title: Structural revision of kynapcin-12 by total synthesis, and inhibitory activities against prolyl oligopeptidase and cancer cells.
abstract: Kynapcin-12 is a prolyl oligopeptidase (POP) inhibitor isolated from Polyozellus multiplex, and its structure was assigned as 1 having a p-hydroquinone moiety by spectroscopic analyses and chemical means. This Letter describes the total syntheses of the proposed structure 1 for kynapcin-12 and 2',3'-diacetoxy-1,5',6',4″-tetrahydroxy-p-terphenyl 2 isolated from Boletopsis grisea, revising the structure of kynapcin-12 to the latter. These syntheses involved double Suzuki-Miyaura coupling, CAN oxidation, and LTA oxidation as key steps. The inhibitory activities of synthetic compounds against POP and cancer cells were also evaluated.
authors.affiliation: RIKEN, Wako-shi, Saitama 351-0198, Japan. Electronic address: shunyat@riken.jp.
authors.forename: Shunya
authors.initials: S
authors.lastname: Takahashi
authors.affiliation: RIKEN, Wako-shi, Saitama 351-0198, Japan; Division of Material Science, Graduate School of Science and Engineering, Saitama University, Saitama 338-8570, Japan.
authors.forename: Ayaka
authors.initials: A
authors.lastname: Yoshida
authors.affiliation: The United Graduate School of Agricultural Sciences, Iwate University, Morioka, Iwate 020-8550, Japan.
authors.forename: Shota
authors.initials: S
authors.lastname: Uesugi
authors.affiliation: RIKEN, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Yayoi
authors.initials: Y
authors.lastname: Hongo
authors.affiliation: The United Graduate School of Agricultural Sciences, Iwate University, Morioka, Iwate 020-8550, Japan.
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Kimura
authors.affiliation: Division of Material Science, Graduate School of Science and Engineering, Saitama University, Saitama 338-8570, Japan.
authors.forename: Koji
authors.initials: K
authors.lastname: Matsuoka
authors.affiliation: RIKEN, Wako-shi, Saitama 351-0198, Japan. Electronic address: koshino@riken.jp.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Koshino
mesh_terms: D000363:Agaricales / Q000737:chemistry; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018922:HL-60 Cells; D006801:Humans; D015394:Molecular Structure; D000085822:Prolyl Oligopeptidases; D012697:Serine Endopeptidases / Q000378:metabolism*; D013329:Structure-Activity Relationship; D013730:Terphenyl Compounds / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D013730:Terphenyl Compounds; C414185:kynapcin 12; D012697:Serine Endopeptidases; C000705287:PREPL protein, human; D000085822:Prolyl Oligopeptidases
keywords: Kynapcin-12; Prolyl oligopeptidase inhibitor; p-Terphenyl