Taxonomic insights from floral scents of western North American sessile-flowered Trillium.

PREMISE: Chemical composition of floral volatiles can be an important complement to morphological characters in describing and identifying species. Four of the five species of western sessile-flowered Trillium are challenging to distinguish morphologically due to wide intraspecific variation and overlapping characters among taxa. Characterizing their floral volatile compositions could aid future taxonomic, ecological, and evolutionary studies of Trillium and related taxa. We addressed two major questions: How do western sessile Trillium taxa vary in floral chemistry? Can floral scent be used to distinguish species? METHODS: We collected petals from 600 individuals at 42 wild populations of four sessile Trillium species across California, Oregon, and Washington. Volatile organic compounds from the petals were extracted using solid-phase microextraction, and the volatiles were identified and quantified by gas chromatography-mass spectrometry. The utility of floral scent composition in distinguishing species was tested using nonmetric multidimensional scaling and random forest analysis. RESULTS: Floral volatiles of the white-petaled T. albidum were dominated by oxygenated monoterpenes and showed considerable geographic variation that paralleled morphological variation. The maroon-petaled T. angustipetalum and T. kurabayashii produced floral scents characterized by aliphatic esters, but each had a distinct chemical composition. Petal color of Trillium chloropetalum is highly variable, as were its scent compositions, which were blends of volatiles from both white-petaled and maroon-petaled congeneric taxa. CONCLUSIONS: Differences in floral scent compositions are consistent with current taxonomy of the western sessile Trillium group. In cases where species delimitations are difficult based on morphology, floral scent composition provides taxonomic insight and suggests a potential hybrid origin for T. chloropetalum.

Chemotaxonomy of Pseudowintera: sesquiterpene dialdehyde variants are species markers.

Two sesquiterpene dialdehydes, the 1beta-E-coumaroyl-5alpha-hydroxypolygodial plus the known 1beta-E-cinnamoyl-5alpha-hydroxypolygodial, were isolated from the recently described species Pseudowintera insperata. This discovery is a further example of the rare sesquiterpene dialdehyde coumarate/cinnamate combination being found exclusively in the family Winteraceae. Another sesquiterpene dialdehyde, isopaxidal, with the rare rearranged drimane skeleton, was isolated from Pseudowintera axillaris. The sesquiterpene dialdehyde contents of leaves of 25 individual plants of the four Pseudowintera species, all endemic to New Zealand, were measured by HPLC. P. insperata individuals all had high levels (3.0-6.9% of leaf dry wt.) of the coumarate, P. axillaris had high levels (2.2-6.9%) of paxidal, and Pseudowintera colorata from different areas of New Zealand contained varying levels of polygodial (1.4-2.9%) and 9-deoxymuzigadial (0-2.9%). Therefore the sesquiterpene dialdehydes are good species markers.

O-nucleophilic amino alcohol acyl-transfer catalysts: the effect of acidity of the hydroxyl group on the activity of the catalyst.

[reaction: see text]. Amino alcohol-derived acyl-transfer catalysts are shown to operate by an O-nucleophilic mechanism, and catalysts bearing electron-withdrawing groups in proximity to the hydroxyl group are found to be more active. This is attributed to an increase in the acidity of the hydroxyl group of the catalyst.