C-糖基黄酮类化合物。荭草素和异荭草素的化学性质。
C-Glycosylflavonoids. The chemistry of orientin and iso-orientin.
作者信息
Koeppen B H
机构信息
Department of Food Science, University of Stellenbosch, Stellenbosch.
出版信息
Biochem J. 1965 Nov;97(2):444-8. doi: 10.1042/bj0970444.
Abstract
- The structures of orientin and iso-orientin have been investigated by periodic acid and ferric chloride oxidation of the tetra-O-methyl derivatives and by identification of the products of oxidation. 2. The preparation and properties of the 3',4',7-trimethyl ethers of orientin and iso-orientin are described, and the nuclear-magnetic-resonance spectra of orientin, iso-orientin and their tri- and tetra-O-methyl derivatives are discussed. 3. Orientin and iso-orientin are formulated as 8- and 6-C-beta-d-glucopyranosyl-luteolin respectively.
摘要
- 已通过对四 - O - 甲基衍生物进行高碘酸和氯化铁氧化以及对氧化产物进行鉴定，研究了荭草苷和异荭草苷的结构。2. 描述了荭草苷和异荭草苷的3'，4'，7 - 三甲醚的制备方法及其性质，并讨论了荭草苷、异荭草苷及其三 - 和四 - O - 甲基衍生物的核磁共振谱。3. 荭草苷和异荭草苷分别被确定为8 - C - β - D - 吡喃葡萄糖基木犀草素和6 - C - β - D - 吡喃葡萄糖基木犀草素。
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本文引用的文献
1
Condensed tannins. 3. Isolation and estimation of (-)-7:3':4':5'-tetrahydroxyflavan-3-ol, (+)-catechin and (+)-gallocatechin from black-wattle-bark extract.缩合单宁。3. 从黑荆树皮提取物中分离并测定（-）-7:3':4':5'-四羟基黄烷-3-醇、（+）-儿茶素和（+）-没食子儿茶素。
Biochem J. 1960 Jan;74(1):44-9. doi: 10.1042/bj0740044.
2
The flavone C-glycosides and flavonol O-glycosides of Aspalathus acuminatus (rooibos tea).尖叶金雀花（路依保斯茶）中的黄酮碳苷和黄酮醇氧苷。
Biochem J. 1962 Jun;83(3):507-11. doi: 10.1042/bj0830507.
3
[On a new glycoside type of the flavone series. III. On the constitution of orientoside and orientin].
Arch Pharm Ber Dtsch Pharm Ges. 1959 Jul;292/64:380-7. doi: 10.1002/ardp.19592920710.
4
STRUCTURE AND INTERRELATIONSHIP OF ORIENTIN AND HOMO-ORIENTIN.
Z Naturforsch B. 1964 Feb;19:173. doi: 10.1515/znb-1964-0225.
5
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