{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1361137045551370752.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1016/s0040-4020(00)01144-3"}},{"identifier":{"@type":"URI","@value":"https://api.elsevier.com/content/article/PII:S0040402000011443?httpAccept=text/xml"}},{"identifier":{"@type":"URI","@value":"https://api.elsevier.com/content/article/PII:S0040402000011443?httpAccept=text/plain"}}],"dc:title":[{"@value":"Isolation of rhododaurichromanic acid B and the anti-HIV principles rhododaurichromanic acid A and rhododaurichromenic acid from Rhododendron dauricum"}],"description":[{"notation":[{"@value":"Abstract—Two novel chromane derivatives (1 and 2) and the known chromene (3) were isolated from the leaves and twigs of Rhodo-dendron dauricum. The absolute stereostructure of 1 was established by spectroscopic examination and X-ray crystallographic analysis. Theabsolute stereostructures of 2 and 3 were also conﬁrmed by photochemical conversion of 3 into 1 and 2. Daurichromenic acid (3)demonstrated potent anti-HIV activity with an EC 50 value of 0.00567 mg/mL and therapeutic index (TI) of 3,710. Rhododaurichromanicacid A (1) also showed relatively potent anti-HIV activity with an EC 50 value of 0.37 mg/mL, and a TI of 91.9, whereas rhododaurichromanicacid B (1) displayed no anti-HIV activity. q 2001 Elsevier Science Ltd. All rights reserved. 1. IntroductionRhododendron dauricum is distributed in the northern partof China, eastern part of Siberia, and Hokkaido. The driedleaves of this plant are known in China as ‘Manshanfong,’and are used medicinally as an expectorant and totreat acute–chronic bronchitis."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1381137045551370761","@type":"Researcher","foaf:name":[{"@value":"Yoshiki Kashiwada"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045551370757","@type":"Researcher","foaf:name":[{"@value":"Kimihisa Yamazaki"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045551370759","@type":"Researcher","foaf:name":[{"@value":"Yasumasa Ikeshiro"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045551370760","@type":"Researcher","foaf:name":[{"@value":"Takashi Yamagishi"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045551370753","@type":"Researcher","foaf:name":[{"@value":"Toshihiro Fujioka"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045551370758","@type":"Researcher","foaf:name":[{"@value":"Kunihide Mihashi"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045551370755","@type":"Researcher","foaf:name":[{"@value":"Koichi Mizuki"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045551370754","@type":"Researcher","foaf:name":[{"@value":"L.Mark Cosentino"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045551370756","@type":"Researcher","foaf:name":[{"@value":"Keith Fowke"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045551370762","@type":"Researcher","foaf:name":[{"@value":"Susan L Morris-Natschke"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045551370752","@type":"Researcher","foaf:name":[{"@value":"Kuo-Hsiung Lee"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00404020"}],"prism:publicationName":[{"@value":"Tetrahedron"}],"dc:publisher":[{"@value":"Elsevier BV"}],"prism:publicationDate":"2001-02","prism:volume":"57","prism:number":"8","prism:startingPage":"1559","prism:endingPage":"1563"},"reviewed":"false","dc:rights":["https://www.elsevier.com/tdm/userlicense/1.0/","https://www.elsevier.com/legal/tdmrep-license"],"url":[{"@id":"https://api.elsevier.com/content/article/PII:S0040402000011443?httpAccept=text/xml"},{"@id":"https://api.elsevier.com/content/article/PII:S0040402000011443?httpAccept=text/plain"}],"createdAt":"2002-07-25","modifiedAt":"2025-09-22","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360004234285558400","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Daurichromenic acid and grifolic acid: Phytotoxic meroterpenoids that induce cell death in cell culture of their producer <i>Rhododendron dauricum</i>"}]},{"@id":"https://cir.nii.ac.jp/crid/1360017282439524608","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Harnessing Fe(II)/α-ketoglutarate-dependent oxygenases for structural diversification of fungal meroterpenoids"}]},{"@id":"https://cir.nii.ac.jp/crid/1360846641543057664","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Combinatorial Biosynthesis of (+)-Daurichromenic Acid and Its Halogenated Analogue"}]},{"@id":"https://cir.nii.ac.jp/crid/1360848654990056832","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Reducing Molecular Flexibility by Cyclization for Elucidation of Absolute Configuration by CD Calculations: Daurichromenic Acid"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001204141347840","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Alkynoxy-Directed C–H Functionalizations: Palladium(0)-Catalyzed Annulations of Alkynyl Aryl Ethers with Alkynes"},{"@value":"Selected Paper : Alkynoxy-Directed C-H Functionalizations : Palladium(0)-Catalyzed Annulations of Alkynyl Aryl Ethers with Alkynes"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001204173359616","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"New Cannabinoid-Like Chromane and Chromene Derivatives from Rhododendron anthopogonoides"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001204625424000","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Antioxidant and Antiviral Activities of Plastoquinones from the Brown Alga <i>Sargassum micracanthum</i>, and a New Chromene Derivative Converted from the Plastoquinones"},{"@value":"Antioxidant and Antiviral Activities of Plastoquinones from the Brown Alga Sargassum micracanthum, and a New Chromene Derivative Converted from the Plastoquinones"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282679147497600","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Tyrosinase Inhibitors from Rhododendron collettianum and Their Structure-Activity Relationship (SAR) Studies"}]},{"@id":"https://cir.nii.ac.jp/crid/1880302168028215936","@type":"Dataset","relationType":["isSupplementedBy"],"jpcoar:relatedTitle":[{"@value":"CCDC 153773: Experimental Crystal Structure Determination"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1016/s0040-4020(00)01144-3"},{"@type":"OPENAIRE","@value":"doi_dedup___::062a497318d8a839faa98c88cc83d696"},{"@type":"CROSSREF","@value":"10.1080/15592324.2017.1422463_references_DOI_PLmLOLigU53qV1sxGx8lZhADMN3"},{"@type":"CROSSREF","@value":"10.1016/j.copbio.2022.102763_references_DOI_PLmLOLigU53qV1sxGx8lZhADMN3"},{"@type":"CROSSREF","@value":"10.1248/cpb.52.1458_references_DOI_PLmLOLigU53qV1sxGx8lZhADMN3"},{"@type":"CROSSREF","@value":"10.1248/bpb.28.374_references_DOI_PLmLOLigU53qV1sxGx8lZhADMN3"},{"@type":"CROSSREF","@value":"10.1002/chir.22606_references_DOI_PLmLOLigU53qV1sxGx8lZhADMN3"},{"@type":"CROSSREF","@value":"10.1248/cpb.59.1409_references_DOI_PLmLOLigU53qV1sxGx8lZhADMN3"},{"@type":"CROSSREF","@value":"10.1021/acs.orglett.7b01288_references_DOI_PLmLOLigU53qV1sxGx8lZhADMN3"},{"@type":"CROSSREF","@value":"10.1246/bcsj.20150180_references_DOI_PLmLOLigU53qV1sxGx8lZhADMN3"}]}