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Lasianosides A-E: New Iridoid Glucosides from the Leaves of Lasianthus verticillatus (Lour.) Merr. and Their Antioxidant Activity

The genus (Rubiaceae) consists of approximately 180 species, of which the greatest species diversity is found in tropical Asia. Some of the species have been used in folk medicine to treat tinnitus, arthritis, fever, and bleeding. (Lour.) Merr. (Syn. auct. non Hemsl.) is a shrub, branchlets terete a...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2019-11, Vol.24 (21), p.3995
Main Authors: Al-Hamoud, Gadah Abdulaziz, Saud Orfali, Raha, Perveen, Shagufta, Mizuno, Kenta, Takeda, Yoshio, Nehira, Tatsuo, Masuda, Kazuma, Sugimoto, Sachiko, Yamano, Yoshi, Otsuka, Hideaki, Matsunami, Katsuyoshi
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cited_by cdi_FETCH-LOGICAL-c493t-a780ff7fe3db07d3789a991d2d09ce9771bc37c87a8570d9d95312731300d073
cites cdi_FETCH-LOGICAL-c493t-a780ff7fe3db07d3789a991d2d09ce9771bc37c87a8570d9d95312731300d073
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container_issue 21
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container_title Molecules (Basel, Switzerland)
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creator Al-Hamoud, Gadah Abdulaziz
Saud Orfali, Raha
Perveen, Shagufta
Mizuno, Kenta
Takeda, Yoshio
Nehira, Tatsuo
Masuda, Kazuma
Sugimoto, Sachiko
Yamano, Yoshi
Otsuka, Hideaki
Matsunami, Katsuyoshi
description The genus (Rubiaceae) consists of approximately 180 species, of which the greatest species diversity is found in tropical Asia. Some of the species have been used in folk medicine to treat tinnitus, arthritis, fever, and bleeding. (Lour.) Merr. (Syn. auct. non Hemsl.) is a shrub, branchlets terete about 1.5-3 m in height. This paper studies the chemical composition of the leaves of for the first time, which resulted in the isolation of five undescribed iridoid glucosides, lasianosides A-E ( - ), together with three known compounds ( - ). The undescribed structures of isolated compounds ( - ) were characterized by physical and spectroscopic data analyses, including one-dimensional (1D) and two-dimensional (2D) NMR, IR, UV, and high-resolution electrospray ionization mass spectra (HR-ESI-MS). Furthermore, the electronic circular dichroism data determined the absolute configurations of the new compounds. The free radical scavenging properties of isolated compounds was assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and their cytotoxicity was assessed toward human lung cancer cell line A549 by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the isolated compounds, and displayed potent radical scavenging activities with IC values of 30.2 ± 1.8 and 32.0 ± 1.2 µM, which were comparable to that of Trolox (29.2 ± 0.39 µM), respectively, while possessed moderate activity with an IC value of 46.4 ± 2.3 µM. None of the isolated compounds exerted cytotoxicity against human cell line A549. As a result, lasianosides C, D, and E have the potential to be non-toxic safe antioxidant agents.
doi_str_mv 10.3390/molecules24213995
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This paper studies the chemical composition of the leaves of for the first time, which resulted in the isolation of five undescribed iridoid glucosides, lasianosides A-E ( - ), together with three known compounds ( - ). The undescribed structures of isolated compounds ( - ) were characterized by physical and spectroscopic data analyses, including one-dimensional (1D) and two-dimensional (2D) NMR, IR, UV, and high-resolution electrospray ionization mass spectra (HR-ESI-MS). Furthermore, the electronic circular dichroism data determined the absolute configurations of the new compounds. The free radical scavenging properties of isolated compounds was assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and their cytotoxicity was assessed toward human lung cancer cell line A549 by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the isolated compounds, and displayed potent radical scavenging activities with IC values of 30.2 ± 1.8 and 32.0 ± 1.2 µM, which were comparable to that of Trolox (29.2 ± 0.39 µM), respectively, while possessed moderate activity with an IC value of 46.4 ± 2.3 µM. None of the isolated compounds exerted cytotoxicity against human cell line A549. 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Merr. and Their Antioxidant Activity</title><author>Al-Hamoud, Gadah Abdulaziz ; Saud Orfali, Raha ; Perveen, Shagufta ; Mizuno, Kenta ; Takeda, Yoshio ; Nehira, Tatsuo ; Masuda, Kazuma ; Sugimoto, Sachiko ; Yamano, Yoshi ; Otsuka, Hideaki ; Matsunami, Katsuyoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c493t-a780ff7fe3db07d3789a991d2d09ce9771bc37c87a8570d9d95312731300d073</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>A549 Cells</topic><topic>Antioxidants</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - pharmacology</topic><topic>Arthritis</topic><topic>Asia</topic><topic>Biphenyl Compounds - chemistry</topic><topic>Cancer therapies</topic><topic>Carbon</topic><topic>Cell Line, Tumor</topic><topic>Chemical composition</topic><topic>Circular dichroism</topic><topic>Cytotoxicity</topic><topic>Dichroism</topic><topic>dpph</topic><topic>Fever</topic><topic>Free radicals</topic><topic>Glucose</topic><topic>Glucosides</topic><topic>Humans</topic><topic>Ionization</topic><topic>Iridoid Glucosides - chemistry</topic><topic>Iridoid Glucosides - pharmacology</topic><topic>Lasianthus</topic><topic>lasianthus trichophlebus</topic><topic>Lung cancer</topic><topic>Magnetic Resonance Spectroscopy - methods</topic><topic>Mass spectra</topic><topic>Metabolites</topic><topic>Molecular Structure</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Picrates - chemistry</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Leaves - chemistry</topic><topic>radical scavenging activity</topic><topic>rubiaceae</topic><topic>Rubiaceae - chemistry</topic><topic>Scavenging</topic><topic>Species diversity</topic><topic>Spectrum analysis</topic><topic>Tinnitus</topic><topic>Two dimensional analysis</topic><topic>Vitamin E</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Al-Hamoud, Gadah Abdulaziz</creatorcontrib><creatorcontrib>Saud Orfali, Raha</creatorcontrib><creatorcontrib>Perveen, Shagufta</creatorcontrib><creatorcontrib>Mizuno, Kenta</creatorcontrib><creatorcontrib>Takeda, Yoshio</creatorcontrib><creatorcontrib>Nehira, Tatsuo</creatorcontrib><creatorcontrib>Masuda, Kazuma</creatorcontrib><creatorcontrib>Sugimoto, Sachiko</creatorcontrib><creatorcontrib>Yamano, Yoshi</creatorcontrib><creatorcontrib>Otsuka, Hideaki</creatorcontrib><creatorcontrib>Matsunami, Katsuyoshi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Health and Medical</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health &amp; Medical Complete (Alumni)</collection><collection>Health &amp; Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>Publicly Available Content (ProQuest)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Al-Hamoud, Gadah Abdulaziz</au><au>Saud Orfali, Raha</au><au>Perveen, Shagufta</au><au>Mizuno, Kenta</au><au>Takeda, Yoshio</au><au>Nehira, Tatsuo</au><au>Masuda, Kazuma</au><au>Sugimoto, Sachiko</au><au>Yamano, Yoshi</au><au>Otsuka, Hideaki</au><au>Matsunami, Katsuyoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lasianosides A-E: New Iridoid Glucosides from the Leaves of Lasianthus verticillatus (Lour.) Merr. and Their Antioxidant Activity</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2019-11-05</date><risdate>2019</risdate><volume>24</volume><issue>21</issue><spage>3995</spage><pages>3995-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>The genus (Rubiaceae) consists of approximately 180 species, of which the greatest species diversity is found in tropical Asia. Some of the species have been used in folk medicine to treat tinnitus, arthritis, fever, and bleeding. (Lour.) Merr. (Syn. auct. non Hemsl.) is a shrub, branchlets terete about 1.5-3 m in height. This paper studies the chemical composition of the leaves of for the first time, which resulted in the isolation of five undescribed iridoid glucosides, lasianosides A-E ( - ), together with three known compounds ( - ). The undescribed structures of isolated compounds ( - ) were characterized by physical and spectroscopic data analyses, including one-dimensional (1D) and two-dimensional (2D) NMR, IR, UV, and high-resolution electrospray ionization mass spectra (HR-ESI-MS). Furthermore, the electronic circular dichroism data determined the absolute configurations of the new compounds. The free radical scavenging properties of isolated compounds was assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and their cytotoxicity was assessed toward human lung cancer cell line A549 by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the isolated compounds, and displayed potent radical scavenging activities with IC values of 30.2 ± 1.8 and 32.0 ± 1.2 µM, which were comparable to that of Trolox (29.2 ± 0.39 µM), respectively, while possessed moderate activity with an IC value of 46.4 ± 2.3 µM. None of the isolated compounds exerted cytotoxicity against human cell line A549. As a result, lasianosides C, D, and E have the potential to be non-toxic safe antioxidant agents.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>31694179</pmid><doi>10.3390/molecules24213995</doi><orcidid>https://orcid.org/0000-0002-5313-7153</orcidid><oa>free_for_read</oa></addata></record>
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subjects A549 Cells
Antioxidants
Antioxidants - chemistry
Antioxidants - pharmacology
Arthritis
Asia
Biphenyl Compounds - chemistry
Cancer therapies
Carbon
Cell Line, Tumor
Chemical composition
Circular dichroism
Cytotoxicity
Dichroism
dpph
Fever
Free radicals
Glucose
Glucosides
Humans
Ionization
Iridoid Glucosides - chemistry
Iridoid Glucosides - pharmacology
Lasianthus
lasianthus trichophlebus
Lung cancer
Magnetic Resonance Spectroscopy - methods
Mass spectra
Metabolites
Molecular Structure
NMR
Nuclear magnetic resonance
Picrates - chemistry
Plant Extracts - chemistry
Plant Extracts - pharmacology
Plant Leaves - chemistry
radical scavenging activity
rubiaceae
Rubiaceae - chemistry
Scavenging
Species diversity
Spectrum analysis
Tinnitus
Two dimensional analysis
Vitamin E
title Lasianosides A-E: New Iridoid Glucosides from the Leaves of Lasianthus verticillatus (Lour.) Merr. and Their Antioxidant Activity
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T23%3A16%3A06IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Lasianosides%20A-E:%20New%20Iridoid%20Glucosides%20from%20the%20Leaves%20of%20Lasianthus%20verticillatus%20(Lour.)%20Merr.%20and%20Their%20Antioxidant%20Activity&rft.jtitle=Molecules%20(Basel,%20Switzerland)&rft.au=Al-Hamoud,%20Gadah%20Abdulaziz&rft.date=2019-11-05&rft.volume=24&rft.issue=21&rft.spage=3995&rft.pages=3995-&rft.issn=1420-3049&rft.eissn=1420-3049&rft_id=info:doi/10.3390/molecules24213995&rft_dat=%3Cproquest_doaj_%3E2312808229%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c493t-a780ff7fe3db07d3789a991d2d09ce9771bc37c87a8570d9d95312731300d073%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2549022553&rft_id=info:pmid/31694179&rfr_iscdi=true