Abstract
The title limonoid compound, C26H28O5·0.5H2O (TS3) [systematic name: (3aS,3bS,4aS,5aS,6S,7aR,8aR,8bS,11aR)-6-(furan-3-yl)-3a,5a,8b,11a-tetra-methyl-3a,4a,5,5a,6,7,7a,8b,11,11a-deca-hydro-oxireno[2',3':4b,5]oxireno[2'',3'':2',3']cyclo-penta-[1',2':7,8]phenanthro[10,1-bc]furan-3(3aH)-one hemihydrate], crystallizes with two independent mol-ecules (1 and 2) in the asymmetric unit and one water mol-ecule. TS3 is composed of three six-membered rings (A, C and D), three five-membered rings (B, E and F) and two epoxide rings. A group of five fused rings (A-E) is bonded to a furan ring (F) with a Csp3-Csp2 bond [1.500 (3) Å in mol-ecule 1 and 1.499 (3) Å in mol-ecule 2]. The absolute structures of the mol-ecules in the crystal were determined by resonant scattering; Flack parameter = 0.05 (5). In the crystal, the individual mol-ecules stack in columns along the b-axis direction. The water mol-ecule bridges mol-ecules 1 and 2 via Owater-H⋯O and C-H⋯Owater hydrogen bonds. Together with further C-H⋯O hydrogen bonds, linking mol-ecules 1 and 2, the columns are linked to form slabs parallel to the ab plane. Within each column, mol-ecules are also linked via C-H⋯π inter-actions involving the five-membered furan (F) rings.
Highlights
Limonoids are a prominent class of secondary metabolites found in plants of the Meliaceae and Rutaceae families
Vilasinin is one of the limonoid classes, to which belongs the title compound (TS3), and all the compounds of the rubescin series have been isolated from Trichilia rubescens (Tontsa et al, 2013; Tsamo et al, 2016)
Among the broad spectrum of biological properties exhibited by vilasinin derivatives, TS3 has been found to induce apoptosis in human hepatoma cell lines, to interfere with NFkB signaling and to enhance cAMP-regulated chloride conductance of cells expressing CFTR
Summary
Limonoids are a prominent class of secondary metabolites found in plants of the Meliaceae and Rutaceae families. They are well known for their wide range of bioactive compounds that exhibit antiplasmodial, antiviral, antitumoral, antibacterial and cytotoxic properties (Krief et al, 2004; Lange et al, 2016). The six-membered rings A and D have envelope conformations with atoms C11/C11B and C16/C16B, respectively, as the flaps, being displaced from the mean plane of the other five atoms by 0.657 (2)/0.672 (2) Afor atoms C11/C11B and by 0.654 (2)/0.670 (2) Afor atoms C16/C16B. The fivemembered rings B and E have envelope conformations with atoms C4/C4B and C15/C15B, respectively, as the flaps, being displaced from the mean plane of the other four atoms by 0.689 (2)/0.702 (2) Aand 0.526 (2)/0.454 (2) A , respectively.
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