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Sainfoin proanthocyanidins (PAs) are complex mixtures of homo- and hetero- polymers consisting of B-type procyanidins and prodelphinidins. Direct analysis by thiolytic degradation revealed a wide range of PA contents and compositions within the HealthyHay germplasm collection (46 accessions). PA contents varied from 0.57% to 2.80% (g PAl100g freeze-dried samples). PAs polymer size ranged from 12 to 84 flavan-3-ol units in terms of their mean degree of polymerisation. Prodelphinidin/procyanidin ratios ranged from 53/47 to 95/5 and trans/cis ratios varied from 12/88 to 34/66. Purified PAs fractions from 4 selected accessions showed a positive correlation between polymer size and prodelphinidin content within each accession (R2 from 0.69 to 0.92). Careful selection of MALDI-TOF MS matrices and analytical conditions made it possible to detect PAs up to 12 subunits and also ion signals that could be assigned to A-type and rarely reported glycosylated A-type PAs. For detecting and confirming the polymer size of underivatised higher molecular weight PAs a new HPLC-GPC technique consisting in a single calibration curve for galloyl glucoses, ellagitannins and PAs was developed. Peak-average molecular weights of sainfoin PA fractions were overestimated by 42.0% at 2436 Dalton and underestimated by 13.9% at 8318 Dalton. Number-average molecular weights were overestimated by 30.0% and underestimated by 25.8%, respectively. Cluster analysis of the HealthyHay germplasm collection revealed that accessions clustered into two main clusters, Western Europe and Eastern Europe/Asia, and that accessions from Armenia, Canada and USA clustered into another group. This seems to be in agreement with the strong links between geographic origin and accession performance found in the HealthyHay sainfoin germplasm. This research made significant contributions to the fields of PA analysis and germplasm screening in terms of novel analytical techniques for determining the average molecular weight distribution, content, subunit composition and linkages, purification and fractionation of proanthocyanidins in sainfoin.

The variation in the genus Adenocarpus DC. (Leguminosae) was sampled as far as possible from its complete distribution range, the Mediterranean and tropical African regions. Characters for taxonomy were obtained from morphology and phytochemistry; a DNA analysis was also undertaken. A detailed study of morphological characters was undertaken and analyzed by one-way ANOVA, discriminant analysis and Cross Tabulation with Chi square. A flavonoid and isoflavonoid survey to provide new taxonomic characters was made using high performance liquid chromatography with diode array detection and atmospheric pressure chemical ionization-mass spectrometry. For ten of these variants, 2-8 samples were examined to investigate flavonoid variation. Nineteen flavonoids belonging to five classes (flavone C- and O-glycosides, flavonol glycosides, isoflavone glycosides and flavanones) were detected. The nuclear ITS and chloroplast trnL-trnF DNA were sequenced to provide the relationships among the variants of Adenocarpus. The phylogenies obtained from both individual and the combined analyses of the data sets were congruent. A good correlation was found in that each of the molecular clades could also be characterised by a combination of flavonoids. For example, the species in clade 4, which are distributed in South and South-East Europe and tropical Africa, are characterised by the presence of flavonol O-glycosides and 5-hydroxyisoflavone O-glycosides. In contrast, flavonol O-glycosides were absent from all but one species of the other three clades, which have a mainly North Africa distribution, and these species produce flavone mono- C-glycosides and/or flavone 7-0-glycosides instead. In addition flavone 41-O-glycosides were only found in species of clade 1 and flavanones were mainly restricted to clade 3. However, the results from the morphology, phytochemistry and phylogeny provided a framework that has been used as a basis for a new classification of the genus. Twenty- four species, including a new species from the Middle Atlas of Morocco, three subspecies and one variety of the genus Adenocarpus (Leguminosae) are recognized in a new systematic account.

Systematics and floral evolution in the order Fabales are addressed through ontogeny, developmental genetics and phylogeny. The Fabales hypothesis (Leguminosae, Polygalaceae, Quillajaceae, Surianaceae) has recently emerged from angiosperm molecular phylogenies. Despite good support for the order, interfamilial relationships are contradictory. Employing parsimony and Bayesian approaches, plastid regions (rbcL, matK) were used to infer interfamilial relationships in Fabales. Five alternative hypotheses were recovered. The Shomodaira-Hasegawa test shows higher probability for a resolved interfamilial topology rather than a hard polytomy scenario. Dating of selected clades using penalized likelihood, indicates rapid radiation of the Leguminosae, Polygalaceae and (Quillajaceae + Surianaceae) crown clades. The actinomorphic Quillajaceae and Surianaceae differ in their reproductive- whorl development, Quillaja more closely resembling Leguminosae in this respect. The origin of the highly. characteristic petaloid lateral sepals in Polygalaceae involves integration of the bracteoles to the flower and reduction or loss of the lateral petals. In taxa where the bracteoles are absent, the lateral sepals are not petaloid and resemble other calyx members. Petaloid lateral sepals are petals (by behaviour) and sepals (by position). Evolution of the petaloid sepals involves the bracteole-wing-lateral petal module, which evolved once in the family. This module is here regarded as a morphological noveltylkey innovation. Inclusion of morphology in cladistic analyses of Fabales contributes significantly to the resolution and support of the interfamilial relationships. Combined phylogenetic analyses suggest more confidently (Polygalaceae (Leguminosae (Quillajaceae+Surianaceae ))) as the preferred hypothesis. In species of Polygalaceae with petaloid sepals, expression patterns of the AP3/DEF and PI/GLG (petal and stamen-identity genes) differ; whereas the former is expressed in several floral and vegetative tissues, the latter is restricted to petals, stamens, and in low levels in sepals and early petaloid sepals. Despite the expression of B-genes in early petaloid sepals, it is not possible to associate the identity of the petaloid sepals with these expression patterns; the petaloid sepals show similar expression patterns to sepals. Putative alternative splicing in B-gene transcripts in Polygalaceae was found. Phylogenetic diversification patterns of B-class genes do not fit expectations from different models previously suggested to explain the petaloid identity of the first-whorl organs. Instead, it appears that floral organs, including the petaloid sepals, have recruited different B-gene copies independently. A putative gen0!lle duplication - evidenced by major diversification events of AP 3/DEF and P I/GLO homologs - could be coincident with or have preceded the origin of petaloid sepals and all the morphological changes implied.

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