A tetramic acid derivative with protein tyrosine phosphatase 1B inhibitory activity and a new nortriterpene glycoside from the Indonesian marine sponge Petrosia sp.

被引:13
|
作者
Maarisit, Wilmar [1 ,2 ]
Yamazaki, Hiroyuki [1 ]
Kanno, Syu-ichi [1 ]
Tomizawa, Ayako [1 ]
Rotinsulu, Henki [3 ]
Wewengkang, Defny S. [3 ]
Sumilat, Deiske A. [2 ]
Ukai, Kazuyo [1 ]
Kapojos, Magie M. [4 ]
Namikoshi, Michio [1 ]
机构
[1] Tohoku Med & Pharmaceut Univ, Fac Pharmaceut Sci, Sendai, Miyagi 9818558, Japan
[2] Sam Ratulangi Univ, Fac Fisheries & Marine Sci, Kampus Bahu, Manado 95115, Indonesia
[3] Sam Ratulangi Univ, Fac Math & Nat Sci, Kampus Bahu, Manado 95115, Indonesia
[4] Univ Pembangunan Indonesia, Fac Nursing, Bahu 95115, Manado, Indonesia
关键词
Tetramic acid; Melophlin; Sarasinoside; Marine sponge; Petrosia sp; Protein tyrosine phosphatase 1B; NATURAL-PRODUCTS; MELOPHLUS-SARASSINORUM; ASTEROPUS-SARASINOSUM; DIABETES TREATMENT; OLIGOGLYCOSIDES; SAPONINS; TARGETS; CELLS; A1; C1;
D O I
10.1016/j.bmcl.2016.12.077
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
During the search for protein tyrosine phosphatase 1B (PTP1B) inhibitors from marine organisms, the known tetramic acid derivative, melophlin C (1), was isolated as an active component together with the new nortriterpenoid saponin, sarasinoside S (2), and three homologues: sarasinosides A1 (3), I-1 (4), and J (5), from the Indonesian marine sponge Petrosia sp. The structure of 2 was elucidated on the basis of its spectroscopic data. Compound 1 inhibited PTP1B activity with an IC50 value of 14.6 mu M, while compounds 2-5 were not active at 15.2-16.0 mu M. This is the first study to report the inhibitory effects of a tetramic acid derivative on PTP1B activity. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:999 / 1002
页数:4
相关论文
共 32 条
  • [21] New natural protein tyrosine phosphatase 1B inhibitors from Gynostemma pentaphyllum
    Wang, Xianting
    Deng, Yidan
    Wang, Jianmei
    Qin, Lin
    Du, Yimei
    Zhang, Qianru
    Wu, Di
    Wu, Xingdong
    Xie, Jian
    He, Yuqi
    Tan, Daopeng
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2024, 39 (01)
  • [22] Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades
    Jiang, Cheng-shi
    Liang, Lin-fu
    Guo, Yue-wei
    ACTA PHARMACOLOGICA SINICA, 2012, 33 (10) : 1217 - 1245
  • [23] Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades
    Cheng-shi Jiang
    Lin-fu Liang
    Yue-wei Guo
    Acta Pharmacologica Sinica, 2012, 33 : 1217 - 1245
  • [24] Antiplasmodial Activities of Homogentisic Acid Derivative Protein Kinase Inhibitors Isolated from a Vanuatu Marine Sponge Pseudoceratina sp.
    Lebouvier, Nicolas
    Jullian, Valerie
    Desvignes, Isabelle
    Maurel, Severine
    Parenty, Arnaud
    Dorin-Semblat, Dominique
    Doerig, Christian
    Sauvain, Michel
    Laurent, Dominique
    MARINE DRUGS, 2009, 7 (04) : 640 - 653
  • [25] A new protein tyrosine phosphatase 1B inhibitory α-pyrone-type polyketide from Okinawan plant-associated Aspergillus sp TMPU1623
    Yamazaki, Hiroyuki
    Takahashi, Kenta
    Iwakura, Natsuki
    Abe, Tatsuki
    Akaishi, Masanari
    Chiba, Satomi
    Namikoshi, Michio
    Uchida, Ryuji
    JOURNAL OF ANTIBIOTICS, 2018, 71 (08) : 745 - 748
  • [26] Asperdichrome, an unusual dimer of tetrahydroxanthone through an ether bond, with protein tyrosine phosphatase 1B inhibitory activity, from the Okinawan freshwater Aspergillus sp TPU1343
    Yamazaki, Hiroyuki
    Ukai, Kazuyo
    Namikoshi, Michio
    TETRAHEDRON LETTERS, 2016, 57 (07) : 732 - 735
  • [27] Protein tyrosine phosphatase 1B (PTP1B) inhibitory constituents from the aerial parts of Tradescantia spathacea Sw.
    Quoc Hung Vo
    Phi Hung Nguyen
    Zhao, Bing Tian
    Ali, Md Yousof
    Choi, Jae Soo
    Min, Byung Sun
    Thi Hoai Nguyen
    Woo, Mi Hee
    FITOTERAPIA, 2015, 103 : 113 - 121
  • [28] Search for Protein Tyrosine Phosphatase 1B Inhibitors from Marine Organisms and Induced Production of New Fungal Metabolites by Modulating Culture Methods
    Yamazaki, Hiroyuki
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2019, 139 (05): : 663 - 672
  • [29] Competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors, prenylated caged xanthones from Garcinia hanburyi and their inhibitory mechanism
    Tan, Xue Fei
    Uddin, Zia
    Park, Chanin
    Song, Yeong Hun
    Son, Minky
    Lee, Keun Woo
    Park, Ki Hun
    BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (08) : 2498 - 2506
  • [30] Protein tyrosine phosphatase 1B inhibitory properties of seco-cucurbitane triterpenes obtained from fruiting bodies of Russula lepida
    Maarisit, Wilmar
    Yamazaki, Hiroyuki
    Kanno, Syu-ichi
    Tomizawa, Ayako
    Lee, Jong-Soo
    Namikoshi, Michio
    JOURNAL OF NATURAL MEDICINES, 2017, 71 (01) : 334 - 337