Altemariol

Saprophytic, dark pigmented fungi such as Alternaria spp. can infect a wide range of plant species, especially tissues that are exposed to other biotic or abiotic stressors and older and senescing plant tissues. Also, wet weather conditions favour attack by Alternaria spp. Inoculum of Alternaria and potentially production of altemariol is further enhanced when cereal straw and stubble is left on the soil surface and not sufficiently incorporated into the soil after harvest (direct seeding and minimum tillage systems). 

Davis V M and Stack M E (1994), Evaluation of altemariol and alterariol methyl ether for mutagenic activity in Salmonella thyphimurium , App. Environ. Microbiol. 60, 3901-3902. 

Griffin G F and Chu F S (1983), Toxicity of the alternaria metabolites altemariol, altemariolmethyl ether, altemuene, and tenuazonic acid in the chicken embryo assay , Appl. Environ. Microbiol., 46, 1420-1421. 

Although most of the compounds produced hy Alternaria are generally nontoxic, altemariol monomethyl ether has been shown to be mutagenic in bacteria (Ames tests) [166]. Tenuazonic acid (TA) is a protein synthesis inhibitor and is capable of chelating metal ions and forming nitrosamines. TA is also produced... 

Delgado, T. and Gomez, C.C. 1998. Natural occurrence of altemariol and altemariol methyl ether in Spanish apple juice concentrates. J. Chromatogr. A 815, 93-97. 

Lau, B.P.Y., Scott, P.M., Lewis, D.A., Kanhere, S.R., Cleroux, C., and Roscoe, V.A. 2003. Liquid chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry of the Altemaria mycotoxins altemariol and altemariol monomethyl ether in fruit juices and beverages. J. Chromatogr. A 998, 119-131. 

Toumas, V.H. and Stack, M.E. 2001. Production of alternariol and altemariol methyl ether by Alternaria alternata grown on fruits at various temperatures. J. Food Prot. 64, 528-532. 

Malonylidene nitrile and a dilorine are transformed into a fused pyran-2-one ring when heated with ethanolic hydrogen chloride [3002]. Reactions in which nitriles and hydrogen chloride interact have been reviewed [2547], When a 2-bromobenzamide is heated with orcinol in dilute sodium hydroxide containing copper(II) sulphate, the bromo and amino groups are lost C—C and C—O bon are formed in a synthesis of the dimethyl ether of altemariol, a compound found in some plants of the Liliacae family [2922]. 

Mixtures of metabolites (e.g. altemariol monomethyl ether, altemariol and altenuene) of the fungus, Altemaria, extracted from Adsorption Corasil II or Either Isooctane/... 

Lucas, G.B., R.W. Pero, J.P. Snow, and D. Harvan Analysis of tobacco for the altemaria toxins, altemariol and altemariol monomethyl ether 1. Agr. Food Chem. 19 (1972) 1274-1275. 

Scheme 11.3 Synthesis of altemariol and altemariol 9-methyl ether by Podlech et al. Reagents and conditions a) K2CO3, cat. Pd(PPh3)4, DMF, 100°C, 4 h, 78% b) NaH2P04 NaC102,2-methyl-...

Raistrick H, Stickings EC, Thomas R (1953) Studies in the Biochemistry of Microorganisms. 90. Altemariol and Altemariol Monomethyl Ether, Metabolic Products of Alternaria tenuis. Biochem J 55 421... 

Freeman GG (1965) Isolation of Altemariol and Altemariol Monomethyl Ether from Alternaria dauci (Kiihn) Groves and Skolko. Phytochemistry 5 719... 

Thomas R (1961) Studies in the Biosynthesis of Fungal Metabolites. 2. The Biosynthesis of Altemariol and its Relation to Other Fungal Phenols. Biochem J 78 748... 

Griffin GF, Chu FS (1983) Toxicity of ths Alternaria Metabolites Altemariol, Altemariol Methyl Ether, Altenuene, and Tenuazonic Acid in the Chicken Embryo Assay. Appl Environ Microbiol 46 1420... 

Pero RW, Main CE (1970) Chlorosis of Tobacco Induced by Altemariol Monomethyl Ether Produced by Altemaria tenuis. Phytopathology 60 1570... 

Spalding JW, Pero RW, Owois RG (1970) Inhibition of the G2 Phase of the Mammalian Cell Cycle by the Mycotoxin, Altemariol. J Cell Biol 47 199... 

Abell C, Bush BD, Staunton J (1986) Biomimetic Syntheses of the Polyketide Fungal Metabolites Altemariol and Rubrofusarin Models for Cyclisation Reactions Catalyzed by Polyketide Synthase Enzymes. J Chem Soc Perkin Trans 1 15... 

Harris TM, Hay JV (1976) Biogenetically Modeled Syntheses of Heptaacetate Metabolites. Altemariol and Lichexanthone. J Am Chem Soc 99 1631... 

Koch K, Podlech J, Pfeiffer E, Metzler M (2005) Total Synthesis of Altemariol. J Org Chem 70 3275... 

The C-methyl group attached to the ring in typical phenols (formed by an aldol condensation step), such as 6-methylsalicyclic acid (I), orsellinic acid (V), and altemariol (III), is derived from the acetyl-CoA primer. In other representative compounds, for example acetyl phloroglucinol (VI), an acetyl residue remains external to the ring as a result of cyclization by a C-acyla-tion process (Birch and Donovan, 1953). 

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