Phenolic constituents of Acorus gramineus

Abstract

The purification of a MeOH extract from the rhizome of Acorus gramineus (Araceae) using column chromatography furnished two new stereoisomers of phenylpropanoid, acoraminol A (1) and acoraimol B (2). It also furnished 17 known phenolic compounds, β-asarone (3), asaraldehyde (4), isoacoramone (5), propioveratrone (6), (1'R,2'S)-1',2'-dihydroxyasarone (7), (1'S,2'S)-1',2'-dihydroxyasarone (8), 3',4'-dimethoxycinnamyl alcohol (9), 3',4',5'-trimethoxycinnamyl alcohol (10), kaempferol 3-methyl ether (11), 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-propanediol (12), hydroxytyrosol (13), tyrosol (14), (2S,5S)-diveratryl-(3R,4S)-dimethyltetrahydrofuran (15), (7S,8R)-dihydrodehydrodiconiferyl alcohol (16), 7S,8S-threo-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan (17), 7S,8R-erythro-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan (18), and dihydroyashsbushiketol (19). The structures of the new compounds were elucidated by analysis of spectroscopic data including 1D and 2D NMR data. The absolute configurations of 1 and 2 were determined using the convenient Mosher ester procedure. Compounds 5-19 were isolated for the first time from this plant source. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamine B (SRB) bioassay.

Termiticidal activity of Acorus calamus Linn. rhizomes and its main constituents against Coptotermes curvignathus Holmgren

“…The n-hexane fraction was subjected to column chromatography to afford yellow oil. Based on 1 H-NMR and 13 C-NMR data (Table 2) and compared to published data, the isolate was in agreement with β-asarone (Park et al, 2011).…”

Qualitative and quantitative analysis of the major constituents in Acorus tatarinowii Schott by HPLC/ESI‐QTOF‐MS/MS

“…Fourteen reference standards of tatarinoids B, tatarinoids A, α ‐asarone, β ‐asarone, 1‐(2,4,5‐trimethoxyphenyl)propan‐1,2‐dione, veraguensin, diasarone I, polysphorin, ( E )‐3‐(2,4,5‐trimethoxyphenyl)acrylaldehyde, tatarine A, asaronaldehyde, 1,3‐dim ethoxy‐2‐[1‐methyl‐2‐(3,4,5‐trimethoxyphenyl)‐ethoxy]‐5‐(1‐propenyl‐1‐yl)‐benzene, 2S‐(2,6‐dimethoxy‐4‐propenyl‐phenoxy)‐1‐(3,4,5‐trimethoxy‐phenyl)‐propane‐1‐one and 2,3,3a,7,8,8a‐hexahydro‐3a‐hydroxy‐1,4‐dimethyl‐7‐(1‐methylethylidene)‐6(1 H )‐azulenone were isolated and purified as described previously. Their chemical structures were unambiguously confirmed by comparing their 1 H NMR, 13 C NMR and MS data with literature precedents (Tong et al ., , ; Park et al ., ; Sebastiao et al ., ; Nawamaki and Kuroyanagi, ). Acetonitrile, methanol and formic acid were purchased from Dikma Company (Dikma, USA).…”

Selective methylation of kaempferol via benzylation and deacetylation of kaempferol acetates

“…Among them, methylated derivatives of kaempferol have attracted attention for a long time due to their broad spectrum of biological activities, including induction of apoptosis in adipocytes, anti-inflammation and anti-atherogenic properties [6–7]. 3- O -Methylkaempferol evidently possesses antiviral [8], antimicrobial [9] and cytotoxic [10] activities. 7- O -Methylkaempferol (rhamnocitrin) shows a very strong inhibition against platelet aggregation induced by sodium arachidonate [11], and antibacterial [12], anti-atherogenic [13], anti-inflammatory and antispasmodic activities [14].…”