New flavonoid chemotypes from Asplenium normale (Aspleniaceae) in Malaysia

Seven Asplenium normale individuals in Malaysia were surveyed for flavonoid com¬pounds. They were divided into two chemotypes, H- and I-types. The flavonoids were isolated by various chromatography and identified by TLC, HPLC, UV spectroscopic, LC-MS and NMR sur¬veys. Two flavone O-glycosides, apigenin 7-O-rhamnosyl-(1→4)-rhamnoside (1) and apigenin 7- O-rhamnosyl-(1→4)-rhamnoside-4'-O-rhamnoside (2), and two flavone C-glycosides, vicenin-2 (6) and lucenin-2 (7), were contained in one chemotype (H-type). On the other hand, two flavonol O-glycosides, kaempferol 3-O-glucosylrhamnoside (3) and kaempferol 3,4'-di-O-glycoside (4) and a flavone O-glycoside, genkwanin 4'-O-glucosyl-(1→3)-rhamnoside (5), were found from another chemotype (I-type) together with 6 and 7. In cases of Japanese Asplenium normale and related species, seven chemotypes have been reported. However, their chemotypes did not include flavonol O-glycosides and apigenin trirhamnoside. Apigenin 7-O-rhamnosyl-(1→4)-rhamnoside (1) and apigenin 7-O-rhamnosyl-(1→4)-rhamnoside-4'-O-rhamnoside (2) were reported in nature for the first time

The Relationship between Mating System and Genetic Diversity in Diploid Sexual Populations of Cyrtomium falcatum in Japan

The impact of variation in mating system on genetic diversity is a well-debated topic in evolutionary biology. The diploid sexual race of Cyrtomium falcatum (Japanese holly fern) shows mating system variation, i.e., it displays two different types of sexual expression (gametangia formation) in gametophytes: mixed (M) type and separate (S) type. We examined whether there is variation in the selfing rate among populations of this species, and evaluated the relationship between mating system, genetic diversity and effective population size using microsatellites. In this study, we developed eight new microsatellite markers and evaluated genetic diversity and structure of seven populations (four M-type and three S-type). Past effective population sizes (Ne) were inferred using Approximate Bayesian computation (ABC). The values of fixation index (FIS), allelic richness (AR) and gene diversity (h) differed significantly between the M-type (FIS: 0.626, AR: 1.999, h: 0.152) and the S-type (FIS: 0.208, AR: 2.718, h: 0.367) populations (when admixed individuals were removed from two populations). Although evidence of past bottleneck events was detected in all populations by ABC, the current Ne of the M-type populations was about a third of that of the S-type populations. These results suggest that the M-type populations have experienced more frequent bottlenecks, which could be related to their higher colonization ability via gametophytic selfing. Although high population differentiation among populations was detected (FST = 0.581, F’ST = 0.739), there was no clear genetic differentiation between the M- and S-types. Instead, significant isolation by distance was detected among all populations. These results suggest that mating system variation in this species is generated by the selection for single spore colonization during local extinction and recolonization events and there is no genetic structure due to mating system

Flavonoid Glycosides from the Fern, Schizaea (Schizaeaceae) in South Pacific Region, and their Distribution Pattern

Abstracts Eight Schizaea species, S. balansae, S. bifida, S. dichotoma, S. fistulosa, S. intermedia, S. laevigata, S. melanesica and S. tenuis, were chemotaxonomically surveyed for flavonoid glycosides. Seventeen flavonoids, e.g. 3-O-glucosides and 3-O-rutinosides of kaempferol and quercetin, isorhamnetin 3-O-glucoside, luteolin 7-O-glucoside and apigenin 6,8-di-C-glucoside, were isolated and identified from the fronds of the species. Nine acylated flavonols such as kaempferol 3-O-(feruloylglucoside) and 3-O-(p-coumaroylglucoside), and quercerin 3-O-(p-coumarolyglucoside) were basically present in all species. On the other hand, 3-O-rutinosides of kaempferol and quercetin were absent in four species, S. intermedia, S. laevigata, S. melanesica and S. tenuis

Flavonol glycosides from Asplenium foreziense and its five related taxa and A. incisum

The flavonoids of Asplenium foreziense, A. fontanum subsp. fontanum and subsp. pseudofontanum. A. obovatum subsp. obovatum var. obovatum and var. protobillotii, A. obovatum subsp. lanceolatum, and A. incisum were isolated and identified for chemotaxonomic survey. A major constituent of all taxa was kaempferol 3-O-gentiobioside. As minor compounds, kaempferol 3,7-O-glycoside and/or kaempferol 3-O-glycoside were found in A. fontanum, A. obovatum and A. foreziense, and kaempferol 3-O-gentiobioside-4'-O-glucoside, kaempferol 3-O- glucoside and quercetin 3-O-diglucoside in A. incisum. It was suggested that A. foreziense, A. fontanum including subsp. pseudofontanum and A. obovatum including subsp. lanceolatum are not only morphologically but also chemotaxonomically related. The East Asian A. incisum was chemically and geographically different from these taxa. (C) 2000 Elsevier Science Ltd.Peer Reviewe

Flavonol glycosides from Asplenium foreziense and its "ve related taxa and A. incisum

Abstract The #avonoids of Asplenium foreziense, A. fontanum subsp. fontanum and subsp. pseudofontanum, A. obovatum subsp. obovatum var. obovatum and var. protobillotii, A. obovatum subsp. lanceolatum, and A. incisum were isolated and identi"ed for chemotaxonomic survey. A major constituent of all taxa was kaempferol 3-O-gentiobioside. As minor compounds, kaempferol 3,7-O-glycoside and/or kaempferol 3-O-glycoside were found in A. fontanum, A. obovatum and A. foreziense, and kaempferol 3-O-gentiobioside-4-O-glucoside, kaempferol 3-O-glucoside and quercetin 3-O-diglucoside in A. incisum. It was suggested that A. foreziense, A. fontanum including subsp. pseudofontanum and A. obovatum including subsp. lanceolatum are not only morphologically but also chemotaxonomically related. The East Asian A. incisum was chemically and geographically di!erent from these taxa

Occurrence of the Primary Cell Wall Polysaccharide Rhamnogalacturonan II in Pteridophytes, Lycophytes, and Bryophytes. Implications for the Evolution of Vascular Plants

Borate ester cross-linking of the cell wall pectic polysaccharide rhamnogalacturonan II (RG-II) is required for the growth and development of angiosperms and gymnosperms. Here, we report that the amounts of borate cross-linked RG-II present in the sporophyte primary walls of members of the most primitive extant vascular plant groups (Lycopsida, Filicopsida, Equisetopsida, and Psilopsida) are comparable with the amounts of RG-II in the primary walls of angiosperms. By contrast, the gametophyte generation of members of the avascular bryophytes (Bryopsida, Hepaticopsida, and Anthocerotopsida) have primary walls that contain small amounts (approximately 1% of the amounts of RG-II present in angiosperm walls) of an RG-II-like polysaccharide. The glycosyl sequence of RG-II is conserved in vascular plants, but these RG-IIs are not identical because the non-reducing l-rhamnosyl residue present on the aceric acid-containing side chain of RG-II of all previously studied plants is replaced by a 3-O-methyl rhamnosyl residue in the RG-IIs isolated from Lycopodium tristachyum, Ceratopteris thalictroides, Platycerium bifurcatum, and Psilotum nudum. Our data indicate that the amount of RG-II incorporated into the walls of plants increased during the evolution of vascular plants from their bryophyte-like ancestors. Thus, the acquisition of a boron-dependent growth habit may be correlated with the ability of vascular plants to maintain upright growth and to form lignified secondary walls. The conserved structures of pteridophyte, lycophyte, and angiosperm RG-IIs suggests that the genes and proteins responsible for the biosynthesis of this polysaccharide appeared early in land plant evolution and that RG-II has a fundamental role in wall structure

Mating system evolution and genetic structure of diploid sexual populations of Cyrtomium falcatum in Japan

Abstract Evolution of mating systems has become one of the most important research areas in evolutionary biology. Cyrtomium falcatum is a homosporous fern species native to eastern Asia. Two subspecies belonging to a sexual diploid race of C. falcatum are recognized: subsp. littorale and subsp. australe. Subspecies littorale shows intermediate selfing rates, while subsp. australe is an obligate outcrosser. We aimed to evaluate the process of mating system evolution and divergence for the two subspecies using restriction site associated DNA sequencing (RAD-seq). The results showed that subsp. littorale had lower genetic diversity and stronger genetic drift than subsp. australe. Fluctuations in the effective population size over time were evaluated by extended Bayesian skyline plot and Stairway plot analyses, both of which revealed a severe population bottleneck about 20,000 years ago in subsp. littorale. This bottleneck and the subsequent range expansion after the LGM appear to have played an important role in the divergence of the two subspecies and the evolution of selfing in subsp. littorale. These results shed new light on the relationship between mating system evolution and past demographic change in fern species