Lupane-type triterpenoids from the steamed leaves of Acanthopanax koreanum and their inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells

Jeong Ah Kim; Seo Young Yang; Jung Eun Koo; Young Sang Koh; Young Ho Kim

doi:10.1016/j.bmcl.2010.09.001

Lupane-type triterpenoids from the steamed leaves of Acanthopanax koreanum and their inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells

Jeong Ah Kim
, Seo Young Yang
, Jung Eun Koo
, Young Sang Koh
, Young Ho Kim

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

32 Scopus citations

Abstract

Two new compounds, (20R)-3α-hydroxy-29-dimethoxylupan-23,28-dioic acid (1) and 3α-hydroxylup-20(29)-ene-23,28-dioic acid 28-O-[β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] ester (2), and eight known lupane-type triterpenoids (3-10), were isolated from steamed leaves of Acanthopanax koreanum. Chemical structures were determined using a combination of spectroscopic analyses and chemical reactivity. Compounds 1-10 were evaluated for their inhibitory activities on lipopolysaccharide (LPS)-stimulated interleukin (IL)-12 production in bone marrow-derived dendritic cells (BMDCs). Compound 1 exhibited inhibitory activity with IC₅₀ value of 26.5 μM on IL-12 production, compared with IC₅₀ value of 29.6 μM for the positive control. Compound 1 also showed significant suppression of LPS-stimulated IL-6 and tumor necrosis factor-alpha (TNF-α) production.

Original language	English
Pages (from-to)	6703-6707
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	22
DOIs	https://doi.org/10.1016/j.bmcl.2010.09.001
State	Published - 15 Nov 2010

Keywords

Acanthopanax koreanum
Bone marrow-derived dendritic cells
IL-12
IL-6
Lupane-type triterpenoids
TNF-α

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10.1016/j.bmcl.2010.09.001

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Kim, J. A., Yang, S. Y., Koo, J. E., Koh, Y. S., & Kim, Y. H. (2010). Lupane-type triterpenoids from the steamed leaves of Acanthopanax koreanum and their inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells. Bioorganic and Medicinal Chemistry Letters, 20(22), 6703-6707. https://doi.org/10.1016/j.bmcl.2010.09.001

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title = "Lupane-type triterpenoids from the steamed leaves of Acanthopanax koreanum and their inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells",

abstract = "Two new compounds, (20R)-3α-hydroxy-29-dimethoxylupan-23,28-dioic acid (1) and 3α-hydroxylup-20(29)-ene-23,28-dioic acid 28-O-[β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] ester (2), and eight known lupane-type triterpenoids (3-10), were isolated from steamed leaves of Acanthopanax koreanum. Chemical structures were determined using a combination of spectroscopic analyses and chemical reactivity. Compounds 1-10 were evaluated for their inhibitory activities on lipopolysaccharide (LPS)-stimulated interleukin (IL)-12 production in bone marrow-derived dendritic cells (BMDCs). Compound 1 exhibited inhibitory activity with IC50 value of 26.5 μM on IL-12 production, compared with IC50 value of 29.6 μM for the positive control. Compound 1 also showed significant suppression of LPS-stimulated IL-6 and tumor necrosis factor-alpha (TNF-α) production.",

keywords = "Acanthopanax koreanum, Bone marrow-derived dendritic cells, IL-12, IL-6, Lupane-type triterpenoids, TNF-α",

author = "Kim, \{Jeong Ah\} and Yang, \{Seo Young\} and Koo, \{Jung Eun\} and Koh, \{Young Sang\} and Kim, \{Young Ho\}",

year = "2010",

month = nov,

day = "15",

doi = "10.1016/j.bmcl.2010.09.001",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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Kim, JA , Yang, SY, Koo, JE, Koh, YS & Kim, YH 2010, 'Lupane-type triterpenoids from the steamed leaves of Acanthopanax koreanum and their inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells', Bioorganic and Medicinal Chemistry Letters, vol. 20, no. 22, pp. 6703-6707. https://doi.org/10.1016/j.bmcl.2010.09.001

Lupane-type triterpenoids from the steamed leaves of Acanthopanax koreanum and their inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells. / Kim, Jeong Ah ; Yang, Seo Young; Koo, Jung Eun et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 20, No. 22, 15.11.2010, p. 6703-6707.

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

TY - JOUR

T1 - Lupane-type triterpenoids from the steamed leaves of Acanthopanax koreanum and their inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells

AU - Kim, Jeong Ah

AU - Yang, Seo Young

AU - Koo, Jung Eun

AU - Koh, Young Sang

AU - Kim, Young Ho

PY - 2010/11/15

Y1 - 2010/11/15

N2 - Two new compounds, (20R)-3α-hydroxy-29-dimethoxylupan-23,28-dioic acid (1) and 3α-hydroxylup-20(29)-ene-23,28-dioic acid 28-O-[β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] ester (2), and eight known lupane-type triterpenoids (3-10), were isolated from steamed leaves of Acanthopanax koreanum. Chemical structures were determined using a combination of spectroscopic analyses and chemical reactivity. Compounds 1-10 were evaluated for their inhibitory activities on lipopolysaccharide (LPS)-stimulated interleukin (IL)-12 production in bone marrow-derived dendritic cells (BMDCs). Compound 1 exhibited inhibitory activity with IC50 value of 26.5 μM on IL-12 production, compared with IC50 value of 29.6 μM for the positive control. Compound 1 also showed significant suppression of LPS-stimulated IL-6 and tumor necrosis factor-alpha (TNF-α) production.

AB - Two new compounds, (20R)-3α-hydroxy-29-dimethoxylupan-23,28-dioic acid (1) and 3α-hydroxylup-20(29)-ene-23,28-dioic acid 28-O-[β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] ester (2), and eight known lupane-type triterpenoids (3-10), were isolated from steamed leaves of Acanthopanax koreanum. Chemical structures were determined using a combination of spectroscopic analyses and chemical reactivity. Compounds 1-10 were evaluated for their inhibitory activities on lipopolysaccharide (LPS)-stimulated interleukin (IL)-12 production in bone marrow-derived dendritic cells (BMDCs). Compound 1 exhibited inhibitory activity with IC50 value of 26.5 μM on IL-12 production, compared with IC50 value of 29.6 μM for the positive control. Compound 1 also showed significant suppression of LPS-stimulated IL-6 and tumor necrosis factor-alpha (TNF-α) production.

KW - Acanthopanax koreanum

KW - Bone marrow-derived dendritic cells

KW - IL-12

KW - IL-6

KW - Lupane-type triterpenoids

KW - TNF-α

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DO - 10.1016/j.bmcl.2010.09.001

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C2 - 20932756

AN - SCOPUS:77958068918

SN - 0960-894X

VL - 20

SP - 6703

EP - 6707

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 22

ER -

Lupane-type triterpenoids from the steamed leaves of Acanthopanax koreanum and their inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells

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