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Historical (mainly 1930s) and contemporary records of 482 vascular plant species or genera of non-littoral areas of 464 islands in the archipelago of SW Finland are compared, to visualise changes in distribution patterns, and to identify environmental variables that exert an influence on the distribution of the species. The environmental variables were measured in a GIS. Logistic regression analysis was used to find variables that affect the probability of species occurrences. Results, including distribution maps, are presented for each species. The families Clusiaceae, Violaceae, Cistaceae, Brassicaceae, Salicaceae, Ericaceae, Pyrolaceae, Monotropaceae, Empetraceae, Primulaceae, Tiliaceae, Malvaceae, Thymelaeaceae, Saxifragaceae, Crassulaceae, Grossulariaceae, Parnassiaceae, and Droseraceae are presented in this part of the series. A synthesis of the study will be presented in the last part of this article series.

P. 99-102 Hemos encontrado en un hayedo submesófilo basófilo orocantábrico una población de la especie Orthilia secunda (L.) House, novedad para la Cordillera Cantábrica y la mitad oeste peninsular. Se estudia la composición florística del sotobosque y se enfatiza la fragilidad de la comunidad derivada de las complejas relaciones tróficas micorríticas de las especies inventariadas. Se propone su inclusión en el Catálogo de Flora Protegida de Castilla y León. SI

Pyroleae species are perennial understory shrubs, many of which are partial mycoheterotrophs. Most fungi colonizing Pyroleae roots are ectomycorrhizal (ECM) and share common mycobionts with their Pyroleae hosts. However, such mycobiont sharing has neither been examined in depth before nor has the interspecific variation in sharing among Pyroleae species. Here, we examined root-associated fungal communities in three co-existing Pyroleae species, including Pyrola alpina, Pyrola incarnata, and Orthilia secunda, with reference to co-existing ECM fungi on the surrounding trees in the same soil blocks in subalpine coniferous forests. We identified 42, 75, and 18 fungal molecular operational taxonomic units in P. alpina, P. incarnata, and O. secunda roots, respectively. Mycobiont sharing with surrounding trees, which was defined as the occurrence of the same mycobiont between Pyroleae and surrounding trees in each soil block, was most frequent among P. incarnata (31 of 44 plants). In P. alpina, sharing was confirmed in 12 of 37 plants, and the fungal community was similar to that of P. incarnata. Mycobiont sharing was least common in O. secunda, found in only 5 of 32 plants. Root-associated fungi of O. secunda were dominated by Wilcoxina species, which were absent from the surrounding ECM roots in the same soil blocks. These results indicate that mycobiont sharing with surrounding trees does not equally occur among Pyroleae plants, some of which may develop independent mycorrhizal associations with ECM fungi, as suggested in O. secunda at our research sites. Electronic supplementary material The online version of this article (doi:10.1007/s00572-017-0788-6) contains supplementary material, which is available to authorized users.

The effects of the ethanolic extracts of 105 plants used in Russian traditional medicine, 26 vegetables and fruits and 2 mushrooms on the release of tumor necrosis factor α (TNF-α) and prostaglandin E 2 (PGE 2) in lipopolysaccharide (LPS)-stimulated differentiated human acute monocytic leukemia THP-1 cells were studied using TNF-α and PGE 2 assays, respectively. We found that 16 plant extracts inhibited TNF-α production and 15 extracts decreased PGE 2 release in the cells in a concentration-dependent manner. Guilder rose, tansy, shrubby cinquefoil, wintergreen and prince's pine, the last two of which belong to the Pyrolaceae family, notably inhibited the levels of both of the inflammatory mediators.

The family Pyrolaceae is represented in Bulgaria by six species, belonging to three genera. The viewpoints for the taxonomical position of the species in this family are not clearly unilateral. The aim of this study is to find molecular markers, allowing the objectively differentiation of the genera in this family, without use of morphological characters. Three species of the family were examined, representing the tree genera distributed in Bulgaria: Moneses uniflora (L.) A.Gray, Orthilia secunda (L.) House and Pyrola minor L. DNA was isolated from leafs and amplified via PCR reactions using 4 primers. The results were processed using cluster analysis and non-metric multidimensional scalling. The consequent cladogram, obtained by the mean euclidean distances, displayed grouping of the samples by genera, independently of their locality. The independent multitudes confirm the accuracy of the method for determination of the species in Pyrolaceae.

The relations between Monotropa hypopitys and four members of Pyrolaceae collected in Bulgaria were investigated using five ISSR markers. The genetic differences given by each used primer were illustrated graphically. The selective ability of each primer was discussed according to the obtained results. The phylogenetic relationships were illustrated using a resulting dendrogram constructed with the data from all polymorphic variants. Monotropa was separated in a single clade only by one marker and displays highest genetic similarity with Orthilia secunda. Our results suggested that Monotropoideae may belong to Pyrolaceae, together with Pyroloideae. Both groups represent two mycoheterotropic lines dependent on the nutrition, which determines their distribution. Monotropa is the terminal result of the gradual passage from authotrophy to mycorrhizal parasitism. In spite of the fact that Monotropaceae is known as a paraphyletic family, it showed a close similarity to Orthilia. The data supported the p...

Bioassay-guided fractionation of Chimaphila umbellata (L.) W. Bart (Pyrolaceae) ethanol extracts led to the identification of 2,7-dimethyl-1,4-naphthoquinone (chimaphilin) as the principal antifungal component. The structure of chimaphilin was confirmed by 1H and 13C NMR spectroscopy. The antifungal activity of chimaphilin was evaluated using the microdilution method with Saccharomyces cerevisiae (0.05mg/mL) and the dandruff-associated fungi Malassezia globosa (0.39mg/mL) and Malassezia restricta (0.55mg/mL). Pronounced antioxidant activity of C. umbellata crude extract was also identified using the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay, suggesting this phytomedicine has an antioxidant function in wound healing. A chemical-genetic profile was completed with chimaphilin using approximately 4700 S. cerevisiae gene deletion mutants. Cellular roles of deleted genes in the most susceptible mutants and secondary assays indicate that the targets for chimaphilin include pathways involved in cell wall biogenesis and transcription.

A new naphthalene glycoside was isolated from the leaves and stems of Chimaphila umbellata Barton. Its chemical structure was elucidated to be 2,7-dimethyl-1,4-dihydroxynaphthalene-1-O-β-d-glucopyranoside (DMDHNG), based on spectroscopic evidence. DMDHNG significantly inhibited the receptor activator of nuclear factor-κB ligand (RANKL)-induced tartrate-resistant acid phosphatase (TRAP) activity and the formation of multinucleated osteoclasts in a dose-dependent manner. In addition, the new glycoside inhibited the RANKL-induced mRNA expression of osteoclast-associated genes that encode TRAP, cathepsin K, and another transcription factor—nuclear factor of activated T-cells c1. We believe that the inhibitory effects of DMDHNG on the osteoclast differentiation may be exploited for a therapeutic benefit.

Starch gel electrophoresis was used to estimate genetic diversity and population structure of Pyrola fauriena H. Andr. in Korea. The percentage of polymorphic loci within enzymes was . The values of genetic diversity at the species level and at the population were higher than average values for herbaceous with similar life history traits (Hes : 0.149; Hep

Five new phenolic glycosides, 2-beta-D-glucopyranosyloxy-5-hydroxyphenylacetic acid methyl ester (4), 4-hydroxy-2-[3-hydroxy-3-methylbutyl]-5-methylphenyl beta-D-glucopyranoside (5), 4-hydroxy-2-[(E)-4-hydroxy-3-methyl-2-butenyl]-5-methylphenyl beta-D-glucopyranoside (7), 4-hydroxy-2-[(2E,6Z)-8-beta-D-glucopyranosyloxy-3,7-dimethylocta-2,6-dien-1-yl]-5-methylphenyl beta-D-glucopyranoside (8), and 2,7-dimethyl-1,4-dihydronaphthalene-5,8-diol 5-O-beta-D-xylopyranosyl(1--6)-beta-D-glucopyranoside (10), were isolated from the whole plants of Pyrola japonica (Pyrolaceae), together with androsin, (-)-syringaresinol glucoside, homoarbutin, pirolatin, hyperin, monotropein and chimaphilin.

A new classification of Ericaceae is presented based on phylogenetic analyses of nuclear and chloroplast DNA sequence data, morphology, anatomy, and embryology. Eight subfamilies and 20 tribes are recognized. In this classification Epacridaceae are included as Styphelioideae and Empetraceae as tribe Empetreae within the Ericoideae. The herbaceous taxa previously recognized as Pyrolaceae and Monotropaceae by some authors are also included within Ericaceae, in the subfamily Monotropoideae. A key, morphological descriptions, and representative images are provided for all named groups. Two new combinations inKalmia (K. buxifolia andK. procumbens) are made, and three new taxa are described: Oligarrheneae, Richeeae, and Cosmelieae (all within Styphelioideae).

Floral scent was collected by headspace methods from intact flowers, petals, and stamens of four species ofPyrolaceae. The scent samples were analyzed by coupled gas chromatography-mass spectrometry (GC-MS). The floral scent inPyrola spp. is differentiated into a characteristic petal scent—phenyl propanoids and a characteristic stamen scent—methoxy benzenes. InMoneses the scent is characterized by isoprenoids and benzenoids, with a larger proportion of benzenoids in the stamens compared to the petals. Specific anther scents may promote foraging efficiency in buzz-pollinated species and enhance flower fidelity. Variation in floral scent composition is consistent with the taxonomic relationships among the genera and species examined.

Several forest understorey achlorophyllous plants, termed mycoheterotrophs (MHs), obtain C from their mycorrhizal fungi. The latter in turn form ectomycorrhizas with trees, the ultimate C source of the entire system. A similar nutritional strategy occurs in some green forest orchids, phylogenetically close to MH species, that gain their C via a combination of MH and photosynthesis (mixotrophy). In orchid evolution, mixotrophy evolved in shaded habitats and preceded MH nutrition. By generalizing and applying this to Ericaceae, we hypothesized that green forest species phylogenetically close to MHs are mixotrophic. Using stable C isotope analysis with fungi, autotrophic, mixotrophic and MH plants as comparisons, we found the first quantitative evidence for substantial fungi-mediated mixotrophy in the Pyroleae, common ericaceous shrubs from boreal forests close to the MH Monotropoideae. Orthilia secunda, Pyrola chlorantha, Pyrola rotundifolia and Chimaphila umbellata acquired between 10.3 and 67.5% of their C from fungi. High N and 15N contents also suggest that Pyroleae nutrition partly rely on fungi. Examination of root fungal internal transcribed spacer sequences at one site revealed that 39 species of mostly endophytic or ectomycorrhizal fungi, including abundant Tricholoma spp., were associated with O. secunda, P. chlorantha and C. umbellata. These fungi, particularly ectomycorrhizal associates, could thus link mixotrophic Pyroleae spp. to surrounding trees, allowing the C flows deduced from isotopic evidence. These data suggest that we need to reconsider ecological roles of understorey plants, which could influence the dynamics and composition of forest communities.

From the water-soluble constituents of the whole herb of Pyrola rotundifolia (Pyrolaceae), one novel phenolic glycoside dimer, pyrolaside A (1), and one novel phenolic glycoside trimer, pyrolaside B (2), together with two known phenolic glycosides homoarbutin (3) and isohomoarbutin (4), were isolated. The structures were elucidated by spectroscopic analysis and confirmed with chemical degradation. In vitro tests for antimicrobial activity showed pyrolaside B (2) to possess significant activity against two Gram-positive organisms, Staphylococcus aureus and Micrococcus luteus.

Cladistic analyses of selected taxa of Ericaceae (and potential relatives) suggest that the family, as traditionally circumscribed, is paraphyletic. The traditionally recognized groups, Monotropaceae, Pyrolaceae, Epacridaceae, and Empetraceae, are nested within the cladistic structure of Ericaceae, and it seems reasonable to expand the circumscription of the latter. Preliminary analyses suggest thatActinidia (Actinidiaceae) likely is cladistically basal within Ericales, withCyrilla (Cyrillaceae) andClethra (Clethraceae) positioned, respectively, as second and first outgroups to Ericaceae. Generic relationships within Ericaceae are highly unresolved due to extensive homoplasy, butEnkianthus appears to be the sister group of the remaining ericad genera. The current division of the family into five subfamilies, i.e., Rhododendroideae, Ericoideae, Vaccinioideae, Pyroloideae, and Monotropoideae, very likely is not in accordance with phylogenetic relationships.

The pollen of 61 of about 80 taxa of Ericales that occur in Canada are described through the use of light and scanning electron microscopy. Five main pollen types are recognized: (I) compact tetrads in which the individual grains are not clearly delimited when rolled and viewed in all positions, and possessing costae endopori or costae endocolpi, (II) tetrads in which the individual grains are clearly and consistently delimited, occasionally possessing costae endopori or costae endocolpi, (III) a category in which grains within the tetrad are not consistently delimited, and lack costae endopori or costae endocolpi, (IV) loose tetrads in which individual grains are poorly fused, and (V) monads. A key identifies general morphological distinctions among the pollen groups or species. This survey of the pollen morphology of the Ericales supports conventional taxonomic treatments. We favour treatment of Monotropaceae and Pyrolaceae as separate families and suggest the elevation of Orthila secunda to its own monotypic family. The Clethraceae and Orthila secunda may be better treated outside the Ericales. We propose that the tetrad pollen of most Ericales is a derived condition from the more primitive trizonocolporate monad of the Cyrillaceae, Clethraceae, and Orthila secunda. Subfamily Vaccinioideae (Ericaceae) and Empetraceae, through subfamily Rhododendroideae (Ericaceae), to Pyrola and Moneses (Pyrolaceae), and finally to Chimaphila (Pyrolaceae) represent the evolutionary progression based on a trend from compact tetrads to loose individual grains within the tetrad. Finally the most advanced group is represented by the zonoaperturate monads of the Monotropaceae. This evolutionary progression based on pollen morphology is in accord with general principles of tetrad formation during microsporogenesis and with evolutionary relationships suggested by the macromorphology, phytochemistry, embryology, and degree of dependence on a fungal symbiont.

The types of mycorrhizal structure seen in the Ericaceae and in the closely related families Pyrolaceae and Monotropaceae are reviewed briefly. Ericoid, arbutoid, and monotropoid mycorrhizas are characterized. The processes of infection and of establishment of the mature ericoid mycorrhizal association are discussed from the structural, ultrastructural, and functional viewpoints. Infection provides an enhancement of N and P supply to the host plant. The enhancement of N supply arises from an improved exploitation of "available" ammonium ions and from the capacity, provided exclusively by the mycorrhizal fungus, to utilize simple organic nitrogen compounds. The endophyte also provides increased phosphatase activity and access to what are otherwise only slightly available organic sources of phosphates. In addition to enhancement of host nutrition in circumstances of low nutrient availability, it is shown that ericoid mycorrhizal infection leads to restriction of uptake of metallic elements when these are present in high concentration. Infection thus provides resistance to heavy metal toxicity. The significance of these observations is discussed in relation to the capacity of plants with ericoid mycorrhizas to exploit marginal ecological situations in temperate, boreal, subarctic, and alpine regions throughout the world.

IT is now generally recognised that the possession of mycorrhiza is not the characteristic only of a few somewhat abnormal families, but is a widespread phenomenon. Janse (I896), in Java, and Gallaud (I905) were among the first workers to indicate the large numbers of species involved. More recent are the observations of Asai (I934), in Japan, who recorded mycorrhiza in 82 per cent. of the I34 families investigated. McDougall and Glasgow (I929), in America, have recorded mycorrhiza on 28 species of Compositae; and Samuel (I926), in Australia, on 27 species of Leguminosae, 30 species of Gramineae, on Liliaceae, Ranunculaceae, Violaceae, Geraniaceae, Euphorbiaceae, Rosaceae, Plantaginaceae and Myrtaceae. A large number of species typically infected is given in the papers of Peyronel (I920, I922, etc.). My own observations in eastern Australia have also shown that the phenomenon is widespread; Myrtaceae, Lauraceae, Saxifragaceae, Cunoniaceae, Sapindaceae, Rutaceae and Epacridaceae all possess members with mycorrhiza. Besides the above are families such as the Orchidaceae, Burmanniaceae, Ericaceae, Pyrolaceae, etc., which have long been recognised as mycotrophic, and also the large numbers of trees with their well-marked ectophytic mycorrhizas. It was found that mycorrhiza fell naturally into several groups distinguished from one another by well-marked features. Ectophytic and endophytic forms were readily separated; in the former the main

This paper presents a review of some of the fungi that parasitize hosts in the Pyrolaceae. Lophodermium pyrolae Parmelee on Pyrola spp. and Strasseria nigra Dearn. on Pyrola spp. are described as new. Mycosphaerella chimaphilae (Ell. & Ev.) Hoehn. is considered to be synonymous with Mycosphaerella chimaphilina (Pk. in Sacc.) House. Ovularia pyrolae Trel. is transferred to the genus Colletotrichum and new hosts and range extensions are listed for other fungi.

Achlorophyllous genera of angiosperms, such as Galeola (Orchidaceae), Leiphaimos (Gentianaceae), and Monotropa (Pyrolaceae), have evolved highly specialized, mycotrophic root systems, along with chlorosis and complex floral morphologies. Productivity rates of most such plants cannot be satisfactorily explained by the saprophytic niche which is often assumed as theirs but is inadequately nutritious. Rather, they parasitize their mycorrhizal fungi. When a mycorrhizal fungus is shared by roots of an achlorophyllous angiosperm an those of a photosynthesizing plant, the former can indirectly parasitize the latter via the connecting mycelium (epiparasitism). The functional mycelial connection between the mycorrhizae of epiparasites and those of associated host trees has been demonstrated by radiotracer techniques. Some epiparasites are very locally distributed. The ecological requirements of their mycorrhizal fungi, such a suitable host trees, may explain much of this localization. A taxonomic survey of the Orc...

A new polyphenol, 6-O-galloylhomoarbutin was isolated from Pyrola incarnata, along with (+)-catechin, (−)-epicatechin gallate, procyanidin B1, B3 B2-3′-O-gallate, B2-3,3′-di-O-gallate, hyperin and hyperin-2″-O-gallate. Hyperin-2″-O-gallate, one of the main components, showed strong tanning activity.

The 1 H and 13 C NMR spectral analysis of the glucoside renifolin, isolated from Pyrola renifolia , demonstrated the so far unknown binding site of the glucose moiety to be at C-8 and hence its structure as 8-β- D -glucosyloxy-2,7-dimethyl-1,4-dihydronaphthalen-5-ol. The earlier reported structure for the glucoside pirolatin, isolated from Pyrola japonica , was also reconfirmed by the 13 C NMR spectral analysis.

As part of a general survey of the flavonoids of Pyrolaceae, the flavonoids of Pyrola virens and P. chlorantha were investigated. Eight flavonol glycosides based upon kaempferol, quercetin and rhamnetin were identified from each of the two species. Two of the glycosides, rhamnetin 3,3′,4′-tri- O -glucoside and rhamnetin 3- O -arabinoside-3′,4′-di- O -glucoside are previously unreported and further, represent an unusual pattern of glycosylation. The similarity of flavonoids and the presence of the unusual substitution pattern supports a conspecific status for the two taxa.

The leaves of Pyrola media contain monotropein, 4-methoxyphenol and its methyl ether, toluquinol, and a glucoside of 5,8-dihydro-2,7-dimethylnaphthalene-1,4-diol, probably renifolin; also present are the quinones chimaphilin, 2-methyl-5-(3-methylbut-2-enyl)-1,4-benzoquinone, 5-geranyl-2-methyl-1,4-benzoquinone, and an unidentified quinone possibly related to renifolin. The coexistence of these compounds suggests that chimaphilin is derived in vivo from 2-methyl-5-(3-methylbut-2-enyl)-1,4-benzoquinone, and in vitro the latter can be cyclised to the former in the presence of boron trifluoride.

Pollen morphology of the Pyrolaceae and Monotropaceae reinforces the view that the Pyrolaceae and Ericaceae are closely related and that the Monotropaceae should be treated as a distinct family. It further supports the separation of Moneses uniflora and Orthilia secunda from the genus Pyrola, and in the Monotropaceae it suggests a realignment of species within the Hypopitys-Monotropa complex. The Pyrolaceae as aligned by Schultze-Motel (1964) constitute a diverse group consisting of two subfamilies Pyroloideae and Monotropoideae, the latter largely saprophytic. Others have reduced one or both taxa to subdivisions of the Ericaceae, either as the tribe Pyroleae (Bentham & Hooker, 1873), or as the subf. Monotropoideae with the Pyroleae included in the subf. Arbutoideae (Copeland, 1941, 1947). A palynological study was made to determine if pollen morphology, a relatively unused attribute, might better characterize the affinities of the taxa involved. Erdtman (1952), largely following the systematic treatment of Drude (1889), described the pollen of 15 species representing eight genera. According to him, species of Pyrola L. have pollen united in tetrads with individual grains 3-colporate; pollen of Chimaphila umbellata Nutt. is in tetrads with apertures not always sharply delimited; pollen of Moneses uniflora (L.) Gray also is united in tetrads in which individual grains are 3-colp(oroid) ate; and Ramischia secunda (L.) Garcke [=Orthilia secunda (L.) House] has single grains which are (2-) 3colporate. In the Monotropoideae, Erdtman described pollen of Monotropa hypophegea Wallr. as (2-) 3-colporate, Pleuricospora fimbriolata Gray as (3-) 4colporoidate, Pterospora andromedea Nutt. as 4 (-5)-colporoidate, and Sarcodes sanguinea Torrey as 4 (-5)-colpate. Erdtman utilized Copeland's (1938) description of Allotropa virgata Torrey & Gray which was noted as three-grooved. Copeland (1934, 1935, 1937, 1938, 1939, 1941, 1947), in an extensive anatomical and systematic study of the tribe Pyroleae and subf. Monotropoideae, included a brief description of pollen of various genera. In his treatment of the Pyroleae (1947), he recognized four genera with the pollen grains of Ramischia Opiz (=Orthilia Raf.) solitary and tricolpate, those of Chimaphila Pursh in easily disrupted tetrads, those of Pyrola united in tetrads with the wall of each individual grain "marked by three half-grooves, continued as half grooves on the three as

AS knowledge of the chemical constitution of plant products extends, types of substances, and individual substances, which were formerly thought to be characteristic of certain taxonomic divisions of plants, are found to occur in divisions, which, on other grounds, are considered to be unrelated. The glucoside asperuloside, first isolated by Herissey1, has hitherto been regarded as a characteristic product of plants of the family Rubiaceae and has been isolated from many of its species. It will be of interest to the student of chemical taxonomy that, in the course of a study of asperuloside, this glucoside has been isolated from Daphniphyllum macropodum, which is a Chinese plant of uncertain affinity, placed in the family Euphorbiaceae, and that a very similar glucoside occurs in the uncommon saprophytic plant Monotropa hypopitys Walt., which is placed in the Ericales, family Pyrolaceae.