Abstract
Two new stereoisomers of tetrahydrofuranoid lignans, 7S,8R,7′S, 8′R- (1) and 7R,8S,7′S,8′R-3,4,3′,4′-tetramethoxy- 9,7′-dihydroxy-8.8′,7.O.9′-lignan (2) along with nine known lignans including tetrahydrofuranoids (3, 4) and tetrahydrofurofuranoids (5-11) were isolated from a CHCl3-soluble fraction of the flower buds of Magnolia fargesii. Two tetrahydrofuranoids, magnostellin A (3) and lariciresinol dimethyl ether (4) were isolated from this species for the first time. The structures of these compounds (1-11) were identified by spectroscopic methods as well as by comparison with published values. Absolute configurations of new stereoisomers (1, 2) were determined by the Mosher's esterification method and Circular Dichroism (CD) studies. All the isolates (1-11) were evaluated for their antioxidant activities using modified superoxide radical-scavenging assay. Compounds 5-8 showed the potent superoxide radical-scavenging activities with the ED50 values of 19.2, 19.2, 16.5, and 27.7 μM, respectively, as compared with standard antioxidants (BHA: 22.8 μM; Trolox: 940 μM).
| Original language | English |
|---|---|
| Pages (from-to) | 137-139 |
| Number of pages | 3 |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 55 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2007 Jan 1 |
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Keywords
- Antioxidant activity
- Lignan
- Magnolia fargesii
- Magnoliaceae
- Superoxide radical
- Tetrahydrofuranoid
- Xinyi
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
- Chemistry(all)
- Pharmacology
Cite this
Two new stereoisomers of tetrahydrofuranoid lignans from the flower buds of Magnolia fargesii. / Lee, Jun; Lee, Dongho; Jang, Dae Sik; Nam, Joo Won; Kim, Jong Pyung; Park, Ki Hun; Yang, Min Suk; Seo, Eun Kyoung.
In: Chemical and Pharmaceutical Bulletin, Vol. 55, No. 1, 01.01.2007, p. 137-139.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Two new stereoisomers of tetrahydrofuranoid lignans from the flower buds of Magnolia fargesii
AU - Lee, Jun
AU - Lee, Dongho
AU - Jang, Dae Sik
AU - Nam, Joo Won
AU - Kim, Jong Pyung
AU - Park, Ki Hun
AU - Yang, Min Suk
AU - Seo, Eun Kyoung
PY - 2007/1/1
Y1 - 2007/1/1
N2 - Two new stereoisomers of tetrahydrofuranoid lignans, 7S,8R,7′S, 8′R- (1) and 7R,8S,7′S,8′R-3,4,3′,4′-tetramethoxy- 9,7′-dihydroxy-8.8′,7.O.9′-lignan (2) along with nine known lignans including tetrahydrofuranoids (3, 4) and tetrahydrofurofuranoids (5-11) were isolated from a CHCl3-soluble fraction of the flower buds of Magnolia fargesii. Two tetrahydrofuranoids, magnostellin A (3) and lariciresinol dimethyl ether (4) were isolated from this species for the first time. The structures of these compounds (1-11) were identified by spectroscopic methods as well as by comparison with published values. Absolute configurations of new stereoisomers (1, 2) were determined by the Mosher's esterification method and Circular Dichroism (CD) studies. All the isolates (1-11) were evaluated for their antioxidant activities using modified superoxide radical-scavenging assay. Compounds 5-8 showed the potent superoxide radical-scavenging activities with the ED50 values of 19.2, 19.2, 16.5, and 27.7 μM, respectively, as compared with standard antioxidants (BHA: 22.8 μM; Trolox: 940 μM).
AB - Two new stereoisomers of tetrahydrofuranoid lignans, 7S,8R,7′S, 8′R- (1) and 7R,8S,7′S,8′R-3,4,3′,4′-tetramethoxy- 9,7′-dihydroxy-8.8′,7.O.9′-lignan (2) along with nine known lignans including tetrahydrofuranoids (3, 4) and tetrahydrofurofuranoids (5-11) were isolated from a CHCl3-soluble fraction of the flower buds of Magnolia fargesii. Two tetrahydrofuranoids, magnostellin A (3) and lariciresinol dimethyl ether (4) were isolated from this species for the first time. The structures of these compounds (1-11) were identified by spectroscopic methods as well as by comparison with published values. Absolute configurations of new stereoisomers (1, 2) were determined by the Mosher's esterification method and Circular Dichroism (CD) studies. All the isolates (1-11) were evaluated for their antioxidant activities using modified superoxide radical-scavenging assay. Compounds 5-8 showed the potent superoxide radical-scavenging activities with the ED50 values of 19.2, 19.2, 16.5, and 27.7 μM, respectively, as compared with standard antioxidants (BHA: 22.8 μM; Trolox: 940 μM).
KW - Antioxidant activity
KW - Lignan
KW - Magnolia fargesii
KW - Magnoliaceae
KW - Superoxide radical
KW - Tetrahydrofuranoid
KW - Xinyi
UR - http://www.scopus.com/inward/record.url?scp=33846046128&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33846046128&partnerID=8YFLogxK
U2 - 10.1248/cpb.55.137
DO - 10.1248/cpb.55.137
M3 - Article
C2 - 17202718
AN - SCOPUS:33846046128
VL - 55
SP - 137
EP - 139
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 1
ER -