Two new stereoisomers of neolignan and lignan from the flower buds of magnolia fargesii

Jun Lee; Eun Kyoung Seo; Dae Sik Jang; Tae Joung Ha; K. I.M. Jong-Pyung; Joo Won Nam; Green Bae; Yun Mi Lee; Min Suk Yang; Jin Sook Kim

doi:10.1248/cpb.57.298

Two new stereoisomers of neolignan and lignan from the flower buds of magnolia fargesii

Jun Lee, Eun Kyoung Seo, Dae Sik Jang, Tae Joung Ha, K. I.M. Jong-Pyung, Joo Won Nam, Green Bae, Yun Mi Lee, Min Suk Yang, Jin Sook Kim

Department of Pharmaceutical Sciences

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

34 Scopus citations

Abstract

A new stereoisomer of 8-O-4′ system neolignan, (7R,8S)-1-(3,4- dimethoxyphenyl)-2-[4-(3-hydroxy-1-propenyl)-2-methoxyphenoxy]-propane-1,3-diol (1) and a new stereoisomer of tetrahydrofuranoid lignan, (7R,8S,7'S,8'R)-(3,4,5, 3′,4′)-pentamethoxy-9,7′-dihydroxy-8.8′,7.0. 9′-lignan (2) along with seven known lignans and neolignans (3-9) were isolated from the methanol extracts of the flower buds of Magnolia fargesii. The structures of these compounds (1-9) were elucidated by spectroscopic methods including 1D- and 2D-NMR as well as by comparison with reported values. Absolute configurations of new stereoisomers 1 and 2 were determined by circular dichroism (CD) spectra. The absolute configuration of (S,8S,10S)-[tetrahydro-4- hydroxy-2-(3,4,5-tri-methoxyphenyl)furan-3-yl]methyl 3,4-dimethoxy benzoate (3) was determined by Mosher's esterification method for the first time in this study. Three lignans, tanegool (4), (+)-dehydrodiconiferyl alcohol (5), and epieudes-min (6), were isolated from this plant for the first time. Superoxide radical scavenging activities of the isolates (1-9) were measured by irradiated riboflavin/ethylenediaminetetraacetic acid (EDTA)/Nitroblue tetrazolium (NBT) system, and their in vitro rat lens aldose reductase (RLAR) inhibitory activities were also evaluated.

Original language	English
Pages (from-to)	298-301
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	57
Issue number	3
DOIs	https://doi.org/10.1248/cpb.57.298
State	Published - Mar 2009

Bibliographical note

Funding Information:
This work was supported, in part, by Field Technology Research Project through the Korea South-East Power Co., Ltd. (KOEN), Korea Institute of Planning and Evaluation for Technology in Food, Agriculture and Forestry (IPET) through Animal Disease Management Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) ( 319078-2 ), and a grant from the Ministry of Science and ICT ( MSIT ) through the National Research Foundation ( NRF ) of Korea [ NRF-2019R1C1C1004572 ; NRF-2019R1A4A1029125 ].

Keywords

Aldose reductase
Diabetic complication
Lignan
Magnolia fargesii
Superoxide radical

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@article{5cbcba78e6784abf9e404d43d6e1d72d,

title = "Two new stereoisomers of neolignan and lignan from the flower buds of magnolia fargesii",

abstract = "A new stereoisomer of 8-O-4′ system neolignan, (7R,8S)-1-(3,4- dimethoxyphenyl)-2-[4-(3-hydroxy-1-propenyl)-2-methoxyphenoxy]-propane-1,3-diol (1) and a new stereoisomer of tetrahydrofuranoid lignan, (7R,8S,7'S,8'R)-(3,4,5, 3′,4′)-pentamethoxy-9,7′-dihydroxy-8.8′,7.0. 9′-lignan (2) along with seven known lignans and neolignans (3-9) were isolated from the methanol extracts of the flower buds of Magnolia fargesii. The structures of these compounds (1-9) were elucidated by spectroscopic methods including 1D- and 2D-NMR as well as by comparison with reported values. Absolute configurations of new stereoisomers 1 and 2 were determined by circular dichroism (CD) spectra. The absolute configuration of (S,8S,10S)-[tetrahydro-4- hydroxy-2-(3,4,5-tri-methoxyphenyl)furan-3-yl]methyl 3,4-dimethoxy benzoate (3) was determined by Mosher's esterification method for the first time in this study. Three lignans, tanegool (4), (+)-dehydrodiconiferyl alcohol (5), and epieudes-min (6), were isolated from this plant for the first time. Superoxide radical scavenging activities of the isolates (1-9) were measured by irradiated riboflavin/ethylenediaminetetraacetic acid (EDTA)/Nitroblue tetrazolium (NBT) system, and their in vitro rat lens aldose reductase (RLAR) inhibitory activities were also evaluated.",

keywords = "Aldose reductase, Diabetic complication, Lignan, Magnolia fargesii, Superoxide radical",

author = "Jun Lee and Seo, {Eun Kyoung} and Jang, {Dae Sik} and Ha, {Tae Joung} and Jong-Pyung, {K. I.M.} and Nam, {Joo Won} and Green Bae and Lee, {Yun Mi} and Yang, {Min Suk} and Kim, {Jin Sook}",

note = "Funding Information: This work was supported, in part, by Field Technology Research Project through the Korea South-East Power Co., Ltd. (KOEN), Korea Institute of Planning and Evaluation for Technology in Food, Agriculture and Forestry (IPET) through Animal Disease Management Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) ( 319078-2 ), and a grant from the Ministry of Science and ICT ( MSIT ) through the National Research Foundation ( NRF ) of Korea [ NRF-2019R1C1C1004572 ; NRF-2019R1A4A1029125 ]. ",

year = "2009",

month = mar,

doi = "10.1248/cpb.57.298",

language = "English",

volume = "57",

pages = "298--301",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "3",

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TY - JOUR

T1 - Two new stereoisomers of neolignan and lignan from the flower buds of magnolia fargesii

AU - Lee, Jun

AU - Seo, Eun Kyoung

AU - Jang, Dae Sik

AU - Ha, Tae Joung

AU - Jong-Pyung, K. I.M.

AU - Nam, Joo Won

AU - Bae, Green

AU - Lee, Yun Mi

AU - Yang, Min Suk

AU - Kim, Jin Sook

N1 - Funding Information: This work was supported, in part, by Field Technology Research Project through the Korea South-East Power Co., Ltd. (KOEN), Korea Institute of Planning and Evaluation for Technology in Food, Agriculture and Forestry (IPET) through Animal Disease Management Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA) ( 319078-2 ), and a grant from the Ministry of Science and ICT ( MSIT ) through the National Research Foundation ( NRF ) of Korea [ NRF-2019R1C1C1004572 ; NRF-2019R1A4A1029125 ].

PY - 2009/3

Y1 - 2009/3

N2 - A new stereoisomer of 8-O-4′ system neolignan, (7R,8S)-1-(3,4- dimethoxyphenyl)-2-[4-(3-hydroxy-1-propenyl)-2-methoxyphenoxy]-propane-1,3-diol (1) and a new stereoisomer of tetrahydrofuranoid lignan, (7R,8S,7'S,8'R)-(3,4,5, 3′,4′)-pentamethoxy-9,7′-dihydroxy-8.8′,7.0. 9′-lignan (2) along with seven known lignans and neolignans (3-9) were isolated from the methanol extracts of the flower buds of Magnolia fargesii. The structures of these compounds (1-9) were elucidated by spectroscopic methods including 1D- and 2D-NMR as well as by comparison with reported values. Absolute configurations of new stereoisomers 1 and 2 were determined by circular dichroism (CD) spectra. The absolute configuration of (S,8S,10S)-[tetrahydro-4- hydroxy-2-(3,4,5-tri-methoxyphenyl)furan-3-yl]methyl 3,4-dimethoxy benzoate (3) was determined by Mosher's esterification method for the first time in this study. Three lignans, tanegool (4), (+)-dehydrodiconiferyl alcohol (5), and epieudes-min (6), were isolated from this plant for the first time. Superoxide radical scavenging activities of the isolates (1-9) were measured by irradiated riboflavin/ethylenediaminetetraacetic acid (EDTA)/Nitroblue tetrazolium (NBT) system, and their in vitro rat lens aldose reductase (RLAR) inhibitory activities were also evaluated.

AB - A new stereoisomer of 8-O-4′ system neolignan, (7R,8S)-1-(3,4- dimethoxyphenyl)-2-[4-(3-hydroxy-1-propenyl)-2-methoxyphenoxy]-propane-1,3-diol (1) and a new stereoisomer of tetrahydrofuranoid lignan, (7R,8S,7'S,8'R)-(3,4,5, 3′,4′)-pentamethoxy-9,7′-dihydroxy-8.8′,7.0. 9′-lignan (2) along with seven known lignans and neolignans (3-9) were isolated from the methanol extracts of the flower buds of Magnolia fargesii. The structures of these compounds (1-9) were elucidated by spectroscopic methods including 1D- and 2D-NMR as well as by comparison with reported values. Absolute configurations of new stereoisomers 1 and 2 were determined by circular dichroism (CD) spectra. The absolute configuration of (S,8S,10S)-[tetrahydro-4- hydroxy-2-(3,4,5-tri-methoxyphenyl)furan-3-yl]methyl 3,4-dimethoxy benzoate (3) was determined by Mosher's esterification method for the first time in this study. Three lignans, tanegool (4), (+)-dehydrodiconiferyl alcohol (5), and epieudes-min (6), were isolated from this plant for the first time. Superoxide radical scavenging activities of the isolates (1-9) were measured by irradiated riboflavin/ethylenediaminetetraacetic acid (EDTA)/Nitroblue tetrazolium (NBT) system, and their in vitro rat lens aldose reductase (RLAR) inhibitory activities were also evaluated.

KW - Aldose reductase

KW - Diabetic complication

KW - Lignan

KW - Magnolia fargesii

KW - Superoxide radical

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U2 - 10.1248/cpb.57.298

DO - 10.1248/cpb.57.298

M3 - Article

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AN - SCOPUS:62549091473

SN - 0009-2363

VL - 57

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EP - 301

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

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ER -

Two new stereoisomers of neolignan and lignan from the flower buds of magnolia fargesii

Abstract

Bibliographical note

Keywords

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