Beilschamide, a New Amide, and Cytotoxic Constituents of Beilschmiedia erythrophloia

Abstract

A new amide, beilschamide (1), has been isolated from the stem of Beilschmiedia erythrophloia, together with seven known compounds, N-trans-feruloyltyramine (2), N-trans-feruloyloctopamine (3), vanillin (4), D-tocopheryl quinone (5), E-sitostenone (6), E-sitosterol (7), and 6D-hydroxystigmast-4-en-3-one (8). The structure of the new compound 1 was determined through spectroscopic and MS analyses. N-trans-Feruloyloctopamine (3) and beilschamide (1) exhibited cytotoxic effects with IC 50 values of 10.3 and 21.2 Pg/mL, respectively, against CCRF-CEM cell line. Beilschmiedia erythrophloia Hay. (Lauraceae) is an evergreen tree, distributed throughout South Mainland China, Hainan Island, the Ryukyus, and Taiwan [1]. Alkaloids [2, 3], flavonoids [4], endiandric acids [5-7], lignans [8, 9], benzenoids [7, 8], steroids [6-9], triterpenoids [7,9], fatty acid esters [7,9], and their derivatives are widely distributed in plants of the genus Beilschmiedia. Many of these compounds exhibit diverse biological activities, including cytotoxic [8] and antitubercular [7,9] activities. In a preliminary screening, the methanolic extract of the root of this species showed cytotoxic activities in vitro. The current phytochemical investigation of the stem of this plant has led to the isolation of a new amide, beilschamide (1), along with seven known compounds. The structural elucidation of 1 and its cytotoxic property are described herein.Extensive fractionation of the EtOAc-soluble portion of a MeOH extract of leaves of Beilschmiedia erythrophloia using silica gel column chromatography (CC), MPLC, and preparative TLC afforded compounds 1-8.Compound 1 was isolated as a yellowish amorphous powder. The HR-ESI-MS gave an [M + Na] + ion at m/z 380.1470 (calcd for C 20 H 23 NO 5 Na, 380.1474), consistent with a molecular formula of C 20 H 23 NO 5 . IR absorptions for NH, OH (3355, 3265 cm -1 ), and carbonyl (1652 cm -1 ) functions were observed. The signals of the 1 H and 13 C NMR spectra of 1 were assigned to a 3,4-dimethoxyphenyl, a 4-hydroxyphenyl, a conjugated double bond, a methoxy, an oxymethine, and a methylene. Comparison of the 1 H and 13 C NMR data of 1 with those of 3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)-2-methoxyethyl]acrylamide [10] suggested that their structures were closely related, except for the 3,4-dimethoxyphenyl group [G H 3.87 (6H, s, 3, 4-OMe), 6.96 (1H, d, J = 8.5 Hz, H-5), 7.13 (1H, dd, J = 8.5, 2.0 Hz, H-6), 7.16 (1H, d, J = 2.0 Hz, H-2); at C-7 of 1 replacing the 4-hydroxy-3-methoxyphenyl group of 3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)-2-methoxyethyl]acrylamide [10].

Endiandric Acid Derivatives and Other Constituents of Plants from the Genera Beilschmiedia and Endiandra (Lauraceae)

“…Additionally, a cyclostachine acid derivative obscurine ( 108 ) was isolated from the stem of B. obscura [ 28 ]. From the stem bark of B. erythrophloia three amides, N - trans -feryoltyramine ( 109 ), N - trans -feryoloctopamine ( 110 ) and beilschamide ( 111 ), were isolated [ 69 ]. …”

“…Some of these compounds are benzaldehyde derivatives such as vanillin ( 160 ), p -hydroxybenzaldehyde ( 161 ), 3,4,5-trimethoxybenzaldehyde ( 162 ), isolated from the root and stem of B. tsangii [ 22 , 23 , 25 ]. Vanillin ( 160 ) was also isolated from the stem bark of B. erythrophloia [ 69 ]. Sarisan ( 163 ), an insect repelling allyl benzenoid, was isolated from the leaves of B. miersii [ 27 , 50 ].…”

“…Its methylated derivative, oligandrol methyl ether ( 165 ), was obtained from the root of B. erythrophloia together with the benzenoids farnesylol ( 166 ) and α-tocopheryl quinone ( 167 ) [ 41 , 49 ]. Compound 167 was also isolated from the stem of B. tsangii and B. erythrophloia [ 25 , 69 ]. Another benzopyran derivative, α-tocopherol ( 168 ), was isolated from the roots of B. tsangii .…”

“…Other amides N - trans -feryoloctopamine ( 110 ) and beilschamide ( 111 ) isolated from the stem of B. erythrophloia exhibited cytotoxic effects in vitro . They were active against CCRF-CEM (human lymphoblastic leukemia) cell line with IC 50 values of 10.3 and 21.2 μg/mL, respectively [ 69 ].…”

Metabolites Identification of Bioactive Compounds Daturataturin A, Daturametelin I, N-Trans-Feruloyltyramine, and Cannabisin F From the Seeds of Datura metel in Rats

“…N -trans-feruloyltyramine could strongly suppress mRNA expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) via suppression of AP-1 and the JNK signaling pathway ( Jiang et al, 2015 ). Meanwhile, N -trans-feruloyltyramine exhibited the strongest DPPH radical-scavenging activity and cytotoxic effects against CCRF-CEM cell line with IC 50 values of 10.3 μg/mL ( Chen et al, 2015 ; Tu et al, 2016 ). Moreover, cannabisin F could successfully inhibit both ErbB1 and ErbB2, exhibiting better MolDock score than other selected inhibitors ( Hu et al, 2016 ).…”