Resin glycosides from the aerial parts of Operculina turpethum.
Three glycosidic acids, turpethic acids A-C, and two intact resin glycosides, turpethosides A and B, all having a common pentasaccharide moiety and 12-hydroxy fatty acid aglycones of different chain lengths, were obtained from the aerial parts of Operculina turpethum. Their structures were elucidated by spectroscopic analyses and chemical correlations. The aglycones were characterized as 12-hydroxypentadecanoic acid in two compounds, 12-hydroxyhexadecanoic acid in two other components, and 12-hydroxyheptadecanoic acid in the fifth compound, which were all confirmed by synthesis. The absolute configurations of these aglycones were all established as S by Mosher's method. These compounds represent the first examples of resin glycosides with a monohydroxylated 12-hydroxy fatty acid as an aglycone, and one compound is the first described resin glycoside having a hydroxylated C(17) fatty acid as its aglycone.
Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Tianhe District, Guangzhou 510650, China.
Wenbing
W
Ding
Zi-Hua
ZH
Jiang
Ping
P
Wu
Liangxiong
L
Xu
Xiaoyi
X
Wei
D000143:Acids / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D029747:Opuntia / Q000737:chemistry*; D035261:Plant Components, Aerial / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry; D012116:Resins, Plant / Q000737:chemistry / Q000302:isolation & purification*; D013045:Species Specificity
D000143:Acids; D005227:Fatty Acids; D006027:Glycosides; D010936:Plant Extracts; D012116:Resins, Plant