Revision of the structures of the naturally occurring acyl tetronic acids: Dehydrocarolic acid, terrestric acid and garlic acid.

Jacobsen, Jens Peter; Reffstrup, Torsten; Cox, Robert E.; Holker, J. S. E.; Boll, Per M.

doi:10.1016/s0040-4039(01)85457-5

Cited by 22 publications

(27 citation statements)

References 9 publications

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“…The use of strongly acidic conditions (0.1% TFA) improved the peak shape and allowed purification of the compound, which was identified as the novel metabolite, dehydroterrestric acid ( t R 3.05 min, 14.9%; λ max 246, 292 nm; ESIMS m/z [M+H 2 O–H] – 225, [M+H] + 209). Analysis of the 1 H and 13 C NMR spectra of dehydroterrestric acid (Table J in S1 File; Figures T and U in S1 File) revealed an equilibrating 5/4 mixture of Z - and E -isomers, which has been previously observed for the closely related Penicillium metabolites terrestric acid, carolic acid and carlic acid [23]. In DMSO- d 6 solution, dehydroterrestric acid exists exclusively as a cyclic ether, while in aqueous solution, the cyclic form is in equilibrium with a ring-opened hydrated form (Fig 3).…”

Section: Resultssupporting

confidence: 52%

Aspergillus hancockii sp. nov., a biosynthetically talented fungus endemic to southeastern Australian soils

Pitt

Lange

Lacey³

et al. 2017

PLoS ONE

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Aspergillus hancockii sp. nov., classified in Aspergillus subgenus Circumdati section Flavi, was originally isolated from soil in peanut fields near Kumbia, in the South Burnett region of southeast Queensland, Australia, and has since been found occasionally from other substrates and locations in southeast Australia. It is phylogenetically and phenotypically related most closely to A. leporis States and M. Chr., but differs in conidial colour, other minor features and particularly in metabolite profile. When cultivated on rice as an optimal substrate, A. hancockii produced an extensive array of 69 secondary metabolites. Eleven of the 15 most abundant secondary metabolites, constituting 90% of the total area under the curve of the HPLC trace of the crude extract, were novel. The genome of A. hancockii, approximately 40 Mbp, was sequenced and mined for genes encoding carbohydrate degrading enzymes identified the presence of more than 370 genes in 114 gene clusters, demonstrating that A. hancockii has the capacity to degrade cellulose, hemicellulose, lignin, pectin, starch, chitin, cutin and fructan as nutrient sources. Like most Aspergillus species, A. hancockii exhibited a diverse secondary metabolite gene profile, encoding 26 polyketide synthase, 16 nonribosomal peptide synthase and 15 nonribosomal peptide synthase-like enzymes.

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Section: Resultssupporting

confidence: 52%

Aspergillus hancockii sp. nov., a biosynthetically talented fungus endemic to southeastern Australian soils

Pitt

Lange

Lacey³

et al. 2017

PLoS ONE

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“…The biosynthesis of nodulisporacid A (1) may be similar to that of lowdenic acid (Angawi et al, 2003), involving the condensation of a modified 12-carbon polyketide (decorating as a side chain, the furylidene ring, and C-1 and C-2 of the tetrahydrofurandione ring) with a four carbon dicarboxylic acid. Such tetronic acid biosynthesis had been experimentally proven, for examples, italicic acid (Arai et al, 1989), and carolic acid (Jacobsen et al, 1978;Simonsen et al, 1980). Lowdenic acid and nodulisporacid A (1) shared the same core structure (Fig.…”

Section: Structural Determinationmentioning

confidence: 93%

“…The evidence from the similarity of 13 C NMR resonances (Table 1) of C-2 (d C 93.3) and C-1 0 (d C 180.1) of lowdenic acid (Angawi et al, 2003) and those [C-2 (d C 93.4) and C-1 0 (d C 179.4)] of nodulisporacid A (1) further confirmed the structure of nodulisporacid A (1). Assignment of 1 H and 13 C resonances for the E-isomer and Z-isomer of nodulisporacid A (1) was accomplished by correlation with E and Z isomers of lowdenic acid and carolic acid (Angawi et al, 2003;Jacobsen et al, 1978). Generally, d C of C-1 of the E-isomer was about 3 ppm lower field than that of the Z-isomer (Angawi et al, 2003;Jacobsen et al, 1978).…”

Section: Structural Determinationmentioning

confidence: 99%

“…Assignment of 1 H and 13 C resonances for the E-isomer and Z-isomer of nodulisporacid A (1) was accomplished by correlation with E and Z isomers of lowdenic acid and carolic acid (Angawi et al, 2003;Jacobsen et al, 1978). Generally, d C of C-1 of the E-isomer was about 3 ppm lower field than that of the Z-isomer (Angawi et al, 2003;Jacobsen et al, 1978). Chemical transformations of nodulisporacid A (1) by methylation, benzylation, and hydrogenation yielded respective products 2, 3, and 4 ( Fig.…”

Section: Structural Determinationmentioning

confidence: 99%

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Cytotoxic and antiplasmodial substances from marine-derived fungi, Nodulisporium sp. and CRI247-01

et al. 2008

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“…CRIF1 and the pestalotic acids A-G 2 Pestalotiopsis yunnanensis. [16][17][18][19][20][21][22][23] Due to the high diversity of side chain substitutions only two representatives of this family are depicted in Fig. 2.…”

Section: Linear Tetronatesmentioning

confidence: 99%

Recent advances in the field of bioactive tetronates

et al. 2014

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Covering: up to mid-2014 Over the last several decades, the number of pharmacologically active natural products has significantly increased and several natural product families have taken shape. This review highlights the family of tetronate and spirotetronate compounds, which show a vast structural and functional diversity. The rapid growth of this group has created the need for a comprehensive overview and classification system, which we have devised based on structural characteristics. An updated overview is provided based on known tetronates, intended to spur further research in this field by identifying common structural features and general principles of their biosynthesis. We also compare a selection of chemical syntheses of representative compounds belonging to individual subtypes, both in terms of their efficiency as well as the extent to which they are biomimetic. This review also summarizes progress in unraveling some of the principles underlying the potent and varied bioactivities of natural tetronate antibiotics, and in identifying and better understanding their structure–activity relationships and modes of action.DFG, EXC 314, Unifying Concepts in Catalysi

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Revision of the structures of the naturally occurring acyl tetronic acids: Dehydrocarolic acid, terrestric acid and garlic acid.

Cited by 22 publications

References 9 publications

Aspergillus hancockii sp. nov., a biosynthetically talented fungus endemic to southeastern Australian soils

Aspergillus hancockii sp. nov., a biosynthetically talented fungus endemic to southeastern Australian soils

Cytotoxic and antiplasmodial substances from marine-derived fungi, Nodulisporium sp. and CRI247-01

Recent advances in the field of bioactive tetronates

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