Dihydrochalcones from the leaves of Pieris japonica

Six new dihydrochalcones, 3-hydroxyasebotin (5), asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside (6), 2' '-acetylasebotin (7), 3',4,5'-trihydroxy-4'-methoxydihydrochalcone 3',5'-di-O-beta-D-glucopyranoside (8), and pierotins A (9) and B (10), along with four k...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2005-03, Vol.68 (3), p.392-396
Hauptverfasser: Yao, G.M, Ding, Y, Zuo, J.P, Wang, H.B, Wang, Y.B, Ding, B.Y, Chiu, P, Qin, G.W
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container_issue 3
container_start_page 392
container_title Journal of natural products (Washington, D.C.)
container_volume 68
creator Yao, G.M
Ding, Y
Zuo, J.P
Wang, H.B
Wang, Y.B
Ding, B.Y
Chiu, P
Qin, G.W
description Six new dihydrochalcones, 3-hydroxyasebotin (5), asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside (6), 2' '-acetylasebotin (7), 3',4,5'-trihydroxy-4'-methoxydihydrochalcone 3',5'-di-O-beta-D-glucopyranoside (8), and pierotins A (9) and B (10), along with four known dihydrochalcones, phloretin (1), phlorizin (2), asebogenin (3), and asebotin (4), were isolated from the leaves of Pieris japonica. Their structures were elucidated on the basis of spectroscopic analysis including HMQC, HMBC, NOESY, and X-ray crystal diffraction. Compounds 1, 3-5, and 7-10 inhibited the proliferation of murine B cells and compounds 5 and 10 inhibited the proliferation of murine T cells in vitro significantly.
doi_str_mv 10.1021/np049698a
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Their structures were elucidated on the basis of spectroscopic analysis including HMQC, HMBC, NOESY, and X-ray crystal diffraction. Compounds 1, 3-5, and 7-10 inhibited the proliferation of murine B cells and compounds 5 and 10 inhibited the proliferation of murine T cells in vitro significantly.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np049698a</identifier><identifier>PMID: 15787442</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>2''-acetylasebotin ; 3-hydroxyasebotin ; Animals ; asebogenin ; B-lymphocytes ; Biological and medical sciences ; cell lines ; cell proliferation ; Chalcone - analogs &amp; derivatives ; Chalcone - chemistry ; Chalcone - isolation &amp; purification ; Chalcone - pharmacology ; Chalcones ; chemical structure ; China ; Crystallography, X-Ray ; dihydrochalcones ; Drug Screening Assays, Antitumor ; Ericaceae - chemistry ; General pharmacology ; Medical sciences ; medicinal plants ; Mice ; Molecular Conformation ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; Pieris japonica ; pierotin ; plant extracts ; Plant Leaves - chemistry ; Plants, Medicinal - chemistry ; poisonous plants ; spectral analysis ; stereochemistry ; T-lymphocytes ; T-Lymphocytes - drug effects ; ulopyranoside ; X-ray diffraction</subject><ispartof>Journal of natural products (Washington, D.C.), 2005-03, Vol.68 (3), p.392-396</ispartof><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=16658144$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15787442$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yao, G.M</creatorcontrib><creatorcontrib>Ding, Y</creatorcontrib><creatorcontrib>Zuo, J.P</creatorcontrib><creatorcontrib>Wang, H.B</creatorcontrib><creatorcontrib>Wang, Y.B</creatorcontrib><creatorcontrib>Ding, B.Y</creatorcontrib><creatorcontrib>Chiu, P</creatorcontrib><creatorcontrib>Qin, G.W</creatorcontrib><title>Dihydrochalcones from the leaves of Pieris japonica</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Six new dihydrochalcones, 3-hydroxyasebotin (5), asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside (6), 2' '-acetylasebotin (7), 3',4,5'-trihydroxy-4'-methoxydihydrochalcone 3',5'-di-O-beta-D-glucopyranoside (8), and pierotins A (9) and B (10), along with four known dihydrochalcones, phloretin (1), phlorizin (2), asebogenin (3), and asebotin (4), were isolated from the leaves of Pieris japonica. Their structures were elucidated on the basis of spectroscopic analysis including HMQC, HMBC, NOESY, and X-ray crystal diffraction. Compounds 1, 3-5, and 7-10 inhibited the proliferation of murine B cells and compounds 5 and 10 inhibited the proliferation of murine T cells in vitro significantly.</description><subject>2''-acetylasebotin</subject><subject>3-hydroxyasebotin</subject><subject>Animals</subject><subject>asebogenin</subject><subject>B-lymphocytes</subject><subject>Biological and medical sciences</subject><subject>cell lines</subject><subject>cell proliferation</subject><subject>Chalcone - analogs &amp; derivatives</subject><subject>Chalcone - chemistry</subject><subject>Chalcone - isolation &amp; purification</subject><subject>Chalcone - pharmacology</subject><subject>Chalcones</subject><subject>chemical structure</subject><subject>China</subject><subject>Crystallography, X-Ray</subject><subject>dihydrochalcones</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Ericaceae - chemistry</subject><subject>General pharmacology</subject><subject>Medical sciences</subject><subject>medicinal plants</subject><subject>Mice</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>Pieris japonica</subject><subject>pierotin</subject><subject>plant extracts</subject><subject>Plant Leaves - chemistry</subject><subject>Plants, Medicinal - chemistry</subject><subject>poisonous plants</subject><subject>spectral analysis</subject><subject>stereochemistry</subject><subject>T-lymphocytes</subject><subject>T-Lymphocytes - drug effects</subject><subject>ulopyranoside</subject><subject>X-ray diffraction</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0E1P20AQBuBVVdQE2gN_gPpSbqaz3_axSvkSoFIlkXpbjdezxNSxgzdB5N-zUgKcRq_m0YxmGDvmcMZB8J_dClRpygI_sTHXAnIDQn9mY-BG5rIwasQOY3wEAAml_sJGXNvCKiXGTP5uFtt66P0CW993FLMw9MtsvaCsJXxOuQ_ZfUNDE7NHXPVd4_ErOwjYRvq2r0dsfnE-m1zlt38urye_bvMgga9zVWlTGqiIAwah0ZaWV4YqKeuySkkYbyloEawmAouBc09G1abw5HVRyyN2upu7GvqnDcW1WzbRU9tiR_0mOmO1Bitsgid7uKmWVLvV0Cxx2Lq3MxP4sQcYPbZhwM438cMZowuuVHL5zjVxTS_vfRz-p2XSaje7n7qbu4u_5WT2z10l_33nA_YOH9KT3HwqgKf7gdtCKPkKT7B4MQ</recordid><startdate>20050301</startdate><enddate>20050301</enddate><creator>Yao, G.M</creator><creator>Ding, Y</creator><creator>Zuo, J.P</creator><creator>Wang, H.B</creator><creator>Wang, Y.B</creator><creator>Ding, B.Y</creator><creator>Chiu, P</creator><creator>Qin, G.W</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20050301</creationdate><title>Dihydrochalcones from the leaves of Pieris japonica</title><author>Yao, G.M ; Ding, Y ; Zuo, J.P ; Wang, H.B ; Wang, Y.B ; Ding, B.Y ; Chiu, P ; Qin, G.W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f301t-4b56960be10af25a7971b6eb33d9ba7926c7ef52f75ee07af11ce64d68cec58d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>2''-acetylasebotin</topic><topic>3-hydroxyasebotin</topic><topic>Animals</topic><topic>asebogenin</topic><topic>B-lymphocytes</topic><topic>Biological and medical sciences</topic><topic>cell lines</topic><topic>cell proliferation</topic><topic>Chalcone - analogs &amp; derivatives</topic><topic>Chalcone - chemistry</topic><topic>Chalcone - isolation &amp; purification</topic><topic>Chalcone - pharmacology</topic><topic>Chalcones</topic><topic>chemical structure</topic><topic>China</topic><topic>Crystallography, X-Ray</topic><topic>dihydrochalcones</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Ericaceae - chemistry</topic><topic>General pharmacology</topic><topic>Medical sciences</topic><topic>medicinal plants</topic><topic>Mice</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phytochemicals</topic><topic>Pieris japonica</topic><topic>pierotin</topic><topic>plant extracts</topic><topic>Plant Leaves - chemistry</topic><topic>Plants, Medicinal - chemistry</topic><topic>poisonous plants</topic><topic>spectral analysis</topic><topic>stereochemistry</topic><topic>T-lymphocytes</topic><topic>T-Lymphocytes - drug effects</topic><topic>ulopyranoside</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yao, G.M</creatorcontrib><creatorcontrib>Ding, Y</creatorcontrib><creatorcontrib>Zuo, J.P</creatorcontrib><creatorcontrib>Wang, H.B</creatorcontrib><creatorcontrib>Wang, Y.B</creatorcontrib><creatorcontrib>Ding, B.Y</creatorcontrib><creatorcontrib>Chiu, P</creatorcontrib><creatorcontrib>Qin, G.W</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yao, G.M</au><au>Ding, Y</au><au>Zuo, J.P</au><au>Wang, H.B</au><au>Wang, Y.B</au><au>Ding, B.Y</au><au>Chiu, P</au><au>Qin, G.W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dihydrochalcones from the leaves of Pieris japonica</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. 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Compounds 1, 3-5, and 7-10 inhibited the proliferation of murine B cells and compounds 5 and 10 inhibited the proliferation of murine T cells in vitro significantly.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>15787442</pmid><doi>10.1021/np049698a</doi><tpages>5</tpages></addata></record>
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subjects 2''-acetylasebotin
3-hydroxyasebotin
Animals
asebogenin
B-lymphocytes
Biological and medical sciences
cell lines
cell proliferation
Chalcone - analogs & derivatives
Chalcone - chemistry
Chalcone - isolation & purification
Chalcone - pharmacology
Chalcones
chemical structure
China
Crystallography, X-Ray
dihydrochalcones
Drug Screening Assays, Antitumor
Ericaceae - chemistry
General pharmacology
Medical sciences
medicinal plants
Mice
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
phytochemicals
Pieris japonica
pierotin
plant extracts
Plant Leaves - chemistry
Plants, Medicinal - chemistry
poisonous plants
spectral analysis
stereochemistry
T-lymphocytes
T-Lymphocytes - drug effects
ulopyranoside
X-ray diffraction
title Dihydrochalcones from the leaves of Pieris japonica
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