title: Tanzawaic acid derivatives from a marine isolate of Penicillium sp. (SF-6013) with anti-inflammatory and PTP1B inhibitory activities.
abstract: Chemical investigation of a marine-derived fungus Penicillium sp. SF-6013 resulted in the discovery of a new tanzawaic acid derivative, 2E,4Z-tanzawaic acid D (1), together with four known analogues, tanzawaic acids A (2) and D (3), a salt form of tanzawaic acid E (4), and tanzawaic acid B (5). Their structures were mainly determined by analysis of NMR and MS data, along with chemical methods. Preliminary screening for anti-inflammatory effects in lipopolysaccharide (LPS)-activated microglial BV-2 cells showed that compounds 1, 2, and 5 inhibited the production of nitric oxide (NO) with IC50 values of 37.8, 7.1, and 42.5 μM, respectively. Compound 2 also inhibited NO production in LPS-stimulated RAW264.7 murine macrophages with an IC50 value of 27.0 μM. Moreover, these inhibitory effects correlated with the suppressive effect of compound 2 on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression in LPS-stimulated RAW264.7 and BV2 cells. In addition, compounds 2 and 5 significantly inhibited the activity of protein tyrosine phosphatase 1B (PTP1B) with the same IC50 value (8.2 μM).
authors.affiliation: College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea; Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Tran Hong
authors.initials: TH
authors.lastname: Quang
authors.affiliation: College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea; Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Nguyen Thi Thanh
authors.initials: NTT
authors.lastname: Ngan
authors.affiliation: College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea; Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Republic of Korea.
authors.forename: Wonmin
authors.initials: W
authors.lastname: Ko
authors.affiliation: College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea; Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Republic of Korea.
authors.forename: Dong-Cheol
authors.initials: DC
authors.lastname: Kim
authors.affiliation: College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea; Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Republic of Korea.
authors.forename: Chi-Su
authors.initials: CS
authors.lastname: Yoon
authors.affiliation: College of Medical and Life Sciences, Silla University, Busan 617-736, Republic of Korea.
authors.forename: Jae Hak
authors.initials: JH
authors.lastname: Sohn
authors.affiliation: Korea Polar Research Institute, KORDI, 7-50 Songdo-dong, Yeonsu-gu, Incheon 406-840, Republic of Korea.
authors.forename: Joung Han
authors.initials: JH
authors.lastname: Yim
authors.affiliation: College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea; Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Republic of Korea. Electronic address: yckim@wonkwang.ac.kr.
authors.forename: Youn-Chul
authors.initials: YC
authors.lastname: Kim
authors.affiliation: College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea; Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Republic of Korea. Electronic address: hoh@wku.ac.kr.
authors.forename: Hyuncheol
authors.initials: H
authors.lastname: Oh
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002460:Cell Line; D051546:Cyclooxygenase 2 / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005231:Fatty Acids, Unsaturated / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000633:toxicity; D008264:Macrophages / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D009569:Nitric Oxide / Q000378:metabolism; D052247:Nitric Oxide Synthase Type II / Q000378:metabolism; D010407:Penicillium / Q000737:chemistry / Q000378:metabolism*; D011485:Protein Binding; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013764:Tetrahydronaphthalenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000893:Anti-Inflammatory Agents; D004791:Enzyme Inhibitors; D005231:Fatty Acids, Unsaturated; D008070:Lipopolysaccharides; D013764:Tetrahydronaphthalenes; D009569:Nitric Oxide; D052247:Nitric Oxide Synthase Type II; D051546:Cyclooxygenase 2; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1
keywords: Anti-inflammatory; Marine-derived fungus; PTP1B; Penicillium