Sulfated Flavonoids Research Articles

Sulfated flavonoids and leaf morphology of the Halophila ovalis—H. minor complex (hydrocharitaceae) in the Pacific Islands and Australia

Sulfated flavonoids showed a systematic pattern among Halophila populations of the Pacific and Australia. Large-leaved plants, typical of H. ovalis (R.Br.) Hook. f., in the Palau Islands (Belau) and in Australia contained sulfated flavonoids, but small-leaved plants that have received various treatments under H. ovalis, including ssp. bullosa (Setchell) den Hartog and ssp. hawaiiana (Doty & Stone) den Hartog, and under H. minor (Zoll.) den Hartog or H. ovata Gaud. in American Samoa, Western Samoa, Tonga, Fiji, Wallis I., New Caledonia, Yap, Guam, Hawaii and Australia lacked sulfated flavonoids. Plants collected in their natural habitats as well as those grown in experimental cultures showed the characteristic patterns of these secondary compounds. Although the large-leaved plants have the potential for producing the largest leaves in the complex, they are not separable from small-leaved plants in leaf dimensions or in number of pairs of cross veins under all environmental conditions. The production of sulfated flavonoids and the potential for greater leaf length are the characteristics that can be used to separate typical H. ovalis and ssp. australis (Doty & Stone) den Hartog from other members of the complex.

Flavonoids as taxonomic markers in some cocosoid palms

Flavonoid surveys of hydrolysed and direct leaf extracts of fifty two cocosoid palms revealed tricin, glycoflavones, proanthocyanidins, quercetin, flavonoid sulphates, isorhamnetin, and luteolin as regular constituents; present in 87, 77, 53, 47, 36, 26 and 26% of species, respectively. Kaempferol was found in 15% of the sample and apigenin in only one taxon ofAttalea. Attalea andSyagrus were chemically heterogeneous groups. The flavonoid evidence suggested the removal ofPolyandrocosus from theAllagoptera unit, the recognition of twoMaximiliana species, the separation ofArecastrum andArikuryroba fromSyagrus and thatJubaea was closer toButia thanJubaeopsis. Five morphologically similar Central AmericanScheelea species were distinguished by their flavonoid profiles.

Leaf flavonoids of primitive dicotyledonous angiosperms: Degeneria vitiensis and Idiospermum australiense

Abstract The leaf flavonoids of Degeneria vitiensis and Idiospermum australiense were examined. Three quercetin (flavonol) glycosides were detected in D. vitiensis , and two flavone glycosides and a C -glycosylflavone were detected in I. australiense . Myricetin, proanthocyanins and flavonoid sulfates were not detected in either species. The results for D. vitiensis agree with the general flavonoid pattern for other families of the Magnoliiflorae and suggest that flavonol glycosides are a “primitive” feature in this group. However, the flavonoids of I. australiense were more “advanced”, and its suggested that the C -glycosylflavone in this species is an “advanced” feature. These data also suggest that C -glycosylflavones are a derived feature in dicotyledons.

Anthocyanin pigments and leaf flavonoids in the family araceae

Anthocyanins, variously identified in inflorescence, fruit, leaf or petiole of 59 representative species of the Araccae, are of a simple type. The most common pigment is cyanidin 3-rutinoside, while pelargonidin 3-rutinoside and cyanidin 3-glucoside are regularly present. Two rare pigments are: cyanidin 3-gentiobioside in Anchomanes and Rhektophyllum, both in the subfamily Lasioideae; and delphinidin 3-rutinoside in Schismatoglottis concinna. In a leaf survey of 144 species from 58 genera, flavone C-glycosides (in 82%) and proanthocyanidins (in 35–45%) were found as the major flavonoids. In the subfamily Calloideae, subtribe Symplocarpeae, flavonols replace glycoflavones as the major leaf components but otherwise flavonols are uncommon in the family (in 27% of the sample) and more usually co-occur with flavone C-glycosides. Two new flavonol glycosides were characterized from Lysichiton camtschatcense: kaempferol 3-(6-arabinosylgalactoside)and kaempferol 3-xylosylgalactoside. Simple flavones, luteolin and chrysoeriol (in 6%) were found only in the subtribes Arinae and Cryptocoryninae, subfamily Aroideae. Flavonoid sulphates were identified in only four taxa: glycoflavone sulphates in two Culcasia species and Philodendron ornatum and a mixture of flavone and flavonol sulphates in Scindapsus pictus. Caffeic ester sulphates were more common and their presence in Anthurium hookeri was confirmed. These results show that the Araceae are unusual amongst the monocots in their simple and relatively uniform flavonoid profile; no one subfamily is clearly distinguished, although at tribal level some significant taxonomic patterns are observed. The best defined groups are the subfamilies Lasioideae and Monsteroideae, and the tribes Symplocarpeae and Arophyteae, and the subtribe Arinae. The greatest chemical diversity occurs in Anthurium and Philodendron, but this may only reflect the fact that these are the two largest genera in the family. The origin and relationship of the Araccae to other monocot groups are discussed in the light of the flavonoid evidence.

Phytochemical Evidence for The Genetic Contamination of Camellia sasanqua Thunberg

A wide range of Camellia species and hybrids have been surveyed for the presence of the eugenol glycoside, sasanquin, and two fluorescent flavonoid sulfates of unknown structure designated here, for convenience, camellin I and camellin II. Sasanquin is restricted to C. sasanqua Thunberg, C. hiemalis Nakai, C.verlealis (Makino) Makino, their hybrids and a very small number of C.japoleica L. cultivars. The camellins are found in all accessions of C. japonica L., C. Iutchuensis T. Ito, C.tralesleohoensis Hayata, most accessions of C. sasalequaThunberg and most hybrids involving these species. Cork-wart variation in some progenies of C.sasanqua Thunberg and C. hiemalis Nakai is also included. The evidence presented here supports the idea that occasional events of hy-bridization between C.japoleica L. and C.sasanqua Thunberg have produced hybrids that backcross to C.sasalequa Thunberg and have introgressed the cultivated forms of C. sasanqua Thunberg.

Taxonomy of the Genus Amphiachyris (Asteraceae: Asterae)

Amphiachyris is a North American genus of two species, A. dracunculoides and A. amoena. Related to Gutierrezia, it has in the past been placed in synonymy under that genus and also under Xanthocephalum. The generic status of A mphiachyris, as recognized by Solbrig, is accepted. Chromosome counts for both species and two species of Gutierrezia are reported. Counts of n = 4 for A. amoena and A. dracun- culoides and n 5 and n = 8 for G. texana are new. Preliminary chromatographic results indicate the presence of sulfated flavonoids in Amphiachyris. The genus Amphiachyris is composed of two annual species, one of which is restricted to the limestone-derived clay soils of the Edward's Plateau region of central Texas. The other, a very weedy species, is distributed widely on black prairie soils in the midwestern United States with scat- tered localities known as far east as South Carolina (Fig. 1). The distri- butions of Amphiachyris and of the annual species of Gutierrezia overlap throughout much of their ranges; these taxa are also quite similar in gross morphology. It is not surprising, therefore, that the taxonomic placement of Amphiachyris has been altered several times by various work- ers. The purpose of the present study is to evaluate the status of the taxon, using morphological, cytological and chemical methods.

Chromosome number and flavonoid synthesis in Briza L. (Gramineae).

Following a recent reidentification of the apigenin C-glycosides in diploid Briza media, the luteolin C-glycosides were reexamined and three acylated derivatives of a luteolin C-glycoside were found. In an attempt to identify the chromosome or group of chromosomes responsible for the change in flavonoid synthesis from 4'-hydroxy- in diploid plants to 3',4'-dihydroxyflavone C-glycosides in autotetraploid plants, leaf flavonoids of artificially produced aneuploids of B. media were examined. Among these plants three different leaf flavonoid profiles were recognized: diploid, tetraploid, and a "modified" tetraploid pattern. All the aneuploids with the normal or "modified" tetraploid pattern were trisomic for one of the small acrocentric chromosomes. Induced polyploids of other Briza species were usually found to have similar flavonoid patterns in the two chromosome races. Flavonoid sulfates were found in three South American species but are absent from all the European species.

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.

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.