharm. Res. 30, 1265 (2007) Abstract
Silibinin sensitizes human glioma cells to TRAIL-mediated apoptosis via DR5 up-regulation and down-regulation of c-FLIP and survivi: Y.G. Son, et al.; Cancer Res. 67, 8274 (2007) Abstract
Silibinin impairs constitutively active TGFalpha-EGFR autocrine loop in advanced human prostate carcinoma cells: A. Tyagi, et al.; Pharm. Res. Epub ahead of print, (2008) Abstract

Further Categories Containing This Product:

Free Radical Scavengers • Flavanones • MAPK Pathway Inhibitors • Cytochrome P450 [CYP450] / Related Products • Natural Products - Antioxidants • MDR Inhibitors • P-glycoprotein [Pgp] / Related Products • Natural Products - Anti-inflammatory Agents • Antitumor Agents (Enzyme Inhibitors)

ALX-385-006

Revised 03-Dec-07

(±)-Taxifolin
SYNONYMS	(±)-Dihydroquercetin (±)-3,3',4',5,7-Pentahydroxyflavanone Taxifoliol Distylin Catechin hydrate
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Flavanones

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-385-006-M010		10 mg	50.00 USD
ALX-385-006-M050		50 mg	200.00 USD

Product Specification

FORMULA:	C₁₅H₁₂O₇
MW:	304.3
CAS NUMBER:	480-18-2
RTECS:	LK6920000
PURITY:	≥90%
APPEARANCE:	White to faintly yellow powder.
SOLUBILITY:	Soluble in 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	HARMFUL.

Product Description

Antioxidant flavonoid.

Product Specific Literature References

Suppression of active oxygen-induced cytotoxicity by flavonoids: T. Nakayama, et al.; Biochem. Pharmacol. 45, 265 (1993) Abstract
Suppression of hydroperoxide-induced cytotoxicity by polyphenols: T. Nakayama; Cancer Res. 54, 1991s (1994) Abstract
Interaction of flavonoids with ascorbate and determination of their univalent redox potentials: a pulse radiolysis study: W. Bors, et al.; Free Radic. Biol. Med. 19, 45 (1995) Abstract
Structure-antioxidant activity relationships of flavonoids and phenolic acids: C.A. Rice-Evans, et al.; Free Radical Biol. & Med. 20, 933 (1996), (Review) Abstract
Modulation of hepatic lipoprotein synthesis and secretion by taxifolin, a plant flavonoid: A. Theriault, et al.; J. Lipid Res. 41, 1969 (2000) Abstract
Inhibitory activity of diacylglycerol acyltransferase (DGAT) and microsomal triglyceride transfer protein (MTP) by the flavonoid, taxifolin, in HepG2 cells: potential role in the regulation of apolipoprotein B secretionInhibitory activity of diacylglycero: A. Casaschi, et al.; Atherosclerosis 176, 247 (2004) Abstract

Further Categories Containing This Product:

Natural Products - Antioxidants

ALX-385-010

Revised 08-Apr-08

(±)-Naringenin
SYNONYMS	(±)-4',5,7-Trihydroxyflavanone
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Flavanones

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-385-010-G001		1 g	15.00 USD

Product Specification

FORMULA:	C₁₅H₁₂O₅
MW:	272.3
CAS NUMBER:	67604-48-2
MERCK INDEX:	14: 6424
PURITY:	≥95%
APPEARANCE:	Light yellow to tan powder.
SOLUBILITY:	Soluble in 100% ethanol; almost insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+20°C
HANDLING:	Protect from light.
HAZARD:	IRRITANT.

Product Description

Antioxidant flavonoid. Has anti-inflammatory and antitumor properties. Induces apoptosis. Stimulates DNA repair following oxidative damage. Inhibits the activity of phosphoinositide 3-kinase (PI(3)K).

Product Specific Literature References

Structure-antioxidant activity relationships of flavonoids and phenolic acids: C.A. Rice-Evans, et al.; Free Radical Biol. & Med. 20, 933 (1996), (Review) Abstract
Naringenin inhibits phosphoinositide 3-kinase activity and glucose uptake in 3T3-L1 adipocytes: A. W. Harmon & Y. M. Patel; BBRC 305, 229 (2003) Abstract
The citrus flavonoid naringenin stimulates DNA repair in prostate cancer cells: K. Gao, et al.; J. Nutr. Biochem. 17, 89 (2006) Abstract
Naringenin-induced apoptosis via activation of NF-kappaB and necrosis involving the loss of ATP in human promyeloleukemia HL-60 cells: S. Kanno, et al.; Toxicol. Lett. 166, 131 (2006) Abstract
Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages: S. Hirai, et al.; Life Sci. 81, 1272 (2007) Abstract

Further Categories Containing This Product:

Natural Products - Other Signal Transduction Pathway Modulators • Active Substances from Fruit and Vegetables • Phosphoinositide 3-kinase [PI(3)K] / Related Products • Natural Products - Apoptosis Inducers & Inhibitors • Natural Products - Anti-inflammatory Agents • Natural Products - Antitumor Reagents • Natural Products - Antioxidants • DNA Repair Other Products

ALX-385-011

Revised 05-Apr-08

(±)-Hesperetin
SYNONYMS	(±)-3',5,7-Trihydroxy-4'-methoxyflavanone
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Flavanones

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-385-011-G001		1 g	21.00 USD

Product Specification

FORMULA:	C₁₆H₁₄O₆
MW:	302.3
CAS NUMBER:	520-33-2
MERCK INDEX:	14: 4670
PURITY:	≥95% (HPLC)
APPEARANCE:	Off-white to yellow powder.
SOLUBILITY:	Soluble in 100% ethanol; slightly soluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C

Product Description

Antioxidant flavonoid. Induces G1-phase cell cycle arrest. Anti-inflammatory. Suppresses NF-κB activation. Reduces cholesterol biosynthesis. Inhibits lipid peroxidation. Neuroprotective against neuronal oxidative damage.

Product Specific Literature References

Structure-antioxidant activity relationships of flavonoids and phenolic acids: C.A. Rice-Evans, et al.; Free Radical Biol. & Med. 20, 933 (1996), (Review) Abstract
Lipid-lowering efficacy of hesperetin metabolites in high-cholesterol fed rats: H. K. Kim, et al.; Clin. Chim. Acta 327, 129 (2003) Abstract
Antioxidant and neuroprotective effects of hesperidin and its aglycone hesperetin: J. Cho; Arch. Pharm. Res. 29, 699 (2006) Abstract
Modulation of the age-related nuclear factor-kappaB (NF-kappaB) pathway by hesperetin: J. Y. Kim, et al.; Aging Cell 5, 401 (2006) Abstract
Hesperetin Induced G1-Phase Cell Cycle Arrest in Human Breast Cancer MCF-7 Cells: Involvement of CDK4 and p21: E.J. Choi; Nutr. Cancer 59, 115 (2007) Abstract

Further Categories Containing This Product:

Cell Cycle Blockers & Inhibitors / Related Products • Active Substances from Fruit and Vegetables • NF-kB Pathway Inhibitors • Natural Products - Antioxidants • Natural Products - Anti-inflammatory Agents • Natural Products - NF-kB Pathway Inhibitors

ALX-385-018

Revised 03-Dec-07

(+)-Taxifolin
SYNONYMS	(+)-Dihydroquercetin (+)-3,3',4',5,7-Pentahydroxyflavanone Taxifoliol Distylin Catechin hydrate
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Flavanones

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-385-018-M010		10 mg	35.00 USD
ALX-385-018-M050		50 mg	140.00 USD

Product Specification

FORMULA:	C₁₅H₁₂O₇
MW:	304.3
CAS NUMBER:	17654-26-1
PURITY:	≥96%
APPEARANCE:	Light yellow to brown powder.
SOLUBILITY:	Soluble in 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HANDLING:	Protect from light.

Product Description

Antioxidant flavonoid. Anti-inflammatory compound. Chemopreventive agent. Decreases hepatic lipid synthesis.

Product Specific Literature References

Structure-antioxidant activity relationships of flavonoids and phenolic acids: C.A. Rice-Evans, et al.; Free Radical Biol. & Med. 20, 933 (1996), (Review) Abstract
Modulation of hepatic lipoprotein synthesis and secretion by taxifolin, a plant flavonoid: A. Theriault, et al.; J. Lipid Res. 41, 1969 (2000) Abstract
Prevention of macrophage adhesion molecule-1 (Mac-1)-dependent neutrophil firm adhesion by taxifolin through impairment of protein kinase-dependent NADPH oxidase activation and antagonism of G protein-mediated calcium influx: Y.H. Wang, et al.; Biochem. Pharmacol. 67, 2251 (2004) Abstract
The chemopreventive effect of taxifolin is exerted through ARE-dependent gene regulation: S.B. Lee, et al.; Biol. Pharm. Bull. 30, 1074 (2007) Abstract

Further Categories Containing This Product:

Natural Products - Chemopreventive Agents • Natural Products - Antioxidants • Natural Products - Anti-inflammatory Agents

ALX-385-025

Revised 07-Apr-08

8-Isopentenylnaringenin
SYNONYMS	8-Prenylnaringenin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Flavanones

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-385-025-M005		5 mg	155.00 USD

Product Specification

FORMULA:	C₂₀H₂₀O₅
MW:	340.4
SOURCE/HOST:	Isolated from hops (Humulus lupulus L.).
PURITY:	≥97% (HPLC)
APPEARANCE:	Light yellow powder
SOLUBILITY:	Soluble in methanol or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C

Product Description

Prenyl flavonoid. Phytoestrogen. Selective, non-steroidal estrogen receptor α (ERα) ligand. Potent inhibitor of angiogenesis in vitro and in vivo. Chemopreventive agent against cancer induced by heterocyclic amines.

Product Specific Literature References

Prenylflavonoids: a new class of non-steroidal phytoestrogen (Part 1). Isolation of 8-isopentenylnaringenin and an initial study on its structure-activity relationship: M. Kitaoka, et al.; Planta Med. 64, 511 (1998) Abstract
Prenylflavonoids: a new class of non-steroidal phytoestrogen (Part 2). Estrogenic effects of 8-isopentenylnaringenin on bone metabolism: M. Miyamoto, et al.; Planta Med. 64, 516 (1998) Abstract
Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer: S.R. Milligan, et al.; J. Clin. Endocrinol. Metab. 84, 2249 (1999) Abstract
Prenylflavonoids from hops inhibit the metabolic activation of the carcinogenic heterocyclic amine 2-amino-3-methylimidazo[4, 5-f]quinoline, mediated by cDNA-expressed human CYP1A2: C.L. Miranda, et al.; Drug Metab. Dispos. 28, 1297 (2000) Abstract; Full Text
The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids: S.R. Milligan, et al.; J. Clin. Endocrinol. Metab. 85, 4912 (2000) Abstract; Full Text
8-prenylnaringenin, a novel phytoestrogen, inhibits angiogenesis in vitro and in vivo: M.S. Pepper, et al.; J. Cell Physiol. 199, 98 (2004) Abstract
Xanthohumol and related prenylflavonoids from hops and beer: to your good health!: J.F. Stevens & J.E. Page; Phytochemistry 65, 1317 (2004), (Review) Abstract
Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types: T.F. Bovee, et al.; J. Steroid Biochem. Mol. Biol. 91, 99 (2004) Abstract
8-Prenylnaringenin, inhibits estrogen receptor-alpha mediated cell growth and induces apoptosis in MCF-7 breast cancer cells: E. Brunelli, et al.; J. Steroid Biochem. Mol. Biol. 107, 140 (2007) Abstract

Further Categories Containing This Product:

Active Substances from Fruit and Vegetables • Estrogen & Estrogen Receptors / Related Products • Natural Products for Angiogenesis Research • Natural Products - Chemopreventive Agents • Other Natural Products - DNA Regulation / Transcription