Drimane-Type Sesquiterpenes fromPolygonum hydropiper

Abstract

One new drimane-type sesquiterpenoid, 3 β-angeloyloxy-7-epifutronolide (1), and one new natural product, polygonumate (2), along with six known drimane-type sesquiterpenes [dendocarbin L (3), (+) winterin (4), (+) fuegin (5), changweikangic acid A (6), futronolide (7), and 7-ketoisodrimenin (8)] were isolated from the whole plant of Polygonum hydropiper Linn. Their structures were determined using spectroscopic techniques. Single-crystal X-ray diffraction study on dendocarbin L (3) and ¹³C-NMR spectroscopic data of (+) winterin (4) are described for the first time. Compound 6 was evaluated for inhibitions of α-chymotrypsin, acetylcholinesterase, and butyrylcholinesterase enzymes.

In vitro and in vivo anti-inflammatory activities of Polygonum hydropiper methanol extract

“…Many anti-oxidative flavonoids, sesquiterpenoids, and coumarin compounds, including 7,4 -dimethylquercetin, 3 -methylquercetin, quercetin, isoquercitrin, polygodial, warburganal, hydropiperoside, rhamnazin, and persicarin are constituents of Polygonum hydropiper (Horhammer and Rao, 1954;Kiem et al, 2008;Yang et al, 2011;Sultana et al, 2011). Of these compounds, quercetin has already been reported as a strong anti-inflammatory drug with Syk and Src inhibitory activities (Lee et al, 2008).…”

Ethnobotanical, Phytochemical, Pharmacological, and Toxicological Aspects of Persicaria hydropiper (L.) Delarbre

“…Various extracts and fractions of P. hydropiper whole plant and herbs were found to contain flavonoids, such as (+)-catechin, (−)-epicatechin, hyperin, isoquercitrin (Figure 1), isorhamnetin (Figure 1), kaempferol, quercetin (Figure 1), quercitrin, rhamnazin and rutin [39–41]; drimane-typed sesquiterpenes, such as 3- β -angeloyloxy-7-epifutronolide, 7-ketoisodrimenin, changweikangic acid A, dendocarbin L, (+)-fuegin, futronolide, polygonumate, and (+)-winterin [42]; phenylpropanoid esters, including hydropiperosides A and B (Figure 1), and vanicosides A (Figure 1), B and E [43]; as well as phenolic acids, such as caffeic acid, chlorogenic acid and ρ -coumaric acid [41]. …”

“…However, the methanol extract, fractions (hexane, dichloromethane, ethyl acetate, butanol, and aqueous) and changweikangic acid A did not exhibit anticholinesterase activity [17, 42]. …”

Terpenoids, Flavonoids and Acetogenins from Some Malagasy Plants

“…General procedure: Optical rotations were measured on a Jasco P-1030 polarimeter (sol. CHCl 3 ), IR spectra on a Shimadzu FTIR 8400S infrared spectrophotometer, and 1 H-and 13…”

“…Reinvestigation of the Et 2 O extract of Cinnamosma fragrans resulted in the isolation of a new drimane sesquiterpenoid, norcinnafragranolide (1), by chromatography on silica gel, Sephadex LH-20, MPLC and prep. HPLC, along with four known sesquiterpenoids, 6,7-epoxy-2,9-humuladiene (2) [11], 9,10-epoxy-2,6-humuladiene (3) [12], (+)-fuegin (4) [13], albicanyl acetate (5) [14], and an aromatic compound -tocotrienol (6) [15], and the identification of volatile mono-and sesquiterpenes; -pinene, limonene, -terpinene, terpinolene, alloaromadendrene, -gurjunene, ledene, -caryophyllene, -caryophyllene, ylangene, -copaene, -cadinene, cadalene, -muurolene, -muurolene, epi-zonarene, -cubebene, -cubebene, -selinene-selinene, -selineneguaiene, -guaiene and -bulnesene by GC-MS analysis. Analysis of 1 H/ 1 H COSY, HMQC, HMBC and NOESY spectra and comparison of their spectral data and signs and values of optical rotation with those of reference and authentic samples determined the structures of 2 -6.…”