Phytochemical Studies and Biological Activity of Three Chinese
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View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Jagiellonian Univeristy Repository Phytochem Rev (2019) 18:109–128 https://doi.org/10.1007/s11101-018-9582-0 (0123456789().,-volV)(0123456789().,-volV) Phytochemical studies and biological activity of three Chinese Schisandra species (Schisandra sphenanthera, Schisandra henryi and Schisandra rubriflora): current findings and future applications Agnieszka Szopa . Magda Barnaś . Halina Ekiert Received: 6 February 2018 / Accepted: 15 June 2018 / Published online: 3 October 2018 © The Author(s) 2018 Abstract Schisandra chinensis (Chinese magnolia butane-type lignans) as the main compounds respon- vine) is the best-known representative of the genus sible for biological activity. The lignans are Schisandra, widely used in the official East-Asian, accompanied by other groups of compounds, includ- North American and European medicine. The article ing triterpenoids and nortriterpenoids. A review of recalls the healing value of this species and, above biological studies, e.g. of empirically confirmed all, presents the current state of knowledge on the hepatoprotective, cytotoxic and anti-HIV-1 activities, chemical composition and biological activity of three proves that these species have a high therapeutic other species of the Schisandra genus: Schisandra potential and may constitute a new East-Asian sphenanthera, Schisandra henryi and Schisandra proposition for European medicine. The article also rubriflora. In addition to dibenzocyclooctadiene lig- draws attention to the possibility of using the nans (the so-called ‘Schisandra chinensis lignans’), biosynthetic potential of the biomass from in vitro they also contain other groups of lignans (e.g. 4- cultures of the described species and biotechnological aryltetralin, aryltetralone, tetrahydrofuran and solutions as an alternative to plant raw materials. A. Szopa (&) · M. Barnas´ · H. Ekiert Chair and Department of Pharmaceutical Botany, Jagiellonian University, Medical College, Medyczna 9, 30-688 Krako´w, Poland e-mail: [email protected] 123 110 Phytochem Rev (2019) 18:109–128 Graphical abstract Phytochemical studies and biological activity of three Chinese Schisandra species (Schisandra sphenanthera, Schisandra henryi and Schisandra rubriflora) - current findings and future applications PHARMACOLOGICAL STUDIES WORLD AND EUROPEAN MEDICINE BIOLOGICAL STUDIES HO Me Me OMe O MeO OMe OMe MeO CHEMICAL STUDIES O HO O OMe Me 1 OMe OH R Me HO Me O MeO BIOTECHNOLOGICAL STUDIES O MeO Me MeO OMe 3 Me Me R 2 R Keywords Schisandra lignans · Triterpenoids · 2002; Chinese Pharmacopoeia Commission 2005; Nortriterpenoids · Schisandra genus · Panossian and Wikman 2008), but also in countries Nan wuweizi · Yi geng wuweizi · of Europe (European Directorate for the Quality of Hong hua wuweizi Medicines 2017) and USA (Upton et al. 2011). Since 2007, they have also been accepted by International Pharmacopoeia edited by WHO (World Health Orga- Introduction nization 2007) as medicinal plant raw material. Also, since 2010, the S. chinensis fruit has been accepted by The genus Schisandra includes from 20 to 30 species the European Food Safety Authority (EFSA) as ‘safe (Hancke et al. 1999; Saunders 2000). The natural nutrition ingredients with tonic for the support of habitats of Schisandra species are located in East and mental and well-being application’ (European Food South-East Asia, twelve of those species are endemic Safety Authority 2010). Moreover, S. chinensis is also to China (Saunders 2000; Wu et al. 2008). The species recognized as a plausible anti-aging and skin condi- of Schisandra differ from one another in small details tioning cosmetics component in the database of the in their morphological structure. The knowledge of the European Inventory of Cosmetic Ingredients (CosIng) chemical composition of different parts of these (Szopa et al. 2016a). species (leaves, stems, flowers, or fruits) is not Recently, we documented the state of the art about satisfactory. Most of them are rooted in Traditional the progression of studies on S. chinensis in our Chinese Medicine (TCM) as medicinal plants (Saun- review article (Szopa et al. 2017a). They deal with ders 2000; Wu et al. 2008; Szopa et al. 2017a). bioactive components, pharmacological properties, The best-known worldwide species from this genus analytical and biotechnological researches. is Schisandra chinensis Turcz. Baill.—Chinese mag- Schisandra chinensis fruit extracts are used in nolia vine. The knowledge of the valuable medicinal medicine because of their valuable biological prop- properties of Schisandra fruits (Bei-wuweizi, Northern erties: hepatoprotective, adaptogenic and ergogenic, magnolia vine fruit) is based on the Traditional anti-cancer, anti-inflammatory, antiulcer, antioxida- Chinese Medicine (Fil’kin 1952; Bensky and Gamble tive and detoxifying (Szopa et al. 2017a). These 1993). Nowadays, monographs on Schisandra chinen- activities are mainly driven by dibenzocyclooctadi- sis fruits are included in numerous pharmacopoeias, ene lignans, which are called, even in the professional not only in Asian countries (China, Japan, South Korea scientific literature, ‘Schisandra chinensis lignans’ and Russia) (Korea Food and Drug Administration due to their complex, and at the same time unique, 123 Phytochem Rev (2019) 18:109–128 111 Table 1 The predominant dibenzocyclooctadiene lignans detected in the fruits of: S. chinensis, S. sphenanthera, S. henryi and S. rubriflora Species Dibenzocyclooctadiene lignans S. chinensis Schisandrin, schisandrins B and C, gomisins A and G, schisantherins A and B, deoxyschisandrin, γ-schisandrin, schisanthenol S. sphenanthera Gomisins: C, S, K3 and J, epigomisin O, 6-O-benzoylgomisin, benzoylgomisin U, methylgomisin, tigloylgomisin P, angeloylgomisin P, schisantherins A–D, deoxyschisandrin, schisanhenol S. henryi Schisantherins A and B, deoxyschisandrin, schisandrin, gomisin G, benzoylgomisin Q, isoanwulignan S. rubriflora Gomisins B, C, G, J, N, O, Q, S and T, isogomisin O, schisandrin, schisandrin A, angeloylgomisins P and Q, benzoylgomisin Q structure (they are present mainly in the fruit, from Europe and North America (World Health Organiza- 7.2 to 19.2% DW) (Opletal et al. 2004; World Health tion 2007; Upton et al. 2011; European Directorate Organization 2007; Szopa et al. 2017a) (Table 1). for the Quality of Medicines 2017). In its mono- The main source of this raw material in Europe and graphs, one can only find descriptions of America are imports from Southeast Asia, primarily morphological and chromatographic methods of from China. The theoretically possible chemical distinguishing S. chinensis fruit against adulteration synthesis of Schisandra lignans involves many stages of the raw material with Schisandrae sphenantherae and is very complicated. So far, only one synthetic fructus. drug is available—Bifendate (BDD, biphenyl Scientific research on the species of the genus dimethyl-dicarboxylate), manufactured in China, it Schisandra is prominent. Some studies have reported is used in medicine as a hepatoprotective agent a high chemical and biological potential of S. henryi (Shuwei and Haodong 2000). C.B. Clarke (翼梗五味子; yi geng wuweizi) and The majority of scientific work on other species of S. rubriflora (Franch.) Rehd. et Wils (红花五味子; the genus Schisandra has been performed in China. hong hua wuweizi) (Wu et al. 2008). These species, Analysis of the reports shows that potential biological along with S. sphenanthera, could be regarded as activities of other species from that genus are very sources of valuable medicinal raw materials in Europe. probable. The major purpose of this review article is to The second in the order of S. chinensis species gain the basic and new knowledge of chemical described in the literature as competing in terms of composition, biological activities and potential medical applications is S. sphenanthera Rehder & E. biotechnological solutions for providing industry H. Wilson (Nan-wuweizi, Southern magnolia vine with raw materials. fruit) (Huyke et al. 2007; Zhu et al. 2007; Lu and Importantly, the available databases contain only Chen 2009). However, the chemical compositions of one review publication comparing the chemical the fruits of the two Schisandra species (Northern and composition of S. sphenanthera and S. chinensis Southern magnolia vines) are quite different (Lu and (Lu and Chen 2009). Furthermore, there are no Chen 2009). Since 2005, the fruits of these two plants publications describing the current state of knowl- have been recognized as two different raw materials, edge on the species S. henryi and S. rubriflora. namely “bei wuweizi” (Fructus Schisandrae chinen- sis) and “nan wuweizi” (Fructus Schisandrae sphenantherae), respectively, by the Chinese Phar- Natural habitats and possibility of cultivation in macopoeia (Chinese Pharmacopoeia Commission Europe 2005; Sun et al. 2010; Wei et al. 2010). On the other hand, the monograph on Schisandrae chinensis fruit All species of Schisandra are scandent, i.e. climbing, has appeared in the European Pharmacopoeia since woody vines; they lack tendrils or other specialized 2008 (European Directorate for the Quality of structures for climbing, but become entangled on Medicines 2013). What is important is the fact that supporting vegetation by spiral stem growth. All of S. chinensis only was approved as a herbal remedy in the species have a very similar growth pattern, but 123 112 Phytochem Rev (2019) 18:109–128 small differences in the morphology