Chemical Constituents from Sambucus adnata and Their Protein–Tyrosine Phosphatase 1B Inhibitory Activities

The MeOH extract from the whole plants of Sambucus adnata has shown significant protein–tyrosine phosphatase 1B (PTP1B) inhibitory activity. Chemical study on the extract resulted in the isolation of thirteen compounds, including a novel triterpene (1). The structure of 1 was determined to be 1α,3β-...

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Published inChemical & pharmaceutical bulletin Vol. 59; no. 11; pp. 1396 - 1399
Main Authors Sasaki, Tatsunori, Li, Wei, Morimura, Haruna, Li, Songpei, Li, Qin, Asada, Yoshihisa, Koike, Kazuo
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 01.11.2011
Pharmaceutical Soc Japan
Subjects
Caprifoliaceae
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Enzyme Activation - drug effects
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - isolation & purification
Enzyme Inhibitors - pharmacology
Kinetics
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
Molecular Conformation
Pharmacology & Pharmacy
Physical Sciences
Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors
Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism
protein–tyrosine phosphatase 1B
Sambucus - chemistry
Sambucus adnata
Science & Technology
triterpene
Triterpenes - chemistry
Triterpenes - isolation & purification
Triterpenes - pharmacology
Sambucus adnata
triterpene
Caprifoliaceae
protein-tyrosine phosphatase 1B
OBESITY
PTP1B
INSULIN-RESISTANCE
NUCLEAR-MAGNETIC-RESONANCE
LIGNANS
TRITERPENES
OLEANOLIC ACID
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Abstract The MeOH extract from the whole plants of Sambucus adnata has shown significant protein–tyrosine phosphatase 1B (PTP1B) inhibitory activity. Chemical study on the extract resulted in the isolation of thirteen compounds, including a novel triterpene (1). The structure of 1 was determined to be 1α,3β-dihydroxy-urs-12-en-11-one-3-yl palmitate on the basis of extensive spectroscopic analyses. Among the isolated compounds, ursolic acid, oleanolic acid and (±)-boehmenan showed the most potent PTP1B inhibitory activity in vitro with the IC50 values of 4.1, 14.4 and 43.5 μm, respectively. The kinetic analysis indicated that (±)-boehmenan inhibits PTP1B activity in a competitive manner.
AbstractList The MeOH extract from the whole plants of Sambucus adnata has shown significant protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity. Chemical study on the extract resulted in the isolation of thirteen compounds, including a novel triterpene (1). The structure of 1 was determined to be 1α,3β-dihydroxy-urs-12-en-11-one-3-yl palmitate on the basis of extensive spectroscopic analyses. Among the isolated compounds, ursolic acid, oleanolic acid and (±)-boehmenan showed the most potent PTP1B inhibitory activity in vitro with the IC(50) values of 4.1, 14.4 and 43.5 µm, respectively. The kinetic analysis indicated that (±)-boehmenan inhibits PTP1B activity in a competitive manner.The MeOH extract from the whole plants of Sambucus adnata has shown significant protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity. Chemical study on the extract resulted in the isolation of thirteen compounds, including a novel triterpene (1). The structure of 1 was determined to be 1α,3β-dihydroxy-urs-12-en-11-one-3-yl palmitate on the basis of extensive spectroscopic analyses. Among the isolated compounds, ursolic acid, oleanolic acid and (±)-boehmenan showed the most potent PTP1B inhibitory activity in vitro with the IC(50) values of 4.1, 14.4 and 43.5 µm, respectively. The kinetic analysis indicated that (±)-boehmenan inhibits PTP1B activity in a competitive manner.
The MeOH extract from the whole plants of Sambucus adnata has shown significant protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity. Chemical study on the extract resulted in the isolation of thirteen compounds, including a novel triterpene (1). The structure of 1 was determined to be 1 alpha,3 beta-dihydroxy-urs-12-en-11-one-3-yl palmitate on the basis of extensive spectroscopic analyses. Among the isolated compounds, ursolic acid, oleanolic acid and (+/-)-boehmenan showed the most potent PTP1B inhibitory activity in vitro with the IC50 values of 4.1, 14.4 and 43.5 mu m, respectively. The kinetic analysis indicated that (+/-)-boehmenan inhibits PTP1B activity in a competitive manner.
The MeOH extract from the whole plants of Sambucus adnata has shown significant protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity. Chemical study on the extract resulted in the isolation of thirteen compounds, including a novel triterpene (1). The structure of 1 was determined to be 1α,3β-dihydroxy-urs-12-en-11-one-3-yl palmitate on the basis of extensive spectroscopic analyses. Among the isolated compounds, ursolic acid, oleanolic acid and (±)-boehmenan showed the most potent PTP1B inhibitory activity in vitro with the IC(50) values of 4.1, 14.4 and 43.5 µm, respectively. The kinetic analysis indicated that (±)-boehmenan inhibits PTP1B activity in a competitive manner.
The MeOH extract from the whole plants of Sambucus adnata has shown significant protein–tyrosine phosphatase 1B (PTP1B) inhibitory activity. Chemical study on the extract resulted in the isolation of thirteen compounds, including a novel triterpene (1). The structure of 1 was determined to be 1α,3β-dihydroxy-urs-12-en-11-one-3-yl palmitate on the basis of extensive spectroscopic analyses. Among the isolated compounds, ursolic acid, oleanolic acid and (±)-boehmenan showed the most potent PTP1B inhibitory activity in vitro with the IC50 values of 4.1, 14.4 and 43.5 μm, respectively. The kinetic analysis indicated that (±)-boehmenan inhibits PTP1B activity in a competitive manner.
Author Li, Songpei
Asada, Yoshihisa
Morimura, Haruna
Li, Qin
Li, Wei
Sasaki, Tatsunori
Koike, Kazuo
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  fullname: Morimura, Haruna
  organization: Faculty of Pharmaceutical Sciences, Toho University
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  fullname: Li, Songpei
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  fullname: Li, Qin
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  fullname: Asada, Yoshihisa
  organization: Faculty of Pharmaceutical Sciences, Tokyo University of Science
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  fullname: Koike, Kazuo
  organization: Faculty of Pharmaceutical Sciences, Toho University
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Issue 11
Keywords Sambucus adnata
triterpene
Caprifoliaceae
protein-tyrosine phosphatase 1B
OBESITY
PTP1B
INSULIN-RESISTANCE
NUCLEAR-MAGNETIC-RESONANCE
LIGNANS
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– reference: 26) Jang J., Na M., Thuong P. T., Njamen D., Mbafor J. T., Fomum Z. T., Woo E., Oh W. K., Chem. Pharm. Bull., 56, 85—88 (2008).
– reference: 23) Batchelor J. G., Cushley R. J., Prestegard J. H., J. Org. Chem., 39, 1698—1705 (1974).
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Snippet The MeOH extract from the whole plants of Sambucus adnata has shown significant protein–tyrosine phosphatase 1B (PTP1B) inhibitory activity. Chemical study on...
The MeOH extract from the whole plants of Sambucus adnata has shown significant protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity. Chemical study on...
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SubjectTerms Caprifoliaceae
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Enzyme Activation - drug effects
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - isolation & purification
Enzyme Inhibitors - pharmacology
Kinetics
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
Molecular Conformation
Pharmacology & Pharmacy
Physical Sciences
Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors
Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism
protein–tyrosine phosphatase 1B
Sambucus - chemistry
Sambucus adnata
Science & Technology
triterpene
Triterpenes - chemistry
Triterpenes - isolation & purification
Triterpenes - pharmacology
Title Chemical Constituents from Sambucus adnata and Their Protein–Tyrosine Phosphatase 1B Inhibitory Activities
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