John E. Dunn

Dihydroacacipetalin–a new cyanogenic glucoside from Acacia sieberiana var. Woodii

Abstract The structure of a new cyanogenic glucoside, dihydroacacipetalin has been established, primarily on the basis of NMR and mass spectral data. This compound co-occurs with acacipetalin and is also derived from l -leucine in the plant Acacia sieberiana var. woodii (Leguminosae).

Frequency and distribution of cyanogenic glycosides in Eucalyptus L'Hérit

In this study approximately 420 of the described species of Eucalyptus were examined for cyanogenesis. Our work has identified an additional 18 cyanogenic species, 12 from living tissues and a further six from herbarium samples. This brings the total of known cyanogenic species to 23, representing approximately 4% of the genus. The taxonomic distribution of the species within the genus is restricted to the subgenus Symphyomyrtus, with only two exceptions. Within Symphyomyrtus, the species are in three closely related sections. The cyanogenic glycoside was found to be predominantly prunasin (1) in the 11 species where this was examined. We conclude that cyanogenesis is plesiomorphic in Symphyomyrtus (i.e. a common basal trait) but has probably arisen independently in the other two subgenera, consistent with recent phylogenetic treatments of the genus. The results of this study have important implications for the selection of trees for plantations to support wildlife, and to preserve genetic diversity.

Tetraphyllin B and epitetraphyillin B sulphates: Novel cyanogenic glucosides from Passiflora caerulea and P. alato-caerulea

Abstract An epimeric mixture of tetraphyllin B-4-sulphate and epitetraphyllin B-4-sulphate was isolated from Passiflora caerulea and P. alato-caerulea .

Cyanogenesis in australian species of Acacia

Abstract In a survey in which approximately 96% of the Australian species of Acacia were examined, 45 species were shown to be cyanogenic. Forty-three of the 45 cyanogenic species occurred in subgenus Phyllodineae and two in subgenus Acacia . Within subgenus Phyllodineae , 37 cyanogenic species occurred in section Juliflorae , five in section Botrycephalae , and one in section Pulchellae . Cyanogenesis was not observed in the four other sections of the subgenus. The cyanogenic glycosides in subgenus Phyllodineae are prunasin and/or sambunigrin, derived from phenylalanine. The two species in subgenus Acacia contain proacacipetalin, derived from leucine. These biochemical studies are discussed in the context of the existing taxonomy of the genus.

Detection and identification of cyanogenic glucosides in six species of Acacia

Abstract The presence of prunasin in Acacia deanei ssp. paucijuga, sambunigrin in Acacia cunninghamii, and acacipetalin in Acacia giraffae has been established by both chromatographic and NMR spectral evidence. Mandelonitrile glucosides of unknown configuration in Acacia parramattensis and Acacia pulchella and (an) as yet unidentified glycoside(s) in Acacia farnesiana are also reported.

Acacipetalin from six species of Acacia of Mexico and Texas

Acacipetalin is the principal cyanogenic glycoside in Acacia chiapensis, A. cochliacantha, A. hindsii, A. macracantha, A. schaffneri var. schaffneri (all from Mexico) and A. schaffneri var. bravoensis (Texas).

Two cyanogenic glucosides, tetraphyllin B and epi-tetraphyllin B, from Adenia volkensii

Abstract Tetraphyllin B and its previously unknown epimer have been isolated from the Kenyan plant Adenia volkensii. The structures were established by their NMR spectra and by GLC.

Cyanogenesis in Acacia subgenus Aculeiferum

Abstract Cyanogenic glycosides are for the first time identified from members of Acacia subgenus Aculeiferum . The aromatic glycosides prunasin and sambunigrin occur in A. caffra and A. hereroensis . These African species are placed in section Aculeiferum subsection Polyacanthae . These data support other evidence derived from pollen and free amino acids in seeds that subgenus Aculeiferum is more closely related to the predominantly Australian subgenus Phyllodineae than to the pan-tropical subgenus Acacia .

Cyanogenesis in the proteaceae

Abstract Living material from 155 species of Proteaceae were tested for cyanogenesis, and 44 species were found to be cyanogenic. The cyanogenic glycosides dhurrin and/or proteacin were identified in eight species.

Cyanogenesis in Acacia sutherlandii

Abstract Two cyano-glucosides have been isolated from leaves of Acacia sutherlandii . One is the previously described cyanogenic glucoside proacacipetalin and the other is the novel, non-cyanogenic, glycoside 1-cyano-2-β- D -glucopyranosyloxymethyl-(Z)-prop-1-en-3-ol which has been given the trivial name sutherlandin.