Shin-Ichi Hatanaka

3,4-dihydroxy-2-hydroxymethylpyrrolidine from Arachniodes standishii

Abstract 3,4-Dihydroxy-2-hydroxymethylpyrrolidine, which has not been encountered naturally before, was isolated from the Pteridophyte Arachniodes standishii . Its configuration was determined as 2,3- cis and 3,4- trans from NMR spectra.

Oligosaccharides in the seeds of Sesamum indicum L

Abstract Sesamum seed trisaccharide was isolated and identified as planteose. The tetrasaccharide fraction obtained from the same plant material was most likely a mixture of lychnose and a new isomer of it, for which the name “Sesamose” is proposed. Experimental results are discussed in relation to the nature of the higher oligosaccharides of the material.

A chlorohydrin amino acid from Amanita abrupta

Abstract A new amino acid, (2 S ,4 Z )-2-amino-5-chloro-6-hydroxy-4-hexenoic acid, has been isolated from Amanita abrupta . Three other unusual amino acids were also isolated from the same fungus.

Stereochemistry of 2-aminopimelic acid and related amino acids in three species of asplenium

Abstract We previously reported two free D -amino acids, D-2-aminopimelic acid ( D -APA) and trans -3,4-dehydro- D -2-aminopimelic acid (D-Δ-APA), from Asplenium unilaterale . In the present work we isolated 4-hydroxy-2-aminopimelic acid (OH-APA) from the same plant and determined it to be the α- L -form. We also investigated the configurations of these amino acids isolated from A. prolongatum and A. wilfordii which are morphologically distinct from A. unilaterale . In A. prolongatum , APA was the D - and OH-APA was the L -isomer. In contrast, APA from A. wilfordii was partially racemized and the degree of racemization was significantly different in plant material collected in July and November, L:D = 3:2 and 3:7, respectively. In A. wilfordii OH-APA was almost pure L - and Δ-APA was mostly the D -isomer.

Cis-5-hydroxy-L-pipecolic acid from Morus alba and Lathyrus japonicus

Abstract cis-5-Hydroxy- L -pipecolic acid was isolated and characterized from the leaves of Morus alba and the seeds of Lathyrus japonicus. The trans-form was also obtained from the former.

A new amino acid isolated from Morchella esculenta and related species

Abstract A new amino acid was isolated from mushrooms, Morchella esculenta , and related species. From the results of elementary analysis, deamination, and NMR spectrum, its structure was shown to be cis -3-amino- l -proline. It is present in a free state in fruit bodies of M. esculenta , M. conica , and M. crassipes , as well as in their cultured mycelia and its occurrence seems to be confined to the genus Morchella .

Amino Acids from Mushrooms

Two dimensional paper chromatography or automated amino acid analysis of the “amino acid-fraction” prepared from ethanol extracts of plants and fungi reveals the existence of many ninhydrin-positive substances. These are mostly protein amino acids in the free state, but also include several non-protein amino acids, i.e., α-aminoadipic acid, ornithine, citrulline, β-alanine, γ-aminobutanoic acid and cysteic acid as well as ethanolamine.

d-2-Aminopimelic acid and trans-3,4-dehydro-d-2-aminopimelic acid from Asplenium unilaterale

Abstract d -2-Aminopimelic acid and a novel amino acid, trans-3,4-dehydro- d -2-aminopimelic acid were isolated and characterized from Asplenium unilaterale. Their distribution in Aspleniaceae was also investigated.

l-2-Aminohex-4-ynoic acid: A new amino acid from Tricholomopsis rutilans

Abstract A new amino acid was isolated from fruit bodies of Tricholomposis rutilans (Fr.) Sing. Its structure was shown to be l -2-aminohex-4-ynoic acid by elementary analysis, catalytic hydrogenation, IR and NMR spectra, and finally confirmed by chemical synthesis.

Chemotaxonomic studies ofAsplenium sect.Hymenasplenium (Aspleniaceae)

We previously isolated and characterized a new free amino acid withd-configuration at the α-carbon,trans-3, 4-dehydro-d-2-aminopimelic acid and its related amino acids,d-2-aminopimelic acid and 4-hydroxy-l-2-aminopimelic acid fromAsplenium unilaterale. In this paper, we report that the biosynthetic relationshps among these three amino acids were studied using14C-and3H-labeled compounds as tracers. Glutamate and aspartate were shown to be good precursors and it was suggested that 4-hydroxy-l-2-aminopimelic acid is biosynthesized first and the twod-amino acids are derived from it. Furthermore, the distribution patterns of these non-protein amino acids inAsplenium sect.Hymenasplenium were examined in detail and they were evaluated by their biosynthetic pathway. Morphological characters especially on their rhizomes were also examined and their character phylogeny was determined by outgroup comparison. Taking all the characters available into account, the phylogenetic relationship among 7 species ofAsplenium sect.Hymenasplenium in Japan and Taiwan is discussed by the transformed cladistic method.