Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata

Min Kyun Na; Seungmi Yang; Long He; Hyuncheol Oh; Beom Seok Kim; Won Keun Oh; Bo Yeon Kim; Jong Seog Ahn

doi:10.1055/s-2005-873194

Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata

Min Kyun Na, Seungmi Yang, Long He, Hyuncheol Oh, Beom Seok Kim, Won Keun Oh, Bo Yeon Kim, Jong Seog Ahn

Research output: Contribution to journal › Article › peer-review

73 Citations (Scopus)

Abstract

Inhibition of protein tyrosine phosphatase IB (PTP1B) has been proposed as a therapy for treatment of type 2 diabetes and obesity. Bioassay-guided fractionation of the MeOH extract of the leaves and stems of Symplocos paniculata (Thunb.) Miq. (Symplocaceae), using an in vitro PTP1B inhibitory assay, resulted in the isolation of three ursane-type triterpenes, ursolic acid (1), corosolic acid (2) and 2α,3α,19α,23-tetrahydroxyurs-12- en-28-oic acid (3). Compounds 1-3 inhibited PTP1B with IC₅₀ values of 3.8 ± 0.5, 7.2 ± 0.8 and 42.1 ± 1.5 μM, respectively. Kinetic studies suggest that 1 is a competitive inhibitor with a K_i value of 2.0 μM, whereas 2 is a mixed-type inhibitor of PTP1B. Our results indicate that the substitution of hydroxy groups on the ursane-type triterpenes is responsible for the loss of activity, and thus 1 and 2 possessing only one or two hydroxy groups can be potential PTP1B inhibitors.

Original language	English
Pages (from-to)	261-263
Number of pages	3
Journal	Planta Medica
Volume	72
Issue number	3
DOIs	https://doi.org/10.1055/s-2005-873194
Publication status	Published - 2006 Feb
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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title = "Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata",

abstract = "Inhibition of protein tyrosine phosphatase IB (PTP1B) has been proposed as a therapy for treatment of type 2 diabetes and obesity. Bioassay-guided fractionation of the MeOH extract of the leaves and stems of Symplocos paniculata (Thunb.) Miq. (Symplocaceae), using an in vitro PTP1B inhibitory assay, resulted in the isolation of three ursane-type triterpenes, ursolic acid (1), corosolic acid (2) and 2α,3α,19α,23-tetrahydroxyurs-12- en-28-oic acid (3). Compounds 1-3 inhibited PTP1B with IC50 values of 3.8 ± 0.5, 7.2 ± 0.8 and 42.1 ± 1.5 μM, respectively. Kinetic studies suggest that 1 is a competitive inhibitor with a Ki value of 2.0 μM, whereas 2 is a mixed-type inhibitor of PTP1B. Our results indicate that the substitution of hydroxy groups on the ursane-type triterpenes is responsible for the loss of activity, and thus 1 and 2 possessing only one or two hydroxy groups can be potential PTP1B inhibitors.",

author = "Na, {Min Kyun} and Seungmi Yang and Long He and Hyuncheol Oh and Kim, {Beom Seok} and Oh, {Won Keun} and Kim, {Bo Yeon} and Ahn, {Jong Seog}",

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doi = "10.1055/s-2005-873194",

language = "English",

volume = "72",

pages = "261--263",

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T1 - Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata

AU - Na, Min Kyun

AU - Yang, Seungmi

AU - He, Long

AU - Oh, Hyuncheol

AU - Kim, Beom Seok

AU - Oh, Won Keun

AU - Kim, Bo Yeon

AU - Ahn, Jong Seog

PY - 2006/2

Y1 - 2006/2

N2 - Inhibition of protein tyrosine phosphatase IB (PTP1B) has been proposed as a therapy for treatment of type 2 diabetes and obesity. Bioassay-guided fractionation of the MeOH extract of the leaves and stems of Symplocos paniculata (Thunb.) Miq. (Symplocaceae), using an in vitro PTP1B inhibitory assay, resulted in the isolation of three ursane-type triterpenes, ursolic acid (1), corosolic acid (2) and 2α,3α,19α,23-tetrahydroxyurs-12- en-28-oic acid (3). Compounds 1-3 inhibited PTP1B with IC50 values of 3.8 ± 0.5, 7.2 ± 0.8 and 42.1 ± 1.5 μM, respectively. Kinetic studies suggest that 1 is a competitive inhibitor with a Ki value of 2.0 μM, whereas 2 is a mixed-type inhibitor of PTP1B. Our results indicate that the substitution of hydroxy groups on the ursane-type triterpenes is responsible for the loss of activity, and thus 1 and 2 possessing only one or two hydroxy groups can be potential PTP1B inhibitors.

AB - Inhibition of protein tyrosine phosphatase IB (PTP1B) has been proposed as a therapy for treatment of type 2 diabetes and obesity. Bioassay-guided fractionation of the MeOH extract of the leaves and stems of Symplocos paniculata (Thunb.) Miq. (Symplocaceae), using an in vitro PTP1B inhibitory assay, resulted in the isolation of three ursane-type triterpenes, ursolic acid (1), corosolic acid (2) and 2α,3α,19α,23-tetrahydroxyurs-12- en-28-oic acid (3). Compounds 1-3 inhibited PTP1B with IC50 values of 3.8 ± 0.5, 7.2 ± 0.8 and 42.1 ± 1.5 μM, respectively. Kinetic studies suggest that 1 is a competitive inhibitor with a Ki value of 2.0 μM, whereas 2 is a mixed-type inhibitor of PTP1B. Our results indicate that the substitution of hydroxy groups on the ursane-type triterpenes is responsible for the loss of activity, and thus 1 and 2 possessing only one or two hydroxy groups can be potential PTP1B inhibitors.

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Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata

Abstract

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