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Chemical Constituents from the Aerial Parts of Cyrtopodium Paniculatum

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Chemical Constituents from the Aerial Parts of Cyrtopodium Paniculatum molecules Article Chemical Constituents from the Aerial Parts of Cyrtopodium paniculatum Florence Auberon 1,*, Opeyemi Joshua Olatunji 1, Gaëtan Herbette 2, Diamondra Raminoson 1, Cyril Antheaume 3, Beatriz Soengas 4, Frédéric Bonté 4 and Annelise Lobstein 1 1 Laboratory of Pharmacognosy and Bioactive Natural Products, Faculty of Pharmacy, Strasbourg University, Illkirch-Graffenstaden 67400, France; [email protected] (O.J.O.); [email protected] (D.R.); [email protected] (A.L.) 2 Spectropôle, FR1739, Aix-Marseille University, Campus de St Jérôme-Service 511, Marseille 13397, France; [email protected] 3 LIVE group, New-Caledonia University, BP R4, Noumea Cedex 98851, New-Caledonia; [email protected] 4 LVMH Recherche, 185 avenue de Verdun, St Jean de Braye 45800, France; [email protected] (B.S.); [email protected] (F.B.) * Correspondence: fl[email protected]; Tel.: +33-679-129-963 Academic Editor: Marcello Iriti Received: 17 September 2016; Accepted: 19 October 2016; Published: 24 October 2016 Abstract: We report the first phytochemical study of the neotropical orchid Cyrtopodium paniculatum. Eight new compounds, including one phenanthrene 1, one 9,10-dihydro-phenanthrene 2, one hydroxybenzylphenanthrene 3, two biphenanthrenes 4–5, and three 9,10 dihydrophenanthrofurans 6–8, together with 28 known phenolic compounds, mostly stilbenoids, were isolated from the CH2Cl2 extract of its leaves and pseudobulbs. The structures of the new compounds were established on the basis of extensive spectroscopic methods. Keywords: Cyrtopodium paniculatum; Orchidaceae; stilbenoids; phenanthrenes derivatives; biphenanthrenes; dihydrophenanthrenofurans 1. Introduction The family Orchidaceae comprises 820 genera with almost 35,000 described species and can be regarded as the largest family of flowering plants. The phytochemical and biological investigations of this family has been mainly conducted in relation with their traditional uses and focused on a large number of Asian orchids from the genus Arundina, Bletilla, Dendrobium, Gastrodia and Pleione at the expense of the New World orchids In fact, the first report on a phytochemical study of South American orchids was in the late 1990s and was mainly focused on species in the genus Scaphyglottis [1–3], Maxillaria [4–7] and Cyrtopodium [8–10]. This genus Cyrtopodium includes 47 endemic species, distributed from Southern Florida to Central America, and they are terrestrial or epiphytic orchids, well recognized by their ovoid to fusiform pseudobulbs as well as their showy flowers [11–14]. To the best of our knowledge, only three Cyrtopodium species have been explored: C. cardiochilum Lindl. and C. andersonnii R.Br. for their polysaccharidic content, which displays anti-inflammatory and gastroprotective activities [8,10], and C. macrobulbon (La Llave & Lex.) G.A. Romero & Carnevali, a species traditionally used for treating urinary infections and whose stilbenoids are considered as its bioactive constituents [9]. C. paniculatum (Ruiz & Pav.) Garay has not yet received any attention since no report on its medicinal uses or chemical composition has been found in the literature. This provides a substantial basis for a detailed phytochemical investigation of this unexplored species. Therefore, in our continuing search for bioactive secondary metabolites from orchids [15–17], we carried out an investigation on Molecules 2016, 21, 1418; doi:10.3390/molecules21101418 www.mdpi.com/journal/molecules Molecules 2016, 21, 1418 2 of 18 the CH2Cl2 extracts from the leaves and pseudobulbs of C. paniculatum. This investigation led to the isolation of eight new compounds 1–8, together with 28 known compounds. In this paper, we describe Molecules 2016, 21, 1418 2 of 18 the structure elucidation of these new compounds, which was performed by means of NMR, HRESIMS data andCH2Cl CD2 extracts spectrum from determination. the leaves and pseudobulbs of C. paniculatum. This investigation led to the isolation of eight new compounds 1–8, together with 28 known compounds. In this paper, we 2. Resultsdescribe and the Discussionstructure elucidation of these new compounds, which was performed by means of NMR, HRESIMS data and CD spectrum determination. Structure Elucidation 2. Results and Discussion The pseudobulbs and the leaves from C. paniculatum were studied separately. The freshly cut pseudobulbsStructure Elucidation (7.5 kg) were ground and macerated in water to get rid of their sugar content, and then in ethanol to afford a crude extract (60 g). The alcoholic crude extract was suspended The pseudobulbs and the leaves from C. paniculatum were studied separately. The freshly cut in water and sequentially extracted with cyclohexane, CH Cl and n-BuOH. The CH Cl extract pseudobulbs (7.5 kg) were ground and macerated in water to 2get 2rid of their sugar content, and2 then2 was concentrated to dryness and subjected to silica gel column chromatography, Sephadex LH-20 in ethanol to afford a crude extract (60 g). The alcoholic crude extract was suspended in water and and preparative thin layer chromatography (PTLC) to afford eight new compounds 1–8 (Figure1) sequentially extracted with cyclohexane, CH2Cl2 and n-BuOH. The CH2Cl2 extract was concentrated togetherto dryness with 28 and previously subjected to described silica gel column compounds chromatography,9–35 which Sephadex were identified LH-20 and as preparativepara-ethoxybenzyl thin alcohollayer (9 )[chromatography18,19], 3,4,6-trimethoxyl-9,10-dihydrophenanthrene-2,7-diol (PTLC) to afford eight new compounds 1–8 (Figure (10)[ 201) ],together confusarin with ( 1128)[ 21], erianthridinpreviously (12 described)[22], para compounds-hydroxybenzaldehyde 9–35 which were identified (13)[18], as nudol para-ethoxybenzyl (14)[23], cephathrene-B alcohol (9) [18,19], (15)[ 24], gigantol3,4,6-trimethoxyl-9,10-dihydrophenanthrene-2,7-diol (16)[25], batatasin III (17)[26], ephemeranthoquinone (10) [20], confusarin (18 (11)[) [21],27], erianthridin coelonin ( 19(12)[) 28], 2,4-dimethoxy-phenanthrene-3,7-diol[22], para-hydroxybenzaldehyde (13) [18], (20)[ nudol29], (14 lusianthridin) [23], cephathrene-B (21)[ 30(15],) [24], densiflorol gigantol (16 B) ([25],22)[ 31], denthyrsininbatatasin (23III)[ 32(17],) bleformins[26], ephemeranthoquinone A (24) and B (25)[ 33(18],) chrysoeriol[27], coelonin (26)[ (3419,)35 [28],], vanillic 2,4-dimethoxy- alcool (27)[36], phenanthrene-3,7-diol (20) [29], lusianthridin (21) [30], densiflorol B (22) [31], denthyrsinin (23) [32], gastrodigenin (28)[37,38], 1-(4-hydroxybenzyl)-4-methoxyl-9,10-dihydrophenanthrene-2,7-diol bleformins A (24) and B (25) [33], chrysoeriol (26) [34,35], vanillic alcool (27) [36], gastrodigenin (28) (29)[39], shancidin (30)[40], blestriarenes A (32) and B (31)[41], velutin (33)[42], (+)-syringaresinol [37,38], 1-(4-hydroxybenzyl)-4-methoxyl-9,10-dihydrophenanthrene-2,7-diol (29) [39], shancidin (30) (34)[43[40],] and blestriarenes (+)-balanophonin A (32) and (35 B)[ (4431],) respectively,[41], velutin ( by33) comparison[42], (+)-syringaresinol of their UV, (34 MS,) [43] and and NMR (+)- data withbalanophonin literature data. (35) [44], respectively, by comparison of their UV, MS, and NMR data with literature Indata. parallel, the leaves (70 g) were ground, lyophilized and successively extracted by maceration with cyclohexane,In parallel, the CH leaves2Cl2 (70and g) nwere-BuOH. ground, The lyophilized CH2Cl2 andextract successively (1.23 g) extracted was fractionated by maceration using vacuumwith liquid cyclohexane, chromatography CH2Cl2 and (VLC)n-BuOH. and The semi-preparative CH2Cl2 extract (1.23 RP-HPLC g) was fractionated to affordgastrodigenin using vacuum (28), coeloninliquid (19 chromatography), ephemeranthoquinone (VLC) and semi-prepa (18), lusianthridinrative RP-HPLC (21), to 1-(4-hydroxybenzyl)-4-methoxyl-9,10- afford gastrodigenin (28), coelonin dihydrophenanthrene-2,7-diol(19), ephemeranthoquinone (29 )(18 and), translusianthridin-feruloyltyramine (21), 1-(4-hydroxybenzyl)-4-methoxyl-9,10- (36)[45]. dihydrophenanthrene-2,7-diol (29) and trans-feruloyltyramine (36) [45]. FigureFigure 1. Chemical 1. Chemical structures structures of of compounds compounds 11––88 fromfrom C.C. paniculatum paniculatum pseudobulbs.pseudobulbs. Molecules 2016, 21, 1418 3 of 18 Compound 1 was obtained as a brown amorphous powder and showed a [M + H]+ peak at m/z 331.1188 (calcd. for C18H19O6 331.1176) in the HRESIMS, indicating a molecular formula of C18H18O6 and suggesting the existence of ten degrees of unsaturation. The UV maximal absorptions at 216, 261, 281, 312 and 344 nm indicated the presence of a phenanthrene derivative [46–48]. The IR spectrum exhibited a broad peak at 3370 cm−1, characteristic of hydroxyl groups, and 1616, 1576, 953 and 860 cm−1, characteristic of aromatic rings. Comparison of the HRMS and the 1H-NMR data of 1 to those of cephathrene-B (15)[16] indicated substantial similarities between the two compounds, thus suggesting that compound 1 is structurally related to cephathrene-B. Extensive analysis of the 1D NMR of 1 (Table1) indicated the presence of two mutually ortho-coupled aromatic protons at δH 7.88 (1H, d, J = 8.9 Hz, H-10) and 7.50 (1H, d, J = 8.9 Hz, H-9), thus suggesting the presence of a tetra-substituted aromatic ring. Additional aromatic proton signals at δH 8.90 (1H, s, H-4) and 7.17 (1H, s, H-8) afforded two penta-substituted aromatic rings. Two hydroxyl signals at δH 7.91 (1H, s, 2-OH) and 8.39 (1H, s, 1 7-OH) were observed. Four methoxyl groups were presumed based on the H-NMR resonances at δH 3.99 (3H, s, 1-OCH3), 4.06 (3H, s, 3-OCH3), 4.03 (3H, s, 5-OCH3) and 4.02 (3H, s, 6-OCH3) and was 13 supported by the corresponding C-NMR signals at δC 61.1, 56.3, 60.5 and 61.4, respectively. HMBC correlations from 1-OCH3 to C-1, 3-OCH3 to C-3, 5-OCH3 to C-5 and 6-OCH3 to C-6 confirmed the position of the methoxyls assigned to C-1, C-3, C-5 and C-6 respectively. In the same way, the locations of the hydroxyl signals at δH 7.91 (1H, s, 2-OH) and 8.39 (1H, s, 7-OH) were positioned on C-2 and C-7 respectively, due to HMBC correlations from 2-OH to C-1, C-2 and C-3 and 7-OH with C-6, C-7, and C-8.
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