Further studies of flavonoids in Saxifraga (original) (raw)
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Externally Accumulated Flavonoids in Three Mediterranean Ononis Species
Zeitschrift für Naturforschung C, 2003
The Mediterranean Ononis species, O. fruticosa, O. natrix subsp. ramosissima and O. tridentata, have been analyzed for their exudate flavonoids. More than 20 flavonoid aglycones were identified, some of which are rather rare natural compounds. One of them, namely hypolaetin-8,3Ј,4Ј-trimethyl ether, had been found only once before. The results are presented in a table along with literature data, and the chemotaxonomic impact of the flavonoid patterns is discussed.
Taxonomic significance of flavonoid variation in temperate species of Nothofagus
Phytochemistry, 2003
Forty-two flavonoids and a stilbene (pinosylvin) were identified in the leaf exudates of 11 temperate species of Nothofagus from South America, Australia and New Zealand. The flavonoid profiles demonstrate significant taxonomic value at the subgeneric level. Most species of subgenus Fuscospora are characterized by the presence of pinosylvin, galangin and galangin methyl ethers. Kaempferol-type flavonols are abundant in subgenus Lophozonia while these flavonols are largely absent from species of subgenus Fuscospora. The flavonoid patterns are largely in agreement with a recent subgeneric classification of Nothofagus.
Foliar flavonoids of the most primitive group, sect. Distegocarpus within the genus Carpinus
Biochemical Systematics and Ecology, 2004
Foliar flavonoids in five taxa of the section Distegocarpus of Carpinus from China, Korea, and Japan were examined. Eleven compounds, mainly mono-glycosides of the flavonols myricetin, kaempferol and quercetin, and the flavones apigenin and luteolin were isolated and identified. The flavonoid profiles were relatively simple, but showed distinct differentiation among taxa. Flavonoid chemistry, morphological characteristics, and geographic distribution patterns were in accord with the idea that section Distegocarpus appeared to have differentiated into two groups from the ancestor; one group (fangiana-type) consisting of C. fangiana and C. rankanensis, and the other (japonica-type) consisting of C. cordata and C. japonica. C. japonica was considered as the most primitive extant species of the section with respect to flavonoid compounds as well as morphological characteristics. Within the fangiana-type, however, C. fangiana represented a more advanced than C. rankanensis only with respect to morphology. The fact that the presence of flavanone, which was a direct precursor to flavones and flavonols, was found in C. fangiana did not show correlation with the result of morphological advancement within the fangiana group. #
The flavonoids of Arnica frigida and A . louiseana (Asteraceae)
Canadian Journal of Botany, 1986
DOWNIE, S. R., and K. E. . The flavonoids of Arnicafrigida and A. louiseana (Asteraceae). Can. J . Bot. 64: 2748-2752. Forty-six populations within the Arnicafrigida Meyer ex Iljinlouiseana Farr complex were examined for flavonoid content. Seven glycosides were isolated and six identified. Members of this complex were found to produce primarily quercetin and kaempferol 3-O-glycosides. Flavonoid profiles obtained from A. frigida ssp. frigida were the most diverse and in some cases the most depauperate. Within this taxon, flavonoid diversity appears to have accompanied high morphological variability. The occurrence of flavonoid-depauperate plants in unglaciated Alaska suggests that flavonoids are of value in identifying refugia. Flavonoid profile similarities between A. frigida ssp. frigida and A. frigida ssp. griscomii corroborate morphological evidence as to the close affinity between these two taxa. DOWNIE, S. R., et K. E. DENFORD. 1986. The flavonoids of Arnicafrigida and A. louiseana (Asteraceae). Can. J . Bot. 64: 2748 -2752. La teneur en flavono'ides a fait l'objet d'Ctudes dans 46 populations i 1'intCrieur du complexe Arnicafrigida Meyer ex Iljin louiseana Farr. Sept glucosides furent isolCs dont six identifies. Les membres de ce complexe produisent principalement les 3-O-glycosides: quercCtine et kaempfkrol. Les profils des flavono'ides obtenus d'A. frigida ssp. frigida sont parmi les plus variCs et en certains cas, les plus pauvres. A 1'intCrieur de ce taxon, la diversit6 en flavonoi'des parait avoir accompagnC une variabilitC morphologique ClevCe. La presence de plantes appauvries en flavonoi'des dans 1'Alaska non glaciC suggkre que les flavonoi'des ont une certaine valeur dans l'identification des refuges. Les similaritks des profils de flavonoi'des entre A. frigida spp. frigida et A. frigida spp. griscomii appuient I'Cvidence morphologique de la grande affinitC entre ces deux taxons. [Traduit par la revue] complex Flavonoid* Locality and collection No. 2 n 1 2 3 4 5 6 7 Arnicafrigida ssp. frigida --*I, quercetin 3-0-galactoside; 2, kaernpfeml 3-0-glucoside; 3, quercetin 3-Odiglucoside; 4, kaernpfeml 3-0-galactoside; 5, quercetin gentiobioside; 6, apigenin 7-0-glucoside; 7, unknown.
Flavonoid chemistry of Calyceraceae
Canadian Journal of Botany, 1995
Flavonoid profiles were determined for I I species representing five genera of Calyceraceae: Acicatpha, Boopis, Calycera, Garnocarpha, and Nastanthus. Kaempferol, quercetin, were unequivocally identified. Kaempferol and quercetin occurred as 3-0-mono-and 3-0-diglycosides, whereas the latter two flavonols were observed only as aglycones. Several unidentified phenolic compounds were also noted. The simplest profile in the family consisted solely of the kaempferol and quercetin glycosides in Acicatpha, Gamocatpha, and one specimen of Calycera leucanthema. Morphological evidence suggests that Acicatpha represents prototypical Calyceraceae and that a close relationship exists between primitive Calyceraceae and some basal members of Asteraceae (subfamily Barnadesioideae). This last possibility is reinforced by the similarity of flavonoid profiles of Acicatpha and members of Barnadesioideae.
Journal of Natural Products, 2017
Eight new flavonoid-based 3′-O-β-D-glucopyranosides (1−8) and three new galloyl glucosides (9, 11, 12), were isolated from the aerial parts of Saxifraga spinulosa, along with 25 known compounds. The structures of the new compounds were elucidated by spectroscopic methods. Most of the isolated compounds exhibited potent DPPH radical-scavenging activities. Further, their inhibitory activities were evaluated against Babesia bovis, Babesia bigemina, Babesia caballi, and Theileria equi, protozoan parasites that cause piroplasmosis in livestock. The results indicated that several of these compounds showed growthinhibitory effects on such organisms that cause piroplasmosis.
Distribution of exudate flavonoids in the genus Plectranthus
Biochemical Systematics and Ecology, 2010
Thirty-four species of the genus Plectranthus (including species of the former genera Coleus and Solenostemon, fam. Lamiaceae) were surveyed for exudate flavonoids to see whether the distribution of these compounds would support a recent classification of the genus based on molecular and morphological characters. In this classification two major groups had been identified, the Coleus and Plectranthus clades. Only about 40% of the species, predominantly from the Plectranthus clade, were found to produce exudate flavonoids, which were mainly flavones. Flavanones were restricted to five species of the Plectranthus clade, whereas flavonols were only found in two species of the Coleus clade, Plectranthus montanus Benth. (synonyms Plectranthus marrubioides Hochst. ex Benth. and Plectranthus cylindraceus Hochst. ex Benth.) and Plectranthus pseudomarrubioides R.H.Willemse. Four of these flavonols were isolated from P. montanus and identified by NMR spectroscopy as the 3,7-dimethyl ether and 3,7,4 0 -trimethyl ether of quercetin and the 3,6,7-trimethyl ether and 3,6,7,4 0 -tetramethyl ether of quercetagetin. The remaining flavonols and flavones were identified by HPLC-UV and LC-MS of crude extracts on the basis of their UV and mass spectra, retention times and comparison with standards. Most flavonols were 3-methyl ethers and many of the flavones and flavonols were oxygenated at the 6-position. The most common flavones, occurring in both clades, were cirsimaritin and salvigenin, which are methoxylated at the 6-and 7-positions. 6-Hydroxylated flavones such as scutellarein and ladanein were restricted to species of the Plectranthus clade.
Leaf flavonoid glycosides as chemosystematic characters in Ocimum
Biochemical Systematics and Ecology, 2002
Thirty-one accessions of nine species belonging to three subgenera of Ocimum (basil, family Lamiaceae) were surveyed for flavonoid glycosides. Substantial infraspecific differences in flavonoid profiles of the leaves were found only in O. americanum, where var. pilosum accumulated the flavone C-glycoside, vicenin-2, which only occurred in trace amounts in var. americanum and was not detected in cv. Sacred. The major flavonoids in var. americanum and cv. Sacred, and also in all other species investigated for subgenus Ocimum, were flavonol 3-O-glucosides and 3-O-rutinosides. Many species in subgenus Ocimum also produced the more unusual compound, quercetin 3-O-(6Љ-O-malonyl)glucoside, and small amounts of flavone O-glycosides. The level of flavonol glycosides produced was reduced significantly in glasshouse-grown plants, but levels of flavone glycosides were unaffected. A single species investigated from subgenus Nautochilus, O. lamiifolium, had a different flavonoid glycoside profile, although the major compound was also a flavonol O-glycoside. This was identified as quercetin 3-O-xylosyl(1ٞ→2Љ)galactoside, using NMR spectroscopy. The species investigated from subgenus Gymnocimum, O. tenuiflorum (=O. sanctum), was characterised by the accumulation of flavone O-glycosides. These were isolated, and identified as the 7-O-glucuronides of luteolin and apigenin. Luteolin 5-O-glucoside was found in all nine species of Ocimum studied, and is considered to be a key character for the genus. : S 0 3 0 5 -1 9 7 8 ( 01 )0 0 1 0 3 -X 328 R.J. Grayer et al. / Biochemical Systematics and Ecology 30 (2002) [327][328][329][330][331][332][333][334][335][336][337][338][339][340][341][342]
Flavonoids and the taxonomy of Cercis
Biochemical Systematics and Ecology, 2000
Flavonoids of 11 samples of Cercis, comprising seven species, were isolated and identi"ed. Only 3-O-monoglycosides of kaempferol, quercetin and myricetin were obtained. Bauhinia (the largest genus in tribe Cercideae) is akin to Cercis because #avones are rarely found in the former. On the other hand, species of Bauhinia often present glycosides of isorhamnetin and a wider diversity of glycosides, and only rarely present myricetin. The frequent occurrence of this #avonol and the simpler #avonoid pro"le of Cercis may re#ect a greater antiquity of Cercis as compared with Bauhinia. With the exception of C. canadensis var. mexicana, Cercis taxa from xerophytic habitats did not yield kaempferol glycosides in detectable amounts, as opposed to taxa from mesophytic habitats. The results obtained are consistent with proposals of merging C. reniformis into synonymy of C. occidentalis, as well as the recognition of two North American species, C. canadensis and C. occidentalis, and the recognition of the Asian C. gigantea.