Components of the heartwood of Populus euphratica from an ancient tomb

Abstract

To probe the organic constituents of over 2000-year-preserved Populus euphratica found in an ancient tomb, a chemical investigation was undertaken, which led to the isolation of a new compound, 2-(4′-hydroxy-3′methoxyphenyl)-2-oxoacetamide (1), together with 12 known compounds (2-13) by column chromatography. Their structures were elucidated on the basis of spectroscopic evidence. It is the first time that compounds 2-13 were isolated from this plant.Key words: Populus euphratica, 2-(4′-hydroxy-3′-methoxyphenyl)-2-oxoacetamide.Populus euphratica is a salt tolerant tree species, which belongs to the family of Salicaceae and is mainly distributed in the desert regions in northwest China [1]. This plant is the only large tree species that can survive and develop into forest in these arid and saline-alkali areas. Glucosides and topolins from this genus have been reported previously [2, 3]. Some wood of P. euphratica was found in an ancient tomb belived to be over 2000 years old in the desert of Xinjiang Province, China, raising questions about its phytochemical constituents. The chemical study on long-term preserved plants showed the presence of natural constituents [4][5][6][7][8][9]. To explore the organic constituents of over 2000-year-preserved P. euphratica, we undertook the chemical investigation of this plant. This paper describes the isolation and elucidation of 13 compounds, including one new compound (1) and twelve known compounds (2-13).3: R 1 = COCH 2 CH 2 OH, R 2 = H; 5: R 1 = CHO, R 2 = H 6: R 1 = COCH 3 , R 2 = H; 7: R 1 = CH=CHCHO, R 2 = H 8: R 1 = CH=CHCHO, R 2 = OCH 3 9: R 1 = CHO, R 2 = OCH 3 Compound 1 was obtained as a yellow amorphous powder, with a melting point of 105-107°C, and its molecular formula C 9 H 9 NO 4 with an unsaturation degree of n = 6 was determined from the quasi-molecular ion peak at m/z 195 in its EI mass spectrum and the 13 C NMR (DEPT) spectrum, which was supported by its HR-ESI observed at m/z 218.0429 (calculated 218.0429, [M+Na] + ). The IR spectrum of compound 1 showed broad absorptions at 3418 and 3159 cm -1 , suggesting the presence of an amide group and a hydroxyl group.

Genome-wide analysis of salt-responsive and novel microRNAs in Populus euphratica by deep sequencing

“…A great majority of P. euphratica are grown in China, and 90% of these are distributed in the Tarim River Basin in Xinjiang Province [28]. P. euphratica has a high tolerance for salinity, drought, cold, and wind, which makes it one of the only tree species in the Taklimakan Desert [29].…”

Bioconstituents from stems of Synsepalum dulcificum Daniell (Sapotaceae) inhibit human melanoma proliferation, reduce mushroom tyrosinase activity and have antioxidant properties

“…The chemical constituents in the stems of S. dulcificum were separated with column chromatography. Thirteen compounds, including dihydro-feruloyl-5-methoxytyramine (1), (+)-syringaresinol (2), (+)-epi-syringaresinol (3) (Chen et al, 1998a,b), 4-acetonyl-3,5-dimethoxy-p-quinol (4) (Luo et al, 2008), cis-p-coumaric acid (5) (Kort et al, 1996), trans-p-coumaric acid (6), p-hydroxybenzoic acid (7) (Hsieh et al, 2003), syringic acid (8), vanillic acid (9) (Chen et al, 1999), veratric acid (10), N-cis-feruloyltyramine (11), N-trans-feruloyltyramine (12) (Lo et al, 2004) and N-ciscaffeoyltyramine (13) (Chen et al, 1998a,b) were isolated from the methanolic extract. Among them, 1 was a new compound; 2-6, 10 and 13 were isolated for the first time from this plant.…”

Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins

“…The resins secreted by the tree, known by the elegant name “the tears of poplar,” have been used to treat tuberculous adenitis, throat, and duodenal ulcer swelling in China [2]. Previous studies revealed the presence of salicin derivatives, volatile oils, and phenolics in the resins of P. euphratica [3,4]. In recent years, we have become interested in chemical investigations of medicinal plant resins.…”