FLAVONOID SURVEY OF OENOTHERA (ONAGRACEAE): SECTS. GAUROPSIS,HARTMANNIA, KNEIFFIA,PARADOXUS, AND XYLOPLEURUM

An analysis of 60 populations of Oenothera sects. Gauropsis, Hartmannia, Kneiffia, Paradoxus, and Xylopleurum showed that 29 flavonols and 4 glycoflavones were present among 19 of the 20 species studied in these five sections. The four glycoflavones, representing the first report for this class of compounds for Oenothera, were present only in O. canescens, a highly specialized and isolated species within the genus. The most closely related species, O. dissecta, had a flavonoid profile more similar to species of sect. Hartmannia and sect. Kneiffia. The most striking feature of the analysis is that roughly 70% of the known flavonoids in the family were found in the group of sections studied. The large number of compounds in this one lineage of Oenothera contrasts sharply to the relatively low numbers found in most other genera of the family. Further, the occurrence of glucuronides and sulfates within Oenothera is restricted to these sections. Each species examined had a unique flavonoid profile, except O. deserticola and O. multicaulis (both sect. Hartmannia) which had identical profiles. This finding contrasts sharply with the uniform profiles of other sections of Oenothera and other genera in Onagraceae, such as Epilobium and Ludwigia. By contrast, O. havardii, a phyletically isolated species of the monotypic sect. Paradoxus, had only five flavonol glycosides, compared with 11–19 compounds in the other species. Based on morphological and seed anatomical data, O. havardii is only distantly related to sects. Gauropsis, Hartmannia, Kneiffia, and Xylopleurum, although along with sect. Lavauxia, it appears to represent the sister group to them. Overall, with the exception of O. havardii and O. canescens, the flavonoid profiles support the hypothesis recently suggested by seed anatomy that these four sections are more closely related to each other than any one of them is to another section of the genus.     

Revisiting of Carex sect. Confertiflorae s.l. (Cyperaceae): New data from molecular and morphological evidence and first insights on Carex biogeography in East Asia

Carex sect. Confertiflorae s.l. is a medium-sized species group (ca. 40 species) with its center of diversity in E Asia (China and Japan). According to morphological traits, the section has been proposed to split into two sections (sects. Confertiflorae sensu Ohwi and Molliculae Ohwi) up to five different ones (sects. Confertiflorae s.s., Molliculae, Dispalatae Ohwi, Ischnostachyae Ohwi, and Alliiformes Akiyama). Recent phylogenetic reconstructions showed Confertiflorae s.l. not to be monophyletic, as species traditionally considered part of it were found to belong to other clades, whereas species traditionally ascribed to other sections were nested within it. In this study, we investigated the phylogenetic structure, morphological affinities, and biogeographic history of sect. Confertiflorae s.l. We employed a taxon-based approach to explore the morphological affinities of the species considered in sect. Confertiflorae and compared the micromorphology of the nutlets of almost all the taxa using SEM. We included 40 samples representing 31 species/subspecies of sect. Confertiflorae s.l. and used two nuclear (ETS and ITS) and three plastid (trnL-F, matK, and rpl32-trnL ^UAG) molecular markers to reconstruct the phylogeny of the group. The phylogenetic analyses confirmed the polyphyly of sect. Confertiflorae s.l., whose representatives were found within five distinct clades. From these, two clades, sect. Confertiflorae and sect. Molliculae, were found to be closely related and contained the majority of the species. The composition of the two clades agreed with the morphological structure of the group, and we confirmed an exclusive combination of features (namely color of basal sheaths, presence of bract sheath, peduncle of lowest spike, inflorescence sex distribution, shape of pistillate glume apex, and color and veins of utricle, among others) characterizing each of the two clades. The origin of the two clades was found to be in the early Pliocene; however, the majority of the diversification events within each clade took place during the Pleistocene. This illustrates that although Asia has been regarded as having little potential ecological space for Carex to diversify due to its climate stability, groups of sedges sub-endemic from that area may have a fairly recent origin related to glaciations. We proposed the rearrangement of sect. Confertiflorae as previously conceived as three independent sections: the monotypic Alliiformes, sect. Molliculae, and sect. Paludosae.     

Correlations between flavonoid chemistry,anatomy and geography in the restionaceae

Comparisons of the flavonoid patterns in stems and inflorescences between Australasian and South African members of the Restionaceae indicate significant differences with geography. Nine of 14 Australasian species contain gossypetin or a related 8-hydroxyflavonoid and proanthocyanidins are uncommon. By contrast, the 33 South African taxa studied contain common flavonols, flavones and glycoflavones, while proanthocyanidins are present in 29. Two anatomically related South African genera, Chondropetalum and Elegia, contain, in addition, myricetin 3-galactoside, together with the 3-galactosides of the myricetin methyl ethers, larycitrin and syringetin. These results confirm the conclusions derived from anatomy that members of Hypolaena, Leptocarpus and Restio, genera represented in both Australia and South Africa, have the distinctive flavonoids characteristic of their geographic origin rather than of their systematic position. The family as a whole is different in flavonoid pattern from other monocotyledonous families with which it is sometimes associated.     

Apigenin di-C-glycosylflavones of Angiopteris (Marattiales)

A survey of the flavonoids of four species of Angiopteris indicates that di-C-glycosylflavones and flavone-O-glycosides may be characteristic of this distinct group of eusporangiate ferns. Derivatives of flavonols, which are typical of leptosporangiate ferns and Ophioglossum, or biflavones, which are characteristic of the Psilotaceae, were not detected in Angiopteris.     

A survey of leaf flavonoids in the portulacaceae

A survey of 26 species in 12 genera of the Portulacaceae showed the presence of flavonoids in 24, and their absence in two, Hectorella caespitosa Hooker fil. and Lyallia kerguelensis Hooker fil. Of the 24 positive species, 16 are reported for the first time. In all 24 however, flavonols and flavones did not occur together suggesting that this dichotomy might be useful for classification at and below the generic level in the Portulacaceae, e.g. the genera Silvaea Philippi (syn. Philippiamara Kuntze), Ceraria Pearson & Stephens and Portulacaria Jacquin which were previously grouped together on palynological characteristics have now been shown to differ in their leaf flavonoids, subsidiary cells of the stomata and geographical location: Silvaea possesses flavones and is endemic to South America, while Ceraria and Portulacaria possess flavonols and are endemic to Africa. The dichotomy also occurs below the generic level. In Calandrinia H.B.K. and Portulaca L. the dichotomy amongst their species is supported by other new taxonomic characters from cytology, palynology, pubescence of surfaces, type of subsidiary cells surrounding the leaf stomata and seed morphology recently elucidated by the author.     

Glycoflavones in Circaea

Hydrolysates of methanolic leaf extracts of Circaea yield the glycoflavones vitexin, isovitexin, vicinin-1, and vicinin-2. Additional flavonoids are found in the unhydrolyzed extracts. Previous studies of Onagraceae report only flavonols and one chalcone. Circaea is assigned to a monogeneric tribe of Onagraceae and has no clear relationship to any other group within the family. The presence of glycoflavones in Circaea serves to underscore the distinctiveness of the genus.     

Trichome anatomy and taxonomy of Saxifraga (Saxifragaceae)

Trichomes on flower pedicels and leaves were examined in 213 species of Saxifraga L. and in the monotypic, segregate genera Zahlbrucknera Reichenb., Saxifragella Engl., Saxifragodes D. M. Moore and Saxifragopsis Small. Pedicel trichomes were found to be better taxonomic characters than foliar ones. Six main trichome types were identified: i) multiseriate, glandular; ii) uniseriate, glandular; iii) sessile, multicellular, glandular; iv) multiseriate, eglandular; v) uniseriate, eglandular; vi) unicellular, eglandular. The different types were distributed (except in certain species) on pedicels as follows. Multiseriate, glandular types occur in four series of Saxifraga sect. Micranthes (Haw.) D. Don, part of sect. Gymnopera D. Don, and in sects Ciliatae Haw., Trachyphyllum Gaudin, Xanthizoon Griseb., Ligulatae Haw., Porophyllum Gaudin, Porphyrion Tausch and Irregulares Haw. They also occur in the genus Saxifragopsis. Uniseriate, glandular types occur in five series of Saxifraga sect. Micranthes , part of sect. Gymnopera and Irregulares , and in sects. Miscopetalum (Haw.) Sternb., Cymbalaria , Griseb. Tridactylites (Haw.) Engl., Saxifraga and Stoloniferae Haw. They also occur in the genus Zahlbrucknera. Eglandular, multicellular trichomes occur occasionally in Saxifraga sects Micranthes and Gymnopera , more frequently in sects Ciliatae and Ligulatae , and are ubiquitous in sects Xanthizoon, Porophyllum and Porphyrion. Eglandular, unicellular trichomes occur only in Saxifragopsis and Saxifragodes. Sessile, glandular trichomes occur in a group of species from Saxifraga sect. Stoloniferae. Saxifragella is glabrous. This taxonomic distribution of trichome types generally supports Engler's classification of the genus, and is compatible with other evidence from palynology, embryology and seed morphology. The taxonomic disposition of the few exceptional species is discussed.     

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 patterns in leaves of the gramineae

In a leaf survey of 274 species from 121 genera of the Gramineae, flavone C-glycosides and tricin were found to be the major flavonoids in 93% of the samples. By contrast, apigenin and luteolin O-glycosides were comparatively rare, as were the flavonols, kaempferol and quercetin. In only one species, Rottboellia exaltata were flavonols the sole flavonoids. 7.3′.4′-Trihydroxyflavone, which has been detected in the Juncaceae, was found in 3 of 5 samples of the species Bothriochloa bladhii. Flavonoid sulphates were present in 16% of the species examined. While in most of these plants tricin glycosides were conjugated with sulphate, in Paspalum convexum quercetin mono- and di-sulphates and 1-caffeylglucose sulphate were identified. Flavonoid sulphates are present in the tropical-subtropical subfamilies: Panicoideae (in 18% of species). Chloridoideae (15%) and Arundinoideae (40%) but were not found at all in tribes of the cool temperate regions. Proanthocyanidins were found in only 3% of the species surveyed. The flavan-4-ol, luteoforol and its apigenin analogue were detected only in the subfamilies Panicoideae and Chloridoideae, where they occured in 12 and 6% of species respectively.     

Chemotaxonomy and flavonoids ofGaillardia sectionHollandia (Asteraceae-Helenieae)

Eleven flavonoids, eight glycoflavones, two 6-methoxyethers, and one dihydroflavonol, were isolated from three “species” ofGaillardia sect.Hollandia. The similarity of the flavonoid profiles suggests that only one species is involved.     

Application of UV/VIS spectrophotometry and multivariate analysis to characterization of the species of Solanum sect. Erythrotrichum CHILD

The UV/VIS spectral characteristics of the standardized extracts of the leaves of 22 Solanum species of the Leptostemonum clade were investigated in the presence of shift reagents with the aid of multivariate analysis, to obtain data in support of the interspecific and subsectional delimitation proposed for Solanum sect. Erythrotrichum. Of these species, 20 belong to the section Erythrotrichum, S. paniculatum is assigned to the section Torva, and S. robustum is not attributed to a defined section. The results indicated characteristic λ(max) (absorbance maxima) for each species as well as the presence of phenolic compounds like flavonoids such as 5-hydroxy flavonols. Hierarchical cluster analysis (HCA) of the data obtained by UV/VIS analysis of the extracts or the extracts with the added shift reagents AlCl? and HCl showed a cophenetic correlation coefficient above 0.92 and the classification of the data into three groups. The principal-component analysis (PCA) revealed that the first three principal components accounted for over 98% of the total variance and showed results similar to those obtained by HCA. The present results supported the current proposal for interspecific delimitation of the studied species and partially supported the division of the section into two subsections. The UV/VIS spectral characteristics along with multivariate analysis appear to be a useful approach for distinguishing among species of the genus Solanum.     

New species and combinations in Vernonia sections Leiboldia and Lepidonia (Asteraceae), with a revisional conspectus of the groups

The wholly North American sectionLeiboldia ofVernonia as revised by Jones (1979) included six species. The present treatment recognizes only three species inLeiboldia, including one newly described from recent collections. The remainder of what Jones consideredLeiboldia has been transferred into a new sect.Lepidonia (Blake) Turner which was first proposed as a monotypic genus. A key to the two sections and 10 species is provided along with an account of their interrelationships. Morphological evidence suggests that sect.Lepidonia is one of the more primitive sections ofVernonia, being as close to certain African sections as they are to the mostly American sect.Vernonia. Consideration is given to the phyletic significance and generic value of receptacular pales in the Vernonieae from which it is concluded that these have persisted in three or more quite unrelated lines of this tribe and undue weight should not be accorded these in generic considerations. Consequently, the paleaceous, monotypic generaLepidonia andBolanosa are sunk into synonymy underVernonia, the former as a distinct section, the latter into the sect.Vernonia.     

Flavonoids as taxonomic markers in old world Lupinus species

In a leaf survey of 54 specimens of 11 Old World Lupinus species three classes of flavonoids were detected: flavones (in 82%), flavonols (in 36%) and flavone C-glycosides (in 55%). The rough-seeded species were clearly distinguished from the smooth-seeded taxa by the presence of a novel 2′-hydroxyflavone, luteolin and flavone C-glycosides as major leaf constituents and by the absence of flavonols. Within the smooth-seeded species, there are three flavonoid patterns: (a) flavonols only, L. albus; (b) flavones and flavonols, L. luteus, L. hispanicus and L. angustifolius; and (c) flavones only, L. micranthus. L. angustifolius further differed in uniquely producing diosmetin as a major leaf constituent. These divisions coincide exactly with previous groupings based on alkaloidal and morphological data. Amongst the 12 samples of L. angustifolius three chemical races were distinguished and a number of diosmetin glucoside malate esters detected. The flower flavonoid aglycone patterns of the nine Old World species surveyed differed markedly from the corresponding leaf profiles by the presence of flavones: luteolin and apigenin in eight and chrysoeriol in seven species as major constituents, while flavone C-glycosides were found only in trace amount in three species. In a leaf flavonoid survey of 13 representative New World Lupinus taxa, glycoflavones were major leaf components, a variety of methylated flavones were identified and flavonols were absent. The presence of the novel 2′-hydroxyflavone in five New World species may indicate some evolutionary link with the rough seeded taxa of the Old World.     

Biosystematics of the monocotyledoneae—flavonoid patterns in leaves of the liliaceae

In a leaf survey of 168 species of the Liliaceae, most of the major flavonoid classes were found to be represented in the family. Flavonols occurred most frequently: quercetin and kaempferol were detected in 40% and 42% of the sample respectively, while the flavones luteolin and apigenin were present in only 24% and 20% of the sample. Methylated derivatives, i.e. isorhamnetin, diosmetin and tricin were rare. Procyanidins were present in 17 species, flavonoid sulphates in only one species and flavone C-glycosides in only three species. Anthraquinone pigments were identified in species of Aloe Asphodeline and Asphodelus. Three new flavonoid glycosides were characterised during the course of the survey: diosmetin 7-diglucoside in Colchicum byzanthinum and tricin 7-fructosylglucoside and tricin 7-rutinoside-4′-glucoside in Hyacinthus orientalis cv. ‘Quean of the Pinks’. On the basis of the flavonoid survey, the subfamilies of the Liliaceae may be grouped into those containing flavonols only, those with flavones only or those having both flavonols and flavones. Members of the related families: Amaryllidaceae (17 species), Agavaceae (1 species) and Xanthorrhoeaceae (1 species) contained only flavonols. The subfamilies Scilloideae, Asphodeloideae and Melanthioideae show the most chemical variation whilst the Wurmbaeoideae and Lilioideae are the most homogeneous groups. The tribe Scilleae is unusual in that both flavone- and flavonol-containing genera occur and a wide variety of flavonoid types are represented. A comparison of the leaf flavonoids of the Liliaceae with those found in families related to the grasses showed that all except two classes of flavonoid compound (5-methylated flavones and 5-deoxyflavonoids) found in the Juncaceae. Cyperaceae, Palmae and Gramineae are present in the Liliaceae thus supporting the view that all four families could have arisen from Liliaceae-like ancestors.     

Ecogeographic distribution of secondary constituents in Parthenium (compositae)

Over 20 taxa of the genus Partenium (Compositae) representing four sections or five ecological groupings from throughout the Americas, were examined for sesquiterpene lactones, flavonoids and alkaloids. The tropical thorn-forest, arborescent members (sect. Parthenichaeta) were found to contain three different sesquiterpene lactone types and derivatives of the flavonols; quercetin, kaempferol and quercetagetin. The desert shrubs were remarkable for their high production of methylated quercetagetin flavonols and alkaloids, but lacked any appreciable amounts of sesquiterpene lactones. The temperate, submontane perennials (sect. Bolophytum), contained lactones and flavonols in extremely low concentrations. The herbaceous annuals (sect. Argyrochaeta) contained pseudoguaianolides only and together with quercetin, and kaempferol $\text{O-}\text{glycosides}$. The herbaceous perennials contained twice as many lactones and flavonoids as the annuals. It is suggested that the ecogeographical distribution of secondary products in Parthenium is probably a result of adaptive responses to various physical and biotic factors (herbivore pressure) in the environment.     

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.     

铁线莲属尾叶铁线莲组(毛茛科)基于形态学证据的分支系统学

选取铁线莲属 (Clematis) 尾叶铁线莲组(sect. Campanella)中37个种以及西南铁线莲组 (sect. Bebaeanthera) 中的2个种为内类群, 以Clematis alternata作为外类群, 通过对全世界10个标本馆的近2 000份腊叶标本的形态学特征统计, 选取了35个性状进行编码, 利用PAUP 4.0 beta 10 软件进行系统发育重建。通过最简约法(maximum parsimony)分析共得到182棵最简约分支树, 树长为182步, 一致性指数(CI)=0.385, 保持性指数(RI)=0.685。结果表明: (1)尾叶铁线莲组并非是一个单系类群; (2)以花序发生位置这一性状建立的sect. Bebaeanthera不能成立, 应并入尾叶铁线莲组; (3)本研究结果不支持 在尾叶铁线莲组中建立subsect. Henryianae或ser. Henryianae; (4) C. ranunculoides等萼片外面具纵翅的一群植物与本组中萼片红色的种类C. lasiandra和C. dasyandra有较近的亲缘关系; (5)C. otophora、C. pogonandra、C. repens和C.barbellata等几个种聚为一支, 且支持率很高, 它们具有一系列的共衍征, 即萼片质地较厚, 花丝扁平, 宽条形, 被短柔毛, 花药被黄色短毛, 药隔先端凸起, 因此不支持建立Ser. Pogonandrae; (6)本组中非洲分布的2个种无论从形态上还是从地理分布和生境上都十分特殊, 是本组植物的特化类群。     

滇西南四个自然保护区鱼类多样性及评价指标探究

为了解滇西南怒江水系的南滚河自然保护区、南捧河自然保护区、永德大雪山自然保护区及澜沧江水系的澜沧江自然保护区鱼类多样性和变化趋势, 探讨其差异和变化的原因, 本文采用β多样性指数分析了4个保护区的鱼类多样性, 并比较了鱼类分类阶元的特有性、单型性和古老成分的有无等多项指标。结果显示, 4个自然保护区共有土著鱼类85种, 隶属于6目13科45属。在中国仅见于怒江水系的4个特有属有异鲴属(Aspidoparia)和新条鳅属(Neonoemacheilus)分布于这3个保护区中; 18种特有种中, 仅分布在这3个保护区的狭域特有种5种。在中国仅分布于澜沧江水系的属有31个, 但仅安巴沙鳅属(Ambastaia)分布于澜沧江保护区; 在澜沧江保护区分布着中国仅见于澜沧江水系的特有种20种, 其中狭域特有种3种。怒江水系的3个保护区分布有1个单型属, 即鳗鲡属(Anguilla), 但没有单型种; 澜沧江自然保护区无单型属与单型种分布。4个保护区中的鱼类均系晚第三纪和第四纪形成的种类或类群, 没有古老或孑遗种类。β多样性结果显示, 在4个保护区中澜沧江自然保护区的鱼类多样性最丰富, 而南滚河自然保护区的丰富程度最低, 但是怒江水系3个自然保护区鱼类多样性的代表性及保护地位比澜沧江自然保护区的要高。而特有阶元和单型性阶元的存在体现出怒江水系3个自然保护区的保护价值及保护意义比澜沧江保护区高。地理范围跨度大小、生境空间异质性高低、保护区面积大小及支流多少等是影响鱼类多样性的主要因素。因此, 规划和设计保护区时, 如果能在水系的上、中、下游分别规划1条一级支流作为保护区, 可使该水系的绝大多数鱼类得到保护。     

Flavonoids and the systematics of Luffa

Flavonoids were characterized from leaves and flowers of six species of Luffa. Each species had a distinct flavonoid pattern. Based on leaf flavonoids, Luffa is separable into two groups of species: L. graveolens and L. operculata contain only flavonols. L. acutangula, L. aergyptiaca, L. echinata and L. forskalii contain only flavones. Flavonoid data indicate that the New World disjunct species. L. operculata, is most closely related to L. graveolens.     

Occurrence of sulphated flavones and caffeic acid esters in members of the fluviales

A survey of 50 species of the Fluviales showed that over 50% have either flavone or caffeic acid sulphates present. Flavone sulphates were detected in 16% of the sample and the 7-sulphates of luteolin, apigenin, diosmetin and chrysoeriol and the 7,3′-disulphate of luteolin were identified variously in Thalassia, Zannichellia and Zostera species. Anionic caffeic esters were found in 46% of the sample; preliminary studies indicate the presence of sulphated caffeylquinic acids in these plants. In confirmation of earlier studies, glycoflavones were found to be widespread and flavonols and proanthocyanidins to be rare. The taxonomic and ecological significance of these results are discussed.