A new carbamic acid from Dryopteris wallichiana

Abstract

The genus Dryopteris, belonging to the Dryopteridaceae family, is a cosmopolitan genus comprising approximately 450 species, mostly occurring in temperate forests and mountainous areas of the tropics. China has more than 300 species distributed across the country, 21 of which can be used for medicine [1]. Many constituents, including sesquiterpenes, phloroglucins, phenolic glycosides, and sitosterols have been isolated from D. crassirhizoma, D. parallelogramma, D. patula, D. hawaiiensis, D. fuscoatra, D. fragrans, D. abbreviate, D. polylepis, and D. dickinssi [2-8]. Phloroglucins are characteristic constituents of Dryopteris plants and are of interest to many pharmaceutical scholars due to multiple physiological activities such as antivirus, antitumor, antibacterial, and anti-inflammatory effects [9][10][11][12]. To the best of our knowledge, there is no research on the chemical constituents of D. wallichiana.In the present study, D. wallichiana growing in Xishuangbanna of Yunnan Province was examined. Samples of the aerial parts of D. wallichiana were collected in May 2006, and a voucher specimen was kept at the Herbarium of the Institute of Natural Products, Henan University. The dried aerial parts of D. wallichiana (3.5 kg) were extracted with ethanol (95%) at room temperature. After evaporation of the ethanol, the residue was suspended in water and extracted with petroleum ether, chloroform, and n-butanol. The n-butanol extract (120 g) was subjected to silica gel column chromatography (200-300 mesh, Qingdao Marine Chemical Inc, China) using chloroform-methanol mixtures (I r =10:1 to 8:2) and divided into three fractions by TLC detection. Fraction 1 was subjected repeatedly to column chromatography over silica gel (10-40 P Qingdao Marine Chemical Inc, China), eluting with chloroform-methanol (I r = 10:1) to afford (1,7a-dihydro-1H-inden-2(7aH)-ylidene) methylcarbamic acid (1, 26.2 mg) and 3,7,11,15-tetramethyl-2-hexadecen-1-ol (4, 11.2 mg). Fraction 2 was chromatographed on Sephadex LH-20 using methanol as eluent and then subjected to C-18 eluting with methanol-water (I r = 7:3) to afford 12-ursen-28-oic acid-3-O-E-D-glucopyranoside (2, 19.4 mg) and 12-ursen-3-O-E-D-glucopyranoside (3, 28 mg). Compound 1 was a new compound, and 2 and 3 were isolated and identified from the genus for the first time.Identification of the isolated compounds was performed by comparison of the physical constants and spectral data with those of known compounds [13][14]. Compound 1, obtained as white needles, had the molecular formula C 11 H 13 NO 2 , as deduced from the molecular-ion peak at m/z 192.1034 [M + H] + (calcd 192.1024) in the HR-EI-MS and from 13 C NMR and DEPT analyses. The 13 C NMR spectrum revealed 11 carbon signals that were sorted by DEPT experiments into a carbonyl group (G 172.3), five olefinic methine groups (G 134.3, 126.9 u 2 and 125.3 u 2), an olefinic quaternary carbon atom (G 126.0), two methylene groups (G 49.1 and 45.2), and two methine groups (G 47.0 and 45.2). The signals of two methine protons [G 1.16...

Antibacterial and cytotoxic activities of new sphingolipids and other constituents isolated from Cissus incisa leaves

“…Phytochemical investigation of CHCl 3 /MeOH extract of C. incisa resulted in the isolation of a new ceramide (1) , new cerebrosides within the genus (5) , of which (5-IV) and (5-V) are reported for the first time, and three known compounds: 2,3-dihydroxypropyl tetracosanoate (2) ( Hernández-Galicia et al., 2007 ), β -sitosterol-D-glucopyranoside (3) ( Njinga et al., 2016 ), and α -amyrin-3- O - β -D-glucopyranoside (4) ( Kang et al., 2011 ) ( Figure 2 ). These compounds were identified by their spectroscopic data and by comparing with those reported above, as well that their acetylated derivates ( Peshin and Kar, 2017 ).…”

Chemical Constituents of <i>Saxifraga umbellulata</i>

“…Compound 3 was isolated as the yellow powder, ESI-MS(m/z): 296(100)[M] + , 1 H-NMR (400MH Z , TMS, CDCl 3 ) δppm: 5.39 (1H, br.t, J=6.8Hz, 13.8Hz, H-2), 4.07 (2H, d, J=6.8Hz, H-1), 1.97 (2H, t, J=6.8Hz, H-4), 1.70 (3H, br.s, H-20), 0.87 (6H, d, J=6.4Hz, H-16, 17), 0.85 (3H, d, J=6.4Hz, H-18), 0.84 (3H, d, J=6.8Hz, H-19), 13 C-NMR (100MH Z , TMS, CDCl 3 ) δppm: 116.7 (C-1), 145.1 (C-2), 73.8 (C-3), 40.1 (C-4), 22.5 (C-5), 31.9 (C-7), 19.6 (C-7a, 11a), 36.7 (C-8), 32.1 (C-11), 36.5 (C-12), 24.1 (C-13), 39.5 (C-14), 29.03 (C-15), 22.4 (C-15a), 22.5 (C-16). All 1 H and 13 C NMR datas suggested that compound 3 was 3, 7, 11, 15-tetramethyl-2-hexadecen-1-ol[4]. Compound 4 was isolated as the white crystal, ESI-MS(m/z): 197[M+H]…”