Studies in the biosynthesis of fungal metabolites. 4. Alternariol monomethyl ether and its relation to other phenolic metabolites of <i>Alternaria tenuis</i>

Thomas, Robert

doi:10.1042/bj0800234

Cited by 50 publications

(19 citation statements)

References 15 publications

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“…[10] In 1957, altertenuol, a minor toxin produced by Alternaria tenuis, was isolated. [12] In 1973, altenuisol, a toxin with identical molecular formula (C 14 H 10 O 6 ) but slightly different melting point was isolated from Alternaria tenuis by Pero et al [13] Although the 1 H NMR spectroscopic data were available for the latter compound, [2] no unambiguous evidence was available for proposed structure 1 given in Figure 1. [12] In 1973, altenuisol, a toxin with identical molecular formula (C 14 H 10 O 6 ) but slightly different melting point was isolated from Alternaria tenuis by Pero et al [13] Although the 1 H NMR spectroscopic data were available for the latter compound, [2] no unambiguous evidence was available for proposed structure 1 given in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Revision of the Structure and Total Synthesis of Altenuisol

2012

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A total synthesis of the reported structure of altenuisol is described. Comparison of the 1H NMR spectra of the synthesized compound and of the natural product revealed that the originally proposed structure was not correct. Consequently, two constitutional isomers were synthesized. The spectra of one of these compounds – a structure originally proposed as the structure of altertenuol – matched perfectly with the spectra of the natural product. The total synthesis of altenuisol was thus achieved starting with phloroglucinic acid and protocatechuic aldehyde in 10 steps and in 23 % yield, where the longest linear sequence consisted of 6 steps. The key step was a Suzuki coupling with concomitant formation of the lactone ring. Whether altertenuol is identical with altenuisol could not be decided.

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Section: Introductionmentioning

confidence: 99%

Revision of the Structure and Total Synthesis of Altenuisol

2012

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“…Some Alternaria-derived dibenzo-α-pyrones were approved as the host-specific phytotoxins including altenuene (1), alternariol (10), alternariol 9-methyl ether (11), alternuisol (15), and dehydroaltenusin (17) [9,10,37,39,41,45].…”

Section: Phytotoxicitymentioning

confidence: 99%

Natural Dibenzo-α-Pyrones and Their Bioactivities

Mao

Sun

et al. 2014

Molecules

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Natural dibenzo-α-pyrones are an important group of metabolites derived from fungi, mycobionts, plants and animal feces. They exhibit a variety of biological activities such as toxicity on human and animals, phytotoxicity as well as cytotoxic, antioxidant, antiallergic, antimicrobial, antinematodal, and acetylcholinesterase inhibitory properties. Dibenzo-α-pyrones are biosynthesized via the polyketide pathway in microorganisms or metabolized from plant-derived ellagitannins and ellagic acid by intestinal bacteria. At least 53 dibenzo-α-pyrones have been reported in the past few decades. This mini-review aims to briefly summarize the occurrence, biosynthesis, biotransformation, as well as their biological activities and functions. Some considerations related to synthesis, production and applications of dibenzo-α-pyrones are also discussed.

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“…has the ability to produce various of terpenoids, including diterpenoids (Visconti et al, 1992), sesquiterpenoids (Gamboa-Angulo et al, 2002), triterpenoids (Gamboa-Angulo et al, 1997) and mixed terpenoids which have a multiple biogenesis (Ichihara et al, 1983;Kjer et al, 2009;Pero et al, 1973;Thomas, 1961). However, to the best of our knowledge, there are rare reports on sesterterpeniods from Alternaria sp.…”

Section: Introductionmentioning

confidence: 78%