Dibenzocyclooctadiene Lignans from Schisandra wilsoniana and Their Anti-HIV-1 Activities

Abstract

Twelve new dibenzocyclooctadiene lignans, marlignans A-L (1-12), together with 16 known compounds, were isolated from the leaves and stems of Schisandra wilsoniana. The structures of 1-12 were elucidated by spectroscopic methods including 1D- and 2D-NMR techniques. Compounds 1-12 were evaluated for their anti-HIV activities, of which compounds 3, 6, 8, and 12 showed modest activities with therapeutic index values of 13.2, 15.6, 17.6, and 16.4, respectively.

Leaves of Eugenia brasiliensis Used as a Folk Medicine Contain Cyclooxygenase Enzyme and Lipid Peroxidation Inhibitory Compounds

“…The NOESY-1D experiment evidenced interactions of H-9 with H-9', and of H-9' with H-9 and H-2'. These results were consistent with a twist boat/chair conformation having C-8 (S) and C-8' (R) absolute configurations[19].The 13 C NMR and DEPT experiments showed signals for 12 aromatic carbons [δ C 148.5 (C-3'), 147.4 (C-3), 145.3 (C-4), 145.0 (C-4'), 135.5 (C-6 and C-6'), 134.4 (C-1'), 130.2 (C-1), 117.3 (C-5), 117.0 (C-5'), 116.5 (C-2'), 113.3 (C-2)], two methylenes [δ C 39.7 (C-7'), 36.0 (C-7)], two methyne groups [δ C 41.8 (C-8), 34.9 (C-8')], two methoxyls [δ C 56.6 (OCH 3 -3'), 56.5 (OCH 3 -3)] and two methyl groups [δ C 22.0 (C-9), 12.7 (C-9')] in the molecule.…”

“…Preliminary TLC of water and methanolic extracts showed similar profiles. Based on literature data [19], signals for methoxy groups at δ C 55-56, indicated their position at C-3 and C-3', whereas signals for methoxy groups at δ C 60.6, suggested their position at C-4, C-4', C-5, or C-5' in its structure. Therefore, the observed signals at δ C 56.5 and 56.6 were assigned to two methoxy groups at C-3 and C-3' [19].…”

A New Dibenzocyclooctadiene Lignan from the Stems of Schisandra neglecta and It Cytotoxicities

“…C28H34O10 by HRESIMS {m/z 553.2058 [M+Na] + (calcd 553.2050)}. The 1 H and 13 C NMR spectra of 1 indicated the presence of 12 aromatic carbons, two aromatic protons, one methylenedioxy group and three methoxyl groups, suggesting the presence of a biphenyl moiety 9 . HMBC correlations of H-11 (δH 6.85, s) with C-9 (δC 36.8, t), C-10 (δC 137.6, s) and C-15 (δC 122.3, s) and of H-4 (δH 7.28, s) with C-5 (δC 133.8, s), C-6 (δC 87.6, s) and C-16 (δC 123.9, s), together with 1 H-1 H COSY correlations of H-9/H-8/H-17 ( Fig.…”

Dibenzocyclooctadiene lignans from the fruits of Schisandra rubriflora and their anti-HIV-1 activities

“…The EtOAc portion (52 g) was subjected to column chromatography on silica gel, Sephadex LH-20, RP-18, and preparative HPLC to afford compounds 1 -19, including two new lignans named rubrilignans A and B (1, 2), together with 17 known lignans, marlignans G (3) [11], schisandrin A (4) [2], gomisin J (5) [2], wilsonilignan C (6) [12], rubschizantherin (7) [13], isogomisin O (8) [2], gomisin N (9) [2], gomisin S (10) [14], benzoylgomisin Q (11) [15], angeloygomisin Q (12) [2], gomisin Q (13) [2], gomisin C (14) [16], gomisin B (15) [16], marlignan L (16) [11], gomisin T (17) [14] schizandrin (18) [17], and (þ )-gomisin K (19) [2]. The structures of the compounds 1 -19 were shown in Figure 1, and 13 C-NMR spectroscopic data of 1 and 2 are listed in Table 1.…”