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01-01-2017 | Note

Protein tyrosine phosphatase 1B inhibitory properties of seco-cucurbitane triterpenes obtained from fruiting bodies of Russula lepida

Authors: Wilmar Maarisit, Hiroyuki Yamazaki, Syu-ichi Kanno, Ayako Tomizawa, Jong-Soo Lee, Michio Namikoshi

Published in: Journal of Natural Medicines | Issue 1/2017

Abstract

The known seco-cucurbitane triterpene, (24E)-3,4-seco-cucurbita-4,24-diene-3,26,29-trioic acid (1), has been isolated as a potent protein tyrosine phosphatase (PTP) 1B inhibitor together with a new analogue, (24E)-3,4-seco-cucurbita-4,24-diene-3-hydroxy-26,29-dioic acid (2), from the fruiting bodies of Russula lepida. Further evaluation of their biological properties against PTPs revealed that compound 1 inhibited T-cell PTP activity similarly to PTP1B and exhibited moderate selectivity against PTP1B over vaccinia H-1-related phosphatase. Moreover, the in vitro growth inhibitory effects of 1 and 2 against three human cancer cell lines were examined in order to evaluate cell-based efficacy. However, neither 1 nor 2 enhanced insulin-stimulated p-Akt levels at non-cytotoxic concentrations.

Elchebly M, Payette P, Michaliszyn E, Cromlish W, Collins S, Loy AL, Normandin D, Cheng A, Himms-Hagen J, Chan CC, Ramachandran C, Gresser MJ, Tremblay ML, Kennedy BP (1999) Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science 283:1544–1548CrossRefPubMed

He RJ, Yu ZH, Zhang RY, Zhang ZY (2014) Protein tyrosine phosphatases as potential therapeutic targets. Acta Pharmacol Sin 35:1227–1246CrossRefPubMedPubMedCentral

Zhang ZY, Dodd GT, Tiganis T (2015) Protein tyrosine phosphatases in hypothalamic insulin and leptin signaling. Trends Pharmacol Sci 36:661–674CrossRefPubMed

Jiang CS, Liang LF, Guo YW (2012) Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades. Acta Pharmacol Sin 33:1217–1245CrossRefPubMedPubMedCentral

Tamrakar AK, Maurya CK, Rai AK (2014) PTP1B inhibitors for type 2 diabetes treatment: a patent review (2011–2014). Expert Opin Ther Pat 24:1101–1115CrossRefPubMed

Lee JS, Maarisit W, Abdjul DB, Yamazaki H, Takahashi O, Kirikoshi R, Kanno S, Namikoshi M (2016) Structures and biological activities of triterpenes and sesquiterpenes obtained from Russula lepida. Phytochemistry 127:63–68CrossRefPubMed

Tiganis T (2013) PTP1B and TCPTP–nonredundant phosphatases in insulin signaling and glucose homeostasis. FEBS J 280:445–458CrossRefPubMed

Pavic K, Duan G, Köhn M (2015) VHR/DUSP3 phosphatase: structure, function and regulation. FEBS J 282:1871–1890CrossRefPubMed

Cheng A, Uetani N, Simoncic PD, Chaubey VP, Lee-Loy A, McGlade CJ, Kennedy BP, Tremblay ML (2002) Attenuation of leptin action and regulation of obesity by protein tyrosine phosphatase 1B. Dev Cell 2:497–503CrossRefPubMed

10.

Zabolotny JM, Bence-Hanulec KK, Stricker-Krongrad A, Haj F, Wang Y, Minokoshi Y, Kim YB, Elmquist JK, Tartaglia LA, Kahn BB, Neel BG (2002) PTP1B regulates leptin signal transduction in vivo. Dev Cell 2:489–495CrossRefPubMed

11.

You-Ten KE, Muise ES, Itié A, Michaliszyn E, Wagner J, Jothy S, Lapp WS, Tremblay ML (1997) Impaired bone marrow microenvironment and immune function in T cell protein tyrosine phosphatase-deficient mice. J Exp Med 186:683–693CrossRefPubMedPubMedCentral

12.

Heinonen KM, Nestel FP, Newell EW, Charette G, Seemayer TA, Tremblay ML, Lapp WS (2004) T-cell protein tyrosine phosphatase deletion results in progressive systemic inflammatory disease. Blood 103:3457–3464CrossRefPubMed

13.

Heinonen KM, Bourdeau A, Doody KM, Tremblay ML (2009) Protein tyrosine phosphatases PTP-1B and TC-PTP play nonredundant roles in macrophage development and IFN-gamma signaling. Proc Natl Acad Sci USA 106:9368–9372CrossRefPubMedPubMedCentral

14.

Berridge MV, Herst PM, Tan AS (2005) Tetrazolium dyes as tools in cell biology: new insights into their cellular reduction. Biotechnol Annu Rev 11:127–152CrossRefPubMed

15.

Abdjul DB, Kanno S, Yamazaki H, Ukai K, Namikoshi M (2016) A dimeric urea of the bisabolene sesquiterpene from the Okinawan marine sponge Axinyssa sp. inhibits protein tyrosine phosphatase 1B activity in Huh-7 human hepatoma cells. Bioorg Med Chem Lett 26:315–317CrossRefPubMed

16.

Yamazaki H, Sumilat DA, Kanno S, Ukai K, Rotinsulu H, Wewengkang DS, Ishikawa M, Mangindaan REP, Namikoshi M (2013) A polybromodiphenyl ether from an Indonesian marine sponge Lamellodysidea herbacea and its chemical derivatives inhibit protein tyrosine phosphatase 1B, an important target for diabetes treatment. J Nat Med 67:730–735CrossRefPubMed

17.

Cui L, Na MK, Oh H, Bae EY, Jeong DG, Ryu SE, Kim S, Kim BY, Oh WK, Ahn JS (2006) Protein tyrosine phosphatase 1B inhibitors from Morus root bark. Bioorg Med Chem Lett 16:1426–1429CrossRefPubMed

18.

Zhang YN, Zhang W, Hong D, Shi L, Shen Q, Li JY, Li J, Hu LH (2008) Oleanolic acid and its derivatives: new inhibitor of protein tyrosine phosphatase 1B with cellular activities. Bioorg Med Chem 16:8697–8705CrossRefPubMed

Title: Protein tyrosine phosphatase 1B inhibitory properties of seco-cucurbitane triterpenes obtained from fruiting bodies of Russula lepida
Authors: Wilmar Maarisit
Hiroyuki Yamazaki
Syu-ichi Kanno
Ayako Tomizawa
Jong-Soo Lee
Michio Namikoshi
Publication date: 01-01-2017
Publisher: Springer Japan
Published in: Journal of Natural Medicines / Issue 1/2017
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-016-1061-6

At a glance: The STEP trials

Springer Medicine

Protein tyrosine phosphatase 1B inhibitory properties of seco-cucurbitane triterpenes obtained from fruiting bodies of Russula lepida

Abstract

At a glance: The STEP trials

Springer Medicine

Abstract

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