The stems of Cinnamomum reticulatum Hay (Lauraceae) were extracted with hexane and chloroform successively. A series of new esters, including a mixture of 4-hydroxy-3-methoxyphenethyl derivatives, along with two butanolides, isoobtusilactone A and obtusilactone A, two amides, N-trans-feruloylmethoxytyramine and N-cis-feruloyl-methoxytyramine, three benzenoids, p-hydroxybenzoic acid, syringic acid and vanillic acid, one lignan, (+)-syringaresinol and one steroid, beta-sitostenone, were isolated. The structures of the new esters were elucidated by chemical and physical evidence.
trans-methyl p-coumarate (7), and p-dihydrocoumaric acid (8), and two amides, N-trans-feruloyltyramine (9) and dihydroferuloyltyramine (10), were isolated from the leaves of Cinnamomum reticulatum Hayata (Lauraceae). These compounds were characterized and identified by physical and spectral evidence.The Cinnamomum species (Lauraceae) have been used in folk medicine for its sweating, antipyretic, and analgesic effects [1]. There are only two papers describing the constituents of leaves of Cinnamomum reticulatum Hayata [1,2]. In the course of screening for biologically and chemically novel agents from Formosan Lauraceous plants [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17], C. reticulatum was chosen for further phytochemical investigation. The H 2 O extract of its leaves was subjected to solvent partitioning and chromatographic separation to afford seven pure substances. The chemical constituents in the leaves of C. reticulatum were separated with column chromatography.Investigation of the MeOH extract of the leaves has led to the isolation of ten compounds, one new butanolide: isoreticulide ((4R,3E)-4-hydroxy-5-methylene-3-octadecylidenedihydrofuran-2-one) (1); one sesquiterpenoid: (3-methoxy-5H-9,11-dioxabenzo[3,4]cyclohepta[1,2-f])inden-7-yl)-methanol (2); six benzenoids: p-hydroxybenzoic acid (3) [18], p-hydroxybenzaldehyde (4) [18], protocatechuic acid (5) [19], ferulic acid (6) [18], trans-methyl p-coumarate (7) [18], and p-dihydrocoumaric acid (8) [18]; and two amides: N-trans-feruloyltyramine (9) [20] and dihydroferuloyltyramine (10) [21]. These compounds were obtained and characterized by comparison of their physical and spectral data (UV, IR, NMR, and MS) with values obtained in the literature. In addition to 3 and 4, all of these compounds were found for the first time from this plant. In this paper, we report the isolation and structural elucidation of butanolide 1 and sesquiterpenoid 2.Isoreticulide (1) was isolated as a pale yellowish liquid. Its molecular formula, C 23 H 40 O 3 , was established by HR-ESI-MS. The UV absorption at 225 nm was similar to that of isoobtusilactone A [22], suggesting the presence of a E-hydroxy-J-methylene-D,E-unsaturated-J-lactone unit [23]. The IR spectrum showed absorption bands of a hydroxyl group at 3440 cm -1 , and an D,E-unsaturated J-lactone moiety at 1770 and 1670 cm -1 . The 1 H NMR spectrum of 1 was similar to that of isoobtusilactone A [22], indicating that 1 has the same E-hydroxy-J-methylene-D,E-unsaturated-J-lactone skeleton and the same E geometry of the trisubstituted double bond. The presence of a broad singlet at G 1.26 was attributed to protons in an aliphatic chain in 1. The exocyclic olefinic protons appeared at G 4.73, 4.96 and one hydroxymethine proton was located at G 5.27. Compound 1 is dextrorotatory, that indicates an R configuration at C-4 [24]. Thus, the structure of isoreticulide is (4R,3E)-4-hydroxy-5-methylene-3-octadecylidenedihydrofuran-2-one, as represented in 1.
This study aims to establish a HPLC method for the simultaneous determination of hesperidin (HE), ferulic acid (FA), cinnamic acid (CA) and cinnamaldehyde (CAD) in a Chinese tonic wine, Ma-Zu-WanShow-Yao-Jyo. After filtering the tonic wine, the filtrate was separated on a C18 column (250´4.6 mm, 5 mm) by gradient elution of acetonitrile-aqueous solution. The regression equations were linear (r ³ 0.9999) in the range of 1.5-150.0 mg/mL for HE, 0.3-60.0 mg/mL for FA, 0.06-6.0 mg/mL for CA, and 0.1-80.0 mg/mL for CAD. The relative standard deviation and relative error were less than 5.0% and 4.0%, respectively, for intra-and inter-day analyses. The limits of detection (LOD) were 0.6, 0.075, 0.012 and 0.02 mg/mL for HE, FA, CA and CAD (S/N = 3, 20 ml injection) respectively. This method can be used to standardize the quality control of Chinese tonic wine to ensure accuracy and efficiency in the future.
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