Floristic Geography of Piper (Piperaceae) in China

Piper is the largest genus and important Pantropical components of the Piperaceae family with approximately 1000-2000 species in the world. China is in the northern verge of its natural distribution. In this study, floristic geography of the Piper genus in China was analyzed to reveal its botanical characteristic, origins of speciation and its dispersal channels. The study results showed Yunnan province is one of the very important distribution regions for Piper species, served as the center of the Piper species dispersal toward to the eastern and northern regions of China with gradually reduced species numbers. The similarity level appeared to be low for its species among different provinces, and the Piper distribution regions could be approximately clustered into three clades: tropical clade, subtropical clade and Taiwan clade. Cladistically, Piper species found in China have the highest proportions which were endemic to China, and then followed by Piper species distributed in Tropical Asia, only few species belonged to Pantropical and East Asia areal types. The floristic geography of Piper genus in China is related to that of Indo Chinese Peninsula, Java Islands and Indian Peninsula in some degrees, but not closely related. This study revealed Yunnan province is one of the central of origins for the Piper species, and or one of the central of regions for its species diversification, and the Piper species of Taiwan mainly came from Philippine islands and further diversified into Taiwan clade. Our study results presented a useful method for the systematic studying of Piper genus taxonomy and the evolution of Piper speciation.     

Efficacy of Piper (Piperaceae) extracts for control of common home and garden insect pests

Extracts from three species of the plant family Piperaceae, Piper nigrum [L.], Piper guineense [Schum & Thonn, and Piper tuberculatum [Jacq.], were tested for efficacy against insects from five orders. All three species contain isobutyl amides, plant secondary compounds that act as neurotoxins in insects. These materials are considered safe to mammals because Piper spp. were used for centuries for spice and medicinal purposes. When 24-h P. nigrum LC50 values were compared between common insect pests from eastern Canada and the northeastern United States, the most sensitive species in order of increasing lethal concentration were eastern tent caterpillar, Malacosoma americanum (F.) < European pine sawfly larvae, Neodiprion sertifer (Geoffroy) < spindle ermine moth larvae, Yponomeuta cagnagella [Hübner] < viburnum leaf beetle larvae, Pyrrhalta viburni [Paykull] < stripped cucumber beetle adults, Acalymma vittatum (F.) < Colorado potato beetle adults, Leptinotarsa decemlineata (Say) < Japanese beetle adults, Popillia japonica [Newman] < hairy chinch bug, Blissus leucopterus hirtis [Montandon]. The life stage tested was the point at which each species causes the greatest amount of damage to the host plant and the point at which most gardeners would likely choose to treat with a conventional synthetic insecticide. Greenhouse trials revealed that the pepper formulations also had a repellent activity, thus protecting plant leaves from 1) herbivory (lily leaf beetle, Lilioceris lilii [Scopoli], adults and larvae and stripped cucumber beetle adults) and 2) oviposition [European corn borer, Ostrinia nubilalis (Hübner)]. Combinations with other botanical extracts were additive at best in toxicity and repellent trials. Nontarget toxicity to beneficial invertebrates is a possibility because the P. nigrum LC50 for beneficial ladybird beetles was 0.2%. P. nigrum extracts can provide a reasonable level of control against lepidopteran and European pine sawfly larvae and also will work as a short-term repellent and feeding deterrent. It is recommended that the use of Piper extracts be restricted to small-scale spot treatments in residential areas where insect pest outbreaks have occurred.     

Piper viridescens sp. nov. (Piperaceae) from Thailand

Piper viridescens sp. nov. is proposed based on material from northern Thailand. The new species is described and illustrated, resulting from a revision of the genus in Thailand. The new species is most closely related to P. boehmeriifolium (Miq.) C. DC. A table comparing diagnostic features of P. viridescens, P. boehmeriifolium and P. retrofractum is provided.     

Taxonomic notes on the genus Piper (Piperaceae)

Sixteen lectotypifications of Asian Piper species are provided. Piper argyrites, P. baccatum, P. leptostachyum, P. majusculum, P. peepuloides, P. quinqueangulatum and P. sulcatum are accepted as species and many new synonyms are proposed. Useful diagnostic characters are described and geographical distribution data of each species are provided.     

Diuretic and antilithiasic activities of ethanolic extract from Piper amalago (Piperaceae)

ObjectivePiper amalago is used in Brazilian folk medicine as diuretic and for the treatment of urinary calculus disease, although no scientific data have been described to support these effects. Thus, this study aims to evaluate the diuretic effects and antilithiatic activity of the ethanolic extract of P. amalago (EEPam).Materials and methodsEthanolic extracts of P. amalago (125, 250 and 500 mg/kg) were orally administered in male Wistar rats (n = 5) and urinary excretion was measured at intervals of up to 24 h after administration. The antilithiasic effect of EEPam on calcium oxalate urolithiasis crystallization was examined in a turbidimetric model.ResultsThe oral administration of all doses of EEPam significantly increased urine output after 24 h when compared to control group. Moreover, the application of EEPam, induced an inhibitory effect on calcium oxalate crystallization.ConclusionsAccording to results, P. amalago extracts showed diuretic and natriuretic activity and antilithiasic effects.     

Clerodane diterpenes from Baccharis sagittalis: insect antifeedant activity

Two clerodane-type diterpene glycosides esters, which were studied as peracetyl derivatives, together with the known diterpene marrubiagenine, were isolated from the aerial part of Baccharis sagittalis (Less). Their structures were established by spectroscopic methods. Antifeedant activity toward Tenebrio molitor larvae of the isolated compounds along with six other diterpenes was evaluated and some structure-antifeedant bioactivity relationships are reported.     

Evolutionary trends in the Central American species of Piper (Piperaceae)

The gross morphology of the Central American species ofPiper is surveyed in respect to habit and habitat, protection of the shoot-tip, form and condensation of the inflorescence and floral parts, and anther-dehiscence. The cap-like structure covering the shoot-tip in many species is interpreted as a modified prophyll. A ligulate development and the inclusion of the inflorescence within the sheathing leaf-base in a few species are discussed. Diminution and compaction of the floral parts are interpreted as an evolutionary response to the activities of small pollen-collecting bees. Compaction of the floral parts is correlated with a truncation of the pistil apex and, in a few species, with a change in the mode of anther dehiscence. Apical and upward dehiscence of the anthers are interpreted as similar adaptations caused by a restriction of the pollinator’s activity to the surface of the spike. A relationship between ants and certain hollow-stemmed species is mentioned. The multiple origins and independent lines of evolutionary development discussed here suggest a complex phyletic history of the genus.     

Ultrastructure and cytochemistry of the pearl gland in Piper regnellii (Piperaceae)

Pearl glands are scattered throughout the lamina of developing leaves and rarely found on adult leaves of Piper regnellii (Piperaceae). The pearl gland is a bicellular secretory trichome composed of a short broad basal cell and a spatula-like, semiglobular apical cell. Four different stages of the pearl gland were determined during its ontogenesis: origin, pre-secretory, secretory and post-secretory. During the pre-secretory stage, mitochondria, ribosomes, dictyosomes, rough endoplasmic reticulum, and plastids with electron dense inclusions were present in the cytoplasm of the apical cell. During the secretory stage, the most remarkable characteristics of the apical cell are the proliferation of dictyosomes and their vesicles, rough endoplasmic reticulum, and modified plastids. At this stage, electron-dense oil drops occur in the plastids as well as scattered within the cytoplasm, proteins and polysaccharides are seen in the plastids, vesicles, and vacuoles. Only polysaccharides are present in the periplasmic space, wall cavities, and on the surface of the apical cell. The polysaccharides are one of the main components of the mucilagenous exudate that covers the developing leaf structures. The apical cell of the senescing trichomes undergoes a progressive degeneration of its cellular components, the plastids being the first organelles to undergo lysis.     

Phylogeny and patterns of floral diversity in the genus Piper (Piperaceae)

With ～1000 species distributed pantropically, the genus Piper is one of the most diverse lineages among basal angiosperms. To rigorously address the evolution of Piper we use a phylogenetic analysis of sequences of the internal transcribed spacers (ITS) of nuclear ribosomal DNA based on a worldwide sample. Sequences from a total of 51 species of Piper were aligned to yield 257 phylogenetically informative sites. A single unrooted parsimony network suggested that taxa representing major geographic areas could potentially form three monophyletic groups: Asia, the South Pacific, and the Neotropics. The position of Pothomorphe was well supported among groups of New World taxa. Simultaneous phylogenetic analysis of an expanded alignment including outgroups suggested that taxa from the South Pacific and Asia formed a monophyletic group, provisionally supporting a single origin of dioecy. Within the Neotropical sister clade, resolution was high and strong bootstrap support confirmed the monophyly of several traditionally recognized infrageneric groups (e.g., Enckea [including Arctottonia], Ottonia, Radula, Macrostachys). In contrast, some of the species representing the highly polytypic subgroup Steffensia formed a clade corresponding to the previously recognized taxon Schilleria, while others were strongly associated with several of the more specialized groups of taxa. The distribution of putatively derived inflorescence and floral character states suggested that both umbellate and solitary axillary inflorescences have multiple origins. Reduction in anther number appears to be associated with highly packaged inflorescences or with larger anther primordia per flower, trends that are consistent with the suppression of later stages of androecial development.     

Piper relictum sp. nov. (Piperaceae) from northern Western Ghats,India

A new species of Piper, P. relictum Lekhak, S. S. Kambale & S. R. Yadav sp. nov. is described and illustrated. It grows as a climber on the edges of high altitude lateritic plateaus in evergreen forests of the northern Western Ghats in India. The new species is similar to P. galeatum, but differs in the characters of the male inflorescence.     

Sesquiterpenes from Xylaria sp., an endophytic fungus associated with Piper aduncum (Piperaceae)

Two new presilphiperfolane sesquiterpenes, 1 and 2, were isolated from the ethyl acetate extract of Xylaria sp., obtained from the leaves of Piper aduncum, along with two known eremophilane sesquiterpenes, phaseolinone (3) and phomenone (4). Chemical structures of 1 and 2 were established by analysis of spectroscopic data. The four compounds were tested in vitro for antifungal and cytotoxicity activities using CHO (Chinese hamster ovary). Compounds 1 and 2 did not show any antifungal and cytotoxic activity. Compounds 3 and 4 displayed moderate cytotoxic activities, as well as 4 antifungal activity.     

Areas of endemism and distribution patterns for Neotropical Piper species (Piperaceae)

Aim The study aimed to establish areas of endemism and distribution patterns for Neotropical species of the genus Piper in the Neotropical and Andean regions by means of parsimony analysis of endemicity (PAE) and track‐compatibility analysis. Location The study area includes the Neotropical region and the Northern Andean region (Páramo‐Punan subregion). Methods We used distribution information from herbarium specimens and recent monographic revisions for 1152 species of Piper from the Neotropics. First, a PAE was attempted in order to delimit the areas of endemism. Second, we performed a track‐compatibility analysis to establish distribution patterns for Neotropical species of Piper. Terminology for grouping Piper is based on recent phylogenetic analyses. Results The PAE yielded 104 small endemic areas for the genus Piper, 80 of which are in the Caribbean, Amazonian and Paranensis subregions of the Neotropical region, and 24 in the Páramo‐Punan subregion of the Andean region. Track‐compatibility analysis revealed 26 generalized tracks, one in the Páramo‐Punan subregion (Andean region), 19 in the Neotropical region, and six connecting the Andean and Neotropical regions. Both the generalized tracks and endemic areas indicate that distribution of Piper species is restricted to forest areas in the Andes, Amazonia, Chocó, Central America, the Guayana Shield and the Brazilian Atlantic coast. Main conclusions Piper should not be considered an Andean‐centred group as it represents two large species components with distributions centred in the Amazonian and Andean regions. Furthermore, areas of greater species richness and/or endemism are restricted to lowland habitats belonging to the Neotropical region. The distribution patterns of Neotropical species of Piper could be explained by recent events in the Neotropical region, as is the case for the track connecting Chocó and Central America, where most of the species rich groups of the genus are found. Two kinds of event could explain the biogeography of a large part of the Piper taxa with Andean–Amazonian distribution: pre‐Andean and post‐Andean events.     

Biostable and PEG polymer-conjugated insect pyrokinin analogs demonstrate antifeedant activity and induce high mortality in the pea aphid Acyrthosiphon pisum (Hemiptera: Aphidae)

The pyrokinins (PK) are multifunctional neuropeptides found in a variety of arthropod species, including the pea aphid Acyrthosiphon pisum (Hemiptera: Aphidae). A series of biostable pyrokinin analogs based on the shared C-terminal pentapeptide core region were fed in solutions of artificial diet to the pea aphid over a period of three days and evaluated for antifeedant and aphicidal activity. The analogs contained either modified Pro residues Oic or Hyp and or a d-amino acid in key positions to enhance resistance to tissue-bound peptidases and retain activity in a number of PK bioassays. A series of PK analogs conjugated with two lengths of polyethyleneglycol (PEG) polymers were also evaluated in the aphid feeding assay. Three of the biostable PK analogs demonstrated potent antifeedant activity, with a marked reduction in honeydew formation and very high mortality after 1 day. In contrast, a number of unmodified, natural pyrokinins and several other analogs containing some of the same structural components that promote biostability were inactive. Two of the most active analogs, Oic analog PK-Oic-1 (FT[Oic]RL-NH(2)) and PEGylated analog PK-dF-PEG(8) [(P(8))-YF[dF]PRL-NH(2)], featured aphicidal activity calculated at LC(50)'s of 0.042nmol/μl [0.029μg/μl] (LT(50) of 1.0 day) and 0.126nmol/μl (LT(50) of 1.3 days), respectively, matching the potency of some commercially available aphicides. Notably, a PEGylated analog of a PK antagonist can block over 55% of the aphicidal effects of the potent PK agonist PK-Oic-1, suggesting that the aphicidal effects are mediated by a PK receptor. The mechanism of this activity has yet to be established, though the aphicidal activity of the biostable analogs may result from disruption of digestive processes by interfering with gut motility patterns, a process shown to be regulated by the PKs in other insects. The active PK analogs represent potential leads in the development of selective, environmentally friendly aphid pest control agents.     

A new benzoic acid derivative isolated from Piper cf. cumanense Kunth (Piperaceae)

New benzoic acid derivative (1), together with five known compounds has been isolated from the inflorescences of Piper cf. cumanense Kunth (Piperaceae). The structure was identified on basis of spectroscopic analysis and comparison with literature data. The compound (1) showed antifungal activity against Fusarium oxysporum f. sp. dianthi and Botrytis cinerea.     

An aromatic amide C-glycoside and a cyclitol derivative from stem barks of Piper guineense Schum and Thonn (Piperaceae)

Two new compounds, an aromatic amide C-glycoside, 4-C-β-D-glucopyranosyl-3,5-dihydroxy-2-methoxybenzamide (1) and a cyclitol derivative, 4-O-caffeoyl-2-C-methoxycarbonyl-1-C-methyl-2,3,6-trihydroxycyclohexanecarboxylic acid (2), were isolated from the methanol soluble extract of the stem barks of Piper guineense Schum and Thonn, together with four known quinic acids derivatives including 3-O-caffeoyl-1-methylquinic acid (3), 3-O-feruloylquinic acid (4), ethyl-4-O-feruloylquinate (5), and 5-caffeoylquinic acid (6). Their structures were established on the basis of detailed spectroscopic analysis. The radical scavenging activity of the isolates were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay. Five of them were found to have significant radical scavenging activities, while compounds 2 and 3 displayed the highest activities with IC₅₀ values of 8.35 and 7.06 μM, respectively.     

Cardamonin,a schistosomicidal chalcone from Piper aduncum L. (Piperaceae) that inhibits Schistosoma mansoni ATP diphosphohydrolase

Background: Schistosomiasis is one of the world's major public health problems, and praziquantel (PZQ) is the only available drug to treat this neglected disease with an urgent demand for new drugs. Recent studies indicated that extracts from Piper aduncum L. (Piperaceae) are active against adult worms of Schistosoma mansoni, the major etiological agent of human schistosomiasis.Purpose: We investigated the in vitro schistosomicidal activity of cardamonin, a chalcone isolated from the crude extract of P. aduncum. Also, this present work describes, for the first time, the S. mansoni ATP diphosphohydrolase inhibitory activity of cardamonin, as well as, its molecular docking with S. mansoni ATPDase1, in order to investigate its mode of inhibition.Methods: In vitro schistosomicidal assays and confocal laser scanning microscopy were used to evaluate the effects of cardamonin on adult schistosomes. Cell viability was measured by MTT assay, and the S. mansoni ATPase activity was determined spectrophotometrically. Identification of the cardamonin binding site and its interactions on S. mansoni ATPDase1 were made by molecular docking experiments.Results: A bioguided fractionation of the crude extract of P. aduncum was carried out, leading to identification of cardamonin as the active compound, along with pinocembrin and uvangoletin. Cardamonin (25, 50, and 100 µM) caused 100% mortality, tegumental alterations, and reduction of oviposition and motor activity of all adult worms of S. mansoni, without affecting mammalian cells. Confocal laser scanning microscopy showed tegumental morphological alterations and changes on the numbers of tubercles of S. mansoni worms in a dose-dependent manner. Cardamonin also inhibited S. mansoni ATP diphosphohydrolase (IC₅₀ of 23.54 µM). Molecular docking studies revealed that cardamonin interacts with the Nucleotide-Binding of SmATPDase 1. The nature of SmATPDase 1–cardamonin interactions is mainly hydrophobic and hydrogen bonding.Conclusion: This report provides evidence for the in vitro schistosomicidal activity of cardamonin and demonstrated, for the first time, that this chalcone is highly effective in inhibiting S. mansoni ATP diphosphohydrolase, opening the route to further studies of chalcones as prototypes for new S. mansoni ATP diphosphohydrolase inhibitors.     

Isolation and characterization of eleven polymorphic microsatellite loci from an endemic species, Piper polysyphonum (Piperaceae)

Piper polysyphonum is an endemic species in southeast Asia, in the narrow habitat located in the Chinese provinces of Guizhou and Yunnan, and the country of Laos. Recently, loss of forests due to agricultural activity has dramatically reduced the habitat and population size of P. polysyphonum. In this study, eleven primer sets of polymorphic microsatellite DNA loci were developed for P. polysyphonum. Allele numbers ranged from two to ten, with observed heterozygosities ranging from 0.222 to 0.889. Four loci exhibited a departure from Hardy–Weinberg equilibrium, possibly due to population admixture. No loci pairs revealed significant linkage disequilibrium. Among the eleven loci, two with extremely high numbers of TCG repeats were obtained. The polymorphic microsatellite DNA markers reported here should provide a helpful means to address questions concerning population structure and demographic history of P. polysyphonum for conservation efforts.