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Potassium Hexacyanoferrate (III)-Catalyzed Dimerization of Hydroxystilbene: Biomimetic Synthesis of Indane Stilbene Dimers

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Potassium Hexacyanoferrate (III)-Catalyzed Dimerization of Hydroxystilbene: Biomimetic Synthesis of Indane Stilbene Dimers Article Potassium Hexacyanoferrate (III)-Catalyzed Dimerization of Hydroxystilbene: Biomimetic Synthesis of Indane Stilbene Dimers Jing-Shan Xie 1,2, Jin Wen 3, Xian-Fen Wang 1, Jian-Qiao Zhang 1, Ji-Fa Zhang 1, Yu-Long Kang 1, You-Wei Hui 2, Wen-Sheng Zheng 1,* and Chun-Suo Yao 1,* Received: 16 November 2015 ; Accepted: 9 December 2015 ; Published: 18 December 2015 Academic Editor: Roman Dembinski 1 State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China; [email protected] (J.-S.X.); [email protected] (X.-F.W.); [email protected] (J.-Q.Z.); [email protected] (J.-F.Z.); [email protected] (Y.-L.K.) 2 School of Chemical Engineering, Northwest University, Xi’an 710069, China; [email protected] 3 Chinese Pharmaceutical Association, Beijing 100022, China; [email protected] * Correspondence: [email protected] (W.-S.Z.); [email protected] (C.-S.Y.); Tel.: +86-010-6316-5233 (W.-S.Z.); +86-010-6021-2110 (C.-S.Y.) Abstract: Using potassium hexacyanoferrate (III)–sodium acetate as oxidant, the oxidative coupling reaction of isorhapontigenin and resveratrol in aqueous acetone resulted in the isolation of three new indane dimers 4, 6, and 7, together with six known stilbene dimers. Indane dimer 5 was obtained for the first time by direct transformation from isorhapontigenin. The structures and relative configurations of the dimers were elucidated using spectral analysis, and their possible formation mechanisms were discussed. The results indicate that this reaction could be used as a convenient method for the semi-synthesis of indane dimers because of the mild conditions and simple reaction products. Keywords: potassium hexacyanoferrate (III); indane stilbene dimer; biomimetic synthesis; hydroxystilbene 1. Introduction Stilbene dimers with indane skeletons possess a wide range of biological activity [1,2] and novel structures which are difficult to achieve by common organic reactions on account of their intricate architectures and chiral centers. As many of these compounds are exclusively obtained by extraction from natural sources, the studies of biological properties are limited by their extreme scarcity. This has made the synthesis of stilbene dimers, especially indane dimers a popular research topic [3]. Indane stilbene dimers such as quadragularin A, pallidol, ampelopsin F, paucifloral F, ampelopsin D, and caraphenol C have been successfully synthesized [4–10]. However, the complexity of the synthetic routes has hindered further studies on these indane derivatives, and the search for simple and convenient synthetic routes to obtain abundant samples is of significant interest. As a conventional inorganic one-electron oxidant, potassium hexacyanoferrate (III) (K3Fe(CN)6) has been reported to generate resveratrol trans-dehydrodimer, "-viniferin and indane dimers in the oxidative coupling reaction of resveratrol (1)[11,12]. However, a detailed study of this reaction has yet to be reported. In our previous paper [13], we reported that the transformation of isorhapontigenin (2) with K3Fe(CN)6/sodium acetate (NaOAc) as oxidant yielded shegansu B (3) as the major product peak (65.2%) and another peak (about 10%) according to high-performance liquid chromatography (HPLC). Further investigation showed that the latter peak comprised two indane dimers, 4 and 5, Molecules 2015, 20, 22662–22673; doi:10.3390/molecules201219872 www.mdpi.com/journal/molecules Molecules 2015, 20, 22662–22673 Molecules 2015, 20, page–page whichwhich indicatesindicates thatthat thethe reactionreaction isis amenableamenable forfor thethe formationformation ofof indaneindane dimers.dimers. To substantiatesubstantiate thisthis hypothesis,hypothesis,Molecules 2015 studiesstudies, 20, page–page on the oxidative coupling reactionreaction of resveratrol employingemploying thethe samesame oxidantsoxidants werewere conducted,conducted, resultingresulting in thethe isolationisolation ofof fivefive resveratrolresveratrol indaneindane dimersdimers 66––1010,, andand thethe benzofuranbenzofuran derivativederivativewhich indicates resveratrolresveratrol that trans transthe reaction-dehydrodimer-dehydrodimer is amenable 1111 for (Figure(Figure the formation1 ).1). AmongAmong of indane thethe dime dimers,dimers,rs. To 4substantiate, 6 and 7 thisare newnew indaneindanehypothesis, dimers.dimers. studiesThis This paper paper on the reports reportsoxidative on on coupling the oxidative reaction coupling of resveratrol of 1 employingand 2 in aqueousaqueousthe same acetoneoxidantsacetone withwith were conducted, resulting in the isolation of five resveratrol indane dimers 6–10, and the benzofuran KK3Fe(CN)6/NaOAc/NaOAc as as oxidant, oxidant, the the isolation isolation and and structural structural identification identification of the products, and thethe 3 derivative6 resveratrol trans-dehydrodimer 11 (Figure 1). Among the dimers, 4, 6 and 7 are new discussion of the mechanisms of formation of all the products. discussionindane ofdimers. the mechanisms This paper reports of formation on the ofoxidative all the products.coupling of 1 and 2 in aqueous acetone with 3 6 K Fe(CN)HO /NaOAc as oxidant, the isolationR and structural identification of the products, and the R1 1 discussion4a of the mechanisms of formationOH of all the products. 4a R HO 11 b OH 1a R HO 1a 13b R R1 H R1 OH HO 7a OH R 4a OH 4a 10b H HO 8a 13 b O 4b HO HO 4a 3b 4a 11b 13a R 1a 7a 1a 7a 9b 13 a 9a 9b HO 11 b OH H 1a 10a R 8b H 10a R 1a 13b H 11bOH HO R 1b 7b 7a 13b OH 4a 9a 7b 10b 9a 7b H HO 8a 13 b O 4b HO 1b HO OH HO 3b 4a 9b 10a 4b OH 1b OH 11b 13aOH 13a 1a 7a 9b 1a 7a OH13 a 9a 9b H 10a 8b 13a 11a 10a 11a OH H 11b 11b 7b 4b 9a 1b 7b HO9a 7b OH 4b 13b 1b OH HO OH 13b OH 1b OH OH R OH 9b 10a 4b ROH OH 1 13a 1 OH 13a 11a10 3 11aR=OCH3 HO 11b 5 R=OH, R14b=OCH3 HO OH 4 R=OH, R1=OCH34b 11 6 R=CN, R =H OHR=H 13b 7 R1 1 OH R=CN, R1=HR1 OH 10 9 R=OH,5 R=OH, R R1=H=OCH 3 R=OCH3 HO 8 R=OH,4 R=OH, R1=H R =OCH 1 3 1 3 6 R=CN, R =H 11 R=H 7 R=CN, R =H 1 1 9 8 R=OH, R =H R=OH, R1=H 1 Figure 1.1. Structures ofof compoundscompounds 33––1111.. Figure 1. Structures of compounds 3–11. 2.2. Results Results and and Discussion Discussion 2. Results and Discussion 2.1.2.1. Treatment ofof 2 with Potassium HexacyanoferrateHexacyanoferrate (III)/Sodium(III)/Sodium AcetateAcetate 2.1. Treatment of 2 with Potassium Hexacyanoferrate (III)/Sodium Acetate AsAs reportedreported inin aa previousprevious paperpaper [[13]13],, thethe oxidativeoxidative couplingcoupling reactionreaction ofof 22 inin aqueousaqueous acetoneacetone As reported in a previous paper [13], the oxidative coupling reaction of 2 in aqueous acetone usingusing KK3Fe(CN)6/NaOAc/NaOAc as as oxidant oxidant at at room room temperature temperature generated generated a a major major product peak 3 inin 65.2%65.2% using3 K3Fe(CN)6 6/NaOAc as oxidant at room temperature generated a major product peak 3 in 65.2% yieldyieldyield and anda a peak peak a peak of of another of another another product product obtained obtained obtained in 10% in 10% yield yield yield with with a with retentiona retention a retention time time of 4.2 timeof min 4.2 of minin 4.2the in HPLC min the HPLC in the HPLCchromatogramchromatogram chromatogram (Figure (Figure (Figure 2). 2). 2). Figure 2. Analysis of isorhapontigenin oxidation products by K3Fe(CN)6/NaOAc (32% CH3CN/H2O, Figure 2. Analysis of isorhapontigenin oxidation products by K3Fe(CN)6/NaOAc (32% CH3 CN/H2O, λ = 230 nm, 1 mL/min). λFigure= 230 2 nm,. Analysis 1 mL/min). of isorhapontigenin oxidation products by K3Fe(CN)6/NaOAc (32% CH3CN/H2O, λ = 230This nm, finding 1 mL/min). indicates that the reaction mainly produced two types of products as compared with Thisthe complex finding products indicates seen that in the the reaction common mainly oxidative produced couplingtwo reactions types of of hydroxylstilbene products as compared [13–16]. with the complexThisFurthermore, finding products indicatesseveral seen reports that in thethe of commonKreaction3Fe(CN) mainly6 oxidative molecules produced couplingcatalyzing two reactions the types oxidative of of products hydroxylstilbene coupling as reactioncompared [13of –with16]. Furthermore,the complexhydroxystilbene products several can reportsseen be found in ofthe Kin 3commonFe(CN) the literature6 oxidatmolecules [11,ive12]. coupling catalyzingHowever, reactions to the the oxidative best of hydroxylstilbeneof our coupling knowledge, reaction [13–16]. a of hydroxystilbeneFurthermore,detailed investigation several can bereports foundon this of inreaction, K the3Fe(CN) literature especially6 molecules [11 for,12 the]. catalyzing K However,3Fe(CN)6 /NaOActhe to oxidative the oxidant best ofcoupling system, our knowledge, has reaction yet of a to be reported. In this study, isorhapontigenin was treated with K3Fe(CN)6/NaOAc in aqueous acetone detailedhydroxystilbene investigation can be on found this reaction,in the literature especially [11, for12]. the However, K3Fe(CN) to6 /NaOActhe best of oxidant our knowledge, system, has a yetdetailed to be investigation reported. In thison this study, reaction, isorhapontigenin especially for was the treated K3Fe(CN) with6/NaOAc K3Fe(CN) oxidant6/NaOAc system, in aqueous has yet 2 to be reported. In this study, isorhapontigenin was treated with K3Fe(CN)6/NaOAc in aqueous acetone 22663 2 Molecules 2015, 20, 22662–22673 acetone at room temperature, followed by silica gel column chromatography, preparative HPLC, and semi-preparativeMolecules 2015, 20 HPLC, page–page to obtain a major product 3 in 52.2% yield, as well as two indane dimers 4 and 5at(Figure room 1temperature,) in 6.0% and followed 3.3% yield,by silica respectively. gel column Amongchromatography, these dimers, preparative5 possesses HPLC, theand same structuresemi-preparative as the natural HPLC product to obtain gnetuhainin a major product I [317 in], 52.2% and yield, compound as well as4, two an indane isomer dimers of 5, 4 is and a new isorhapontigenin5 (Figure 1) in dimer.
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