Publisher Summary This chapter summarizes the methods available for the synthesis of cyclic hydroxamic acids––to outline their characteristic reactions, and to present some useful physical data. Their synthesis, some biological and physical properties are also reviewed. A classification of naturally occurring hydroxamic acids in terms of their biological function or activity is provided. They are distinguished as: (1) growth factors, (2) antibiotics, and (3) microbial pigments. The naturally occurring compounds are arranged in order of increasing molecular complexity. A vast majority of syntheses methods of cyclic hydroxamic acids depend on condensation reactions involving only familiar processes of acylation or alkylation of hydroxylamine derivatives. The principles of such syntheses are outlined by condensation reactions, oxidative processes, displacement reactions, and ring expansions. Alicyclic hydroxamic acids undergo several specific characteristic reactions—namely, thermal decomposition, oxidation, reduction, reactions in acidic or basic media, and alkylation. The presence of a cyclic hydroxamic acid function in a molecule is recognized by the red or violet color given with ferric chloride and by the characteristic changes in the infrared spectra of the alkyl and acyl derivatives with respect to the spectrum of the free acid.

Hydroxyaspergillic Acid as Growth Inhibitant against Hiochi-bacteria

Cyclic Hydroxamic Acids

Host plant specificity depends on recognition of the host and the ability to discriminate it from nonhost plants. Chilo suppressalis (Walker) (Lepidoptera: Crambidae), an important insect pest of rice, is considered to be polyphagous, although few papers have ever reported infestation of C. suppressalis on most of the recorded hosts. The present investigation was designed to test whether two important gramineous crops, wheat and corn, are host plants of C. suppressalis based on the host-plant finding process in cage and Y-tube olfactometer tests, oviposition and egg hatching, and larval feeding and survival. In the cage tests, gravid C. suppressalis females did not differentiate rice plants from wheat or corn plants when only visual cues were involved, but were more attracted to rice plants when only olfactory cues or both vision and olfaction were present. The Y-tube olfactometer tests further confirmed that the females did not prefer wheat or corn plants, and revealed that they responded equally to clean air and odors from wheat or corn plants. Under no-choice and choice condition alike, the females laid eggs on a lower proportion of wheat and corn plants and egg number and hatching rate were significantly reduced on wheat and/or corn plants than on rice plants. Larval feeding was not observed in wheat and lower in corn than in rice plants, and no pupae or surviving larvae were collected from wheat and corn plants. The results suggest that wheat and corn are not host plants of C. suppressalis. These findings are discussed in context of host-finding process in C. suppressalis and management of resistance to transgenic Bt rice.

https://bioone.org/journals/Environmental-Entomology/volume-39/issue-6/EN10081/Host-Status-of-Wheat-and-Corn-for-Chilo-suppressalis-Lepidoptera/10.1603/EN10081.pdf

Host Status of Wheat and Corn for Chilo suppressalis (Lepidoptera: Crambidae)

Synthesis of neoaspergillic acid

Synthesis of 1-hydroxy-3-isobutyl,-6-(1-hydroxy-1-methylethyl)-2-pyrazinone and the structure of muta-aspergillic acid

Publisher Summary The fungal alkaloids seem to be characteristic in utilizing amino acid itself as its component in contrast to the higher plant alkaloids, which are biosynthesized mainly from the amine produced by decarboxylation of amino acid. This chapter provides an overview of the fungal alkaloidal metabolites isolated from Aspergillus species, which are classified by biogenetic category. Aspergillic acid , C 12 H 20 N 2 O 2 , is a monobasic acid that also possesses a weakly basic group. A deep red coloration with FeCl 3 and formation of a green cupric salt suggests that aspergillic acid is a hydroxamic acid derivative. Aspergillic acid is produced by Asp. flavus grown on a medium supplemented with radioactive leucine and isoleucine, and hydrolysis of the labeled metabolite shows that it is biosynthesized from one molecule each of leucine and isoleucine. Few fungal metabolites consist of a diketopiperazine ring derived from tryptophan and an amino acid other than alanine and proline. Those known in Aspergillus species include ditryptophenaline and D-valyl-L-tryptophan anhydride.

Hydroxyaspergillic Acid as Growth Inhibitant against Hiochi-bacteria

Citations

Cyclic Hydroxamic Acids

Host Status of Wheat and Corn for Chilo suppressalis (Lepidoptera: Crambidae)

Synthesis of neoaspergillic acid

Synthesis of 1-hydroxy-3-isobutyl,-6-(1-hydroxy-1-methylethyl)-2-pyrazinone and the structure of muta-aspergillic acid

Chapter 4 Alkaloidal Substances from Aspergillus Species

Related Papers (5)

Hydroxyaspergillic Acid as Growth Inhibitant against Hiochi-bacteria:Studies on Growth Inhibiton of Hiochi-bacteria, Specific Saprophytes of Saké. Part 4

Muta-aspergillic Acid, A New Growth Inhibitant Against Hiochi-bacteria

Repressive Effect of Barrel Materials on the Growth of Hiochi-Bacteria

Studies on Growth Inhibition of Hiochi-bacteria, Specific Saprophytes of Sake:Part VIII. Structure of Muta-aspergillic Acid (2)

The lactice acid bacteria