The flavonoids of Xylonagra (onagraceae)

Xylonagra arborea is a monotypic genus of the tribe Onagreae of the Onagraceae. The species is restricted to the desert regions of central Baja California in western Mexico. Four flavonol glycosides, myricetin 3-O-glucoside, myricetin 3-O-rhamnoside, quercetin 3-O-glucoside and quercetin 3-O-rhamnoside were found to occur in methanolic leaf extracts of each of the populations sampled. The data are consistent with earlier investigations of leaf flavonoids in the Onagreae and suggest interesting changes in B-ring hydroxylation patterns within the tribe.     

The flavonoids of Stenosiphon (Onagraceae)

Stenosiphon linifolius is a monotypic genus of the tribe Onagreae of the Onagraceae. The species is widespread in, but restricted to, the Great Plains of the United States. Three flavonol glycosides, kaempferol 3-O-rhamnoside, quercetin 3-O-rhamnoside and myricetin 3-O-rhamnoside, were found to occur in methanolic extracts of Stenosiphon leaves. Similar compounds are found in the leaves of such related genera as Oenothera and Gaura, but in the latter genera, additional flavonols exhibiting greater substitutional variation also are found.     

Chemosystematic implications of flavonoids in Aniba riparia

The trunk wood of Aniba riparia (Nees) Mez (Lauraceae) contains flavokawin-B, (2S)-pinostrombin, (2S)-5, 7-di-O-methylpinocembrin, (2R, 3R)-5, 7-di-O-methylpinobanksin, izalpinin and 3,5, 7-tri-O-methylgalangin. Structural comparison of these flavonoids with the pyrones and neolignans, which characterized all previously examined Aniba spp., leads to a chemical classification of the genus.     

Flavonoid chemistry of the generic segregates Ascyrum and Crookea of Hypericum

Leaf flavonoids were isolated and characterized from the seven taxa of Hypericum, formerly segregated as Ascyrum and Crookea. These included flavonol 3-glycosides based on quercetin and kaempferol and flavone-O-glycosides and C-glycosides based on apigenin and luteolin. The flavonoid data do not indicate that the taxe of Ascyrum and Crookea form a single coherent group and hence support their merger with Hypericum.     

Flavonoid variation in Xanthisma texanum: Infrapopulation and interpopulation variation

Fourteen flavonoids were isolated from Xanthisma texanum. Chemosystematic interpretations are made concerning the origin and distribution of the infraspecific taxa of the species.     

Flavonoids in Parahebe and Veronica: a chemosystematic study

Flavone glycosides are the main flavonoid leaf constituents in the related genera Parahebe and Veronica (Scrophulariaceae), in agreement with former chemical studies of the family. In Parahebe there are groups of species in which there are mainly luteolin glycosides, and groups in which 6-hydroxyluteolin dominates. Small amounts of apigenin occur in many taxa. Glycosylation is usually in the 7-position but 4′- and 5-glycosides were also found. In Veronica a larger variety of flavone aglycones was found: e.g. luteolin, apigenin, chrysoeriol, tricin and three different 6-hydroxyflavones. They are often present in the plants in the form of glucuronides. Glycosylation is in the 7-or-5-position. Most species of both genera have a distinctive pattern of flavonoid glycosides in their leaves which can be used for identification. Populations of P. catarractae are an exception in showing three different patterns, but here the variety in flavone profiles corresponds to the pattern of morphological and geographic variation within this taxon. Anthocyanins are responsible for the blue, mauve and pink colours of the flowers in the two genera. In Veronica they are based on delphinidin, whereas in Parahebe catarractae on both delphinidin and cyanidin.     

Flavonoid and anthocyanin patterns and the systematic relationships in Collomia

Analyses of extracts among populations of the 14 species of Collomia revealed the occurrence of 13 mono-, di- and triglycosides based on the flavonoids, acacetin, kaempferol, patuletin and quercetin. The glycosides included those having arabinose, galactose, glucose and rhamnose as mono-, bio- or triosides at the 3-, 5-, 3,7- or 7-position. Analyses of floral extracts from ten species revealed the occurrence of two anthocyanins, cyanidin and delphinidin 3-(p-coumarylglucosyl)-5-glucoside. Nearly all the species express distinctive flavonoid patterns, although the differences are based on relatively minor changes in position or type of glycosidic substitution. Use of the minimum biosynthetic step distance (MBSD), an index of similarity, revealed that a mean of 5.6 steps separated the 14 species. The four perennial species of section Collomiastrum showed a high degree of similarity and differed consistently from species of the two annual sections Courtoisia and Collomia by lacking quercetin-5-glucoside and kaempferol-3-arabinosylgalactoside. In contrast, flavonoid patterns among species within sections Courtoisia and Collomia showed a relatively low degree of similarity. The dissimilarity between C. diversifolia and C. heterophylla (section Courtoisia) is consistent with their divergent patterns of pollen morphology and ecological distribution. Three groups of species within section Collomia were defined generally by shared patterns of flavonoids, which are correlated to some degree with floral, pollen and vegetative morphology.     

Distribution of flavonoids and their systematic significance in Clematis subsection Viornae

Fifteen flavonoids were identified in the eight taxa of Clematis subsection Viornae. Flavonols, flavones, and C-glycosyl flavones were present. The compounds were based primarily on luteolin, apigenin, quercetin, and kaempferol. The systematic significance of the distribution of these compounds among the taxa is discussed.     

A chemosystematic survey of the fern genus Bommeria

A phytochemical survey of the species of Bommeria showed that foliage of the members of this genus contains a variety of flavonol and flavone glycosides. The distributions of chemical and morphological characters in Bommeria correlated to circumscribe infrageneric affinities: B. hispida and B. subpalaecea comprise one evolutionary line, while B. pedata and B. ehrenbergiana form a second. Flavonoid data may also be applied in concert with spore morphology in defining intergeneric species groups within Bommeria and Hemionitis.     

Flavonoids of Heterogaura (Onagraceae)

Heterogaura is a monotypic genus of the tribe Onagreae of the Onagraceae. It is endemic to south western Oregon and California. Four flavonol glycosides, kaempferol 3-O-rhamnoside, quercetin 3-O-glucoside, quercetin 3-O-rhamnoglucoside and myricetin 3-O-glucoside, were found to occur in methanolic leaf extracts of each of the populations sampled. The presence of only flavonols is consistent with flavonoid analyses from other genera of the Onagreae, including Clarkia, the closest relative of Heterogaura.     

Systematic implicationsofflavonoid patterns in Haplopappus segregates

Complex flavonoid patterns are correlated with primitive woody taxa and high base chromosome numbers among Haplopappus segregates. Variability among flavonoid complements supports the polyphyletic interpretation of the genus.     

Flavonoids of the Muhlenbergia montana complex

Specimens from natural populations of Muhlenbergia montana (Nutt.) Hitch. and related species were analysed for their flavonoid content. Twenty-four flavonoids from 14 species were separated and 22 of the compounds identified. Most were glycosylated derivatives of luteolin, apigenin and tricin. Two flavonols, quercetin 3-O-rutinoside and quercetin 3-O-glycoside, and two flavanones were also identified. Flavonoid patterns were distinct for all perennial species and identical for the two annual species examined. Phenetic analysis of the flavonoid characters does not support the inclusion of the annual species M. crispiseta and M. peruviana as part of the M. montana complex.     

The phylogenetic content of flavonoid point scores

The history of flavonoid point scores is discussed and the advantages of each system are described. A variation of the Wagner Groundplan-divergence Method can be used to reveal the phylogenetic content of flavonoid point scores. Flavonoid features evolving on more than one occasion are readily detectable.     

The flavonoids of Margaranthus

Four flavonols based on either quercetin or kaempferol are found in Margaranthus. The compounds are uniform throughout the populations examined and no evidence is present for the recognition of more than one species. The flavonols are similar to those found in related in genera, and do not provide a basis for the exclusion of Margaranthus from the subtribe Solaninae.     

Altered Glycoflavone expression in induced Autotetraploids of Phlox drummondii

The effects of colchicine induced autotetraploidy on non-anthocyanin flavonoid expression were determine for 15 cultivars of Phlox drummondii and for the naturally occuring P. drummondii ssp. mcallisteri. Collectively, the taxa express a total of nine glycoflavonoid derivatives (C, O-diglycosides or di-C-glycosides) of either apigenin or luteolin. The autotetraploids of 14 cultivars and those of the natural subspecies exhibit altered glycoflavone profiles relative to their respective diploid sources. The qualitative alternations in the cultivars may be grouped into three phenotypic categories: (1) the expression of novel glycoflavones, (2) the absence of diploid glycoflavones, and (3) the deregulation of tissue-specific glycoflavone production. Alterations in mcallisteri autotetraploids include only the latter two categories. Each of the novel compounds is otherwise expressed among other diploid cultivars or in other wild P. drummondii subspecies. Quantitatively, the phenolic content of most autotetraploid flowers is significantly greater than in respective diploid flowers. However, on a dry weight basis, phenolic titre in comparable 4n and 2n floral or leaf tissues is not significantly different. Floral tissues express from 5 to 10 times the phenolic titre of leaves. The results are discussed in terms of the possible origins of novel flavonoids in natural polyploid Phlox species.     

Chemosystematics of the hydrophyllaceae: Flavonoids of three species of eriodictyon

Eleven flavonoids, nine aglycones and two glycosides were isolated from Eriodictyon tomentosum, E. angustifolium and E. Californicum. Aglycones included the flavanone homoeriodictyol, the flavones apigenin, luteolin, chrysoeriol, 6-methoxyapigenin, 6-methoxyapigenin 7-methyl ether, 6-methoxyapigenin 4′-methyl ether, 6-methoxyluteolin and 6-methoxyluteolin 3′-methyl ether, glycosides were the 3-O-glucosides of quercetin and kaempferol.     

Geographic variation of flavonoids in Phlox carolina

Non-anthocyanin flavonoid expression was determined among 64 continuous range and nine disjunct range populations of Phlox carolina. The species contains four flavone nuclei and a total of 25 derivatives, most of which are $\text{C-}\text{glycosides}$. Nearly all populations express unique flavone patterns. Using a qualitative similarity index of minimum biosynthetic step distance (MBSD), the average population contains only ca. 50% of the overall substitutional diversity. The separate ranges are distinctive in the % occurrence of most compounds but only weakly divergent in comparative mean MBSD. Proximity and MBSD are significantly correlated overall but local variability is extensive and no discrete racism is apparent. Within the continuous range 18 compounds are distributed in independent but overlapping gradients and 13 of these extend consistently through the disjunct range. The patch-work continuum of flavone variation is the apparent consequence of dissection and contraction of a historically more widespread distribution. Other general aspects of the variation patterns are discussed.     

Protective mechanisms and acclimation to solar ultraviolet-B radiation in Oenothera stricta

Abstract Mechanisms of plant protection and acclimation to potentially damaging solar ultraviolet-B (UV-B, 280–320 nm) radiation incident on the Earth's surface were examined in Oenothera stricta. Attenuation of this radiation in the upper leaf epidermis reduces the penetration of UV-B radiation to the mesophyll where damage to physiologically sensitive targets can occur. The epidermis is a highly selective radiation filter that can attenuate up to 95% of the incident UV-B radiation and yet transmit between 70% and 80% of the visible radiation. Exposure to UV-B radiation significantly reduced the degree of epidermal UV-B transmittance by as much as 33%. No significant reduction in epidermal transmittance of visible radiation was observed as a result of UV-B exposure. The plasticity in epidermal UV-B transmittance results from production of flavonoid and related phenolic compounds in the tissue. Absorbance of UV-B radiation in llavonoid extract solutions from epidermal and mesophyll tissues significantly increased by as much as 100% and 35%, respectively, after exposure to UV-B radiation. Photosynthetic rates of leaves exposed to UV-B radiation were not significantly reduced at dose rates representative of the radiation flux found in the habitat of this species, but significant photosynthetic depression was observed at dose rates that exceed the field UV-B flux. The phenotypic plasticity in epidermal UV-B transmittance resulting in decreased penetration of damaging UV-B radiation to the mesophyll may reduce the rate of damage to a level where repair mechanisms can keep pace with reduced injury.     

Flavonoids of Sullivantia: Taxonomic implications at the generic level within the saxifraginae

Sullivantia species were found to produce quercetin 3-O-glycosides, several of which contain glucuronic acid, as well as pedalitin (6-hydroxy-7-O-methyl luteolin), pedalitin 6-O-glycosides, and small amounts of luteolin. Sullivantia has a unique combination of compounds that distinguishes it from other genera in the Saxifraginae for which flavonoid data are available. The nature of the flavonoid compounds is in accordance with a general trend within the Saxifragaceae of reduction and replacement of flavonols by flavones.