Arylbenzofurans from Dalbergia parviflora

The isolation of two polysubstituted arylbenzofurans from the heartwood of Dalbergia parviflora is described. Their structures were elucidated mainly by spectroscopic techniques (UV, IR, ¹H and ¹³C NMR). They were named parvifuran (5-hydroxy-6-methoxy-3-methyl-2-phenylbenzofuran) and isoparvifuran (5-hydroxy-6-methoxy-2-methyl-3-phenylbenzofuran) and are the first compounds of this class isolated from a Dalbergia species.     

Amino acids of Caesalpinia tinctoria and some allied species

Two previously unreported amino acids have been found to form major constituents of seed of Caesalpinia tinctoria; they have been characterized as 4-hydroxy-3-hydroxymethylphenylalanine and 3-hydroxymethylphenylalanine. The seed also contains a large amount of the imino acid baikiain. The amino acid content of seeds of this species is compared with that for 12 other species of Caesalpinia and 14 species in closely related genera.     

A new dihydrobenzofuran from Liatris provincialis

A chloroform extract of Liatris provincialis Godfrey gave as a minor component a new dihydrobenzofuran, whose structure was established as I.     

Aliphatic hydroxy-ketones from Curculigo orchioides rhizomes

Two new aliphatic hydroxy-ketones, isolated from the rhizomes of Curculigo orchioides, have been characterized as 27-hydroxytriacontan-6-one and 23-hydroxytriacontan-2-one, respectively, by spectral data and chemical studies.     

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

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.     

Carotenoids in petals of some perennial Medicago species

The petal carotenoids of several Medicago species, some of them considered as intermediate between the genera Medicago L. and Trigonella L. were investigated. Characteristics common to all species were: (a) the carotene fraction was small (0·2–4·4%) compared with the xanthophylls and their epoxy derivatives, (b) lutein, lutein-5,6-epoxide and violaxanthin constituted 83·7–98·1% of total content and thus were the prominent group in all species, (c) no single carotenoid of appreciable amount was characteristic to any species, (d) groups of related species tended to have similar quantities of major carotenoids.     

Flavonoids from the external leaf resins of four hemizonia species (asteraceae)

The external leaf resins of four Hemizonia species afforded nine methylated flavonoids, including flavanones, flavones and flavonols. Besides the rare compounds 7-methyleriodictyol and 3,6,8-trimethoxy-5,7,3′,4′-tetrahydroxyflavone the new 6-methoxy-5,7,8,3′,4′-pentahydroxyflavone was isolated and identified by spectroscopic means.     

Structure and synthesis of the growth inhibitor batatasin I from Dioscorea batatas

The synthesis of 6-hydroxy-2,4,7-trimethoxyphenanthrene is described and its identity with the growth inhibitor, batatasin I, is confirmed.     

The isolation of methyl β-orsellinate from Stereocaulon alpinum and comments on the isolation of 4,6-dihydroxy-2- methoxy-3-methylacetophenone from stereocaulon species

Methyl β-orsellinate has been isolated from chloroform extracts of Stereocaulon alpinum. It is shown that methyl β-orsellinate was probably previously misidentified as 4,6-dihydroxy-2-methoxy-3-methylacetophenone during work on Stereocaulon vesuvianum. Reports of the isolation of the latter thus appear to be erroneous. The status of methyl β-orsellinate as a naturally occurring metabolite is discussed.     

Surface wax of Andreaea and Pogonatum species

The mosses Andreaea rupestris, Pogonatum aloides and P. urnigerum contain surface waxes in amounts of 0.05–0.12% dry wt. The waxes consisted of esters (C₃₈-C₅₄), primary alcohols (C₂₀-C₃₂), free fatty acids (C₁₆-C₃₀), and alkanes (C₂₁-C₃₁). Additionally, aldehydes (C₂₂-C₃₀) were major constituents in the wax of P. urnigerum. The classes and their chain length distributions in the surface waxes of these mosses are comparable to those of epicuticular waxes of higher plants.     

Isolation of glucosinolates and the identification of o-(α-l-rhamnopyranosyloxy)benzylglucosinolate from Reseda odorata

A method has been developed for the quantitative isolation of glucosinolates by ion-exchange chromatography and high voltage electrophoresis avoiding strongly alkaline and acidic conditions. The compounds were identified by ¹H and ¹³C NMR spectroscopy and through the products arising from enzymatic, acid and alkaline hydrolysis. The method is well suited for the isolation and identification of glucosinolates containing aglucone parts which produce non-volatile compounds on enzymatic hydrolysis. The method has been used in the isolation and identification of 2-hydroxy-2-methylpropylglucosinolate from Reseda alba, 2-hydroxy-2-phenylethylglucosinolate from R. luteola and a new glucosinolate, o-(α-l-rhamnopyranosyloxy)benzylglucosinolate, occurring in R. odorata. The glucosinolate content in different parts of this plant has been determined and the metabolism of glucosinolates is briefly discussed.     

Systematic implications of flavonols in Zaluzania

The distribution of flavonols based on quercetin and kaempferol in the leaves of Zaluzania supports phyletic interpretations based on morphology and cytology.     

Structures of some minor pterocarpans of Neorautanenia edulis

The constitution of five new compounds, (?)-neorautenol, (?)-neodunol, (?)-homoedudiol, neorauteen and neoduleen, has been established in the root bark of Neorautanenia edulis.     

Glucosides of ionone-related compounds in several nicotiana species

The β-glucosides of 3-oxo-α-ionol and 5,6-epoxy-5,6-dihydro-3-hydroxy-β-ionol were isolated from fresh leaves of Nicotiana rustica. Two or more of the glucosides of 3-oxo-α-ionol, 5,6-epoxy-5,6-dihydro-3-hydroxy-β-ionol, 3-hydroxy-β-damascone, blumenol A, 4-(3-hydroxybutylidene)-3,5,5-trimethyl-2-cyclohexenl-one and blumenol C were shown to be present and the amounts measured in N. alata, N. repanda, N. rustica, N. undulata, N. accuminata, N. sylvestris and N. tabacum. No glucosides were detected in N. paniculata.     

Structure and biosynthesis of a new anthraquinone from Streptocarpus dunnii

A new anthraquinone (1-hydroxy-2-hydroxymethylanthraquinone has been isolated from the title plant. The structure was determined by spectroscopy and synthesis. Investigation on the biosynthesis showed that this quinone is formed via o-succinoylbenzoic acid.     

Lipids of Fontinalis antipyretica

Fatty acid compositions of the lipids of Fontinalis antipyretica shows the presence of octadeca-9, 12-dien-6-ynoic, octadeca-9,12,15-trien- 6-ynoic and eicosa-11,14-dien-8-ynoic acids as the major components of the triglycerides. These acetylenic acids were not present in the galactosyl diglycerides. The moss lipids also contained relatively large amounts of two novel acetylenic methyl ketones with an unsaturation pattern analogous to that of the C₁₈ acetylenic acids.     

The steam volatile leaf oils of some species of Eucalyptus subseries Strictinae

The volatile leaf oils of Eucalyptus stenostoma, E. fraxinoides, E. triflora, E. dendromorpha, E. burgessiana, E. rupicola, E. approximans subsp. approximans, E. approximans subsp. codonocarpa and E. paliformis were qualitatively very similar to each other but significantly different from the leaf oils of the remaining species of the subseries. Their leaf oils were characterized by high concentrations of p-cymene and by the presence of α- and β-phellandrene, variable amounts of piperitone, trans- and cis-piperitol and trans- and cis-p-menth- 2-en-1-ol. The three last named alcohols have not been previously reported from the Myrtaceae.     

UV-mediated antibiotic activity of some compositae species

Roots, leaves, and flowers of 80 species of Compositae were tested for phototoxic activity against Candida albicans. Many genera showed activity, especially in the roots. No active genera were found in the tribe Cichorieae. Phototoxic compounds were isolated from Chrysanthemum leucanthemum florets and Cirsium arvense roots. Chemotaxonomic evidence plus preliminary chemical data suggests that the compounds are polyacetylenic in nature. Unlike other phototoxic compounds, these are inactive against human skin.     

Naphthoquinones and triterpenes from some asian Diospyros species

Investigation of the stem bark, wood and/or fruit of nine Asian Diospyros spp. (Ebenaceae) has revealed a range of triterpenes and naphthoquinones     

Biological implications of flavonoid chemistry in Baptisia and Thermopsis

An analysis of flavonoid distributional data from detailed biochemical systematic investigations of Baptisia and Thermopsis species supports the contention that the two genera are closely related with Baptisia being the more advanced evolutionarily and exhibiting greater evolutionary vigor. B. megacarpa may represent an ancestral complex which gave rise to several major Baptisia lines. Enzymes involved in methoxylation and 4′-glucosylation of flavonoids in Thermopsis have higher substrate specificities than those involved in 7-glucosylation.