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Mycotoxins
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ALX-270-111 Revised 31-Jul-08
Patulin
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SYNONYMS 4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one
Clairformin
Clavacin
Clavatin
Claviformin
Leucopin
Mycoin C3
Mycosin
Penicidin
Terinin
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Antibiotics - Other Signal Transduction Pathway Modulators
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Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-270-111-M001   1 mg 20.00 USD Add To Cart
ALX-270-111-M005   5 mg 80.00 USD Add To Cart
ALX-270-111-M025   25 mg 320.00 USD Add To Cart
Product Specification
FORMULA: C7H6O4
MW: 154.1
CAS NUMBER: 149-29-1
MERCK INDEX: 14: 7053
RTECS: LV2625000
SOURCE/HOST: Isolated from Penicillium expansum.
PURITY: ≥98% (HPLC)
APPEARANCE: White to off-white solid.
SOLUBILITY: Soluble in water, 100% ethanol, ethyl acetate or DMSO (10mg/ml).
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HAZARD: MAY BE CARCINOGENIC. TOXIC.

Product Description
Inhibitor of protein farnesylation in a cell free assay. Inhibits incorporation of tritiated mevalonate into proteins in whole cells. Mycotoxin with anti-bacterial, potassium uptake inhibitory and possibly carcinogenic activities. Known contaminant of spoiled apples.
Product Specific Literature References
M. Birkinshaw, et al.; Lancet 245, 625 (1943)
J. Kahn; J. Pharmacol. Exp. Ther. 121, 234 (1957)
IARC Monographs 10, 205 (1976)
Chronology of patulin-induced alterations in membrane function of cultured renal cells, LLC-PK: R.T. Riley, et al.; Toxicol. Appl. Pharmacol. 102, 128 (1990) Abstract
Inhibition of protein prenylation by patulin: S. Miura, et al.; FEBS Lett. 318, 88 (1993) Abstract
Aneuploidogenic and clastogenic potential of the mycotoxins citrinin and patulin: E. Pfeiffer, et al.; Carcinogenesis 19, 1313 (1998) Abstract
Hplc detection of patulin in apple juice with GC/MS confirmation of patulin identity: J.A. Roach, et al.; Adv. Exp. Med. Biol. 504, 135 (2002), Review Abstract
Further Categories Containing This Product:
Mycotoxins • Farnesylation / Isoprenylation Reagents
 
 
ALX-350-017 Revised 18-Nov-08
Fumonisin B1
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Tumor Promoters
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ALX-350-017-M001   1 mg 60.00 USD Add To Cart
ALX-350-017-M005   5 mg 245.00 USD Add To Cart
Product Specification
FORMULA: C34H59NO15
MW: 721.8
CAS NUMBER: 116355-83-0
MERCK INDEX: 14: 4289
RTECS: TZ8350000
SOURCE/HOST: Isolated from Fusarium moniliforme.
PURITY: ~98% (TLC)
APPEARANCE: White to off-white powder.
SOLUBILITY: Soluble in water (10mg/ml), methanol (5mg/ml), DMSO (20mg/ml) or acetonitrile.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HAZARD: MAY BE MUTAGENIC. MAY BE TERATOGENIC. MAY BE CARCINOGENIC. HARMFUL.

Product Description
Mycotoxin. Induces DNA damage in the liver and cancer. Inhibitor of sphingosine biosynthesis. Induces apoptosis. Activates Akt (protein kinase B; PKB), which leads to increased survival, inhibition of GSK-3β activity and post-translational stabilization of cyclin D1.
Product Specific Literature References
Inhibition of sphingolipid biosynthesis by fumonisins. Implications for diseases associated with Fusarium moniliforme: E. Wang, et al.; J. Biol. Chem. 266, 14486 (1991) Abstract; Full Text
Fumonisin B1 inhibits sphingosine (sphinganine) N-acyltransferase and de novo sphingolipid biosynthesis in cultured neurons in situ: A.H. Merrill Jr., et al.; J. Biol. Chem. 268, 27299 (1993) Abstract; Full Text
Biological activities of fumonisins, mycotoxins from Fusarium moniliforme, in jimsonweed (Datura stramonium L.) and mammalian cell cultures: H.K. Abbas, et al.; Toxicon 31, 345 (1993) Abstract
Fumonisins and Alternaria alternata lycopersici toxins: sphinganine analog mycotoxins induce apoptosis in monkey kidney cells: H. Wang, et al.; PNAS 93, 3461 (1996) Abstract
A potential mechanism for fumonisin B(1)-mediated hepatocarcinogenesis: cyclin D1 stabilization associated with activation of Akt and inhibition of GSK-3beta activity: D. Ramljak, et al.; Carcinogenesis 21, 1537 (2000) Abstract
Implications of apoptosis for toxicity, carcinogenicity, and risk assessment: fumonisin B(1) as an example: Y.P. Dragan, et al.; Toxicol. Sci. 61, 6 (2001), Review Abstract
Fumonisin B(1): oxidative status and DNA damage in rats: A.M. Domijan, et al.; Toxicology 232, 163 (2007) Abstract
Further Categories Containing This Product:
Akt [PKB] / Related Products • Sphingolipids & Glycosphingolipids Other Products • Carcinogens & Tumor Promoters Other Products • Mycotoxins • DNA Damage & Repair Other Products • Natural Products - Apoptosis Inducers & Inhibitors
 
 
ALX-350-023 Revised 03-Jun-08
Cyclopiazonic acid
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SYNONYMS CPA
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - ATPase Inhibitors
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ALX-350-023-M005   5 mg 42.00 USD Add To Cart
ALX-350-023-M025   25 mg 145.00 USD Add To Cart
ALX-350-023-M100   100 mg 460.00 USD Add To Cart
Product Specification
FORMULA: C20H20N2O3
MW: 336.4
CAS NUMBER: 18172-33-3
RTECS: UY8587000
SOURCE/HOST: Isolated from Penicillium griseofulvum.
PURITY: ≥98% (TLC)
APPEARANCE: Off-white to yellow powder.
SOLUBILITY: Soluble in DMSO (50mg/ml), methylene chloride or methanol (10mg/ml).
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HAZARD: TOXIC.

Product Description
Mycotoxin. Cell permeable, reversible inhibitor of Ca2+-ATPases.
Product Specific Literature References
Cyclopiazonic acid is a specific inhibitor of the Ca2+-ATPase of sarcoplasmic reticulum: N.W. Seidler, et al.; J. Biol. Chem. 264, 17816 (1989) Abstract; Full Text
Acetylcholine Ca2+ stores refilling directly involves a dihydropyridine- sensitive channel in dog trachea: J.P. Bourreau, et al.; Am. J. Physiol. 261, C497 (1991) Abstract
Discrimination of Ca(2+)-ATPase activity of the sarcoplasmic reticulum from actomyosin-type ATPase activity of myofibrils in skinned mammalian skeletal muscle fibres: distinct effects of cyclopiazonic acid on the two ATPase activities: N. Kurebayashi & Y. Ogawa; J. Muscle Res. Cell Motility 12, 355 (1991) Abstract
Coupling between intracellular Ca2+ stores and the Ca2+ permeability of the plasma membrane. Comparison of the effects of thapsigargin, 2,5-di- (tert-butyl)-1,4-hydroquinone, and cyclopiazonic acid in rat thymic lymphocytes: M.J. Mason, et al.; J. Biol. Chem. 266, 20856 (1991) Abstract; Full Text
Cyclopiazonic acid depletes intracellular Ca2+ stores and activates an influx pathway for divalent cations in HL-60 cells: N. Demaurex, et al.; J. Biol. Chem. 267, 2318 (1992) Abstract; Full Text
Cyclopiazonic acid, an inhibitor of the sarcoplasmic reticulum Ca(2+)- pump, reduces Ca(2+)-dependent K+ currents in guinea-pig smooth muscle cells: M. Suzuki, et al.; Br. J. Pharmacol. 107, 134 (1992) Abstract
Effects of cyclopiazonic acid, a novel Ca(2+)-ATPase inhibitor, on contractile responses in skinned ileal smooth muscle: Y. Uyama, et al.; Br. J. Pharmacol. 106, 208 (1992) Abstract
Effects of cyclopiazonic acid and ryanodine on cytosolic calcium and contraction in vascular smooth muscle: F. Abe, et al.; Br. J. Pharmacol. 118, 1711 (1996) Abstract
Natural and in vitro coproduction of cyclopiazonic acid and aflatoxins: M.L. Martins & H.M. Martins; J. Food Prot. 62, 292 (1999) Abstract
Recent advances in analytical methodology for cyclopiazonic acid: J.W. Dorner; Adv. Exp. Med. Biol. 504, 107 (2002), Review Abstract
Cyclopiazonic acid reduces the coupling factor of the Ca2+-ATPase acting on Ca2+ binding: F. Martinez-Azorin; FEBS Lett. 576, 73 (2004) Abstract
Further Categories Containing This Product:
Ca2+-ATPase / Related Products • Neurotoxins • Mycotoxins
 
 
ALX-350-127 Revised 07-May-08
Fumitremorgin C
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SYNONYMS FTC
SM-Q
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Mycotoxins
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ALX-350-127-C250   250 µg 130.00 USD Add To Cart
Product Specification
FORMULA: C22H25N3O3
MW: 379.5
CAS NUMBER: 118974-02-0
SOURCE/HOST: Isolated from Aspergillus fumigatus.
PURITY: ≥96% (HPLC)
APPEARANCE: Off-white to light brown powder.
SOLUBILITY: Soluble in DMSO, methanol or chloroform.
SHIPPING: AMBIENT
LONG TERM STORAGE: +4°C
HAZARD: TOXIC.

Product Description
Mycotoxin. Tremorgenic. Potent and specific inhibitor of the breast cancer resistance protein (BCRP; ABCG2). Reverses multidrug resistance mediated by BCRP and increases cytotoxicity of several anticancer agents in vitro.
Product Specific Literature References
Mycotoxins produced by Aspergillus fumigatus species isolated from molded silage: R.J. Cole, et al.; J. Agric. Food Chem. 25, 826 (1977) Abstract
Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. I. Taxonomy, fermentation, isolation and biological properties: C.B. Cui, et al.; J. Antibiot. 49, 527 (1996) Abstract
Reversal of a novel multidrug resistance mechanism in human colon carcinoma cells by fumitremorgin: S.K. Rabindran, et al.; Cancer Res. 58, 5850 (1998) Abstract
Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein.: S.K. Rabindran, et al.; Cancer Res. 60, 47 (2000) Abstract
Characterization of drug transport, ATP hydrolysis, and nucleotide trapping by the human ABCG2 multidrug transporter. Modulation of substrate specificity by a point mutation.: Ozvegy, et al.; J. Biol. Chem. 277, 47980 (2002) Abstract
The role of breast cancer resistance protein in acute lymphoblastic leukemia.: S.L. Plasschaert, et al.; Clin. Cancer Res. 9, 5171 (2003) Abstract
Plasma pharmacokinetics and tissue distribution of the breast cancer resistance protein (BCRP/ABCG2) inhibitor fumitremorgin C in SCID mice bearing T8 tumors: T.S. Garimella, et al.; Cancer Chemother. Pharmacol. 55, 101 (2005) Abstract
General Information
BACKGROUND/TECHNICAL INFORMATION Optical Rotation: [α]D= +19° ±1° (c=1.0 in methanol).
Further Categories Containing This Product:
Other Natural Products for Cancer Research • Breast Cancer Resistance Protein [BCRP / MXR] / Related Products • MDR Inhibitors
 
 
ALX-350-139 Revised 18-Feb-08
Alternariol
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SYNONYMS AOH
3,7,9-Trihydroxy-1-methyl-6H-dibenzo(b,d)pyran-6-one
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Mycotoxins
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ALX-350-139-M001   1 mg 110.00 USD Add To Cart
Product Specification
FORMULA: C14H10O5
MW: 258.2
CAS NUMBER: 641-38-3
RTECS: HP8757000
SOURCE/HOST: Isolated from Alternaria sp.
PURITY: ≥97% (HPLC)
APPEARANCE: Off-white to brown solid.
SOLUBILITY: Soluble in DMSO or 100% ethanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Protect from light.
HAZARD: VERY TOXIC. MAY BE MUTAGENIC.
IDENTITY: Identity determined by MS, 1H-NMR.

Product Description
Mycotoxin contaminant of fruit and cereal products. Exhibits antifungal and phytotoxic activity. Cholinesterase inhibitor.
Product Specific Literature References
Studies in the biochemistry of micro-organisms. 90. Alternariol and alternariol monomethyl ether, metabolic products of Alternaria tenuis: H. Raistrick, et al.; Biochem. J. 55, 421 (1953) Abstract; Full Text
Studies in the biosynthesis of fungal metabolites. 2. The biosynthesis of alternariol and its relation to other fungal phenols: R. Thomas; Biochem. J. 78, 748 (1961) Abstract; Full Text
Effect of substrate on metabolite production of Alternaria alternata: R. Burroughs, et al.; Appl. Environ. Microbiol. 31, 685 (1976) Abstract; Full Text
Light inhibits the production of alternariol and alternariol monomethyl ether in Alternaria alternata: K. Soderhall, et al.; Appl. Environ. Microbiol. 36, 655 (1978) Abstract; Full Text
Toxicity of the Alternaria metabolites alternariol, alternariol methyl ether, altenuene, and tenuazonic acid in the chicken embryo assay: G.F. Griffin and F.S. Chu; Appl. Environ. Microbiol. 46, 1420 (1983) Abstract; Full Text
Alternariol, a dibenzopyrone mycotoxin of Alternaria spp., is a new photosensitizing and DNA cross-linking agent: F. DiCosmo and N.A. Straus; Experientia 41, 1188 (1985) Abstract
Nitrogen inhibition of mycotoxin production by Alternaria alternata: M. Orvehed, et al.; Appl. Environ. Microbiol. 54, 2361 (1988) Abstract; Full Text
Evaluation of alternariol and alternariol methyl ether for mutagenic activity in Salmonella typhimurium: V.M. Davis and M.E. Stack; Appl. Environ. Microbiol. 60, 3901 (1994) Abstract; Full Text
The inhibitory effect of extracts from Fructus lycii and Rhizoma polygonati on in vitro DNA breakage by alternariol: D.S. Xu, et al.; Biomed. Environ. 9, 67 (1996) Abstract
Total synthesis of alternariol: K. Koch, et al.; J. Org. Chem. 70, 3275 (2005) Abstract
Mutagenicity of the mycotoxin alternariol in cultured mammalian cells: E.M. Brugger, et al.; Toxicol. Lett. 164, 221 (2006) Abstract
Estrogenic and clastogenic potential of the mycotoxin alternariol in cultured mammalian cells: L. Lehmann, et al.; Food Chem. Toxicol. 44, 398 (2006) Abstract
Further examination of the effects of nitrosylation on Alternaria alternata mycotoxin mutagenicity in vitro: T.J. Schrader, et al.; Mutat. Res. 606, 61 (2006) Abstract
Novel oxidative in vitro metabolites of the mycotoxins alternariol and alternariol methyl ether: E. Pfeiffer, et al.; Mol. Nutr. Food Res. 51, 307 (2007) Abstract
Further Categories Containing This Product:
Natural Products - Antifungal Agents
 
 
ALX-350-237 Revised 21-Apr-08
Fumonisin B2
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Tumor Promoters
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ALX-350-237-M001   1 mg 155.00 USD Add To Cart
Product Specification
FORMULA: C34H59NO14
MW: 705.8
CAS NUMBER: 116355-84-1
MERCK INDEX: 14: 4289 (Fumonisin B1)
RTECS: TZ8335000
SOURCE/HOST: Isolated from Fusarium moniliforme.
PURITY: ≥96%
APPEARANCE: White to off-white solid.
SOLUBILITY: Soluble in methanol (5mg/ml).
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HAZARD: MAY BE CARCINOGENIC. VERY TOXIC.

Product Description
Mycotoxin, structurally similar to fumonisin B1 (Prod. No. ALX-350-017). Found as contaminant mostly in corn silage; was detected recently for the first time in the industrially important Aspergillus niger. Induces cancer. Inducer of apoptosis.
Product Specific Literature References
Biological activities of fumonisins, mycotoxins from Fusarium moniliforme, in jimsonweed (Datura stramonium L.) and mammalian cell cultures: H.K. Abbas, et al.; Toxicon 31, 345 (1993) Abstract
Liquid chromatographic determination of the mycotoxin fumonisin B2 in physiological samples: G.S. Shephard, et al.; J. Chromatogr. A 692, 39 (1995) Abstract
Fumonisins and Alternaria alternata lycopersici toxins: sphinganine analog mycotoxins induce apoptosis in monkey kidney cells: H. Wang, et al.; PNAS 93, 3461 (1996) Abstract
Liquid chromatographic determination of fumonisins B1, B2, and B3 in corn silage: E.K. Kim, et al.; J. Agric. Food Chem. 52, 196 (2004) Abstract
Fumonisin B2 Production by Aspergillus niger: J.C. Frisvad, et al.; J. Agric. Food Chem. 55, 9727 (2007) Abstract
Further Categories Containing This Product:
Carcinogens & Tumor Promoters Other Products • Mycotoxins • Natural Products - Apoptosis Inducers & Inhibitors
 
 
ALX-350-239 Revised 22-Apr-08
Gliotoxin
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SYNONYMS [3R-(3α, 5aβ,6β,10aα)]-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epi-dithiopyrazino[1,2-a]indole-1,4-dione
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Antibiotics - Apoptosis Inducers & Inhibitors
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Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-350-239-M001   1 mg 60.00 USD Add To Cart
Product Specification
FORMULA: C13H14N2O4S2
MW: 326.4
CAS NUMBER: 67-99-2
MERCK INDEX: 14: 4441
RTECS: KB4725000
SOURCE/HOST: Isolated from Gladiocladium fimbriatum.
PURITY: ≥98% (HPLC)
APPEARANCE: White to light yellow solid.
SOLUBILITY: Soluble in DMSO or methanol (10mg/ml).
SHIPPING: AMBIENT
LONG TERM STORAGE: +4°C
USE/STABILITY: Stock solutions are stable for up to 3 months when stored at -20°C.
HAZARD: TOXIC.

Product Description
Immunomodulating mycotoxin which acts by blocking membrane thiol groups. Causes apoptotic cell death in macrophages and thymocytes. Induces Ca2+ release from intact rat liver mitochondria. Inhibits the activation of transcription factor NF-κB. Antioxidant.
Product Specific Literature References
Identification of an agent in cultures of Aspergillus fumigatus displaying anti-phagocytic and immunomodulating activity in vitro: A. Müllbacher, et al.; J. Gen. Microbiol. 131, 1251 (1985) Abstract
R.J. Jones & J.G. Hancock; J. Gen. Microbiol. 134, 2067 (1988)
Gliotoxin stimulates Ca2+ release from intact rat liver mitochondria: M. Schweizer & C. Richter; Biochemistry 33, 13401 (1994) Abstract
Extracellular calcium is not required for gliotoxin or dexamethasone- induced DNA fragmentation: a reappraisal of the use of EGTA: P. Waring & A. Sjaarda; Int. J. Immunopharmacol. 17, 403 (1995) Abstract
Gliotoxin and related epipolythiodioxopiperazines: P. Waring & J. Beaver; Gen. Pharmacol. 27, 1311 (1996), Review Abstract
The immunosuppressive fungal metabolite gliotoxin specifically inhibits transcription factor NF-kappaB: H.L. Pahl, et al.; J.Exp. Med. 183, 1829 (1996) Abstract
Aspergillus fumigatus suppresses the human cellular immune response via gliotoxin-mediated apoptosis of monocytes: M. Stanzani, et al.; Blood 105, 2258 (2005) Abstract
Discovery of gliotoxin as a new small molecule targeting thioredoxin redox system: H.S. Choi, et al.; BBRC 359, 523 (2007) Abstract
Further Categories Containing This Product:
Antioxidants, Flavonoids & Free Radical Scavengers Other Products • Natural Products - NF-kB Pathway Inhibitors • Mycotoxins • Antibiotics - Immunomodulators
 
 
ALX-350-317 Revised 08-Apr-08
Tenuazonic acid
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Antitumor Antibiotics
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ALX-350-317-MC05   0.5 mg 150.00 USD Add To Cart
Product Specification
FORMULA: C10H15NO3
MW: 197.3
CAS NUMBER: 610-88-8
MERCK INDEX: 14: 9149
RTECS: UY7425000
SOURCE/HOST: Isolated from Alternaria sp.
PURITY: ≥97% (HPLC)
APPEARANCE: Brown oily solid.
SOLUBILITY: Soluble in DMSO or 100% ethanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Protect from light.
IDENTITY: Identity determined by 1H-NMR, 13C-NMR and MS.

Product Description
Antineoplastic compound exhibiting antitumor, antiviral and antibacterial activity. Inhibits protein synthesis by suppression at the ribosome. May act as a mycotoxin.
Product Specific Literature References
Microbial metabolites with insecticidal properties: M. Cole & G.N. Rolinson; Appl. Microbiol. 24, 660 (1972) Abstract
Microbial production of tenuazonic acid analogues: S. Gatenbeck & J. Sierankiewicz; Antimicrob. Agents Chemother. 3, 308 (1973) Abstract
Inhibition of mouse skin tumor promotion by tenuazonic acid: M. Antony, et al.; Cancer Lett. 61, 21 (1991) Abstract
Further Categories Containing This Product:
Antitumor Agents (Anti-proliferative) • Mycotoxins • Antibiotics - Antiviral / Anti-HIV
 
 
ALX-350-322 Revised 20-Feb-08
Equisetin