Structure of cymbidine A, a monomeric peptidoglycan-related compound with hypotensive and diuretic activities, isolated from a higher plant, Cymbidium goeringii (Orchidaceae).
The structure of a new monomeric peptidoglycan-related compound with hypotensive and diuretic activities, cymbidine A (1) isolated from the orchid Cymbidium goeringii, was elucidated mainly by spectroscopic analysis. The structure of 1 was shown to involve four amino acids (D-alanin, meso-diaminopimelic acid, D-gultamic acid, and L-valine) and two amino sugars (N-acetylglucosamine and 1,6-anhydro-N-acetylmuramic acid). The sequence of the amino acids and amino sugars was determined by the analysis of 2D NMR data. The absolute stereochemistries of the three amino acids (D-Ala, D-Glu and L-Val) were determined by the modified Marfey's method, and the (6S,10R) configurations of meso-diaminopimelic acid in 1 were indicated on the basis of the CD analysis. The absolute stereochemistry of 1,6-anhydro-N-acetylmuramic acid was also determined by CD data.
Watanabe
Kinzo
K
School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan .
Tanaka
Rina
R
Sakurai
Hitomi
H
Iguchi
Kazuo
K
Yamada
Yasuji
Y
Hsu
Chau-Shin
CS
Sakuma
Chiseko
C
Kikuchi
Hiroyuki
H
Shibayama
Humio
H
Kawai
Tadahide
T
D000818:Animals; D000959:Antihypertensive Agents / Q000302:isolation & purification* / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D004232:Diuretics / Q000302:isolation & purification* / Q000494:pharmacology*; D006020:Glycopeptides / Q000302:isolation & purification* / Q000494:pharmacology*; D006868:Hydrolysis; D006973:Hypertension / Q000139:chemically induced / Q000188:drug therapy / Q000503:physiopathology; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D029595:Orchidaceae / Q000737:chemistry*; D051381:Rats; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared
D000959:Antihypertensive Agents; D004232:Diuretics; D006020:Glycopeptides; C520863:cymbidine A