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Characterization of Proanthocyanidin Oligomers of Ephedra Sinica

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Characterization of Proanthocyanidin Oligomers of Ephedra Sinica molecules Article Characterization of Proanthocyanidin Oligomers of Ephedra sinica Joanna Orejola, Yosuke Matsuo ID , Yoshinori Saito and Takashi Tanaka * ID Department of Natural Product Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan; [email protected] (J.O.); [email protected] (Y.M.); [email protected] (Y.S.) * Correspondence: [email protected]; Tel.: +81-95-819-2432 Received: 14 July 2017; Accepted: 3 August 2017; Published: 6 August 2017 Abstract: Ephedra sinica, an important plant in Chinese traditional medicine, contains a complex mixture of proanthocyanidin oligomers as major constituents; however, only the minor components have been chemically characterized. In this study, oligomers with relatively large molecular weights, which form the main body of the proanthocyanidin fractions, were separated by adsorption and size-exclusion chromatography. Acid-catalyzed degradation in the presence of mercaptoethanol or phloroglucinol led to the isolation of 18 fragments, the structures of which were elucidated from their experimental and TDDFT-calculated ECD spectra. The results indicated that (−)-epigallocatechin was the main extension unit, while catechin, the A-type epigallocatechin–gallocatechin dimer, and the A-type epigallocatechin homodimer, were identified as the terminal units. Among the degradation products, thioethers of gallocatechin with 3,4-cis configurations, a B-type prodelphinidin dimer, a prodelphinidin trimer with both A- and B-type linkages, and a prodelphinidin dimer with an α-substituted A-type linkage were new compounds. In addition, a phloroglucinol adduct of an A-type prodelphinidin dimer, a doubly-linked phloroglucinol adduct of epigallocatechin, and a unique product with a flavan-3-ol skeleton generated by the rearrangement of the aromatic rings were also isolated. Keywords: Ephedra sinica; proanthocyanidin; oligomer; thiolysis; phloroglucinolysis; TDDFT; ECD 1. Introduction Ephedra sinica Stapf (Fam. Ephedraceae) is one of the most important plants in traditional medicine, and is used as a diuretic, antipyretic, diaphoretic, and for relieving a cough and asthma [1]. As the crude drug, it has an official monograph in both the Chinese and Japanese Pharmacopoeias, where it is standardized against the major alkaloids, ephedrine and pseudoephedrine [2]. Thus, the main emphasis is conventionally given to its alkaloidal content, despite the fact that this only constitutes about 0.7–0.8% of the whole plant [3,4]. Clearly, the motivation for this is the proven clinical effects of these alkaloids on the respiratory, central nervous, and cardiovascular systems [5]. However, many species of Ephedra have also been shown to contain significant amounts of proanthocyanidins [6]. Recently, many health benefits of foods and medicinal plants have been attributed to proanthocyanidins [7], and some of their biological activities, including hypotensive and vasorelaxant effects [8,9], improvement of the airway microenvironment in asthma [10], and the inhibition of inflammation and remodeling in murine models of chronic asthma [11], are responsible for the aforementioned activities of E. sinica, especially its respiratory and cardiovascular effects. A number of studies have shown that Ephedra spp. also display other biological activities that are not attributed to alkaloids, including antimicrobial [12,13], antioxidant [14], anti-inflammatory [15,16], immunosuppressive [17], antiviral [18], anti-invasive, antiangiogenic, antitumor [19], and cytotoxic [20] Molecules 2017, 22, 1308; doi:10.3390/molecules22081308 www.mdpi.com/journal/molecules Molecules 2017, 22, 1308 2 of 18 Molecules 2017, 22, 1308 2 of 18 cell lines SGC-7901, HepG2, and HeLa [21]. In addition, a decrease in the uremic toxin parameters of cellproperties.rats lineswas reportedlySGC The-7901, dimeric inducedHepG2, proanthocyanidins andby the HeLa administration [21]. ofIn E.addition, sinica of proanthocyanidinshow a decrease cytotoxic in the activity oligomers uremic against toxin of E. theparameters sinica tumor [22,23 cell of]. ratslines wasAs SGC-7901, for reportedly the composition HepG2, induced and of by HeLa the the proanthocyanidins [administration21]. In addition, of a proanthocyanidinof decrease E. sinica in, monomeric the uremic oligomers toxinflavan of parameters-3 E.-ols sinica [12,24 [22,23 of] and rats]. wasdimeric reportedlyAs forproanthocyanidins the composition induced by theofwith the administration A proanthocyanidins-type linkage ofs proanthocyanidin have of beenE. sinica isolated, monomeric oligomers [12,21,25 flavan of–28E.]. sinica- 3The-ols p [[12,2422resence,23].] and of dimericprodelphinidinAs forproanthocyanidins the compositiontrimers and with of tetramers the A proanthocyanidins-type withlinkage A-s andhave ofB beenE.-type sinica isolated linka, monomericges [12,21,25 has also flavan-3-ols–28 ]been. The shownp [resence12,24 ][12] and of. prodelphinidinHowever,dimeric proanthocyanidins these trimersflavan-3 -andols with andtetramers proanthocyanidins A-type with linkages A- and have are B been -minortype isolatedlinka componentsges [12 has,21 , 25alsoof– the28 been]. total The shown polyphenol presence [12] of. However,prodelphinidincontent, and these our trimers flavanpreliminary- and3-ols tetramers andHPLC proanthocyanidins and with TLC A- andanalysis B-type are of linkagestheminor extract components has suggested also been of that shownthe thetotal [ 12main polyphenol]. However, body of contentthethese polyphenols flavan-3-ols, and our preliminarywas and a proanthocyanidinscomplex HPLC mix andture TLC of are analysisoligomers minor of components, thedetected extract as ofsuggested a the broad total thathump polyphenol the onmain the content,body HPLC of thebaselineand polyphenols our and preliminary at the was origin HPLCa complex of the and TLC TLCmix plateture analysis ( Figureof oligomers of 1a the). Thus, extract, detected the suggestedpresent as a study broad that aimed thehump main at characterizingon body the HPLC of the baselinepolyphenolsthese proanthocyanidin and at was the a origin complex oligomersof the mixture TLC byplate of acid oligomers, (Figure-catalyzed 1a detected). Thus, degradation the as present a broad in studythe hump presence aimed on the at of HPLC characterizing nucleophilic baseline theseagents,and at proanthocyanidin thethat origin is, 2-mercaptoethanol of the TLC oligomers plate (Figureor by phloroglucinol. acid1a).-catalyzed Thus, the The degradation present degradation study in aimed theinvolve presence atd characterizing the ofcleavage nucleophilic of these the agents,proanthocyanidininterflavan that bondsis, 2-mercaptoethanol oligomersunder acidic by acid-catalyzedconditions or phloroglucinol., generating degradation The flavan degradation in- the3-ols presence from involve the ofd nucleophilic terminalthe cleavage unitsagents, of andthe interflavanflavanylthat is, 2-mercaptoethanol-4 cations bonds fromunder the oracidic extension phloroglucinol. conditions units, , whichThegenerating degradation were trappeflavan involvedd-3 -byols nucleophilic from the cleavage the terminal agents of the ( interflavanSchemeunits and 1) flavanyl[29]bonds. under-4 cations acidic from conditions, the extension generating units, flavan-3-ols which were from trappe thed terminal by nucleophilic units and agents flavanyl-4 (Scheme cations 1) [29]from. the extension units, which were trapped by nucleophilic agents (Scheme1)[29]. CH-09 [MaxABS (200.0--550.0 nm)] alkaloids CH-09 [MaxABS (200.0--550.0 nm)] alkaloids 400000 proanthocyanidin oligomers proanthocyanidin oligomers 400000 proanthocyanidin oligomers proanthocyanidin oligomers 300000 300000 200000 Intensity[µAU] UV (max abs) (max UV 200000 Intensity[µAU] UV (max abs) (max UV 100000 100000 0 0 0.0 10.0 20.0 30.0 40.0 50.0 60.0 0 10 20 Retention 30 Time [min] 40 50 (min) 0 10 20 30 40 50 (min) 0 0.0 10.010 20.020 30.030 4040.0 50.050 (min)60.0 0 10 20 30 40 50 (min) Retention(a) Time [min] (b) (a) (b) Figure 1. HPLC profiles of 60% EtOH extract of E. sinica (a) and proanthocyanidin oligomer fraction Figure(b). 1. HPLC profiles ofof 60%60% EtOH EtOH extract extract of ofE. E. sinica sinica(a )(a and) and proanthocyanidin proanthocyanidin oligomer oligomer fraction fraction (b). (b). Scheme 1. Reaction mechanism of the acid-catalyzed cleavage of the interflavan bond in the presence Scheme 1. Reaction mechanism of the acid-catalyzed cleavage of the interflavan bond in the presence Schemeof nucleophiles 1. Reaction (Nu). mechanism of the acid-catalyzed cleavage of the interflavan bond in the presence of nucleophiles (Nu). of nucleophiles (Nu). 2. Results and Discussion 2. Results and Discussion 2.1. Composition of the Intact Proanthocyanidin Oligomer 2.1. Composition of the Intact Proanthocyanidin Oligomer The drieddried aerialaerial parts parts of ofE. E. sinica sinicawere were extracted extracted with with aqueous aqueous acetone acetone and fractionatedand fractionated by a series by a The dried aerial parts of E. sinica were extracted with aqueous acetone and fractionated by a seriesof chromatographic of chromatographic separation sepa methods,ration methods, including including size-exclusion size-exclusion chromatography chromatography [30]. The [30 fractions]. The series of chromatographic separation methods, including size-exclusion chromatography [30]. The fcontainingractions containing only oligomeric only oligomeric proanthocyanidins proantho accountedcyanidins foraccount
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