Isolation of polyacetylenes with proprotein convertase/kexin type 9 downregulating activity and two new sesquiterpenes from the aerial parts of Aster koraiensis

Nhoek, Piseth; Ahn, Jongmin; Chae, Hee‐Sung; Pel, Pisey; Kim, Youngmi; Lee, Seung Eun; Lee, Jeong Hoon; Kim, Jinwoong; Choi, Young Hee; Lee, Kyeong; Chin, Young‐Won

doi:10.1016/j.tetlet.2020.151957

Cited by 7 publications

(6 citation statements)

References 32 publications

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“…Although numerous types of sesquiterpene have been reported from the Compositae family, until now, only eudesmane-type sesquiterpenes have been isolated from A. koraiensis [15][16][17], except for the presence of an oplopane-type sesquiterpene [15].…”

Section: Structure Elucidation Of 1-7mentioning

confidence: 99%

“…Previous chemical studies on A. koraiensis have led to the identification of several types of secondary metabolites, such as polyacetylenes [ 3 , 10 , 11 , 12 , 14 ], sesquiterpenoids [ 4 , 15 , 16 , 17 ], triterpenoids [ 18 ], flavonoids [ 4 , 16 , 17 ], ionones [ 17 ], caffeoylquinic acids [ 16 ], and benzofurans [ 16 , 19 ]. However, active compounds with anti-inflammatory activities in this plant has been poorly studied.…”

Section: Introductionmentioning

confidence: 99%

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New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of Aster koraiensis

Kim

Seo

Lee

et al. 2020

Plants

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Four new eudesmane-type sesquiterpenoids, (1R,5S,6R,7S,9S,10S)-1,6,9-trihydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside (1), (1R,5S,6S,7R,9S,10S)-1,6,9,11-tetrahydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside (3), (1R,5S,6R,7S,9S,10R)-9-O-(Z-p-coumaroyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside (6), and (1R,5S,6R,7S,9S,10R)-9-O-(E-feruloyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside (7), were isolated from a 95% EtOH extract of the leaves of Aster koraiensis by repeated chromatography. Moreover, three sesquiterpenoids (2, 4, and 5) and two caffeoylquinic acids (8 and 9) having previously known chemical structures were isolated during the isolation procedure. The four new compounds (1, 3, 6, and 7) were elucidated by spectroscopic data (1D- and 2D-NMR, MS, and ECD) interpretation and hydrolysis. Moreover, the absolute configurations of 2, 4, and 5 were determined for the first time in this study. The compounds isolated were tested for their viability on nitric oxide (NO) and prostaglandin E2 (PGE2) production on LPS-stimulated RAW 264.7 cells. Among them, only 7 presented weak inhibitory effects on both NO and PGE2 production.

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Section: Structure Elucidation Of 1-7mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of Aster koraiensis

Kim

Seo

Lee

et al. 2020

Plants

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“…[8] The presence of conjugated triple bonds in polyacetylene natural products also makes them a class of compounds wide variety of biological properties. [3,[9][10][11][12][13][14][15][16][17][18][19][20][21] Polyacetylene glycosides (PAGs) are natural derivatives of polyyne compounds, consisting of one or more units of carbohydrates and a polyacetylene alcohol connected through an acetal bond. [22] The combination of these two structural units into a single molecule makes PAGs a class of attractive compounds, due to the polyacetylene unit being hydrophobic, achiral, rigid, and linear, while the sugar unit is hydrophilic, chiral, occurs in several acyclic and cyclic isomers, and can be easily oxidized.…”

Section: Introductionmentioning

confidence: 99%

Polyacetylene Glycosides: Isolation, Biological Activities and Synthesis

Santos

Filho

et al. 2021

The Chemical Record

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Polyacetylene glycosides (PAGs) constitute a relatively small class of secondary metabolites characterized by the presence of a sugar unit anomerically connected to a polyacetylene. These compounds are found in fungi, seaweed, and more often in plants. PAGs exhibit a wide range of biological and pharmacological activities and, as a result, the literature of these compounds has grown exponentially in recent years.

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“…In particular, extracts or individual constituents from P. chinense displayed therapeutic potentials for hepatic disorders such as hepatitis [5,6], fatty liver [3,4], and hepatocarcinoma [2]. As our ongoing project to pursue naturally occurring inhibitors on proprotein convertase subtilisin/kexin type 9 (PCSK9) [9][10][11], 39 compounds including two new neolignans and two naturally occurring chalcone glycosides were isolated and all isolates were evaluated for their inhibitory activities on the expression of PCSK9 which is involved in degrading low-density lipoprotein receptor (LDLR) and thereby results in inhibiting LDL uptake into cells [12][13][14]. In addition, PCSK9-LDLR interaction was tested for all isolated compounds.…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents with Inhibitory Activities on Proprotein Convertase Subtilisin/kexin Type 9 Expression from the Aerial Parts of Penthorum chinense

Pel¹,

Chae²,

Cho³

et al. 2020

Preprint

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Background: Penthorum chinense has been used in East Asia for the treatment of cholecystitis, infectious hepatitis, and jaundice. So far there is no report regarding proprotein convertase subtilisin/kexin type 9 inhibitory constituents from this plant. The aim of the present study was to discover new active constituents with PCSK9 expression inhibitory activities from P. chinenseMethods: All structures were established by interpreting NMR spectroscopic data and MS data. Further experimental and calculated ECD data were used to determine the absolute configuration of the two new neolignans. To monitor the inhibitory activity on proprotein convertase subtilisin/kexin type 9 (PCSK9) mRNA expression and PCSK9-low density lipoprotein receptor (LDLR) interaction, quantitative real time-PCR, Western blot analysis, and an enzyme-linked immunosorbent assay (ELISA) method by a PCSK9-biotinylated-LDLR binding assay were performed.Results: 39 compounds were isolated and identified including two new oxepine-type neolignans, penthorinols A (1) and B (2) and a naturally occurring chalcone, 6'-hydroxy-2'-methoxychalcone-4'-O-β-D-glucopyranoside (20). Of all tested compounds, penthorin A (4) and methyl gallate (25) were found to suppress PCSK9 mRNA expression with IC50 values of 15.56 and 11.66 µM, respectively. Furthermore, penthorin A (4) and methyl gallate (25) downregulated PCSK9 protein expression. However, all compounds seemed to be inactive in PCSK9-LDLR interaction.Conclusion: In the present study, two new compounds was discovered from this plant and active constituents with PCSK9 expression inhibitory activities were suggested.

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Isolation of polyacetylenes with proprotein convertase/kexin type 9 downregulating activity and two new sesquiterpenes from the aerial parts of Aster koraiensis

Cited by 7 publications

References 32 publications

New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of Aster koraiensis

New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of Aster koraiensis

Polyacetylene Glycosides: Isolation, Biological Activities and Synthesis

Chemical Constituents with Inhibitory Activities on Proprotein Convertase Subtilisin/kexin Type 9 Expression from the Aerial Parts of Penthorum chinense

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