Isolation and characterization of sesquiterpenes from Arecophila saccharicola YMJ96022401 with NO production inhibitory activity

Lin Wen Lee, Guei Jane Wang, Mei Hsiang Lin, Yu Min Ju, Yen Wen Lin, Fang Yu Chen, Zong-Huei Li

Research output: Contribution to journalArticle

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Abstract

Sesquiterpenes, arecoic acids A-F and arecolactone, were isolated from the ethyl acetate extracts of the fermented broth of Arecophila saccharicola YMJ96022401 along with two known analogues 1,7α,10α- trihydroxyeremophil-11(13)-en-12,8-olide and 1,10α,13-trihydroxyeremophil- 7(11)-en-12,8-olide. Their structures were elucidated on the basis of spectroscopic data analyses. The inhibitory effects of all of these compounds on nitric oxide (NO) production in lipopolysaccharide (LPS, 200 μg/mL)-activated murine macrophage RAW264.7 cells were also evaluated. Among these compounds, 1,7α,10α-trihydroxyeremophil-11(13)-en-12,8-olide significantly inhibited NO production without any cytotoxicity, and its average maximum inhibition (Emax) at 100 μM and median inhibitory concentration (IC50) were 85.7% ± 0.8% and 16.5 ± 1.0 μM, respectively. Arecolactone was the most potent, with the Emax at 12.5 μM and IC50 being 94.7% ± 0.8% and 1.32 ± 0.1 μM, respectively, but displayed cytotoxicity at considerable higher concentrations than 25 μM. Analyses of Western blotting indicated that arecolactone (0.8-12.5 μM) inhibited induction of inducible NO synthase (iNOS) by LPS, which involved suppression of NF-κB activation and the phosphorylation of extracellular signal-regulated kinase (ERK), c-Jun NH(2)-terminal kinase (JNK) and p38 mitogen-activated protein kinases (MAPKs) in activated RAW 264.7 cells. In addition, arecolactone concentration-dependently prevented the vascular hyporeactivity to phenylephrine induced by LPS (300 ng/mL) through iNOS pathway in isolated rat thoracic aortic rings. These results indicated that both of these naturally occurring iNOS inhibitors may provide a rationale for the potential anti-inflammatory effect of A. saccharicola YMJ96022401.

Original languageEnglish
Pages (from-to)129-136
Number of pages8
JournalPhytochemistry
Volume85
DOIs
Publication statusPublished - Jan 2013

Fingerprint

Sesquiterpenes
Cytotoxicity
mitogen-activated protein kinase
Nitric Oxide Synthase
sesquiterpenoids
Inhibitory Concentration 50
nitric oxide
Nitric Oxide
MAP Kinase Kinase 4
Phosphorylation
inhibitory concentration 50
cytotoxicity
JNK Mitogen-Activated Protein Kinases
Macrophages
Extracellular Signal-Regulated MAP Kinases
Phenylephrine
p38 Mitogen-Activated Protein Kinases
Nitric Oxide Synthase Type II
Blood Vessels
Lipopolysaccharides

Keywords

  • Anti-inflammation
  • Arecophila saccharicola
  • Ascomycete
  • Nitric oxide
  • Sesquiterpene

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Horticulture

Cite this

Isolation and characterization of sesquiterpenes from Arecophila saccharicola YMJ96022401 with NO production inhibitory activity. / Lee, Lin Wen; Wang, Guei Jane; Lin, Mei Hsiang; Ju, Yu Min; Lin, Yen Wen; Chen, Fang Yu; Li, Zong-Huei.

In: Phytochemistry, Vol. 85, 01.2013, p. 129-136.

Research output: Contribution to journalArticle

Lee, Lin Wen ; Wang, Guei Jane ; Lin, Mei Hsiang ; Ju, Yu Min ; Lin, Yen Wen ; Chen, Fang Yu ; Li, Zong-Huei. / Isolation and characterization of sesquiterpenes from Arecophila saccharicola YMJ96022401 with NO production inhibitory activity. In: Phytochemistry. 2013 ; Vol. 85. pp. 129-136.
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abstract = "Sesquiterpenes, arecoic acids A-F and arecolactone, were isolated from the ethyl acetate extracts of the fermented broth of Arecophila saccharicola YMJ96022401 along with two known analogues 1,7α,10α- trihydroxyeremophil-11(13)-en-12,8-olide and 1,10α,13-trihydroxyeremophil- 7(11)-en-12,8-olide. Their structures were elucidated on the basis of spectroscopic data analyses. The inhibitory effects of all of these compounds on nitric oxide (NO) production in lipopolysaccharide (LPS, 200 μg/mL)-activated murine macrophage RAW264.7 cells were also evaluated. Among these compounds, 1,7α,10α-trihydroxyeremophil-11(13)-en-12,8-olide significantly inhibited NO production without any cytotoxicity, and its average maximum inhibition (Emax) at 100 μM and median inhibitory concentration (IC50) were 85.7{\%} ± 0.8{\%} and 16.5 ± 1.0 μM, respectively. Arecolactone was the most potent, with the Emax at 12.5 μM and IC50 being 94.7{\%} ± 0.8{\%} and 1.32 ± 0.1 μM, respectively, but displayed cytotoxicity at considerable higher concentrations than 25 μM. Analyses of Western blotting indicated that arecolactone (0.8-12.5 μM) inhibited induction of inducible NO synthase (iNOS) by LPS, which involved suppression of NF-κB activation and the phosphorylation of extracellular signal-regulated kinase (ERK), c-Jun NH(2)-terminal kinase (JNK) and p38 mitogen-activated protein kinases (MAPKs) in activated RAW 264.7 cells. In addition, arecolactone concentration-dependently prevented the vascular hyporeactivity to phenylephrine induced by LPS (300 ng/mL) through iNOS pathway in isolated rat thoracic aortic rings. These results indicated that both of these naturally occurring iNOS inhibitors may provide a rationale for the potential anti-inflammatory effect of A. saccharicola YMJ96022401.",
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AU - Ju, Yu Min

AU - Lin, Yen Wen

AU - Chen, Fang Yu

AU - Li, Zong-Huei

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N2 - Sesquiterpenes, arecoic acids A-F and arecolactone, were isolated from the ethyl acetate extracts of the fermented broth of Arecophila saccharicola YMJ96022401 along with two known analogues 1,7α,10α- trihydroxyeremophil-11(13)-en-12,8-olide and 1,10α,13-trihydroxyeremophil- 7(11)-en-12,8-olide. Their structures were elucidated on the basis of spectroscopic data analyses. The inhibitory effects of all of these compounds on nitric oxide (NO) production in lipopolysaccharide (LPS, 200 μg/mL)-activated murine macrophage RAW264.7 cells were also evaluated. Among these compounds, 1,7α,10α-trihydroxyeremophil-11(13)-en-12,8-olide significantly inhibited NO production without any cytotoxicity, and its average maximum inhibition (Emax) at 100 μM and median inhibitory concentration (IC50) were 85.7% ± 0.8% and 16.5 ± 1.0 μM, respectively. Arecolactone was the most potent, with the Emax at 12.5 μM and IC50 being 94.7% ± 0.8% and 1.32 ± 0.1 μM, respectively, but displayed cytotoxicity at considerable higher concentrations than 25 μM. Analyses of Western blotting indicated that arecolactone (0.8-12.5 μM) inhibited induction of inducible NO synthase (iNOS) by LPS, which involved suppression of NF-κB activation and the phosphorylation of extracellular signal-regulated kinase (ERK), c-Jun NH(2)-terminal kinase (JNK) and p38 mitogen-activated protein kinases (MAPKs) in activated RAW 264.7 cells. In addition, arecolactone concentration-dependently prevented the vascular hyporeactivity to phenylephrine induced by LPS (300 ng/mL) through iNOS pathway in isolated rat thoracic aortic rings. These results indicated that both of these naturally occurring iNOS inhibitors may provide a rationale for the potential anti-inflammatory effect of A. saccharicola YMJ96022401.

AB - Sesquiterpenes, arecoic acids A-F and arecolactone, were isolated from the ethyl acetate extracts of the fermented broth of Arecophila saccharicola YMJ96022401 along with two known analogues 1,7α,10α- trihydroxyeremophil-11(13)-en-12,8-olide and 1,10α,13-trihydroxyeremophil- 7(11)-en-12,8-olide. Their structures were elucidated on the basis of spectroscopic data analyses. The inhibitory effects of all of these compounds on nitric oxide (NO) production in lipopolysaccharide (LPS, 200 μg/mL)-activated murine macrophage RAW264.7 cells were also evaluated. Among these compounds, 1,7α,10α-trihydroxyeremophil-11(13)-en-12,8-olide significantly inhibited NO production without any cytotoxicity, and its average maximum inhibition (Emax) at 100 μM and median inhibitory concentration (IC50) were 85.7% ± 0.8% and 16.5 ± 1.0 μM, respectively. Arecolactone was the most potent, with the Emax at 12.5 μM and IC50 being 94.7% ± 0.8% and 1.32 ± 0.1 μM, respectively, but displayed cytotoxicity at considerable higher concentrations than 25 μM. Analyses of Western blotting indicated that arecolactone (0.8-12.5 μM) inhibited induction of inducible NO synthase (iNOS) by LPS, which involved suppression of NF-κB activation and the phosphorylation of extracellular signal-regulated kinase (ERK), c-Jun NH(2)-terminal kinase (JNK) and p38 mitogen-activated protein kinases (MAPKs) in activated RAW 264.7 cells. In addition, arecolactone concentration-dependently prevented the vascular hyporeactivity to phenylephrine induced by LPS (300 ng/mL) through iNOS pathway in isolated rat thoracic aortic rings. These results indicated that both of these naturally occurring iNOS inhibitors may provide a rationale for the potential anti-inflammatory effect of A. saccharicola YMJ96022401.

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