Flavonoid systematics of ten sections of Ludwigia (Onagraceae)

Data for the flavonoids of 19 species in 10 sections of Ludwigia are presented. Eight flavonoids, comprising four glycoflavones, of which vitexin and isovitexin are reported for the first time in Ludwigia, and four flavonol glycosides, based on quercetin, are present in these species. Each section treated here has either glycoflavones or flavonols; presence of only onte class is considered to be advanced in the genus as a whole, compared with the presence of both glycoflavones and flavonols in the more generalized sects Myrtocarpus Cinerascentes, and Pterocaulon, which were examined earlier. Only glycoflavones are present in sects Macrocarpon (four species), Seminuda (five species), the ditypic African sect. Africana, the monotypic African sects Brenania, Cryptosperma, and Prieurea, the monotypic east Asian sect. Nipponia, and the monotypic pantropical section Fissendocarpa. Only flavonols are present in the monotypic Old Wodd section Caryophylloidea and sect. Oligospermum, which comprises nine species widespread in the OId and New Worlds.     

不同育性三角梅品种之间的形态、花粉活力、造访昆虫及黄酮醇含量的比较研究

三角梅高度不育,到目前为止其不育机理仍未理解透彻。本研究通过比较三角梅中可育和不育品种之间的生殖器官特征、花粉的活力、造访昆虫以及花粉中的类黄酮积累差异,为揭示其不育机理提供更多的证据。四个可育和两个不育三角梅品种的花萼管比较结果显示,可育品种的花萼管饱满呈长卵形,而不育品种的花萼管细长管状。可育品种的花粉形态均匀,而不育品种的花粉大小不一。花粉活性结果显示,可育品种的花粉萌发率在11.1%~46.5%,不育品种的花粉在相同的培养条件下几乎不萌发。在可育和不育品种间,共有七种昆虫造访,但昆虫的种类没有表现出明显的差异和偏好。类黄酮积累调查结果显示山奈酚/槲皮素糖苷衍生物是花粉中的主要类黄酮组分。利用花粉荧光染料DPBDA对四个可育和两个不育三角梅品种花器官中的黄酮醇含量比较显示,可育材料中的两种黄酮醇的含量显著高于不育材料,花粉管尖端的荧光信号相比花粉管的其他位置更丰富。我们推测黄酮醇含量差异,特别是槲皮素含量可能对三角梅花粉的活力有一定的积极作用。     

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.     

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.     

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.     

Exudate flavonoids in three persian asteraceae species

Aereal parts of three Asteraceae from Iran have been analysed for exudate flavonoids. Artemisia oliveriana, Pulicaria gnaphalodes and Tanacetum polycephalum are shown to accumulate mostly 6-methoxylated flavonols and flavones as external aglycones.     

笃斯越桔化学成分及其功能活性的研究进展

笃斯越桔(Vaccinium uliginosum)因其富含花青苷等生物活性成分而备受关注。迄今为止, 从笃斯越桔果实中已鉴定出24种花青苷、32种黄酮醇苷、24种有机酸、28种芳香成分及少量儿茶素及其低聚物。同时, 笃斯越桔还含有丰富的矿质元素、维生素及氨基酸等营养成分。大量的体内和体外实验结果表明, 笃斯越桔具有强大的抗氧化、抗衰老、抗炎、抗癌、提高记忆力、预防心血管疾病和保护视力等生理活性。该文介绍了笃斯越桔资源分布情况及其遗传背景, 综述了其果实和叶片中的主要功能成分、营养物质及芳香成分的组成和含量, 讨论了遗传和环境等因素对其活性物质合成和积累的影响, 以期为其新品种选育及综合利用提供参考依据。     

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.     

Flavonoids of the Hydrangeaceae Dumortier

Fourteen species representing nine genera of the Hydrangeaceae Dumortier were surveyed for their flavonoid pigments. All taxa exhibited profiles based upon common flavonols. Myricetin was seen in two genera: Jamesia and Decumaria. Jamesia was further distinguished by the absence of kaempferol or its glycosides. A complex array of 3-O-mono-, 3-O-di- and 3-O-triglycosides was observed, although not all species had all levels of glycosylation. Decumaria barbara was unique within the species studied in its possession of 3,7-di- and 3,7-triglycosides. The overall pattern of flavonol glycosides observed for the Hydrangeaceae closely resembles that found in herbaceous genera of Saxifragaceae. The comparatively low frequency of myricetin contrasts with its high occurrence in herbaceous genera.     

Anthochlors and other flavonoids as honey guides in the compositae

Anthochlor pigments have been recorded for the first time in three species of Helianthus and in Viguiera laciniata. Yellow flavonols based on quercetagetin or gossypetin have been found in yellow flowered species of Eriophyllum and Geraea. In Eriophyllum, all seven species studied contain quercetagetin and/or patuletin 7-glucosides. In those species containing UV honey guides, either yellow flavonoid or colourless quercetin glycosides can be responsible for producing strongly UV absorbent zones on the flowers. Thus in Helianthus, honey guides in some species result from UV absorbance by the chalcone coreopsin and the aurone sulphurein, whilst in H. annuus they result from absorbance by quercetin 3- and 7-glucosides. Furthermore, the occurrence of yellow flavonoids in flowers is not directly correlated with the presence of UV nectar guides. A detailed study of the distribution of chalcone in Coreopsis bigelovii flowers revealed that the anthochlor was present in epidermal cells on both upper and lower surfaces.     

Identification of eupalitin, eupatolitin and patuletin glycosides in Ipomopsis aggregata

Eupalitin, eupatolitin and patuletin 3-O-galactosides as well as eupalitin and patuletin 3-O-diglucosides have been isolated and identified from Ipomopsis aggregata (Polemoniaceae). These 6-methoxylated flavonols are important taxonomic markers in the family, occurring as they do in nine of the eighteen known genera. Microscale methods of identifying these and other related highly substituted flavonols are discussed. Studies of the mass spectral fragmentation patterns have shown that quercetagetin derivatives methylated in the A-ring can be distinguished from similar compounds methylated in the B-ring and from the analogous gossypetin derivatives.     

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.     

Flavonoids of Pallenis spinosa (Asteraceae)

Pallenis spinosa was investigated for its flavonoid content. Two mono- and diglycosides of patuletin, a quercetin monoglycoside, two tricin monoglycosides, and four methoxylated flavonols were reported.     

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.     

External flavonoid aglycones of Viguiera series Viguiera (asteraceae: heliantheae)

Distribution of external flavonoid aglycones supports other data to suggest that Viguiera series Viguiera (series Dentatae Blake) is a mixed taxonomic grouping. Two species, V. dentata and V. potosina, lack external flavonoid aglycones, whereas the remaining species of the series all produce external flavonoid aglycones and appear to form a natural taxonomic group. The latter group, which consists of species from Baja California and nearby xeric areas, exhibits a diversity of flavonoid types, with different diploid species variously producing flavonols, simple flavones, 6-methoxyflavones, 6-hydroxy,7-methoxyflavones and a chalkone as major compounds. Polyploid species exhibit combinations of flavonoid types from possible diploid ancestors. Compounds of the 6-hydroxy,7-methoxyflavone type appear to characterize the group of species from Baja California and nearby areas within Viguiera.     

Flavonols from Pterogyne nitens and their evaluation as myeloperoxidase inhibitors

A myeloperoxidase inhibitory kaempferol derivative, namely pterogynoside (1), was isolated from fruits of Pterogyne nitens, along with six known flavonols, kaempferol, afzelin, kaempferitrin, quercetin, isoquercetrin and rutin. The structures of all compounds were elucidated primarily from 1D and 2D NMR spectroscopic analyses, as well as by high resolution mass spectrometry. All flavonols were screened to identify secondary metabolites as potential myeloperoxidase (MPO) inhibitors, and at concentrations of 0.50–50 nM, quercetin (5), isoquercitrin (6) and rutin (7) exhibited strong inhibitory effects with IC₅₀ values of 1.22 ± 0.01, 3.75 ± 0.02 and 3.60 ± 0.02, respectively. The MPO activity detected for the new derivative 1 was markedly decreased (IC₅₀ 10.3 ± 0.03) when compared with known flavonols 5–7, and interestingly increased when tested against ABTS scavenging activity.     

Flavonoid variability within and between natural populations of Pinus uncinata

A total of 120 individual trees representative of Pinus uncinata were analysed for their foliar flavonoid content. The ratio of two extracted anthocyanidins, prodelphinidin and procyanidin, is a constant. Among the flavonols quercetin, kaempfrerol and isorhamnetin, the percentage of quercetin discriminates the five studied populations. Its distribution conforms to the Hardy-Weinberg law, but the ratio of the two implicit alleles proves the originality of each population, and leads to the recognition of distinct chemotypes.     

über die Beziehungen zwischen flavonolaufbauenden Enzymen,einem flavonolumwandelnden Enzym und der Akkumulation phenylpropanoider Verbindungen während der Antherenentwicklung

Summary The difference in activity of enzymes which are involved in the biosynthesis of flavonols (phenylalanineammonium-lyase, chalcone-flavanone isomerase) and of an enzyme which converts flavonols is studied during the development of anthers in Tulipa cv. Apeldoorn. The results are considered in relation to the accumulation of simple phenylpropanes, of an intermediate a chalcone and of different flavonoid compounds.In the stages of development with high activities of flavonol synthesizing enzymes there are also high activities in the flavonol converting enzymes. In these stages a large amount of derivates of p-coumaric acid and ferulic acid is accumulated as well as the intermediate product 2,3,4,4,6-pentahydroxychalcone; accordingly only traces of flavonols can be found.An intensive accumulation of different flavonols does not start before the late phase of development of the anthers in which the stationary concentration of chalcones decreases. It is the stage when the activity of the flavonol converting enzyme decreases rapidly.The relations between the stationary concentration of flavonoid compounds and the interlacing of synthesis and turnover are discussed.     

Chemodiversity of surface flavonoids in Solanaceae

Several species of Nicotiana and Solanum and further members of the Solanaceae have been examined for their exudate flavonoids. Most of the aglycones are widespread flavonols, but rare and unusual flavonols were also found, e.g. in exudates of Physalis and Solanum species. Flavones occur throughout the family, but flavanones are rare. Our data are presented in comparison to previous results. The chemodiversity of the observed structures is discussed in relation to literature reports. Morphological and systematic aspects are briefly addressed.     

Mutagenicity of plant flavonols in the Salmonella/mammalian microsome test: activation of flavonol glycosides by mixed glycosidases from rat cecal bacteria and other sources.

Over 70 naturally occurring and synthetic flavonoids were screened for mutagenicity with 5 tester strains in the Salmonella/mammalian microsome assay: TA1535, TA100, TA1537, TA1538 and TA98. Frameshift mutagenicity was confined to the flavonols (flavon-3-ols) in strain TA98, TA1537 and TA100. The two most mutagenic falvonols, namely, quercetin (3,3',4',5,7-pentahydroxyflavone) and kaempferol (3,4',5,7-tetrahydroxyflavone), exhibiting 12 and 7 revertants/nmol in TA98 respectively, are also the most common flavonols occurring in plants. Other flavonols exhibited less activity (revertants/nmol): galangin (2.0), rhamnetin (0.45), kaempferide (0.24), fisetin (0.14), myricetin (0.12), robinetin (0.06) and morin (0.05). All of these flavonols apparently exhibited significant activation by Aroclor 1254 induced rat-liver microsome preparations (S9). However, subsequent study revealed that only those flavonols either lacking or possessing one B ring hydroxyl group had an absolute requirement for microsomal activation. Alternatively, quercetin with two B-ring OH groups is not activated by microsomal enzymes, but by soluble (S100) enzymes from liver which are apparently constitutive and not subject to the usual chemical induction. 3 flavonol glycosides, namely, quercetrin (quercetin-3-O-rhamnoside), rutin (quercetin-3-O-rutinoside) and robinin (kaempferol-3-O-galactosido-rhamnoside-7-O-rhamnoside), were found to be nonmutagenic. They could, however, be activated by a variety of mixed glycosidases incorporated in the usual pour plate procedure. The most effective enzyme mixtures were obtained from rat cecal bacteria and from the snail Helix pomatia.