DOCSLIB.ORG

Mosquito Larvicidal and Antifungal Isoquinoline Alkaloids from Papaveraceae

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Mosquito Larvicidal and Antifungal Isoquinoline Alkaloids from Papaveraceae Jpn. J. Environ. Entomol. Zool. 30（２）：51－61（2019） 環動昆 第 30 巻 第２号：51－61（2019） Original Article Mosquito larvicidal and antifungal isoquinoline alkaloids from Papaveraceae Shingo Ueno1), Park Pyoyun1), Yukio Tosa1), Takashi Maoka2), Naoto Kojima3), Masayuki Yamashita3), Masafumi Inoue4)* and Tamio Ueno5) 1) Graduate School of Agricultural Science, Kobe University, Kobe 657-8501, Japan 2) Research Institute for Production Development, Kyoto 606-0805, Japan 3) Kyoto Pharmaceutical University, Kyoto 607-8412, Japan 4) Research & Development Laboratory, Dainihon Jochugiku Co., Ltd, Toyonaka, Osaka 561-0827, Japan 5) Prof. Emeritus of Kyoto University, Graduate School of Agriculture, Kyoto University, Kyoto, 606-8502, Japan （Received：October 17, 2018；Accepted: Aprli: 24, 2019） Abstract From the extracts of three Papaveraceous plants, i.e., Macleaya cordata (Willd.) R.Br., Corydalis incisa (Thunb.) Pers., and Chelidonium majus L. var. asiaticum (Hara) Ohwi., eight isoquinoline alkaloid compounds, i.e., protopine, allocryptopine, sanguinarine, chelerythrine, coryincine, (±)-corynoline, (+)-chelidonine, and (±)-stylopine, were isolated. Furthermore, their structures were spectroscopically determined. Among them, the absolute structure of coryincine was directly determined by X-ray crystallography for the first time. Seven compounds showed larvicidal activity in the mosquito Culex pipiens pallens Coquillett (1898), with corynoline, chelidonine, and stylopine showing particular activity even at low concentrations (1 ppm). In an antifungal test against rice blast fungus, Pyricularia oryzae Cavara involving six compounds, sanguinarine and chelerythrine exhibited almost the same excellent level of activity as isoprothiolane. The toxicity of the M. cordata extract to the fish Oryzias latipes Temminck & Schlegel (1846) was weaker than that of nicotine, which suggests that the fish toxicity of sanguinarine and chelerythrine are low. We believe that these aromatic quaternary benzo[c]phenanthridine alkaloids, especially sanguinarine and chelerythrine, are potentially highly suited as new treatments against the blast fungi and mosquito larvae in aquatic environments, including paddy fields, because of their efficacy and low fish toxicity. Keywords: antifungal, Chelidonium majus, Corydalis incisa, isoquinoline alkaloids,Macleaya cordata, mosquito larvicidal Introduction killer” and has been used as a folk-remedy insecticide by putting the dried plants into toilets to control house fly larvae. Papaveraceous plants have long been used as private Based on these interesting biological characteristics, the medicinal herbs as their tissues contain various biologically alkaloid components of M. cordata and two other plants in active alkaloids (Yu et al., 2014). Macleaya cordata (Willd.) Papaveraceae, i.e., Corydalis incisa (Thunb.) Pers. and R.Br. (Papaveraceae) is distributed in eastern Asia and North Chelidonium majus L. var. asiaticum (Hara) Ohwi, were America and has been used in traditional Chinese medicine for investigated. its analgesic, antiedemic, carminative, depurative, diuretic, Mosquito-borne infections, malaria, and Japanese anti-inflammatory, and antimicrobial properties (Baek et al., encephalitis have been problematic for many years, but 2013). In Japan, M. cordata has been called the “maggot recently, new infections, such as dengue fever and Zika fever, ＊Correspondig author：[email protected] - 51 - Inoue et al have also become prevalent (Alshammari et al., 2018). To the following chromatographic procedures. reduce the occurrence of these infectious diseases, it is The alkaloid phase was washed with water, dried over important to reduce the number of adult mosquitoes, by killing sodium sulfate, and evaporated to dryness to afford a both the larvae and the adults using insecticides. Therefore, we reddish-brown solid (5–7 g) containing alkaloids. After focused on the effect of Papaveraceous alkaloids against evaporation of the solvent, the precipitate and solid were mosquito larvae. applied to an aluminum oxide column and eluted with a Paddy fields are a potential habitat for mosquito larvae; benzene-chloroform mixture to produce a stepwise increase in therefore, prior to use of a new insecticide in this environment, polarity (9:1 to 1:9 each 200 mL). Each fraction was monitored it is necessary to ensure that its toxicity to fish is low in by TLC and LC-MS. The fractions containing components with consideration of outflow to rivers and fields and take into the same Rf value on TLC and the same m/z peak account the chemical balance of the aquatic environment. corresponding to [M+H]+ or [M]+ at the same retention time on Effects of the active components in the extracts on the fish LC-MS were collected, evaporated, and recrystallized to afford were preliminarily examined based on toxicity against the fish the following crystal alkaloid compounds: 1, 2, 3 and 4 from M. Oryzias latipes Temminck & Schlegel (1846). cordata; 1, 5, and 6 from Cor. incisa; and 1 and 7 from Chel. Furthermore, the antifungal activity of some of the extracted majus. alkaloids was examined against rice blast fungus, Pyricularia The basic component of the former hexane phase was oryzae Cavara, one of the most problematic pathogens partitioned into 1.0 L of 2 N L-(+)-tartaric acid and extracted infecting rice in the paddy fields, thus significantly reducing with 0.5 L of chloroform twice under basic conditions (pH rice production. 10.0) by the addition of 2 N sodium carbonate. Evaporation of Here, we report the potential development of a pesticide the chloroform phase of Chel. majus afforded a yellow-brown with unique alkaloid ingredients active against mosquito larvae solid, which yielded yellow crystal needles (compound 8) on and the rice blast fungus, with low fish toxicity and usage in recrystallization from ethanol (Fig. 1). aquatic environments, such as paddy fields. Reverse phase HPLC using a Gemini C6-Phenyl column (4.6 mm ID × 150 mm, Phenomenex Inc.) and eluting with 70% Materials and Methods MeOH-NH4HCO3 at pH 10.7 at a flow rate of 1 mL/min, showed the following retention times: 8.47, 0.68, 2.42, 2.26, 2.00, 2.13, 1.85, and 2.16 min for compound 1–8, respectively. Plant materials Three species of Papaveraceae native to Japan, M. cordata, Elucidation of chemical structure Cor. incisa, and Chel. majus, were harvested in the flowering Compound 1: protopine (1) period in May from the Kyoto and Osaka areas. The whole A colorless prism; mp. 205°C–206°C; TLC (Aluminum plants were dried in the shade for 3 weeks, chopped (1.5 Oxide, 100% CHCl ) R : 0.20; IR (KBr): ν 2891, 2802, kg/plant), and extracted with Methanol (15 L, 3 times, each 10 3 f max 2359, 1640, 1610 cm−1; HR-ESIMS : found [M+H]+ m/z days) at room temperature. The combined Methanol extracts 354.1341, calcd. for C H NO : 354.1328; EIMS m/z (%): 353 were filtered, concentrated, and stored at room temperature. 20 20 5 (M+, 8.0), 281 (6.1), 267 (9.1), 252 (7.6), 190 (12.8), 163 (20.6), 148 (100), 134 (6.8); 1H NMR (400 MHz, CDCl , δ ) Extraction and isolation 3 H 1.98 (3H, s, N-CH ), 2.54 (2H, bm, H-6), 3.00 (2H, bm, H-5), The reserved Methanol extracts were evaporated in vacuo 3 3.58 (2H, bm, H-13), 3.80 (2H, bm, H-8), 5.93 (2H, s, yielding a brown paste (40–50 g), which was suspended in 2.0 -OCH O-), 5.95 (2H, s, -OCH O-), 6.64 (1H, s, H-4), 6.66 (1H, L of water (pH 6.0) and successively extracted with 1.0 L of 2 2 d, J = 5.2 Hz, H-11), 6.72 (1H, d, J = 5.2 Hz, H-12), 6.91 (1H, n-hexane three times to afford a hexane phase and a water s, H-1); 13C NMR (100 MHz, CDCl , δ ): 31.8 (C-5), 41.5 phase. The water phase was extracted with 1.0 L of 3 C (N-CH ), 46.5 (C-13), 50.8 (C-8), 57.8 (C-6), 100.9 (-OCH O-), chloroform three times. The chloroform phase was partitioned 3 2 101.2 (-OCH O-), 106.7 (C-11), 108.2 (C-1), 110.5 (C-4), with 1.0 L of 1 N HCl twice to afford an HCl phase. The HCl 2 117.9 (C-8a), 125.1 (C-12), 129.0 (C-12a), 132.8 (C-4a), 136.2 phase was re-extracted with 1.0 L of chloroform twice under (C-14a), 145.9 (C-2), 146.0 (C-10), 146.3 (C-9), 148.0 (C-3), basic conditions at pH 10.0, adjusted by the addition of sodium 195.0 (C-14). carbonate to afford a chloroform phase, named the alkaloid These data were in agreement with the values of 1 in phase. This phase was used for the fish toxicity bioassay and - 52 - 殺ボウフラ活性型アルカロイド Takahashi et al. (1985). -OCH2O-), 7.76 (1H, s, H-1), 8.26 (1H, d, J = 9.0 Hz, H-9), 8.27 (1H, s, H-4), 8.29 (1H, d, J = 9.0 Hz, H-12), 8.76 (1H, d, Compound 2: allocryptopine (2) J = 9.0 Hz, H-11), 8.80 (1H, d, J = 9.0 Hz, H-10), 10.05 (1H, s, 13 A colorless prism; mp. 161°C–163°C; TLC (Aluminum H-6); C NMR (125 MHz, DMSO-D6, δC) 52.5 (N-CH3), 57.4 Oxide, 100% CHCl3) Rf: 0.12; IR (KBr): νmax 2891, 2802, (C-8 -OCH3), 62.5 (C-7 -OCH3), 103.1 (-OCH2O-), 104.6 2359, 1640, 1610 cm−1; HR-ESIMS : found [M+H]+ m/z (C-4), 106.1 (C-1), 119.0 (C-6a), 119.6 (C-11), 119.6 (C-10), 370.1655, calcd. for C21H24NO5: 370.1654; EIMS m/z (%): 369 120.5 (C-4a), 125.6 (C-14), 126.4 (C-9), 128.3 (C-10a), 131.4 (M+, 100), 352 (20.1), 290 (9.5), 206 (11.5), 188 (40.8); 1H (C-12), 132.0 (C-13), 132.6 (C-12a), 145.8 (C-7), 149.0 (C-3), NMR (400 MHz, CDCl3, δH) 1.86 (3H, s, N-CH3), 2.64 (2H, 149.1 (C-2), 150.9 (C-8), 151.1 (C-6).
Load more

Recommended publications
  • The Developmental and Genetic Bases of Apetaly in Bocconia Frutescens
    Arango‑Ocampo et al. EvoDevo (2016) 7:16 DOI 10.1186/s13227-016-0054-6 EvoDevo RESEARCH Open Access The developmental and genetic bases of apetaly in Bocconia frutescens (Chelidonieae: Papaveraceae) Cristina Arango‑Ocampo1, Favio González2, Juan Fernando Alzate3 and Natalia Pabón‑Mora1* Abstract Background: Bocconia and Macleaya are the only genera of the poppy family (Papaveraceae) lacking petals; how‑ ever, the developmental and genetic processes underlying such evolutionary shift have not yet been studied. Results: We studied floral development in two species of petal-less poppies Bocconia frutescens and Macleaya cordata as well as in the closely related petal-bearing Stylophorum diphyllum. We generated a floral transcriptome of B. frutescens to identify MADS-box ABCE floral organ identity genes expressed during early floral development. We performed phylogenetic analyses of these genes across Ranunculales as well as RT-PCR and qRT-PCR to assess loci- specific expression patterns. We found that petal-to-stamen homeosis in petal-less poppies occurs through distinct developmental pathways. Transcriptomic analyses of B. frutescens floral buds showed that homologs of all MADS-box genes are expressed except for the APETALA3-3 ortholog. Species-specific duplications of other ABCE genes inB. frute- scens have resulted in functional copies with expanded expression patterns than those predicted by the model. Conclusions: Petal loss in B. frutescens is likely associated with the lack of expression of AP3-3 and an expanded expression of AGAMOUS. The genetic basis of petal identity is conserved in Ranunculaceae and Papaveraceae although they have different number of AP3 paralogs and exhibit dissimilar floral groundplans.
    [Show full text]
  • Isolation and Identification of Alkaloids from Macleaya Microcarpa by UHPLC–Q-TOF-MS and Their Cytotoxic Activity in Vitro, An
    Sai et al. BMC Chemistry (2020) 14:5 https://doi.org/10.1186/s13065-020-0660-1 BMC Chemistry RESEARCH ARTICLE Open Access Isolation and identifcation of alkaloids from Macleaya microcarpa by UHPLC– Q-TOF-MS and their cytotoxic activity in vitro, antiangiogenic activity in vivo Chunmei Sai1,2, Jian’an Wang1, Binjie Li3, Lin Ding1, Huiyun Wang1, Qibao Wang1, Huiming Hua3, Fangpeng Zhang2 and Qiang Ren1* Abstract Background: Extensive bioactivities of alkaloids from the genus Macleaya (Macleaya cordata (Willd.) R. Br. and Macleaya microcarpa (Maxim.) Fedde) have been widely reported, as well as more and more concerned from the sci- entifc communities. However, systematic research on the phytochemical information of M. microcarpa is incomplete. The aim of this study was to rapidly and conveniently qualitative analyze alkaloids from M. microcarpa by ultra-perfor- mance liquid chromatography/quadrupole-time-of-fght mass spectrometry (UHPLC–Q-TOF-MS) using accurate mass weight and characteristic fragment ions, furthermore separate and identify the main alkaloids, test antitumor activity in vitro and antiangiogenic activity in vivo. Results: A total of 14 alkaloids from fruits of M. microcarpa were identifed by UHPLC–Q-TOF-MS, including 5 pro- topines, 2 benzophenanthridines, 1 dimer, 1 dihydrobenzophenanthridines and 5 unknown structure compounds. Two major alkaloids were isolated by various column chromatographic methods. Their structures were determined by NMR data and related literatures. The two major alkaloids were evaluated for intro cytotoxic activities against HL-60, MCF-7, A-549, and in vivo antiangiogenic activity using transgenic zebrafsh. Conclusions: Current qualitative method based on UHPLC–Q-TOF-MS technique provided a scientifc basis for isola- tion, structural identifcation, and in vitro or in vivo pharmacological further study of alkaloids from M.
    [Show full text]
  • Big Island Invasive Species Committee (BIISC) Highlights BIISC
    Big Island Invasive Species Committee (BIISC) Highlights BIISC surveyed 6,244 acres for 5 key target species, and two incidental species and controlled a total of 16,608 acres, 17,610 individual plants were treated, and a total of 4,357 worker hours were used. An additional 165 miles of road were surveyed by the early detection crew looking for and mapping 138 potentially incipient invasive species. Miconia calvescens • BIISC continues to focus containment strategy along a 40-mile containment buffer between Malama Ki in lower Puna to Ninole in the Hamakua districts. Surveys focused in the Hilo, Hamakua and Puna districts. • Completed aerial surveys in the upper Hamakua district at elevations between 1,400' and 1,600'. A total of 1,598 acres were surveyed by air, while ground crews removed a total of 687 plants in this area. • Expanded survey and control effort from 1,600' to the 1,800' elevation above the core population in Onomea after finding a small number of plants at the 1,700' elevation. • Began work in a 52-acre control block in the Nanawale Forest Reserve. This project was terminated after data analysis revealed the feasibility to complete the mission was questionable after finding a large number of plants within the control area, as well as adjacent private parcels. • Completed survey and control blocks in the Makuu Forest Reserve. DOFAW donated 12 hours of air time to this effort which allowed BIISC to drop the ground crew at the far southern end of the survey sites to limit walk time to the survey and control blocks.
    [Show full text]
  • Landscape Plants Rated by Deer Resistance
    E271 Bulletin For a comprehensive list of our publications visit www.rce.rutgers.edu Landscape Plants Rated by Deer Resistance Pedro Perdomo, Morris County Agricultural Agent Peter Nitzsche, Morris County Agricultural Agent David Drake, Ph.D., Extension Specialist in Wildlife Management The following is a list of landscape plants rated according to their resistance to deer damage. The list was compiled with input from nursery and landscape professionals, Cooperative Extension personnel, and Master Gardeners in Northern N.J. Realizing that no plant is deer proof, plants in the Rarely Damaged, and Seldom Rarely Damaged categories would be best for landscapes prone to deer damage. Plants Occasionally Severely Damaged and Frequently Severely Damaged are often preferred by deer and should only be planted with additional protection such as the use of fencing, repellents, etc. Success of any of these plants in the landscape will depend on local deer populations and weather conditions. Latin Name Common Name Latin Name Common Name ANNUALS Petroselinum crispum Parsley Salvia Salvia Rarely Damaged Tagetes patula French Marigold Ageratum houstonianum Ageratum Tropaeolum majus Nasturtium Antirrhinum majus Snapdragon Verbena x hybrida Verbena Brugmansia sp. (Datura) Angel’s Trumpet Zinnia sp. Zinnia Calendula sp. Pot Marigold Catharanthus rosea Annual Vinca Occasionally Severely Damaged Centaurea cineraria Dusty Miller Begonia semperflorens Wax Begonia Cleome sp. Spider Flower Coleus sp. Coleus Consolida ambigua Larkspur Cosmos sp. Cosmos Euphorbia marginata Snow-on-the-Mountain Dahlia sp. Dahlia Helichrysum Strawflower Gerbera jamesonii Gerbera Daisy Heliotropium arborescens Heliotrope Helianthus sp. Sunflower Lobularia maritima Sweet Alyssum Impatiens balsamina Balsam, Touch-Me-Not Matricaria sp. False Camomile Impatiens walleriana Impatiens Myosotis sylvatica Forget-Me-Not Ipomea sp.
    [Show full text]
  • Influence of Different Elicitors on BIA Production in Macleaya Cordata
    www.nature.com/scientificreports OPEN Infuence of diferent elicitors on BIA production in Macleaya cordata Peng Huang1,2,7, Liqiong Xia3,7, Li Zhou1,7, Wei Liu1,4, Peng Wang1, Zhixing Qing5* & Jianguo Zeng1,6* Sanguinarine (SAN) and chelerythrine (CHE) have been widely used as substitutes for antibiotics for decades. For a long time, SAN and CHE have been extracted from mainly Macleaya cordata, a plant species that is a traditional herb in China and belongs to the Papaveraceae family. However, with the sharp increase in demand for SAN and CHE, it is necessary to develop a new method to enhance the supply of raw materials. Here, we used methyl jasmonate (MJ), salicylic acid (SA) and wounding alone and in combination to stimulate aseptic seedlings of M. cordata at 0 h, 24 h, 72 h and 120 h and then compared the diferences in metabolic profles and gene expression. Ultimately, we found that the efect of using MJ alone was the best treatment, with the contents of SAN and CHE increasing by 10- and 14-fold, respectively. However, the increased SAN and CHE contents in response to combined wounding and MJ were less than those for induced by the treatment with MJ alone. Additionally, after MJ treatment, SAN and CHE biosynthetic pathway genes, such as those encoding the protopine 6-hydroxylase and dihydrobenzophenanthridine oxidase enzymes, were highly expressed, which is consistent with the accumulation of SAN and CHE. At the same time, we have also studied the changes in the content of synthetic intermediates of SAN and CHE after elicitor induction.
    [Show full text]
  • J\V1ERICANI Iorticulturisf DECEMBER 1981
    j\V1ERICANI IORTICULTURISf DECEMBER 1981 / lOmatoes in OCtober, November, and December? f course.. .and in January and February too with nutrients too. Your plants gradually absorb wnat they require Windowsill Gardens Nutriponics® Kits. If you simply and easily, eliminating the main causes of house O nave a sunny window you can grow tomatoes, plant failure; inadequate moisture and overwatering. peppers, geraniums, sunflowers, or whatever you wish in Nutriponics is a fully tested system. Over 65% of our our Gro-thru N Pots combined with our handsome planters customers reorder equipmemt and supplies, and kits are shown above. You can even grow your Nutriponic plants immediately available to get you started. Each includes our from seed. beautifully illustrated 50-page book on Nutriponics, to­ The lower container in this new system acts as a reservoir gether with Liqui-Soil, N Gro-thru Pots, and planting which enables the plant to take moisture as it needs it..and medium. Fill out the order coupon today. Windowsill Gardens, Grafton, N.H. 03240, Dept. AH D Senti Information Name, ___________~ =~_ D Send $4.95 kit Street'--______________ D Send $9.95 kit City State: _____Zip __ Include $2.00 for shipping WINDOWSILL GARDENS Grafton, New Hampshire 03240 #1ERICAN HORfICULTURIST DECEMBER 1981 FEATURES COLUMNS Camellias in Containers 16 Guest Editorial: Lessons We Can Learn Text and Photography by Anthony DeBlasi from Chelsea 2 A. St. Clair Wright Book Reviews 4 Gilbert S. Daniels Pronunciation Guide 8 Strange Relatives: The Cashew Family 9 Jane Steffey The Herb Garden: Thyme 13 Betty Ann Laws The Gotelli Dwarf Conifer Collection 20 Text by Steve Bender Photography by Barbara W.
    [Show full text]
  • Downloaded from Protein Data Bank for Illustration in Ccp4mg
    bioRxiv preprint doi: https://doi.org/10.1101/2020.10.12.333484; this version posted March 23, 2021. The copyright holder for this preprint (which was not certified by peer review) is the author/funder, who has granted bioRxiv a license to display the preprint in perpetuity. It is made available under aCC-BY 4.0 International license. Jurassic NLR: conserved and dynamic evolutionary features of the atypically ancient immune receptor ZAR1 Hiroaki Adachi1, Toshiyuki Sakai1, Jiorgos Kourelis1, Jose L. Gonzalez Hernandez2, Abbas Maqbool1 and Sophien Kamoun1* 1The Sainsbury Laboratory, University of East Anglia, Norwich Research Park, NR4 7UH, Norwich, UK 2Agronomy, Horticulture and Plant Sciences Department, South Dakota State University, Brookings, South Dakota, US *For correspondence: [email protected] ABSTRACT In plants, NLR immune receptors generally exhibit hallmarks of rapid evolution even at the intraspecific level. We reconstructed the evolutionary history of ZAR1, an atypically conserved NLR that traces its origin to early flowering plant lineages ~220 to 150 million years ago (Jurassic period). Ortholog sequence analyses revealed highly conserved features of ZAR1, including regions for pathogen effector recognition, intramolecular interactions and cell death activation. This uncovered a new conserved surface on the ZAR1 resistosome underside that is required for cell death induction. Throughout its evolution, ZAR1 acquired novel features, such as a C-terminal integration of a thioredoxin-like domain. ZAR1 duplicated into two paralog families, which underwent distinct evolutionary paths. We conclude that ZAR1 stands out among angiosperm NLRs for having experienced relatively limited gene duplication and expansion throughout its deep evolutionary history. Nonetheless, ZAR1 did also give rise to non-canonical NLR proteins with integrated domains and degenerated molecular features.
    [Show full text]
  • The Botanic Garden
    www.e-rara.ch The botanic garden Maund, Benjamin London, 1825-1836 ETH-Bibliothek Zürich Shelf Mark: Rar 1386 Persistent Link: http://dx.doi.org/10.3931/e-rara-16398 Chrysanthemum Sinense / Macleaya cordata / Leucocarpus alatus / Melittis melissophyllum. www.e-rara.ch Die Plattform e-rara.ch macht die in Schweizer Bibliotheken vorhandenen Drucke online verfügbar. Das Spektrum reicht von Büchern über Karten bis zu illustrierten Materialien – von den Anfängen des Buchdrucks bis ins 20. Jahrhundert. e-rara.ch provides online access to rare books available in Swiss libraries. The holdings extend from books and maps to illustrated material – from the beginnings of printing to the 20th century. e-rara.ch met en ligne des reproductions numériques d’imprimés conservés dans les bibliothèques de Suisse. L’éventail va des livres aux documents iconographiques en passant par les cartes – des débuts de l’imprimerie jusqu’au 20e siècle. e-rara.ch mette a disposizione in rete le edizioni antiche conservate nelle biblioteche svizzere. La collezione comprende libri, carte geografiche e materiale illustrato che risalgono agli inizi della tipografia fino ad arrivare al XX secolo. Nutzungsbedingungen Dieses Digitalisat kann kostenfrei heruntergeladen werden. Die Lizenzierungsart und die Nutzungsbedingungen sind individuell zu jedem Dokument in den Titelinformationen angegeben. Für weitere Informationen siehe auch [Link] Terms of Use This digital copy can be downloaded free of charge. The type of licensing and the terms of use are indicated in the title information for each document individually. For further information please refer to the terms of use on [Link] Conditions d'utilisation Ce document numérique peut être téléchargé gratuitement.
    [Show full text]
  • Insights Into Triterpene Synthesis and Unsaturated Fatty-Acid Accumulation Provided by Chromosomal- Level Genome Analysis of Akebia Trifoliata Subsp
    Huang et al. Horticulture Research (2021) 8:33 Horticulture Research https://doi.org/10.1038/s41438-020-00458-y www.nature.com/hortres ARTICLE Open Access Insights into triterpene synthesis and unsaturated fatty-acid accumulation provided by chromosomal- level genome analysis of Akebia trifoliata subsp. australis Hui Huang 1,2,JuanLiang1,QiTan1,LinfengOu1, Xiaolin Li3, Caihong Zhong1, Huilin Huang1, Ian Max Møller 4, Xianjin Wu1 and Songquan Song1,5 Abstract Akebia trifoliata subsp. australis is a well-known medicinal and potential woody oil plant in China. The limited genetic information available for A. trifoliata subsp. australis has hindered its exploitation. Here, a high-quality chromosome- level genome sequence of A. trifoliata subsp. australis is reported. The de novo genome assembly of 682.14 Mb was generated with a scaffold N50 of 43.11 Mb. The genome includes 25,598 protein-coding genes, and 71.18% (485.55 Mb) of the assembled sequences were identified as repetitive sequences. An ongoing massive burst of long terminal repeat (LTR) insertions, which occurred ~1.0 million years ago, has contributed a large proportion of LTRs in the genome of A. trifoliata subsp. australis. Phylogenetic analysis shows that A. trifoliata subsp. australis is closely related to Aquilegia coerulea and forms a clade with Papaver somniferum and Nelumbo nucifera, which supports the well-established hypothesis of a close relationship between basal eudicot species. The expansion of UDP-glucoronosyl 1234567890():,; 1234567890():,; 1234567890():,; 1234567890():,; and UDP-glucosyl transferase gene families and β-amyrin synthase-like genes and the exclusive contraction of terpene synthase gene families may be responsible for the abundant oleanane-type triterpenoids in A.
    [Show full text]
  • Buffer Handbook Plant List
    THE BUFFER HANDBOOK PLANT LIST Originally Developed by: Cynthia Kuhns, Lake & Watershed Resource Management Associates With funding provided by U.S. Environmental Protection Agency and Maine Department of Environmental Protection,1998. Revised 2001 and 2009. Publication #DEPLW0094-B2009 TABLE OF CONTENTS Page Acknowledgements 1 Introductory Information Selection of Plants for This List 1 Plant List Organization & Information 3 Terms & Abbreviations 4 Plant Hardiness Zone Map 5 General Tree & Shrub Planting Guidelines 5 Tips for Planting Perennials 7 Invasive Plants to Avoid 7 Plant Lists TREES 8 (30 to 100 ft.) SHRUBS 14 Small Trees/Large Shrubs 15 (12 to 30 ft.) Medium Shrubs 19 (6 to 12 ft.) Small Shrubs 24 (Less than 6 ft.) GROUNDLAYERS 29 Perennial Herbs & Flowers 30 Ferns 45 Grasses 45 Vines 45 References 49 ACKNOWLEDGEMENTS Original Publication: This plant list was published with the help of Clean Water Act, Section 319 funds, under a grant awarded to the Androscoggin Valley Soil and Water Conservation District and with help from the Maine Department of Environmental Protection and the U.S. Environmental Protection Agency. Graphics and ‘clip-art’ used in this document came from the University of Wisconsin-Extension and from Microsoft Office 97(Small Business Edition) and ClickArt 97 (Broderbund Software, Inc). This publication was originally developed by Cynthia Kuhns of Lake & Watershed Resource Management Associates. Substantial assistance was received from Phoebe Hardesty of the Androscoggin Valley Soil and Water Conservation District. Valuable review and advice was given by Karen Hahnel and Kathy Hoppe of the Maine Department of Environmental Protection. Elizabeth T. Muir provided free and cheerful editing and botanical advice.
    [Show full text]
  • Plant TDP1 (Tyrosyl-DNA Phosphodiesterase 1): a Phylogenetic Perspective and Gene Expression Data Mining
    G C A T T A C G G C A T genes Article Plant TDP1 (Tyrosyl-DNA Phosphodiesterase 1): A Phylogenetic Perspective and Gene Expression Data Mining 1, 1,2, , 1 2 Giacomo Mutti y , Alessandro Raveane * y , Andrea Pagano , Francesco Bertolini , Ornella Semino 1 , Alma Balestrazzi 1 and Anca Macovei 1,* 1 Department of Biology and Biotechnology ‘L. Spallanzani’, University of Pavia, via Ferrata 9, 27100 Pavia, Italy; [email protected] (G.M.); [email protected] (A.P.); [email protected] (O.S.); [email protected] (A.B.) 2 Laboratory of Hematology-Oncology, European Institute of Oncology IRCCS, via Ripamonti 435, 20141 Milan, Italy; [email protected] * Correspondence: [email protected] or [email protected] (A.R.); [email protected] (A.M.); Tel.: +39-0382-985-583 (A.M.) Equal contribution. y Received: 30 October 2020; Accepted: 3 December 2020; Published: 7 December 2020 Abstract: The TDP1 (tyrosyl-DNA phosphodiesterase 1) enzyme removes the non-specific covalent intermediates between topoisomerase I and DNA, thus playing a crucial role in preventing DNA damage. While mammals possess only one TDP1 gene, in plants two genes (TDP1α and TDP1β) are present constituting a small gene subfamily. These display a different domain structure and appear to perform non-overlapping functions in the maintenance of genome integrity. Namely, the HIRAN domain identified in TDP1β is involved in the interaction with DNA during the recognition of stalled replication forks. The availability of transcriptomic databases in a growing variety of experimental systems provides new opportunities to fill the current gaps of knowledge concerning the evolutionary origin and the specialized roles of TDP1 genes in plants.
    [Show full text]
  • Long Blooming Perennials
    Things to think about when planting your perennial garden… WE CAN HELP YOU…. To identify plants Diagnose common insect and disease problems Plan your perennial gardens carefully to get the Find answers to your gardening questions most even blooming. Most perennials actually Provide soil test kits Long bloom only three to four weeks, some even less. You can see us at many local events: Local Farmers Markets Without knowing when they bloom, you could Chisago County Fair Blooming end up with a lot of color in late June and early Almelund Threshing Show July, but very sparse color in August and Chisago Lakes Home and Garden Show September, or vice-versa. Spring Gardening Expo Perennials An all-day gardening event held in March: Foliage plays an important part in the perennial Classes on a variety of horticultural topics garden as well. Even though a plant isn't Info booth staffed by Master Gardeners Local businesses display and sell merchandise blooming, its leaves add color, form, and texture. This may be particularly valuable in shady Bare root plant sale gardens, where fern fronds and hosta leaves can Each spring the Master Gardeners offer for sale several be as important as any perennial flowers that varieties of fruit and vegetable plants as bare root stock. These varieties are University recommended for might bloom there. our area and are often hard to find at local nurseries. Order forms are available in January Voice Mail Line651-277-0151 http://www3.extension.umn.edu/county/chisago “Friend” us on Facebook Chisago County Extension Office Our office is located at the Ag Service Building in North Branch at 38814 Third Avenue.
    [Show full text]