Tanzawaic acid derivatives from a marine isolate of Penicillium sp. (SF-6013) with anti-inflammatory and PTP1B inhibitory activities

  • Bioorg Med Chem Lett. 2014 Dec 15;24(24):5787-5791. doi: 10.1016/j.bmcl.2014.10.035.
Tran Hong Quang  1 ,  Nguyen Thi Thanh Ngan  1 ,  Wonmin Ko  2 ,  Dong-Cheol Kim  2 ,  Chi-Su Yoon  2 ,  Jae Hak Sohn  3 ,  Joung Han Yim  4 ,  Youn-Chul Kim  5 ,  Hyuncheol Oh  6
Affiliations
  • 1. 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.
  • 2. College of Pharmacy, Wonkwang University, Iksan 570-749, Republic of Korea; Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Republic of Korea.
  • 3. College of Medical and Life Sciences, Silla University, Busan 617-736, Republic of Korea.
  • 4. Korea Polar Research Institute, KORDI, 7-50 Songdo-dong, Yeonsu-gu, Incheon 406-840, Republic of Korea.
  • 5. 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: [email protected].
  • 6. 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: [email protected].
PMID: 25453820 DOI: 10.1016/j.bmcl.2014.10.035
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).

Keywords
Anti-inflammatory; Marine-derived fungus; PTP1B; Penicillium.