BIOCHEMICAL SYSTEMATICS AND ECOLOGY

Biodiversity of Convolvulaceous species that contain Ergot Alkaloids, Indole Diterpene Alkaloids, and Swainsonine
Cook D, Lee ST, Panaccione DG, Leadmon CE, Clay K and Gardner DR
Convolvulaceous species have been reported to contain several bioactive principles thought to be toxic to livestock including the calystegines, swainsonine, ergot alkaloids, and indole diterpene alkaloids. Swainsonine, ergot alkaloids, and indole diterpene alkaloids are produced by seed transmitted fungal symbionts associated with their respective plant host, while the calystegines are produced by the plant. To date, and represent the only species and members of the Convolvulaceae known to contain indole diterpene alkaloids, however several other Convolvulaceous species are reported to contain ergot alkaloids. To further explore the biodiversity of species that may contain indole diterpenes, we analyzed several Convolvulaceous species (n=30) for indole diterpene alkaloids, representing four genera, , , , and , that had been previously reported to contain ergot alkaloids. These species were also verified to contain ergot alkaloids and subsequently analyzed for swainsonine. Ergot alkaloids were detected in 18 species representing all four genera screened, indole diterpenes were detected in two species and eight species of the 18 that contained ergot alkaloids, and swainsonine was detected in two species. The data suggest a strong association exists between the relationship of the species associated with each host and the occurrence of the ergot alkaloids and/or the indole diterpenes reported here. Likewise there appears to be an association between the occurrence of the respective bioactive principle and the genetic relatedness of the respective host plant species.
Marine actinomycete sp. ISP2-49E, a new source of Rhamnolipid
Yan X, Sims J, Wang B and Hamann MT
A comparative study of with related species: Morphological characteristics, ITS sequences and active compounds
Wang Q, Quan Q, Zhou X, Zhu Y, Lan Y, Li S, Yu Y and Cheng Z
Morphological characteristics, ITS sequences, and active compounds have been used to differentiate between species of used in the traditional Chinese medicines Flos Lonicerae Japonicae (FLJ) and Flos Lonicerae (FL). FLJ includes whereas FJ includes , , and . FLJ could be distinguished from FL using four quantitative and 10 qualitative characters, ITS sequences, chlorogenic acid and luteoloside contents. Analyses revealed that was very different from the other species. The results have implications for the identification and quality control of species of used medicinally, suggesting that species should not be interchanged in medicinal preparations.
Triterpenoids and flavonoids from Miq. (Urticaceae)
Li J, Coleman CM, Wu H, Burandt CL, Ferreira D and Zjawiony JK
Phytochemical investigation of the leaves of Miq. (Urticaceae) led to the isolation of four triterpenoids (), three flavone C-glycosides (), two flavan-3-ols (, ), two flavanolignans (, ), and two proanthocyanidins (, ). All compounds were isolated from for the first time. This is the first report demonstrating the presence of arjunolic acid (), cinchonain Ia (), and cinchonain Ib () in the Urticaceae family. The occurrence of flavanolignans within the family Urticaceae supports the likelihood that such compounds are more common within the class Magnoliopsida than previously thought.
Phytoecdysteroids from Lamium spp: identification and distribution within plants
Savchenko T, Blackford M, Sarker SD and Dinan L
Bioassay/radioimmunoassay (RIA) analysis of the seeds of four Lamium species, L. album, L. galeobdolon, L. maculatum and L. pupureum revealed the presence of phytoecdysteroids in all of them. Bioassay/RIA-guided and photo-diode array-monitored HPLC analysis of the aerial parts of L. album and L. purpureum led to the isolation of four known ecdysteroids (abutasterone, inokosterone, polypodine B and pterosterone) from the former, and 20-hydroxyecdysone from the latter. Distribution and identities of ecdysteroids in different parts of these two species and also in the seed extract of L. maculatum have been analysed by RIA and bioassay.
Phylogenetic relationships among four species of Mullidae (Perciformes) inferred from DNA sequences of mitochondrial cytochrome b and 16S rRNA genes
Apostolidis AP, Mamuris Z and Triantaphyllidis C
DNA sequence comparisons of two mitochondrial DNA genes were used to infer phylogenetic relationships among four species of mullids. Approximately 238bp of the mitochondrial 16S ribosomal RNA (rRNA) and 261bp of the cytochrome b (cytb) genes were sequenced from representatives of three mullid genera (Mullus, Upeneus, Pseudopeneus), present in the Mediterranean Sea. Trees were constructed using three methods: maximum likelihood (ML), neighbor joining (NJ) and parsimony (MP). The results of the analyses of these data together with published data of the same mtDNA segments of two other perciform species (Sparus aurata, Perca fluviatilis), support the previous taxonomic classification of the three genera examined, as well as the classification of the two red mullet species in the same genus.
Differential expression for tissue-specific isozymes in three species of Hypostomus Lacépède, 1803 (Teleostei: Loricariidae)
Zawadzki CH, Machado MF and Renesto E
The expression patterns of 14 enzymatic systems in skeletal muscle, liver and heart tissues of three species of Hypostomus from the Iguaçu River basin (Brazil) were investigated. Although the patterns were similar for the three species, different tissues showed differential expressions, and the data showed that differential tissue expressions of isoperoxidases may be due to preferential combination or association of polypeptide subunits. The detected patterns for SOD isozymes showed that the quaternary structures of these enzymes were in disagreement with the subunit number reported for the majority of other vertebrate groups. Tissue-specific restriction on heterotetramer formation also were described in LDH and MDHP isozymes. Thus, these tissue-specific gene expression character in the species of Hypostomus have the greatest potential to be recognized and applied in systematic studies among species of Hypostomus.
The role of lipophilic and polar flavonoids in the classification of temperate members of the Anthemideae
Williams CA, Greenham J and Harborne JB
Lipophilic and vacuolar flavonoids were separately identified in representative temperate species of the genera Anthemis, Chrysanthemum, Cotula, Ismelia, Leucanthemum and Tripleurospermum. The four Anthemis species investigated variously produced four main surface constituents, in leaf and flower: santin, quercetagetin 3,6,3'-trimethyl ether, scutellarein 6,4'-dimethyl ether and 6-hydroxyluteolin 6,3'-dimethyl ether. By contrast, surface extracts of disc and ray florets of the species of Chrysanthemum, Cotula, Ismelia, Leucanthemum and Tripleurospermum surveyed yielded five common flavones in the free state: apigenin, luteolin, acacetin, apigenin 7-methyl ether and chrysoeriol. Polar flavonoids were isolated and identified in leaf, ray floret and disc floret of all the above plants. Anthemis species were distinctive in having flavonol glycosides in the leaves, whereas the leaf flavonoids of the other taxa were generally flavone O-glycosides. The 3-glucoside and 3-rutinoside of patuletin were characterised for the first time from Anthemis tinctoria ssp. subtinctoria. Two new flavonol glycosides, the 5-glucuronides of quercetin and kaempferol, were obtained from the leaf of Leucanthemum vulgare, where they co-occur with the related 5-glucosides and with several flavone glycosides. The ray florets of these Anthemideae generally contain apigenin and/or luteolin 7-glucoside and 7-glucuronide, whereas disc florets have additional flavonol glycosides, notably the 7-glucosides of quercetin and patuletin and the 7-glucuronide of quercetin. A comparison of the flavonoid pattern encountered here with those previously recorded for Tanacetum indicate some chemical affinity between Anthemis and Tanacetum. Flavonoid patterns of the other five genera are more distinct from those of Tanacetum and suggest that those genera form a related group. All 14 species surveyed for their flavonoid profiles have distinctive constituents and the chemical data are in harmony with modern taxonomic treatments of the "Chrysanthemum complex" as a series of separate genera.
Flavonoids as chemotaxonomic markers for Asteraceae
Emerenciano VP, Militão JS, Campos CC, Romoff P, Kaplan MA, Zambon M and Brant AJ
Flavonoids have been shown to be good taxonomic markers for Asteraceae. More than 800 compounds comprising 4700 flavonoid occurrences were included in a computational system specially made for chemotaxonomic purposes. Some implications of flavonols, flavones and other types as well as structural features of them are discussed for tribes and subtribes of Asteraceae.
Constituents of three Icelandic Alchemilla species
Olafsdottir ES, Omarsdottir S and Jaroszewski JW
3-Methoxyflavones and a novel coumarin from Psiadia dentata
Jakobsen TH, Marcussen HV, Adsersen A, Strasberg D, Smitt UW and Jaroszewski JW
Sesquiterpene lactones from Centaurea tweediei
Fortuna AM, de Riscala EC, Catalan CA, Gedris TE and Herz W
Aerial parts of Centaurea tweediei from Argentina afforded as the main constituent the sesquiterpene lactone onopordopicrin and minor amounts of a new heliangolide, a new guaianolide, a new eudesmanolide, a new eudesmane acid and the lignans arctigenin and matairesinol.
Acyclic diterpenes and sterols from the genera Bifurcaria and Bifurcariopsis (Cystoseiraceae, Phaeophyceae)
Daoudi M, Bakkas S, Culioli G, Ortalo-Magné A, Piovetti L and Guiry MD
Flavonoid sequestration by the common blue butterfly Polyommatus icarus: quantitative intraspecific variation in relation to larval hostplant, sex and body size
Burghardt F, Proksch P and Fiedler K
Common blue butterflies (Polyommatus icarus) sequester flavonoids from their larval food and store these pigments as part of their adult wing colouration. Insects were reared on 10 different diets to assess effects of host plants on variation in flavonoid sequestration in this moderately polyphagous butterfly. Rearing experiments revealed an unexpectedly large gradient in flavonoid richness, ranging from individuals with high flavonoid loads (reared on inflorescences of Medicago sativa, Trifolium repens, T. pratense) to butterflies which contained almost no such pigments (fed with foliage of M. sativa or Robinia pseudoacacia). Flavonoid sequestration was much more effective from natural hostplants than from experimentally offered diets which would not be accepted in the field. Female butterflies on average sequestered almost 60% more flavonoids than males. This sex difference was more pronounced on natural than on experimental diets. Flavonoid load was significantly and positively related to dry mass and forewing length as two important fitness correlates of butterflies. This correlation was particularly strong on experimental diets (i.e. under constraining conditions for development). On natural hostplants, in contrast, when butterflies generally were flavonoid-rich, no clear relationship between flavonoid load and size or mass emerged. Our analytical data are consistent with field results according to which females rich in UV-absorbing flavonoid wing pigments are more attractive to mate-searching males. In P. icarus, flavonoid richness might therefore increase visibility (by more effective sensory stimulation of the visual system), but could also confer information about the feeding history, and thus ontogenetically determined 'quality' of a potential mate.
Phytoecdysteroids in seeds of Lloydia serotina (Liliaceae)
Dinan L, Whiting P and Savchenko T
Seeds of a number of species in the Liliaceae (sensu Brummitt, 1992) were examined for the presence of ecdysteroid agonist and antagonist activities. No species were antagonistic to 20-hydroxyecdysone action on the ecdysteroid-responsive Drosophila melanogaster B(II) cell line and only one extract, that of Lloydia serotina, was agonistic. This activity is attributable to the presence of phytoecdysteroids as detected by ecdysteroid-specific radioimmunoassay and the agonist version of the B(II) bioassay. HPLC in conjunction with radioimmunoassay and bioassay have been used to determine the ecdysteroid profile. The major ecdysteroids present are identified as 20-hydroxyecdysone and polypodine B (5beta,20-dihydroxyecdysone).
Cyclopropyl amino acids of Amanita
Scott Chilton W and Drehmel DC
Secondary metabolites of Scilla plumbea, Ledebouria cooperi and Ledebouria ovatifolia (Hyacinthaceae)
Pohl T, Koorbanally C, Crouch NR and Mulholland DA
Tagetes tenuifolia Cav. (Asteraceae): some chemosystematic implications of their flavonoids
Abdala LR
Comparative chemical composition of the resinous exudates from Senecio adenotrichius and S. viscosissimus
Urzúa A and Andrade L
Sesquiterpene lactones from Lugoa revoluta
Triana J, Eiroa JL, López M, Ortega JJ, González AG and Barrera JB
The identification of fusidic acid, a steroidal antibiotic from marine isolate of the fungus Stilbella aciculosa
Kuznetsova TA, Smetanina OF, Afiyatullov SS, Pivkin MV, Denisenko VA and Elyakov GB