New phenalenone derivatives from the Hawaiian volcanic soil-associated fungus Penicillium herquei FT729 and their inhibitory effects on indoleamine 2,3-dioxygenase 1 (IDO1)

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dc.contributor.authorJ S Yu-
dc.contributor.authorS Y Jeong-
dc.contributor.authorC Li-
dc.contributor.authorTaehoon Oh-
dc.contributor.authorMincheol Kwon-
dc.contributor.authorJong Seog Ahn-
dc.contributor.authorSung-Kyun Ko-
dc.contributor.authorY J Ko-
dc.contributor.authorS Cao-
dc.contributor.authorK H Kim-
dc.date.accessioned2022-03-07T15:30:44Z-
dc.date.available2022-03-07T15:30:44Z-
dc.date.issued2022-
dc.identifier.issn0253-6269-
dc.identifier.urihttps://oak.kribb.re.kr/handle/201005/25541-
dc.description.abstractPhenalenone derivatives sourced from fungi are polyketides that have attracted significant interest because of their diverse chemical structures and potential bioactivities. As part of our ongoing quest to discover novel natural products with biological properties from diverse natural resources, three unreported phenalenone derivatives (1-3), named ent-12-methoxyisoherqueinone (1), (-)-scleroamide (2), and (+)-scleroamide (3), together with four known phenalenone derivatives, ent-atrovenetinone (4), isoherqueinone (5), herqueinone (6), and ent-peniciherquinone (7) were isolated from the Hawaiian soil fungus Penicillium herquei FT729, collected on the Big Island, Hawaii. Compounds 2 and 3 were enantiomers, which were separated using a chiral-phase HPLC column, which provided optically pure compounds 2 and 3. The structures of the novel compounds were established by extensive spectroscopic analyses, including 1D and 2D NMR and high-resolution ESIMS. Their absolute configurations were determined using quantum chemical electronic circular dichroism (ECD) calculations. The inhibitory activity of the isolated compounds (1-7) against indoleamine 2,3-dioxygenase 1 (IDO1) was assessed. Compounds 1, 5-7 inhibited IDO1, with IC50 values of 32.59, 36.86, 19.05, and 24.18 μM, respectively. These findings demonstrated that the phenalenone derivatives 1 and 5-7, as IDO1 inhibitors, are promising anticancer immunotherapeutic agents.-
dc.publisherPharmaceutical Soc Korea-
dc.titleNew phenalenone derivatives from the Hawaiian volcanic soil-associated fungus Penicillium herquei FT729 and their inhibitory effects on indoleamine 2,3-dioxygenase 1 (IDO1)-
dc.title.alternativeNew phenalenone derivatives from the Hawaiian volcanic soil-associated fungus Penicillium herquei FT729 and their inhibitory effects on indoleamine 2,3-dioxygenase 1 (IDO1)-
dc.typeArticle-
dc.citation.titleArchives of Pharmacal Research-
dc.citation.number2-
dc.citation.endPage113-
dc.citation.startPage105-
dc.citation.volume45-
dc.contributor.affiliatedAuthorTaehoon Oh-
dc.contributor.affiliatedAuthorMincheol Kwon-
dc.contributor.affiliatedAuthorJong Seog Ahn-
dc.contributor.affiliatedAuthorSung-Kyun Ko-
dc.contributor.alternativeName유재식-
dc.contributor.alternativeName정세윤-
dc.contributor.alternativeNameLi-
dc.contributor.alternativeName오태훈-
dc.contributor.alternativeName권민철-
dc.contributor.alternativeName안종석-
dc.contributor.alternativeName고성균-
dc.contributor.alternativeName고윤주-
dc.contributor.alternativeNameCao-
dc.contributor.alternativeName김기현-
dc.identifier.bibliographicCitationArchives of Pharmacal Research, vol. 45, no. 2, pp. 105-113-
dc.identifier.doi10.1007/s12272-022-01372-8-
dc.subject.keywordPenicillium herquei FT729-
dc.subject.keywordPhenalenone derivative-
dc.subject.keywordStructural elucidation-
dc.subject.keywordECD calculation-
dc.subject.keywordIndoleamine 2,3-dioxygenase 1-
dc.subject.localPenicillium herquei FT729-
dc.subject.localPhenalenone derivative-
dc.subject.localStructural elucidation-
dc.subject.localECD calculation-
dc.subject.localIndoleamine 2,3-dioxygenase 1-
dc.subject.localIndoleamine 2,3-dioxygenase 1 (IDO1)-
dc.description.journalClassY-
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