37 シュンラン(Cymbidium goeringii)から単離された降圧および利尿作用を有する新規ペプチドグリカンcymbidine Aの構造(口頭発表の部)

概要

論文の詳細を見る
In 1972, cymbidine A (1) was isolated from the 80% ethanol extract of the orchidaceous plant Cymbidium goeringii as a hypotensive and diuretic principle. In those days, compound 1 was suggested to contain several amino acids and amino sugars, but further structure elucidation was difficult because of its structural complexity. Our recent investigation on cymbindine A (1) resulted in the elucidation of the whole structure. The molecular formula of cymbidine A (|α|_D^<22>-28.4°) was found to be C_<39>H_<63>N_7O_<20> by HRESIMS and ^<13>C NMR data (Table 1). Based on the amino acid analysis of the hydrolysate of 1 (Figure 2), valine (Val), glutamic acid (Glu), alanine (Ala) and an unusual amino acid were detected. The HMQC revealed the direct correlations between ^<13>C and ^1H signals (Table 1). The analysis of ^1H-^1H COSY and/or TOCSY indicated the partial structures a〜g (Figure 3) in 1. The partial structures were connected by HMBC correlations to give the plane structure of 1 (Figure 3). The absolute configurations of the three amino acid residues in 1 were determined to be L-Val, D-Glu and D-Ala by the advanced Marfey method. The unusual amino acid was found to be 2,6-diaminopimelic acid (A_2pm) whose meso stereochemistry was assigned by comparison of HPLC retention time with those of DD-, LL- and meso-A_2pm. The relative configurations of two aminosugars were elucidated by the analysis of ^1H-^1H spin coupling constants as well as NOESY spectral data (Figure 4), to exhibit that these aminosugars were N-acetylglucosamine and 1,6-anhydro-N-acetyl muramic acid.
天然有機化合物討論会の論文
2005-09-15

37 シュンラン(Cymbidium goeringii)から単離された降圧および利尿作用を有する新規ペプチドグリカンcymbidine Aの構造(口頭発表の部)

スポンサーリンク

概要

著者

関連論文

スポンサーリンク