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New 30-Noroleanane Triterpenoid Saponins from Holboellia Coriacea Diels

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New 30-Noroleanane Triterpenoid Saponins from Holboellia Coriacea Diels molecules Article New 30-Noroleanane Triterpenoid Saponins from Holboellia coriacea Diels Wenbing Ding 1,2, Ye Li 1, Guanhua Li 1, Hualiang He 1, Zhiwen Li 1 and Youzhi Li 1,2,* 1 Hunan Provincial Engineering & Technology Research Center for Biopesticide and Formulation Processing, Hunan Agricultural University, Changsha 410128, China; [email protected] (W.D.); [email protected] (Y.L.); [email protected] (G.L.); [email protected] (H.H.); [email protected] (Z.L.) 2 Hunan Co-Innovation Center for Utilization of Botanical Functional Ingredients, Changsha 410128, China * Correspondence: [email protected]; Tel.: +86-731-8461-8163 Academic Editor: Derek J. McPhee Received: 10 May 2016; Accepted: 2 June 2016; Published: 4 June 2016 Abstract: Three new 30-noroleanane triterpenoid saponins, akebonoic acid 28-O-b-D-glucopyranosyl-(111Ñ61)-b-D-glucopyranosyl ester (1), akebonoic acid 28-O-(611-O-caffeoyl)- b-D-glucopyranosyl-(111Ñ61)-b-D-glucopyranosyl ester (Holboelliside A, 2) and 3b,20a,24-trihydroxy- 29-norolean-12-en-28-oic acid 3-O-(61-O-caffeoyl)-b-D-glucopyranoside (Holboelliside B, 3) were isolated from the stems of Holboellia coriacea Diels, together with five known compounds, eupteleasaponin VIII (4), 3a-akebonoic acid (5), quinatic acid (6), 3b-hydroxy-30-norhederagenin (7) and quinatoside A (8). The structures of these compounds were determined on the basis of spectral and chemical evidence. Compounds 1–5 were evaluated for their inhibitory activity against three human tumors HepG2, HCT116 and SGC-7901 cell lines in vitro. Keywords: Holboellia coriacea; nortriterpenoids; saponins; cytotoxicity 1. Introduction Holboellia coriacea Diels belonging to family Lardizabalaceae, is an evergreen woody vines mainly distributed in Qinling Mountain region of China at altitudes of 500–2000 m [1]. The fruit of H. coriacea, edible berries, can be used to wine, while the stems and roots of the plant have been used as Chinese folk medicine for treating arthritis and rheumatism paralysis [1,2]. To date there are very few reports about the chemical constituents of this species. Recently, a phytochemical study revealed six triterpenoid saponins, including two noroleanane-type ones from a methanol extract of root of H. coriacea [2]. Noroleanane triterpenoids are recognized as characteristic constituents of the family Lardizabalaceae, some of which were revealed to show significant bioactivities [3–5]. Our interest in the chemistry of noroleanane triterpenoids prompted us to continue the phytochemical study of H. coriacea, whereby three new 30-noroleanane triterpenoid saponins (1–3) and five known ones (4–8) were obtained from the stem of the plant. Herein, we report the isolation, structure elucidation, and cytotoxic activity of these compounds. 2. Results and Discussion The dried stems of H. coriacea were extracted using 95% aq. EtOH. The EtOH extract residue was suspended in water and then partitioned successively with petroleum ether and EtOAc. Column chromatography of the EtOAc-soluble fraction yielded three new triterpenoid saponins (1–3), which were identified by NMR techniques and HRESIMS, and five known compounds 4–8 that were identified as by comparison of their NMR and MS data with those reported in the literature as eupteleasaponin Molecules 2016, 21, 734; doi:10.3390/molecules21060734 www.mdpi.com/journal/molecules Molecules 2016, 21, 734 2 of 8 VIII (4)[6], 3α-akebonoic acid (5)[7], quinatic acid (6)[8], 3b-hydroxy-30-norhederagenin (7)[9] and quinatosideMolecules 2016 A (8, 21)[, 10734] (Figure1). 2 of 8 Figure 1. Structures of compounds 1–8 isolated from H. coriacea, as well as structures of 1a and 3a Figure 1. Structures of compounds 1–8 isolated from H. coriacea, as well as structures of 1a and 3a mentioned in the text. mentioned in the text. 2.1. Identification of New Compounds 2.1. Identification of New Compounds Compound 1 was obtained as white solid powder (MeOH). The positive HR-ESIMS of 1 showed Compoundan [M + Na]+ 1at wasm/z 787.4248, obtained which, as white taken solidtogether powder with the (MeOH). 13C-NMR Thedata positiveanalysis, indicated HR-ESIMS the of 1 showedmolecular an [M formula + Na] C+ 41atH64m/zO13. 787.4248,The 13C-NMR which, spectrum taken displayed together 41 signals, with the of which13C-NMR 12 carbons data were analysis, assignable to sugar moieties and 29 carbons to13 the aglycone moiety (Table 1). On the basis of indicated the molecular formula C41H64O13. The C-NMR spectrum displayed 41 signals, of which 13 12 carbonsC-NMR were and DEPT assignable spectra, to the sugar carbons moieties for the aglycone and 29 were carbons identified to the as five aglycone methyls, moiety four olefinic (Table 1). carbons, an oxy-methine carbon, a carbonyl carbon, 10 methylenes, three methines, and five On the basis of 13C-NMR and DEPT spectra, the carbons for the aglycone were identified as five quaternary carbons. The HSQC spectrum of 1 displayed corresponding five angular methyl groups methyls, four olefinic carbons, an oxy-methine carbon, a carbonyl carbon, 10 methylenes, three (δH 0.94 (s, 3H); 1.02 (s, 3H); 1.12 (s, 3H); 1.20 (s, 3H); 1.22 (s, 3H)), a broad singlet olefinic proton at methines, and five quaternary carbons. The HSQC spectrum of 1 displayed corresponding five δH 5.45, and two exo-methylene protons at δH 4.65 (s) and 4.71 (s). These NMR data suggested that angularthe structure methyl groups of 1 should (δH be0.94 a noroleanane (s, 3H); 1.02 triterpenoid (s, 3H); 1.12 saponin (s, 3H); [4]. 1.20After (s, comparison 3H); 1.22 of (s, the 3H)), 1H and a broad singlet13C-NMR olefinic data proton with those at δH of5.45, closely and related two exo-methyleneanalogues, the aglycone protons was at characterizedδH 4.65 (s) and as 3β 4.71-hydroxy- (s). These NMR30-norolean-12,20(29)-dien-28-oic data suggested that the structure acid of(akebonoic1 should acid) be a [7], noroleanane a common triterpene triterpenoid aglycon saponin occurring [4]. After comparisonin the genera of the of1 HLardizabalaceae. and 13C-NMR The data β-orientation with those of of the closely hydroxyl related group analogues, at C-3 was theconfirmed aglycone by was characterizedan NOE correlation as 3b-hydroxy-30-norolean-12,20(29)-dien-28-oic of H-3 with Hα-5 (Figure S7) and the proton acid spin-coupling (akebonoic constant acid) [of7], H-3 a common (δH 1 13 triterpene3.44 (dd, aglycon J = 9.9, occurring 5.6 Hz)). In in addition, the genera the H of and Lardizabalaceae. C-NMR spectra The exhibitedb-orientation two anomeric of the proton hydroxyl signals at δH 6.21 (d, J = 8.0 Hz) and 5.00 (d, J = 7.7 Hz), as well as twelve carbon signals at δC 95.2 (glc- group at C-3 was confirmed by an NOE correlation of H-3 with Hα-5 (Figure S7) and the proton 1′), 73.3 (glc-2′), 78.1 (glc-3′), 70.4 (glc-4′), 77.3 (glc-5′), 69.0 (glc-6′), 104.8 (glc-1′′), 74.6 (glc-2′′), 77.8 spin-coupling constant of H-3 (δ 3.44 (dd, J = 9.9, 5.6 Hz)). In addition, the 1H and 13C-NMR (glc-3′′), 71.0 (glc-4′′), 77.9 (glc-5′′H), and 62.1 (glc-6′′), which correspond with that of published data for δ spectraa sugar exhibited moiety two of anomericβ-D-glucopyranosyl proton signals (1′′→6′ at) β-DH-glucopyranosyl6.21 (d, J = 8.0 [11]. Hz) andFurthermore, 5.00 (d, Jthe= 7.7sugar Hz), as 1 1 1 1 1 well asmoiety twelve was carbon found to signals be attached at δC to95.2 C-28 (glc-1 via an ),ester 73.3 linkage (glc-2 from), 78.1 correlations (glc-3 ), 70.4between (glc-4 H-1),′ ( 77.3δH 6.21) (glc-5 ), 1 11 11 11 11 11 11 69.0 (glc-6and carboxyl), 104.8 carborn (glc-1 (δ),C 74.6175.3) (glc-2 observed), 77.8 in the (glc-3 HMBC), 71.0spectrum (glc-4 (Figure), 77.9 S6). (glc-5 Based), upon and all 62.1 of (glc-6the ), whichabove correspond evidence, with the thatstructure of published of 1 was dataelucidated for a as sugar akebonoic moiety acid of b28--DO-glucopyranosyl-β-D-glucopyranosyl- (111Ñ61) b-D-glucopyranosyl(1′′→6′)-β-D-glucopyranosyl [11]. Furthermore, ester. the sugar moiety was found to be attached to C-28 via an 1 ester linkage from correlations between H-1 (δH 6.21) and carboxyl carborn (δC 175.3) observed in the HMBC spectrum (Figure S6). Based upon all of the above evidence, the structure of 1 was elucidated as akebonoic acid 28-O-b-D-glucopyranosyl-(111Ñ61)-b-D-glucopyranosyl ester. Molecules 2016, 21, 734 3 of 8 Table 1. NMR spectroscopic data for compound 1 in pyridine-d5. No. δc δH (mult., J in Hz) No. δc δH (mult., J in Hz) Ag-1 38.5 CH2 0.98 (m); 1.52 (m) 23 28.2 CH3 1.22 (s) 2 27.5 CH2 1.79–1.82 (m) 24 16.0 CH3 1.02 (s) 3 77.6 CH 3.44 (dd, 9.9, 5.6) 25 15.1 CH3 0.94 (s) 4 38.8 qC 26 17.0 CH3 1.12 (s) 5 55.3 CH 0.84 (d, 11.2) 27 25.5 CH3 1.20 (s) 6 18.3 CH2 1.36 (m); 1.51 (m) 28 175.3 qC 7 32.6 CH2 1.35 (m); 1.47 (m) 29 106.7 CH2 4.65 (s); 4.71 (s) 8 39.4 qC 9 47.6 CH 1.63 (dd, 9.7, 7.4) Glc-11 95.2 CH 6.21 (d, 8.0) 10 36.8 qC 21 73.3 CH 4.12 (m) 1 11 23.2 CH2 1.90 (m) 3 78.1 CH 4.19 (m) 12 122.9 CH 5.45 (br s) 41 70.4 CH 4.33 (m) 13 143.0 qC 51 77.3 CH 4.07 (m) 1 14 41.5 qC 6 69.0 CH2 4.35 (dd, 12.1, 4.9) 15 27.7 CH2 1.18 (m); 2.34 (m) 4.69 (br d, 12.1) 11 16 23.0 CH2 2.06 (m); 2.14 (m) Glc-1 104.8 CH 5.00 (d, 7.7) 17 46.8 qC 211 74.6 CH 4.00 (t, 7.7) 18 47.0 CH 3.13 (dd, 4.7, 13.4) 311 77.8 CH 4.21 (m) 11 19 41.2 CH2 2.20 (m); 2.59 (t, 13.4) 4 71.0 CH 4.19 (m) 20 147.9 qC 511 77.9 CH 3.88 (m) 11 21 29.5 CH2 2.09 (m); 2.20 (m) 6 62.1 CH2 4.48 (br d, 10.5) 22 37.1 CH2 1.74 (m); 2.03 (m) 4.32 (m) δ in ppm; 1H-NMR: 400 MHz and 13C-NMR 100 MHz.
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