New taxa and nomenclatural changes in arceuthobium (viscaceae)

The following new taxa are recognized inArceuthobium: subgeneraArceuthobium andVaginata; sectionsVaginata, Campylopoda, andMinuta; seriesCampylopoda,Rubra, andStricta; speciesA. apachecum,A. californicum,A. guatemalense,A. hondurense, andA. pini; new formae spécialesA. abietinum f. sp.concoloris,A. abietinum f. sp.magnificae. New combinations:A. abietinum (Engelm.) Hawksworth & Wiens, andA. microcarpum (Engelm.) Hawksworth & Wiens.     

Flavonoid chemistry of Coreopsis grandiflora (Compositae)

The leaf flavonoid chemistryof Coreopsis grandiflora, which includes var.harveyana, var.longipes, var.saxicola and the typical var.grandiflora, is quite uniform with 6-hy-droxyquercetin 7-O-glucoside, luteolin 7-O-glucoside, marein-maritimein chal-cone-aurone pair and lanceolin-leptosin chalcone-aurone pair as consistent com-ponents. Flavonoid data lend support to the hypothesis that the hexaploid var.longipes originated from parents which would be included withinC. grandiflora, i.e., there is no evidence that other species were involved in its formation. One population of var.grandiflora and several collections of var.saxicola contain additional flavonoid components in the form of flavonol 3-O-glycosides. In nearly all instances the additional compounds are attributable to hybridization withC. lanceolata orC. pubescens because these flavonols are characteristic of these two species and morphological considerations also suggest it. Flavonoid chemistry supports the treatment of var.saxicola as a variety ofC. grandiflora rather than as a distinct species.     

Flavonoid chemistry ofWeigela (Caprifoliaceae) in Korea

Fifteen flavonoids were isolated from flowers and leaves of four species ofWeigela [W. florida (Bunge) A. DC.,W. praecox (Lemoine) Bailey,W. hortensis (Sieb. et Zucc.) K. Koch, andW. subsessilis (Nakai) Bailey] of Korea and one species (W. coraeensis Thunb.) of Japan. The flavonoid data indicated the presence of two distinct chemical groups: the “yellow flower” type producing flavonols and the “red flower” type producing flavonols and flavones. Two cyanidin 3-O-glycosides (glucoside and glucose-xylose) also occurred in all examined taxa. In the floral color-changing species,W. subsessilis, only quercetin glycosides predominated in floral tissue at first, decreasing in number and quantity with time. Instead, cyanidin 3-O-glycosides became present predominantly in flower color changing tissue from yellow to mauve.Weigela florida produced apigenin and luteolin glycosides, along with cyanidin 3-O-glycosides, which were also found inW. subsessilis. Within a relatively limited number of individuals (five),W. hortensis was unique in its production of all flavonols, flavones, and anthocyanins, although two individuals lacked flavone compounds but possessed all flavonols and anthocyanins. In effect, the putative hybrid,W. hortensis of Korea showed additive profiles of the parental marker compounds ofW. subsessilis andW. florida. Pollinator (andrenid bees) non-discrimination betweenWeigela flower-color morphs leading to non-assortive mating was a common, which indicated no breeding barrier among species. This flavonoid study indicated that species of both sections,Weigela andCalysphyrum appeared in each chemical grouping and it was obvious that the arrangement based on flavonoids cut across the sectional treatment of Hara. Floral tissues may be directly involved in the evolutionary strategy of pollination mechanisms and hence, their inherent flavonoids may no longer support taxonomic relationships. The presence of flavone glycosides inWeigela would support that tribe Dievilleae have a closer affinity to tribe Lonicereae within the Family Caprifoliaceae.     

Flavonoid chemistry of Fallopia section Fallopia (Polygonaceae)

Five controversial species of Fallopia sect. Fallopia sensu Holub were examined for leaf flavonoid constituents. Twenty-one flavonoid compounds were isolated and identified; they were glycosylated derivatives of the flavonols kaempferol, quercetin, and myricetin, and of the flavones apigenin and luteolin. Among them, quercetin 3-O-galactoside and quercetin 3-O-glucoside were major flavonoid constituents and present in all species. Although the flavonoid data for some species are lacking, those available appear to be useful for species delimitation and for recognizing species relationships in the section. The flavonoid data, in conjunction with morphological evidence, strongly suggest that F. scandens, F. dentatoalata, F. dumetorum, and F. convolvulus are closely allied but distinct species. In addition, the flavonoid data for F. cilinodis lend additional support to the segregation of sect. Parogonum from sect. Fallopia.     

Flavonoid chemistry ofBlennospermatinae, a trans-Pacific disjunct subtribe ofSenecioneae (Asteraceae)

The flavonoid profiles of seven species ofAbrotanella and one species ofIschnea have been shown to be based upon kaempferol 3- and quercetin 3-O-glycosides and a delphinidin glycoside. Glucosides, glucuronides, arabinosides, diglucosides, and rutinosides of the flavonols were identified. The profile ofIschnea consisted solely of quercetin 3-O-glucoside and 3-O-arabinoside whereas the profiles of theAbrotanella species were more varied. Although infraspecific variation was not investigated in this study, the flavonoid chemistry of the two genera is in accordance with the flavonoid variation described for other members ofSenecioneae which are primarily flavonol producers. Based on the known phylogeny and biogeography, the flavonoid distribution from the perspective of long-distance dispersals across the Pacific is discussed. Such events should lead to genetic bottle-neck situations and depauperate flavonoid profiles. A summary of current flavonoid knowledge in theSenecioneae is supplied.     

Flavonoid chemistry and angiosperm evolution

A consideration of the distribution of flavonoid compounds in angiosperms indicates that exceptions exist to current thought on the presence of particular structural types occurring in primitive versus advanced flowering plants. As additional thorough survey work is done, the exceptions become increasingly common and the generalizations are weakened. A methodological problem in flavonoid surveys concerns documenting the “absence” of particular compounds and the question of quantitative versus qualitative variation of certain constituents. Consideration of flavonoid biosynthesis suggests that simple genetic differences likely control the classes of compounds present and this in turn indicates that caution be used in placing phylogenetic significance on such differences. Features of floral morphology used in studying angiosperm phylogeny have a complex genetic-developmental basis as compared to the genetic factors governing the presence of various flavonoid classes. This ostensibly is an important factor in explaining why reversals in certain trends of floral morphology are rarely noted and why these features are usually constant at higher taxonomic levels. By contrast, variation of flavonoid classes (by virtue of the small genetic differences controlling the presence of different classes) occurs at lower taxonomic levels. Genetic and enzymological studies of flavonoid biosynthesis also indicate that a single compound may be synthesized via different pathways, and this has significant implications for the use of flavonoid distribution in a phylogenetic sense. Given similar selection pressures, the same compounds may arise independently in distantly related plants. Clearly, this has occurred with floral anthocyanidins, where the distribution of particular compounds is related to pollinators. Flavonoid compounds will continue to be useful systematically at the generic level or lower, and possibly at the familial level in some instances. However, studies of the genetics and enzymology of flavonoid compounds in different groups of plants are needed if flavonoids are to be employed in a phylogenetic or evolutionary sense at higher taxonomic levels in the angiosperms. Much additional work in the difficult area of flavonoid functions is to be desired. Many more investigations of comparative flavonoid chemistry of fossil and extant members of what are considered the same genus must be carried out if any appreciation of flavonoid change through evolutionary time is to be achieved.     

Flavonoid chemistry ofPolygonum sect.Tovara (Polygonaceae): A systematic survey

Polygonum sect.Tovara includes three controversial species;P. virginianum, P. filiforme, andP. neofiliforme. The flavonoid chemistry of these was examined to provide additional information on their delimitation and levels of differentiation. Eight flavonoid compounds were isolated and identified, all of which were 3-O-glycosides of the flavonols kaempferol, quercetin, and myricetin, and their acylated derivatives. Although they exhibit relatively simple flavonoid profiles, the three taxa are readily distinguished by their flavonoid constituents. In addition, they show fundamental differences in flavonol types and glycosylation patterns. These results, in conjunction with evidence from the morphology, strongly suggest thatP. virginianum, P. filiforme, andP. neofiliforme are closely allied but distinct species.     

Flavonoid chemistry and plant geography in the Cyperaceae

A leaf survey of 59 tropical (43 African, and 16 South American) Cyperaceae showed that in addition to the expected flavonoid constituents, i.e. glycoflavones and tricin derivatives, a representative number of them (33%) contained luteolin 5-methyl ether. An equal sample of temperate Cyperaceae failed to show any species with this substance. Thus it appears that this rare 5-methylated flavone is restricted to tropical members of the family. In four species of the South American genus, Lagenocarpus, 6-hydroxyluteolin 7-glucoside was identified. This is the first report of this 6-hydroxyflavone in the Cyperaceae and in the monocotyledons. A new glycoside of iso-orientin, the 3'-glucuronide, was identified in Rhynchospora eximia. The new data have been collected in a revised summary of the leaf flavonoid pattern of the Cyperaceae and compared with those of the Gramineae and Juncaceae. The discovery of luteolin 5-methyl ether in the Cyperaceae brings it closer in chemical terms to the Juncaceae, from which family this compound was first isolated     

Flavonoid chemistry and taxonomy in Ulmus

There is evidence in Ulmus of impoverishment of flavonoid constituents with evolutionary advancement and dispersal, but this is less marked in Ulmus than in Geranium and Dillenia. lnfraspecific variability is present in U. minor and U. macrocarpa. The phylogeny of Ulmus, systematic relationships within the Ulmaceae and the systematic position of the Urticales are discussed.     

Flavonoid antioxidants: chemistry,metabolism and structure-activity relationships

Flavonoids are a class of secondary plant phenolics with significant antioxidant and chelating properties. In the human diet, they are most concentrated in fruits, vegetables, wines, teas and cocoa. Their cardioprotective effects stem from the ability to inhibit lipid peroxidation, chelate redox-active metals, and attenuate other processes involving reactive oxygen species. Flavonoids occur in foods primarily as glycosides and polymers that are degraded to variable extents in the digestive tract. Although metabolism of these compounds remains elusive, enteric absorption occurs sufficiently to reduce plasma indices of oxidant status. The propensity of a flavonoid to inhibit free-radical mediated events is governed by its chemical structure. Since these compounds are based on the flavan nucleus, the number, positions, and types of substitutions influence radical scavenging and chelating activity. The diversity and multiple mechanisms of flavonoid action, together with the numerous methods of initiation, detection and measurement of oxidative processes in vitro and in vivo offer plausible explanations for existing discrepancies in structure-activity relationships. Despite some inconsistent lines of evidence, several structure-activity relationships are well established in vitro. Multiple hydroxyl groups confer upon the molecule substantial antioxidant, chelating and prooxidant activity. Methoxy groups introduce unfavorable steric effects and increase lipophilicity and membrane partitioning. A double bond and carbonyl function in the heterocycle or polymerization of the nuclear structure increases activity by affording a more stable flavonoid radical through conjugation and electron delocalization. Further investigation of the metabolism of these phytochemicals is justified to extend structure-activity relationships (SAR) to preventive and therapeutic nutritional strategies.     

Flavonoid races in lasthenia (Compositae)

Nine of the 13 taxa ofLasthenia in which two or more populations were examined for flavonoid constituents exhibited interpopulation variation in these constituents. In certain species entire classes of compounds were present in some races and absent from others. Some of these biochemical differences are due to the failure of certain steps to occur in the biosynthesis of various flavonoids from precursor compounds. Another pattern of variation involves intraspecific differences in the nature of flavonoid glycosides that are produced. In view of the close biosynthetic relationships among all the flavonoids produced byLasthenia, the genetic differences among the flavonoid races of a species may be small. Whether or not these biochemical differences have any adaptive significance is problematical at present.     

Flavonoid glycosides of Lotus corniculatus (leguminosae)

Two-dimensional TLC of stems and leaves of Lotus corniculatus revealed the presence of ca 25 flavonoid glycosides. Among these, 14 were identified; 10 are new for this species. This pattern is qualitatively the same among different populations of this plant but the relative amounts of mono- and diglycosides varies considerably from one population to another.     

Flavonoid B-ring chemistry and antioxidant activity: fast reaction kinetics

Rapid scavenging of the model stable radical cation, ABTS(*+), has been applied to screen for the antioxidant activity of flavonoids. The reaction follows two distinct phases. For compounds with a monophenolic B-ring there is a rapid initial phase of reduction of ABTS(*+) within 0.1 s with no further change in the subsequent 2.9 s. In contrast, compounds with a catechol-containing B ring follow a fast initial scavenging phase with a slow secondary phase. Flavonoids with an unsubstituted B ring do not react within this time scale. The findings suggest that the structure of the B ring is the primary determinant of the antioxidant activity of flavonoids when studied through fast reaction kinetics.     

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 systematics of the genus Perideridia (Umbelliferae)

A survey of flavonoids in sixteen of the seventeen taxa in the genusPerideridia (Umbelliferae) showed the presence of thirteen glycosides of the flavonols kaempferol, quercetin, and isorhamnetin, and seven glycosides of the flavones apigenin, luteolin and chrysoeriol. An anthocyanin and four other flavonoids also occur, but remain unidentified dueto their low concentration. Several species characteristically produce speciesspecific compounds. The majority of species, however, produce flavonoids common to one or more taxa, but each taxon can be distinguished by its own specific complement of these flavonoids. Based on classes of flavonoids the genus can be divided into three groups: (1) those species which produce only flavonols; (2) those which produce mainly flavonols and a few flavones; and (3) those which produce predominantly flavones with flavonols absent or present only in trace amounts. Geographically, the flavonol-producing species are centered in California, extending northeastward to Idaho and eastward into Arizona. The flavonol/flavone producers are concentrated more towards the Pacific Northwest and eastward through the Rocky Mountains to the midwestern United States.     

Flavonoid chemistry of the endemic species of Myrceugenia (Myrtaceae) of the Juan Fernandez Islands and relatives in continental South America

Twenty-one flavonoids were isolated from the leaves of two endemic species ofMyrceugenia on the Juan Fernandez Islands,M. fernandeziana andM. schulzei, from two related species from Brazil,M. campestris andM. rufescens, and from five species from continental Chile,M. colchaguensis, M. exsucca, M. lanceolata, M. pinifolia, andM. rufa. A phenetic analysis was used to evaluate chemical similarities.Myrceugenia campestris andM. rufescens appear most closely related to each other based on flavonoid profiles, and they are also different from the other seven species. The two endemic species in the Juan Fernandez Islands,M. fernandeziana andM. schulzei, group with the continental Chilean species. The former is most closely related toM. lanceolata, and the latter clusters withM. exsucca, although somewhat distantly. The results suggest that the two Juan Fernandez endemics are derived from two introductions from the Chilean continent and not from immigrants from the eastern side of the Andes.     

Flavonoid distribution of Mulinum (Apiaceae, Hydrocotyloideae, Mulineae)

Flavonoid chemistry of the genusMulinum and selected Mulineae taxa was studied. Both flavones and flavonols were identified as C- and O-glycosides. AllMulinum species contain 6,8-di-C-glycosyl chrysoeriol (flavone) and, with the exception of one, quercetin (flavonol). The presence of both flavones and flavonols in this genus weakens previous generalizations that the mulineae contain only flavonols and are primitive compared to other Apiaceae tribes. Based on the selected taxa studied,Azorella appears to differ from bothMulinum andGymnophyton in producing more kinds of flavonols, andGymnophyton appears similar toMulinum in the production of both chrysoeriol and quercetin as well as relatively few compounds. The flavonoid profile ofAsteriscium glaucum is reported as well. In general, a more homogeneous flavonoid compound composition for the Apiaceae is suggested.     

Flavonoid variation of theAconitum jaluense complex (Ranunculaceae) in Korea

Thirteen flavonoid compounds were isolated and identified from five Korean species in theA. jaluense complex; they were glycosylated derivatives of the flavonols kaempferol, quercetin, and isorhamnetin, and of the flavone apigenin. The flavonoid data revealed the presence of two entities in the complex in Korea; one includesA. jaluense s. str. and the other includes the remaining four species which have identical flavonoid profiles. Based on these results, in conjunction with evidence from the morphology, it is suggested that the taxa should be recognized as two sub-species ofA. jaluense s. l. The flavonoid data also provide strong evidence for the occurrence of hybridization betweenA. jaluense s. str. andA. japonicum subsp.napiforme at Mt. Chiri in southern Korea.     

Flavonoid systematics of Potamogeton subsections Perfoliati and Praelongi (Potamogetonaceae)

The flavonoid pigments of Potamogeton praelongus Wulfen, P. perfoliatus L., and P. richardsonii (A. Benn.) Rydberg were isolated and identified. Five flavone glycosides based on three aglycone types and one C-glycosylflavone were identified. Potamogeton perfoliatus and P. richardsonii are most similar in flavonoid composition. The greatest number of compounds are found in P. praelongus with the other two species having a subset of its profile. The flavonoid data suggest that P. richardsonii arose by means other than hybridization between P. perfoliatus and P. praelongus.