Biotechnological Approaches to Enhance Salidroside, Rosin and Its Derivatives Production in Selected Rhodiola Spp. in Vitro Cultures

Phytochem Rev DOI 10.1007/s11101-014-9368-y Biotechnological approaches to enhance salidroside, rosin and its derivatives production in selected Rhodiola spp. in vitro cultures Marta Grech-Baran • Katarzyna Sykłowska-Baranek • Agnieszka Pietrosiuk Received: 10 April 2013 / Accepted: 7 June 2014 Ó The Author(s) 2014. This article is published with open access at Springerlink.com Abstract Rhodiola (Crassulaceae) an arctic-alpine CCR Cinnamoyl-CoA reductase plant, is extensively used in traditional folk medicine CNS Central Nervous System in Asian and European countries. A number of DW Dry weight investigations have demonstrated that Rhodiola prep- IAA Indole-3-acetic acid arations exhibit adaptogenic, neuroprotective, anti- IBA Indole-3-butyric acid tumour, cardioprotective, and anti-depressant effects. KT Kinetin The main compounds responsible for these activities MS Murashige and Skoog (1962) medium are believed to be salidroside, rosin and its derivatives NAA Naphthaleneacetic acid which became the target of biotechnological investi- PAL Phenylalanine ammonia-lyase gations. This review summarizes the results of the Phe L-Phenylalanine diverse biotechnological approaches undertaken to SA Salicylic acid enhance the production of salidroside, rosin and its TDZ Thidiazuron derivatives in callus, cell suspension and organ in vitro Trp L-Tryptophan cultures of selected Rhodiola species. TGase Tyrosol-glucosyltransferase 2,4-D 2,4-Dichlorophenoxyacetic acid Keywords Biotransformation Á In vitro cultures Á 4CL Hydroxycinnamic acid CoA-ligase Rhodiola spp. Á Rosin derivatives Á Salidroside 4-HPAA 4-Hydroxyphenylacetaldehyde Tyr L-Tyrosine TyrDC Tyrosine decarboxylase Abbreviations UDP UDP-glucose:tyrosol glucosyltransferase BA 6-Benzylaminopurine UGT Uridine diphosphate dependent CA Cinnamyl alcohol glucosyltransferase CAD Cinnamyl alcohol dehydrogenase CCA Compact callus aggregates M. Grech-Baran (&) Á K. Sykłowska-Baranek Á A. Pietrosiuk Introduction Department of Pharmaceutical Biology and Medicinal Plant Biotechnology, Faculty of Pharmacy, Medical Rhodiola spp., herbaceous perennial plants of the University of Warsaw, Banacha 1 St., 02-097 Warsaw, Poland Crassulaceae family, are extensively used in tradi- e-mail: [email protected] tional medicine in Asian and European countries 123 Phytochem Rev (Tolonen et al. 2003; Yousef et al. 2006; Galambosi The roots and rhizomes of Rhodiola spp. have been et al. 2010; Panossian et al. 2010). The Rhodiola reported to contain distinct groups of chemical com- species grows in regions of cool temperature, in the pounds (Table 1). Initially, in the 1970s, the com- sub-arctic areas of the northern hemisphere, including pound responsible for its unique pharmacological North and Central Europe, Asia and North America properties was believed to be salidroside (Saratikov (GBIF 2010 http://www.gbif.org; Galambosi 2006; and Krasnov 1987). According to the Russian Phar- Guest and Allen 2014). The genus Rhodiola is macopeia (1989), the raw material of R. rosea should believed to originate from the mountainous regions of contain 0.8 % salidroside (Furmanowa et al. 1999). Southwest China and the Himalayas and nowadays is However, further studies revealed that not only distributed in mountainous as well as coastal habitats salidroside but also rosin derivatives are important (Brown et al. 2002). bioactive compounds (Sokolov et al. 1985, 1990; The current taxonomic status of the genus Rhodiola Wagner et al. 1994; Zapesochnaya et al. 1995). is quite complex due to the generally similar mor- Wiedenfeld et al. (2007a) summarized the results of phology (Brown et al. 2002; Liu et al. 2013). comparative studies on the activities of salidroside and According to GBIF (2010) the genus Rhodiola com- rosin derivatives by Sokolov et al. (1985, 1990) which prises of 136 accepted species while the Plant List showed CNS, adaptogenic and immunostimulating (http://www.theplantlist.org) includes 135 scientific properties, however he concluded that total Rhodiola plant names of species rank for the genus Rhodiola.Of rosea extracts are superior to the single components these 61 are accepted species names, 16 have not been which indicates that the glycosides mentioned are not clarified. the only compounds responsible for the medicinal The morphologicals of Rhodiola plants are as effect. In the subsequent studies it was reported that follows: stems dimorphic with usually very stout aqueous and hydroalcoholic extracts of R. rosea caudex or rhizome, usually with brown or blackish, exhibited stronger neovascular reaction than rosavin membranous, scalelike leaves, sharply differentiated applied alone (Skopin´ska-Ro´zewska_ et al. 2008b). from much more slender, erect or ascending, leafy Rhodiola rosea extracts used in most pharmaco- flowering stems (Liu et al. 2013). The plant is logical studies were standardized to a minimum 3 % dioecious with male and female flowers located on of rosin and its derivatives and 0.8–1 % salidroside different plants, and rarely hermaphroditic (Tutin because the naturally occurring ratio of these com- 1964). Among the distinguishing characters of the pounds in R. rosea root is approximately 3:1 (Brown genus are two series of stamens totaling twice the et al. 2002). number of petals; free or nearly free petals (not joined In numerous in vitro and in vivo studies on cells and in a tube); a stout rhizome from whose axils the animals, the extracts or pure salidroside have been flowering stems rise (Flora of China 2001). examined and have shown strong biological activity. Recently, genotyping and chemotaxonomic mark- The main effects described to date are the following: ers have been used to identify Rhodiola species within adaptogenic and stress protective (Darbinyan et al. the genus. On the basis of the chemical profiles of the 2000; Spasov et al. 2000; De Bock et al. 2004; Olsson 47 collected Rhodiola samples of R. crenulata, R. et al. 2009), antioxidant (Chen et al. 2009b; Schriner sachalinensis, R. himalensis, R. serrata, R. rosea, R. et al. 2009; Calcabrini et al. 2010; Mao et al. 2010), kirilowii and R. fastigiata it was demonstrated that anti-tumour (Skopin´ska-Ro´zewska_ et al. 2008a, different kinds of characteristics reference markers 2008c, Hu et al. 2010a, b; Sun et al. 2012), anti- occurred at various concentrations in the different depressive (Chen et al. 2009a, Diermen et al. 2009), Rhodiola species. The eight compounds: rosarin, neuroprotective (Zhang et al. 2007b,Yuetal.2008, rosavin, and rosin, tyrosol and salidroside, catechin, Chen et al. 2009a,Yuetal.2010), cardioprotective rhodionin and gallic acid have been proposed as (Wu et al. 2009, Cheng et al. 2012) hepatoprotective reference chemotaxonomic markers. Salidroside and (Nan et al. 2003), and immunostimulating (Seo et al. gallic acid were found in all species while rosarin and 2001,Wo´jcik et al. 2009, Siwicki et al. 2012). Also the rosin were detected in R. sachalinnsis, R. himalensis, cinnamyl alcohol derivate rosavin shows a stimulating R. rosea. Rosavin was characteristic only for R. effect on the CNS (Wagner et al. 1994), demonstrated himalensis, R. serrata, R. rosea (Liu et al. 2013). as spontaneous motor action and antihypnotic 123 Phytochem Rev Table 1 Chemical composition of Rhodiola spp. Plant species Compound References R. crenulata (in Salidroside and tyrosol, 2-(4-hydroxyphenyl)-ethyl-O- Wang and Wang (1992), Du and Xie (1995), Peng total over 26 b-D-glucopyranosyl-6-O-b-D-glucopyranoside, p- et al. (1995), Su et al. (2007), Nakamura et al. compounds) hydroxyphenacyl-b-D-glucopyranoside, icariside D2, (2008), Chen et al. (2012) rutin, picein, lotaustralin, rodiocyanoside A, crenulatin, rhodionin, rhodiosin, daucosterol, b- sitosterol, hydroxycinnamic, gallic acid, creosides I, II, III, IV, and V R. kirilowii (in Salidroside and tyrosol, rosin, rosavin, rosarin, cinnamyl Kang et al. (1992), Krasnov et al. (1978), Krajewska- total over 49 alcohol, herbacytrin, umbeliferon, esculetin, luteolin, Patan et al. (2006), Wiedenfeld et al. (2007b), Zuo compounds) tricetin, epigallocatechin, epigallocatechin gallate, et al. (2007), Wong et al. (2008), Krajewska-Patan lotaustralin, rodiocyanoside A, tannins, daucosterol et al. (2009), Krajewska-Patan et al. (2013) and b-sitosterol, hydroxycinnamic, gallic acid, chlorogenic acid R. quadrifida Salidroside and tyrosol, rosin, rosavin, rosarin, cinnamyl Yoshikawa et al. (1996), Altantsetseg et al. (2007), alcohol, rhodiooctanoside, rhodiolin, mongrhoside, Wiedenfeld et al. (2007a) rhodiocyanosides A and B, rhodioflavonoside, rhodiooctanoside, tricetin, L-rhamnopyranoside, osmaronin, chlorogenic acid R. rosea (in total salidroside and tyrosol, rosin, rosavin, rosarin, cinnamyl Saratikov et al. (1967), Kurkin et al. (1985, 1986), over 140 alcohol, epigallocatechin, epigallocatechin gallate, Kurkin and Zapesochnaya (1986), Akgul et al. compounds) lotaustralin, rodiocyanoside A, herbacetin, kaemferol, (2004), Yousef et al. (2006), Altantsetseg et al. rosiridol and rosaridin, daucosterol and b-sitosterol, (2007), Ali et al. (2008), Ma et al. (2013) Rhodiolosid A- C, organic acids, tannins, waxes, fats, proanthocyanidins, sachaliside, gallic, hydroxycinnamic acid, acetylrodalgin and tricin R. sachalinensis salidroside and tyrosol, rosarin, rosavin, cinnamyl Lee et al. (2000), Nakamura et al. (2007), Zhang et al. (in total over 44 alcohol, multiflorin B, tricetin, afzelin, kaempferol, (2007a), Choe et al. (2012) compounds) rhodionin, rhodiosin, gallic acid, sachalosides I –V, sacranoside A, rhodiocyanoside

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