cis-Aconitic Anhydride Ethyl Ester and Phenolic Compounds from the Seeds of Alisma orientale

Abstract

From the seeds of Alisma orientale, cis-aconitic anhydride ethyl ester and cis-2,4,5-trihydroxycinnamic acid were isolated, together with nine known phenolic compounds and a megastigmane sesquiterpene. All compounds are reported for the first time from Alisma species.

A 90-Day Repeated Oral Dose Toxicity Study of Alismatis Rhizoma Aqueous Extract in Rats

“…Chromatograms of ARAE detected main compounds with four peaks: compound 1 ( m / z 281.1641 [M+H] + ), compound 2 ( m / z 295.1812 [M+H] + ), compound 3 ( m / z 265.1696 [M+H] + ) and compound 4 ( m / z 279.1854 [M+H] + ). These compound 1 ((R)-1-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)pent-4-en-1-one (101c); C 18 H 21 N 2 O), compound 2 (trans-N-Benzyl-1-methyl-4-phenylpyrrolidine-3-carboxamide; C 19 H 23 N 2 O), compound 3 (N-{(E,2E)-2-[(2,6-Dimethylphenyl)imino]ethyliden}-2,6-dimethylaniline; C 18 H 21 N 2 ) and compound 4 ((E)-N-(2-phenyl-1-(piperidin-1-yl)ethylidene)aniline; C 19 H 23 N 2 ) were identified as phenolic compounds based on MS data and reference (12,21–24).…”

“…AR compounds that have been discovered include terpenoids (11), phenolic (12), polysaccharides (13), carbohydrates, proteins, amino acids, etc (5). Diuretic activity investigations have shown that the alisol A content in AR has a similar diuretic effect with hydrochlorothiazide, and alisol A 24-acetate and hydrochlorothiazide increased the excretion of Na + and K + in rats (14).…”

Alisma genus: Phytochemical constituents, biosynthesis, and biological activities

“…Recently, only five phenylpropionic acids were obtained from A. orientale and A. plantago‐aquatica through preparative HPLC eluted with MeOH‐H 2 O as mobile phase (Figure 6), namely N‐trans‐ feruloyl‐ N′‐cis ‐feruloyl‐cadaverine ( 110 ), N,N′‐trans ‐diferuloyl‐3‐oxo‐cadaverine ( 111 ), N‐trans‐ feruloyl‐ N′ ‐ cis ‐feruloyl‐3‐hydroxy‐ cadaverine ( 112 ), N,N′‐cis‐ diferuloyl‐3‐hydroxy‐cadaverine ( 113 ), N‐trans‐p‐ coumaroyl‐ N′ ‐ trans ‐feruloyl‐3‐hydroxy‐cadaverine ( 114 ), and plantain A ( 115 ) (Xin et al, 2017). In addition, cis ‐2,4,5‐trihydroxycinnamic acid ( 116 ) and cis ‐aconitic anhydride ethyl ester ( 117 ) were also isolated from the seeds of A. orientale by Zhao et al (2012).…”