title: The Halicylindramides, Farnesoid X Receptor Antagonizing Depsipeptides from a Petrosia sp. Marine Sponge Collected in Korea.
abstract: Three new structurally related depsipeptides, halicylindramides F-H (1-3), and two known halicylindramides were isolated from a Petrosia sp. marine sponge collected off the shore of Youngdeok-Gun, East Sea, Republic of Korea. Their planar structures were elucidated by extensive spectroscopic data analyses including 1D and 2D NMR data as well as MS data. The absolute configurations of halicylindramides F-H (1-3) were determined by Marfey's method in combination with Edman degradation. The absolute configurations at C-4 of the dioxyindolyl alanine (Dioia) residues of halicylindramides G (2) and H (3) were determined as 4S and 4R, respectively, based on ECD spectroscopy. The C-2 configurations of Dioia in 2 and 3 were speculated to both be 2R based on the shared biogenesis of the halicylindramides. Halicylindramides F (1), A (4), and C (5) showed human farnesoid X receptor (hFXR) antagonistic activities, but did not bind directly to hFXR.
authors.affiliation: New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation , Daegu, 41061, Republic of Korea.
authors.forename: Dongyup
authors.initials: D
authors.lastname: Hahn
authors.affiliation: School of Earth and Environmental Sciences, Seoul National University , NS-80, Seoul, 08826, Republic of Korea.
authors.forename: Hiyoung
authors.initials: H
authors.lastname: Kim
authors.affiliation: School of Earth and Environmental Sciences, Seoul National University , NS-80, Seoul, 08826, Republic of Korea.
authors.forename: Inho
authors.initials: I
authors.lastname: Yang
authors.affiliation: New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation , Daegu, 41061, Republic of Korea.
authors.forename: Jungwook
authors.initials: J
authors.lastname: Chin
authors.affiliation: School of Earth and Environmental Sciences, Seoul National University , NS-80, Seoul, 08826, Republic of Korea.
authors.forename: Hoosang
authors.initials: H
authors.lastname: Hwang
authors.affiliation: School of Earth and Environmental Sciences, Seoul National University , NS-80, Seoul, 08826, Republic of Korea.
authors.forename: Dong Hwan
authors.initials: DH
authors.lastname: Won
authors.affiliation: School of Earth and Environmental Sciences, Seoul National University , NS-80, Seoul, 08826, Republic of Korea.
authors.forename: Byoungchan
authors.initials: B
authors.lastname: Lee
authors.affiliation: Department of Chemistry and Nano Science, Global Top 5 Program, Ewha Womans University , Seoul, 03760, Republic of Korea.
authors.forename: Sang-Jip
authors.initials: SJ
authors.lastname: Nam
authors.affiliation: Queensland Museum , P.O. Box 3300, South Brisbane, Queensland 4101, Australia.
authors.forename: Merrick
authors.initials: M
authors.lastname: Ekins
authors.affiliation: College of Pharmacy, Yeungnam University , Gyeongsan, 38541, Republic of Korea.
authors.forename: Hyukjae
authors.initials: H
authors.lastname: Choi
authors.affiliation: School of Earth and Environmental Sciences, Seoul National University , NS-80, Seoul, 08826, Republic of Korea.
authors.forename: Heonjoong
authors.initials: H
authors.lastname: Kang
mesh_terms: D000818:Animals; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D047130:Petrosia / Q000737:chemistry*; D018160:Receptors, Cytoplasmic and Nuclear / Q000187:drug effects*; D056910:Republic of Korea; D000099150:Receptor, Farnesoid X-Activated
chemical_list: D047630:Depsipeptides; D018160:Receptors, Cytoplasmic and Nuclear; D000099150:Receptor, Farnesoid X-Activated; C538741:halicylindramide A; C000609829:halicylindramide G; C000609830:halicylindramide H