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Natural Products - Other Signal Transduction Pathway Modulators
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ALX-350-240 Revised 05-Dec-07
Ilimaquinone
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SYNONYMS 3-[(Decahydro-1β,2β,4αβ-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Signal Transduction Pathway Modulators
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ALX-350-240-C100   100 µg 140.00 USD Add To Cart
Product Specification
FORMULA: C22H30O4
MW: 358.5
CAS NUMBER: 71678-03-0
PURITY: ≥98%
APPEARANCE: Yellow powder.
SOLUBILITY: Soluble in DMSO or 100% ethanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

Product Description
Displays antimicrobial, anti-HIV and anti-inflammatory properties. Induces reversible breakdown of Golgi membranes. Inhibits the association of β-COP and ADP-ribosylation factor to Golgi membranes. Interacts with methylation enzymes. Shows anticancer activity.
Product Specific Literature References
R.T. Luibrand, et al.; Tetrahedron 35, 609 (1979)
Complete vesiculation of Golgi membranes and inhibition of protein transport by a novel sea sponge metabolite, ilimaquinone: P.A. Takizawa, et al.; Cell 73, 1079 (1993) Abstract
Interactions of (-)-ilimaquinone with methylation enzymes: implications for vesicular-mediated secretion: H.S. Radeke, et al.; Chem. Biol. 6, 639 (1999) Abstract
Ilimaquinone inhibits gap-junctional communication prior to Golgi fragmentation and block in protein transport: V. Cruciani, et al.; Exp. Cell Res. 287, 130 (2003) Abstract
Natural products with anti-HIV activity from marine organisms: L.A. Tziveleka, et al.; Curr. Top. Med. Chem. 3, 1512 (2003), Review Abstract
Interaction of the smooth endoplasmic reticulum and mitochondria: J.G. Goetz & I.R. Nabi; Biochem. Soc. Trans. 34, 370 (2006), Review Abstract
Ilimaquinone, a marine sponge metabolite, displays anticancer activity via GADD153-mediated pathway: P.H. Lu, et al.; Eur. J. Pharmacol. 556, 45 (2007) Abstract
Further Categories Containing This Product:
Natural Products - Anti-inflammatory Agents • Golgi Apparatus • ADP Ribosylation Factor [ARF] / Related Products • Natural Products - Chemopreventive Agents • Natural Products - Antiviral / anti-HIV Agents • PRMTs, Mono- & Dimethylarginine / Related Products • Marine Natural Products
 
 
ALX-350-279 Revised 02-Jun-08
Isoxanthohumol
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Other Natural Products - DNA Regulation / Transcription
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ALX-350-279-M001   1 mg 60.00 USD Add To Cart
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-350-311 Revised 07-Feb-05
Stellettamide A . trifluoroacetate
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Signal Transduction Pathway Modulators
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ALX-350-311-C100   100 µg 460.00 USD Add To Cart
Product Specification
FORMULA: C26H45N2O . CF3CO2
MW: 401.7 . 113.0
CAS NUMBER: 129744-24-7
SOURCE/HOST: Isolated from the marine sponge Stellata sp.
PURITY: ≥95%
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
HAZARD: TOXIC.

Product Description
Inhibits intrinsic tyrosine fluorescence in a concentration-dependent manner. Binds to calmodulin and inhibits Ca2+/calmodulin-dependent enzyme activities.
Product Specific Literature References
Stellettamide-A, a novel inhibitor of calmodulin, isolated from a marine sponge: Y. Abe, et al.; Br. J. Pharmacol. 121, 1309 (1997) Abstract
Further Categories Containing This Product:
Calmodulin Inhibitors • Alkaloids • Marine Natural Products
 
 
ALX-350-314 Revised 20-Dec-07
(+)-Calystegine B2
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SYNONYMS (1R,2S,3R,4S,5R)-8-Azabicyclo[3.2.1]octane-1,2,3,4-tetrol
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Signal Transduction Pathway Modulators
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ALX-350-314-M001   1 mg 90.00 USD Add To Cart
ALX-350-314-M005   5 mg 360.00 USD Add To Cart
Product Specification
FORMULA: C7H13NO4
MW: 175.2
CAS NUMBER: 127414-85-1
SOURCE/HOST: Isolated from Lycopersicon sp.
PURITY: ≥98%
APPEARANCE: White to off-white solid.
SOLUBILITY: Soluble in water.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

Product Description
Selective glycosidase inhibitor sharing such activity with other hydroxylated nitrogen containing bicyclic compounds like swainsonine (Prod. No. ALX-350-077), castanospermine (Prod. No. ALX-270-160), monocyclic deoxynojirimycin (Prod. No. ALX-580-003) or fagomine. Most abundant form is calystegine B2 occurring in almost all plants displaying calystegines. Inhibitory potency of calystegine B2 is comparable to other alkaloidal glycosidase inhibitors showing Ki values below 1µM.
Product Specific Literature References
Identification of the glycosidase inhibitors swainsonine and calystegine B2 in Weir vine (Ipomoea sp. Q6 [aff. calobra]) and correlation with toxicity: R.J. Molyneux, et al.; J. Nat. Prod. 58, 878 (1995) Abstract
The effects of calystegines isolated from edible fruits and vegetables on mammalian liver glycosidases: N. Asano, et al.; Glycobiology 70, 1085 (1997) Abstract
Synthesis and evaluation of calystegine B2 analogues as glycosidase inhibitors: M.I. Garcia-Moreno, et al.; J. Org. Chem. 66, 7604 (2001) Abstract
Biosynthesis of calystegines: 15N NMR and kinetics of formation in root cultures of Calystegia sepium: Y. Scholl, et al.; Phytochemistry 62, 325 (2003) Abstract
Chemistry and biology of calystegines: B. Drager; Nat. Prod. Rep. 21, 211 (2004) Abstract
Calystegines in potatoes with genetically engineered carbohydrate metabolism: U. Richter, et al.; J. Exp. Bot. 58, 1603 (2007) Abstract
Related Products
Further Categories Containing This Product:
Active Substances from Fruit and Vegetables • Glycosidases / Related Products • Alkaloids
 
 
ALX-350-323 Revised 20-Jun-08
Psoralidin
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Antitumor Reagents
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ALX-350-323-M001   1 mg 170.00 USD Add To Cart
Product Specification
FORMULA: C20H16O5
MW: 336.3
CAS NUMBER: 18642-23-4
SOURCE/HOST: Isolated from Psoralea corylifolia.
PURITY: ≥97% (HPLC)
APPEARANCE: Yellow solid.
SOLUBILITY: Soluble in DMSO.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Protect from light.
HAZARD: TOXIC.
IDENTITY: Identity determined by 1H-NMR, 13C-NMR and MS.

Product Description
Antineoplastic compound. Cytotoxic against stomach cancer cell lines. Shows antibacterial activity against Shigella sonnei and S. flexneri. Shows strong antioxidant activity and inhibits tyrosine phosphatase 1B (PTP1B) activity. Was shown to possess potent antidepressant properties.
Product Specific Literature References
Influence of nitrogen on accumulation of isosojagol (a newly detected coumestan in soybean) and associated isoflavonoids in roots and nodules of mycorrhizal and non-mycorrhizal soybean: D. Morandi and J.L. Le Quere; New Phytol. 117, 75 (1991) Full Text
The cytotoxicity of psoralidin from Psoralea corylifolia: Y.M. Yang, et al.; Planta Med. 62, 353 (1996) Abstract
Coumarins: A. Estevez-Braun and A.G. Gonzalez; Nat. Prod. Rep. 14, 465 (1997) Abstract
Cytotoxic constituents of Psoralea corylifolia: W. Mar, et al.; Arch. Pharm. Res. 24, 211 (2001) Abstract
Antibacterial compounds from the seeds of Psoralea corylifolia: N.A. Khatune, et al.; Fitoterapia 75, 228 (2004) Abstract
Inducible flavone in oats (Avena sativa) is a novel defense against plant-parasitic nematodes: I. R. Soriano, et al.; Nematology 94, 1207 (2004) Full Text
Antioxidants from a Chinese medicinal herb - Psoralea corylifolia L.: G. Jiangning, et al.; Food Chem. 91, 287 (2005)
In vitro protein tyrosine phosphatase 1B inhibitory phenols from the seeds of Psoralea corylifolia: Y.C. Kim, et al.; Planta Med. 71, 87 (2005) Abstract
Antidepressant-like effects of psoralidin isolated from the seeds of Psoralea Corylifolia in the forced swimming test in mice: L.T. Yi, et al.; Prog. Neuropsychopharmacol. Biol. Psychiatry 32, 510 (2008) Abstract
Further Categories Containing This Product:
Monoamine Neurotransmitters & Receptors Other Products • Antitumor Agents (Anti-proliferative) • Natural Products with Antibiotic Activity • Natural Products - Antioxidants • Natural Products - Other Signal Transduction Pathway Modulators • Protein Tyrosine Phosphatases Other Products
 
 
ALX-350-328 Revised 07-Apr-08
(+)-Madindoline A
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SYNONYMS MadA
MDL-A
[(2R), 3aR, 8aS]-8-[4-(n-Butyl)-2,5-dimethyl-1, 3-dioxo-2-(4-cyclopentyl)methyl]-3, 3a, 8,8a-tetrahydro-3a-hydroxy-2H-furo[2,3-b] indole
PRODUCT LINE Chemokines & Cytokines
PRODUCT CATEGORY Interleukin & Interleukin Receptors Other Products
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ALX-350-328-MC05   0.5 mg 330.00 USD Add To Cart
ALX-350-328-M001   1 mg 580.00 USD Add To Cart
Product Specification
FORMULA: C22H27NO4
MW: 370.2
SOURCE/HOST: Synthetic.
PURITY: ≥97%
APPEARANCE: Light yellow needles
SOLUBILITY: Soluble in methanol or 100% ethanol; insoluble in hexane.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

Product Description
Madindolines are noncytotoxic indole alkaloids originally isolated from a fermentation broth of Streptomyces nitrosporeus K93-071. (+)-Madindoline A (MadA; MDL-A) and (+)-madindoline B (MadB; MDL-B) are diastereomers with MadA being the more potent compound. MadA binds competitively but noncovalently to the extracellular domain of the membrane glycoprotein gp130 and inhibits the homodimerization of the trimeric IL-6/IL-6R/gp130 or the IL-11/gp130 complex, thus inhibiting activation of the JAK/STAT signal transduction pathway. MadA inhibits IL-6 and IL-11-induced osteoclastogenesis in vitro in a dose dependent manner and postmenopausal osteoporosis in vivo, by a mechanism different from that of 17β-estradiol. IL-6 activity is known to cause various diseases such as cancer cachexia, Castleman’s disease, Crohn’s disease, rheumatoid arthritis, hypercalcemia, and multiple myeloma. Madindolines are no longer available from natural sources due to mutation of the originating bacterial strain. Thus, synthetic routes have been developed to produce madindolines. Recently analogs of madindolines have been synthesized as potent IL-6 inhibitors.
Product Specific Literature References
Madindoline, a novel inhibitor of IL-6 activity from Streptomyces sp. K93-0711. I. Taxonomy, fermentation, isolation and biological activities: M. Hayashi, et al.; J. Antibiot. 49, 1091 (1996) Abstract
Madindolines, novel inhibitors of IL-6 activity from streptomyces sp. K93-0711. II. Physico-chemical properties and structural elucidation: S.Takamatsu, et. al.; J. Antibiot. 50, 1069 (1997) Abstract
Binding of madindoline A to the extracellular domain of gp130: A.Z. Saleh, et al.; Biochemistry 44, 10822 (2005) Abstract
Association of transcription factor APRF and protein kinase Jak1 with the interleukin-6 signal transducer gp130: C. Lutticken, et al.; Science 263, 89 (1994) Abstract
Suppression of bone resorption by madindoline A, a novel nonpeptide antagonist to gp130: M. Hayashi, et al.; PNAS 99, 14728 (2002) Abstract
Mechanisms of experimental cancer cachexia. Local involvement of IL-1 in colon-26 tumor: G. Strassmann, et.al.; J. Immunol. 150, 2341 (1993) Abstract
Pathogenic significance of interleukin-6 (IL-6/BSF-2) in Castleman’s disease: K. Yoshizaki, et al.; Blood 74, 1360 (1989) Abstract
Inhibition of IL-6 for the treatment of inflammatory diseases: N. Nishimoto & T. Kishimoto; Curr. Opin. Pharmacol. 4, 386 (2004) Abstract
Blockage of interleukin-6 receptor ameliorates joint disease in murine collagen-induced arthritis: N. Takagi, et al.; Arthritis Rheum. 41, 2117 (1998) Abstract
Interleukin-6 enhances hypercalcemia and bone resorption mediated by parathyroid hormone-related protein in vivo: J. de la Mata, et al.; J. Clin. Invest. 95, 2846 (1995) Abstract
Granulocyte-macrophage colony-stimulating factor synergizes with interleukin-6 in supporting the proliferation of human myeloma cells: X.G. Zhang, et al.; Blood 76, 2599 (1990) Abstract
Synthesis of (+)-madindoline A and (+)-madindoline B: L. Wan & M.A. Tius; Org. Lett. 9, 647 (2007) Abstract
Design, synthesis, and biological activities of madindoline analogues: D. Yamamoto, et al.; Bioorg. Med. Chem. Lett. 16, 2807 (2006) Abstract
Efficient total synthesis of novel bioactive microbial metabolites: T. Sunazuka, et al.; Acc. Chem. Res. 41, 302 (2008) Abstract
General Information
MANUFACTURER Manufactured by the Kitasato Institute, Tokyo.
Further Categories Containing This Product:
Natural Products - Other Signal Transduction Pathway Modulators • Alkaloids • Bone Metabolism Other Products
 
 
ALX-350-338 Revised 16-Jun-08
Ophiobolin B
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SYNONYMS Cochliobolin B
Zizanin B
Ophiobolsin A
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Signal Transduction Pathway Modulators
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ALX-350-338-M001   1 mg 330.00 USD Add To Cart
Product Specification
FORMULA: C25H38O4
MW: 402.6
CAS NUMBER: 5601-74-1
SOURCE/HOST: Isolated from Bipolaris leersia MST-FP107.
APPEARANCE: White to off-white solid.
FORMULATION: ≥95% (HPLC)
SOLUBILITY: Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

Product Description
Originally isolated from Helminthosporium sp. Inhibitor of calmodulin action in calcium regulation. Exhibits antibacterial, antitumor and nematocidal activities.
Product Specific Literature References
The structure of ophiobolin, a C25 terpenoid having a novel skeleton: S. Nozoe, et al.; JACS 87, 4968 (1965) Abstract
Microbial metabolites of ophiobolin A and antimicrobial evaluation of ophiobolins: E. Li, et al.; J. Nat. Prod. 58, 74 (1995) Abstract
The biology of ophiobolins: T.K. Au, et al.; Life Sci. 67, 733 (2000), (Review) Abstract
Further Categories Containing This Product:
Calmodulin Inhibitors • Natural Products with Antibiotic Activity • Natural Products - Antitumor Reagents • Natural Products - Antitumor Reagents
 
 
ALX-350-362 Revised 26-Mar-08
(+)-Egenine
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SYNONYMS 6-(6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6,8-dihydrofuro[3,4-E][1,3]benzodioxol-8-ol
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Signal Transduction Pathway Modulators
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ALX-350-362-M025   25 mg 95.00 USD Add To Cart
ALX-350-362-M100   100 mg 285.00 USD Add To Cart
Product Specification
FORMULA: C20H19NO6
MW: 369.4
CAS NUMBER: 6883-44-9
SOURCE/HOST: Isolated from Fumaria vaillantii or Corydalis decumbens.
PURITY: ≥98% (HPLC)
APPEARANCE: White to off-white crystalline solid.
SOLUBILITY: Soluble in ethyl acetate or chloroform; sparingly soluble in 100% ethanol or ether; practically insoluble in water.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

Product Description
First phthalideisoquinoline hemiacetal from a natural source. Inhibits Ca2+ currents and contractile responses in vitro.
Product Specific Literature References
Egenine: A possible intermediate in phthalideisoquinoline biogenesis: B. Gotzler, et al.; Tetrahedron 39, 577 (1983)
Synthesis of (-)-egenine (decumbensine) by asymmetric carbonyl addition: K.S. Rein & R.E. Gawley; Tetrahedron Lett. 31, 3711 (1990)
Synthesis of phthalide isoquinoline alkaloides (-)-egenine, (-)-corytensine, and (-)-bicuculline by asymmetric carbonyl addition of chiral dipole-stabilized organometallics: K.S. Rein & R.E. Gawley; J. Org. Chem. 56, 1564 (1991)
β-Phenylethylamines and the isoquinoline alkaloids: K.W. Bentley; Natural Prod. Rep. 11, 555 (1994), (Review)
1-Magnesiotetrahydroisoquinolyloxazolines as chiral nucleophiles in stereoselective additions to aldehydes: Auxiliary optimization, asymmetric synthesis of (+)-corlumine, (+)-bicuculline, (+)-egenine, and (+)-corytensine, and preliminary (13)C NMR studies: R.E. Gawley & P. Zhang; J. Org. Chem. 61, 8103 (1996) Abstract
Effects of alkaloids from Corydalis decumbens on contraction and electrophysiology of cardiac myocytes: S. Kadota, et al.; Phytother. Res. 10, 18 (1998)
Further Categories Containing This Product:
Calcium Signalling (Intracellular) Other Products • Alkaloids
 
 
ALX-350-366 Revised 03-Apr-08
Azaspiracid-1
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SYNONYMS AZA-1
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Other Toxins
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ALX-350-366-C001   1 µg 180.00 USD Add To Cart
Product Specification
FORMULA: C47H71NO12
MW: 842.1
CAS NUMBER: 214899-21-5
SOURCE/HOST: Islolated from marine mussel.
CONCENTRATION:

2μg/ml
PURITY: ≥95%
FORMULATION: Liquid. In methanol.
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
HAZARD: VERY TOXIC. MAY BE TERATOGENIC.

Product Description
Activator of JNK (c-Jun-N-terminal kinase). Cellular growth inhibitor and inducer of cytoskeletal alterations. Activator of caspases. Modulator of intracellular cAMP (cyclic adenosine monophosphate) and calcium levels. Inhibitor of cholesterol biosynthesis in human T lymphocyte cells. Potent teratogen to finfish. Cytotoxic to mammalian cells.
Product Specific Literature References
Multiple organ damage caused by a new toxin azaspiracid, isolated from mussels produced in Ireland: E. Ito, et al.; Toxicon 38, 917 (2000) Abstract
Azaspiracid-1, a potent, nonapoptotic new phycotoxin with several cell targets: Y. Roman, et al.; Cell. Signal. 14, 703 (2002) Abstract
Teratogenic effects of azaspiracid-1 identified by microinjection of Japanese medaka (Oryzias latipes) embryos: J.R. Coleman, et al.; Toxicon 45, 881 (2005) Abstract
Cytotoxic and cytoskeletal effects of azaspiracid-1 on mammalian cell lines: M.J. Twiner, et al.; Toxicon 45, 891 (2005) Abstract
Azaspiracids modulate intracellular pH levels in human lymphocytes: A. Alfonso, et al.; BBRC 346, 1091 (2006) Abstract
Cell growth inhibition and actin cytoskeleton disorganization induced by azaspiracid-1 structure-activity studies: N. Vilarino, et al.; Chem. Res. Toxicol. 19, 1459 (2006) Abstract
The c-Jun-N-terminal kinase is involved in the neurotoxic effect of azaspiracid-1: C. Vale, et al.; Cell Physiol. Biochem. 20, 957 (2007) Abstract
Effects of azaspiracid-1, a potent cytotoxic agent, on primary neuronal cultures. A structure-activity relationship study: C. Vale, et al.; J. Med. Chem. 50, 356 (2007) Abstract
Irreversible cytoskeletal disarrangement is independent of caspase activation during in vitro azaspiracid toxicity in human neuroblastoma cells: N. Vilarino, et al.; Biochem. Pharmacol. 74, 327 (2007) Abstract
Transcriptional profiling and inhibition of cholesterol biosynthesis in human T lymphocyte cells by the marine toxin azaspiracid: M.J. Twiner, et al.; Genomics 91, 289 (2008)