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2-Phenylnaphthalenes and a polyoxygenated cyclohexene from the stem and root extracts of Uvaria cherrevensis (Annonaceae)

Auranwiwat, Chiramet; Wongsomboon, Puttandon; Thaima, Thanaphat; Rattanajak, Roonglawan; Kamchonwongpaisan, Sumalee; Willis, Anthony; Lie, Wilford; Pyne, Stephen G; Ritthiwigrom, Thunwadee

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Three new 2-phenylnaphthalene derivatives, cherrevenaphthalenes A–C (1–3), and a new polyoxygenated cyclohexene derivative, (−)-uvaribonol F (4) together with six known compounds, 5–10, were isolated from the stem and root extracts of Uvaria cherrevensis (Annonaceae). The structures of all isolated compounds were elucidated by spectroscopic analysis. The structures of 3 and 4 were further confirmed by single crystal X-ray diffraction methods. Compound 2 exhibited modest antiplasmodial activity...[Show more]

dc.contributor.authorAuranwiwat, Chiramet
dc.contributor.authorWongsomboon, Puttandon
dc.contributor.authorThaima, Thanaphat
dc.contributor.authorRattanajak, Roonglawan
dc.contributor.authorKamchonwongpaisan, Sumalee
dc.contributor.authorWillis, Anthony
dc.contributor.authorLie, Wilford
dc.contributor.authorPyne, Stephen G
dc.contributor.authorRitthiwigrom, Thunwadee
dc.date.accessioned2021-04-23T01:08:12Z
dc.identifier.issn0367-326X
dc.identifier.urihttp://hdl.handle.net/1885/230987
dc.description.abstractThree new 2-phenylnaphthalene derivatives, cherrevenaphthalenes A–C (1–3), and a new polyoxygenated cyclohexene derivative, (−)-uvaribonol F (4) together with six known compounds, 5–10, were isolated from the stem and root extracts of Uvaria cherrevensis (Annonaceae). The structures of all isolated compounds were elucidated by spectroscopic analysis. The structures of 3 and 4 were further confirmed by single crystal X-ray diffraction methods. Compound 2 exhibited modest antiplasmodial activity against the P. falciparum stains TM4/8.2 and K1CB1 with IC50 values of 18.8 ± 3.63 and 23.4 ± 4.08 μM, respectively, and weak cytotoxicity to a Vero cell line. Furthermore, compound 4 displayed cytotoxic activity against a KB cell line with an IC50 value of 22.1 ± 0.42 μM but was non-cytotoxic to the Vero cell line. Compound 5 revealed stronger cytotoxicity towards the KB cell line, with an IC50 value of 5.05 ± 0.86 μM and was nearly equally cytotoxic to the Vero cell line
dc.description.sponsorshipThis work was supported by a CMU Short Term Research Fellowships in Overseas. CA and PW acknowledged the Science Achievement Scholarship of Thailand (SAST), the Graduate School and The Association of Students supported by the Development and Promotion for Science and Technology talents project (ASDPST). We would like also to thank the bioassay laboratory, BIOTEC, NSTDA, Thailand for KB and Vero cells and NSTDA's Cluster Program Management for financial support to SK
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherElsevier
dc.rights© 2017 Published by Elsevier B.V
dc.sourceFitoterapia
dc.subjectUvaria cherrevensis
dc.subjectAnnonaceae
dc.subjectPhenylnaphthalene
dc.subjectPolyoxygenated cyclohexene
dc.subjectAntiplasmodial activity
dc.subjectCytotoxic activity
dc.title2-Phenylnaphthalenes and a polyoxygenated cyclohexene from the stem and root extracts of Uvaria cherrevensis (Annonaceae)
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume120
dc.date.issued2017
local.identifier.absfor060101 - Analytical Biochemistry
local.identifier.ariespublicationa383154xPUB6168
local.publisher.urlhttps://www.elsevier.com/en-au
local.type.statusPublished Version
local.contributor.affiliationAuranwiwat, Chiramet, Chiang Mai University
local.contributor.affiliationWongsomboon, Puttandon, Chiang Mai University
local.contributor.affiliationThaima, Thanaphat, University of Wollongong
local.contributor.affiliationRattanajak, Roonglawan, National Center for Genetic Engineering and Biotechnology
local.contributor.affiliationKamchonwongpaisan, Sumalee, National Center for Genetic Engineering and Biotechnology
local.contributor.affiliationWillis, Anthony, College of Science, ANU
local.contributor.affiliationLie, Wilford, University of Wollongong
local.contributor.affiliationPyne, Stephen G, University of Wollongong
local.contributor.affiliationRitthiwigrom, Thunwadee, University of Wollongong
local.description.embargo2099-12-31
local.bibliographicCitation.startpage103
local.bibliographicCitation.lastpage107
local.identifier.doi10.1016/j.fitote.2017.06.002
dc.date.updated2020-11-23T10:04:06Z
local.identifier.scopusID2-s2.0-85020308911
local.identifier.thomsonID000407404000015
CollectionsANU Research Publications

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