Journal article
[ 13C]-Specific labeling of 8–2′ linked (−)- cis-blechnic, (−)- trans-blechnic and (−)-brainic acids in the fern Blechnum spicant
Phytochemistry (Oxford), Vol.62(3), pp.501-511
2003
Handle:
https://hdl.handle.net/2376/106864
PMID: 12620363
Abstract
In vivo administration experiments using stable (
13C) and radio (
14C) labeled precursors established that the optically active 8–2′ linked lignans, (−)-
cis-blechnic, (−)-
trans-blechnic and (−)-
trans-brainic acids, were directly derived from
l-phenylalanine, cinnamate, and
p-coumarate.
In vivo administration experiments using stable (
13C) and radio (
14C) labeled precursors established that the optically active 8–2′ linked lignans, (−)-
cis-blechnic, (−)-
trans-blechnic and (−)-
trans-brainic acids, were directly derived from
l-phenylalanine, cinnamate, and
p-coumarate but not either from tyrosine or acetate. The radiochemical time course data suggest that the initial coupling product is (−)-
cis-blechnic acid, which is then apparently converted into both (−)-
trans-blechnic and (−)-
trans-brainic acids in vivo. These findings provide additional evidence for vascular plant proteins engendering distinct but specific phenolic radical-radical coupling modes, i.e., for full control over phenylpropanoid coupling in vivo, whether stereoselective or regiospecific.
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Details
- Title
- [ 13C]-Specific labeling of 8–2′ linked (−)- cis-blechnic, (−)- trans-blechnic and (−)-brainic acids in the fern Blechnum spicant
- Creators
- Laurence B Davin - Institute of Biological Chemistry, Washington State University, Pullman, WA 99164-6340, USAChang-Zeng Wang - Institute of Biological Chemistry, Washington State University, Pullman, WA 99164-6340, USAGregory L Helms - Nuclear Magnetic Resonance Center, Washington State University, Pullman, WA 99164, USANorman G Lewis - Institute of Biological Chemistry, Washington State University, Pullman, WA 99164-6340, USA
- Publication Details
- Phytochemistry (Oxford), Vol.62(3), pp.501-511
- Academic Unit
- Biological Chemistry, Institute of; NMR Center
- Publisher
- Elsevier Ltd
- Identifiers
- 99900546965001842
- Language
- English
- Resource Type
- Journal article