Polyphenolic compounds from callus cultures of Iris pseudacorus

June 14, 2017 | Autor: Victor Bulgakov | Categoria: Organic Chemistry, Plant Biology, Polyphenols, Lignans, Plant tissue Culture Techniques
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2013 Vol. 8 No. 10 1419 - 1420

Natural Product Communications

Polyphenolic Сompounds from Сallus Сultures of Iris pseudacorus Darya V. Tarbeevaa,*, Sergey A. Fedoreyeva, Marina V. Veselovaa, Anatoliy I. Kalinovskiya, Ludmila D. Seletskayab, Tamara I. Mazurokb and Victor P. Bulgakovb,c a

G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Vladivostok, Russia, 690022 b Institute of Biology and Soil Science, Far Eastern Branch, Russian Academy of Sciences, Vladivostok, Russia, 690022 c Far Eastern Federal University, Vladivostok, Russia, 690950 [email protected] Received: February 24th, 2013; Accepted: July 2nd, 2013

A callus culture of Iris pseudacorus L. (Iridaceae) was established from plant leaves using a modified Murashige and Skoog medium. A derivative of cinnamic acid (lavandoside) (1), a neolignan (dehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside) (2) as well as three isoflavonoids, tectoridin (3), tectorigenin (4), and iristectorigenin A (5) were isolated from the callus culture. Under normal conditions, the calli accumulated 0.4% DW of polyphenols. The addition of phenylalanine to a concentration of 1 mM resulted in a 1.5-fold increase in isoflavonoid production, allowing the accumulation of 0.69% of polyphenols in the callus dry weight. Tectorigenin, a promising chemotherapeutic and chemopreventive agent for the treatment of carcinomas, was produced in I. pseudacorus calli in high quantities (0.3% DW). Keywords: Iris pseudacorus, Polyphenolic compounds, Isoflavonoids, Cell culture.

Iris is the largest genus within the Iridaceae family and comprises approximately 300 species occurring in Eurasia, North Africa and North America [1]. The major polyphenolic compounds found in Iridaceae are isoflavonoids. Though the application of various biotechnological methods can lead to an increase in the production of polyphenols [2a-2c,3a], little is known about polyphenolic metabolites from cell cultures of Iridaceae. Iris pseudacorus (yellow-flag Iris) is one of the most widely cultivated and horticulturally important Iridaceae species, with numerous commercially important cultivars [3b]. A number of isoflavonoids were previously isolated from I. pseudacorus leaves treated with cupric chloride [3c]. A cell culture of this species producing only terpenoids (iridals) has been established [4a]. However, polyphenols from cultured cells of I. pseudacorus have not been previously studied. The objectives of the present investigation were to establish a callus culture producing isoflavonoids and to study their composition. The ethanolic extract of the callus culture of I. pseudacorus was analyzed using HPLC. The most abundant polyphenolic compounds were isolated and identified by HPLC-PDA-MS, CD, 1D and NMR experiments as lavandoside (1), dehydrodiconiferyl alcohol-4-O-βD-glucoside (2), tectoridin (3), tectorigenin (4) and iristectorigenin A (5) (Figure 1) [4b-4d]. HPLC-PDA-MS analysis data for polyphenols 1-5 are given in Table 1. Lavandoside (1) and dehydrodiconiferyl alcohol-4-O-β-D-glucoside (2) were previously isolated from Lavandula spica and Euphrasia rostkoviana, respectively [4b,4c]. This is the first time these compounds have been isolated from a cell culture of an Iridacae species. Tectorigenin (4) and tectorigenin glucosides were found in I. crocea and I. carthaliniae [4e]. The Ip-ISO callus line has been analyzed using HPLC and HPLC-PDA-MS (Table 1). The total amounts of polyphenols produced by the calli were equal to 0.4% DW. Tectorigenin (3) was the main compound (0.19% DW). A derivative of cinnamic acid, lavandoside (1), accumulated at a level up to 0.1% DW; neolignan 2 was produced in the smallest quantities (0.05% DW). These biosynthetic patterns of the callus

HO

O 2'

6

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OH

8

10

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5

4

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9 6 7

7a

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OCH3

5'

9

O

7

1'

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8

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3'

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OCH3

2 3

5

4

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2' 1'

3'

5'

2. R = β-D-Glc

R2

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3. R1 = β-D-Glc; R2 = H; R3 = H 4. R1 = H; R2 = H; R3 = H 5. R1 = H; R2 = OH; R3 = CH3

Figure 1: Chemical structures of polyphenols from the Ip-ISO callus culture of I. pseudacorus. Table 1: HPLC-PDA-MS data for polyphenols 1-5. Compound tR, min 1 3.33 2 5.87 3 5.90 4 8.06 5 8.46

MW Positive ion mode; m/z of molecular ions 356 520 503 (M-H2O+H)+ 462 463 (M+H)+ 300 301 (M+H)+ 330 331 (M+H)+

Negative ion mode; m/z of molecular ions 355 (M-H)461 (M-H)299 (M-H)329 (M-H)-

UV (λmax) 225, 291, 315 232, 277 213, 266 229, 264 235, 265

line were stable for long-time cultivation (three years). Addition of biosynthetic precursors is often used to activate biosynthesis of polyphenols [2c]. Because phenylalanine (Phe) is a precursor of phenylpropanoid metabolites, we tested whether the addition of Phe to nutrient media would increase the polyphenol content. Phe added at the concentration of 0.1 mM did not change the accumulation of polyphenols, whereas a 1 mM concentration of Phe caused the activation of polyphenol accumulation (Table 2). Lavandoside content increased more than two-fold, whereas the content of isoflavonoids increased by 1.6–1.8 times for tectoridin (3), tectorigenin (4) and iristectorigenin A (5). Dehydrodiconiferyl alcohol-4-O-β-D-glucoside (2) production was not affected by the addition of Phe suggesting that neolignan 2 was biosynthesized via a different biosynthetic route. The medium with added Phe enabled the polyphenols to accumulate to 0.69% without decreasing callus growth. Therefore, this medium was selected as the basic medium for further cultivation of the Ip-ISO callus line. Thus, the Ip-ISO callus line of I. pseudacorus represents a biotechnological source of valuable polyphenols, which may potentially be used to improve human health. The occurrence of tectorigenin (4) in the Iris calli is especially interesting. Recent studies of tectorigenin in combination

1420 Natural Product Communications Vol. 8 (10) 2013

therapies have shown promising clinical effects in ovarian carcinoma [4e] as well as for the treatment of hepatocellular carcinoma [5a]. Our work represents a first example of high accumulation of tectorigenin (0.3% DW, Table 2) in plant cell cultures. Experimental Plant material and cell cultures: Samples of wild-growing I. pseudacorus plants were collected from Sakhalin Island (southSakhalin lowland). Plants were identified at the Botany Department of the Institute of Biology and Soil Science. I. pseudacorus callus cultures were established from leaves of the plants using essentially the same method described previously [5b]. Calli were cultivated in 100 mL Erlenmeyer flasks containing 30 mL of WB/2,4-D medium [3a] supplemented with the following components (mg/L): thiamine-HCl (0.2), nicotinic acid (0.5), pyridoxine-HCl (0.5), meso-inositol (100), peptone (100), sucrose (25000), agar (6000), 6benzyladenine (BA, 0.5) and 2,4-dichlorophenoxyacetic acid (2,4D, 1.0). Calli were cultivated at 25°C in the dark at 30-day subculture intervals. The actively growing callus culture of leaf origin was selected and designated as the Ip-ISO line. DLphenylalanine was dissolved in hot water and aseptically added to the culture medium at final concentrations of 0.1 mM and 1 mM. Extraction and isolation of polyphenolic compounds: Cells of I. pseudacorus (76 g) were extracted twice with 96% EtOH for 24 h at room temperature. The combined extract was concentrated under vacuum. The residue was dissolved in 70% EtOH, and lipophilic substances were removed by triple liquid-liquid partitioning between n-hexane and residual ethanolic solution. The ethanolic solution was evaporated under reduced pressure and applied to a Toyopearl HW-50 (3 × 20) column. The column was eluted with H2O – EtOH (containing 0.02% of formic acid) with gradually increasing amounts of EtOH to give 20 fractions. Fractions 5 (187 mg) and 7 (152 mg) were subsequently fractionated on a C-18 column to afford compounds 1 (4.2 mg), 2 (10.5 mg) and 3 (4.5 mg). Fractions 14 (43 mg) and 15 (21 mg) were chromatographed over silica gel using a CHCl3 – MeOH mixture with gradually

Tarbeeva et al.

increasing amounts of MeOH and yielded compounds 4 (8.8 mg) and 5 (3.9 mg). Analytical HPLC: The analytical HPLC was carried out using an Agilent Technologies 1100 series HPLC system equipped with a VWD detector (λ = 280 nm). The extracts were analyzed using a Supelco Analytical HS-C18 column (3 µm, 4.6 × 75 mm) thermostated at 30°C. The mobile phase consisted of 1% aqueous acetic acid (A) and acetonitrile containing 1% acetic acid (B). For the analysis, the following 8 gradient steps were programmed: 0-2 min, 5-10% B, 2-4 min, 10-20% B, 4-10 min, 20-30% B, 10-12 min, 30-40% B, 12-15 min, 40-50% B, 15-17 min, 50-90% B, 1720 min, 90-5% B. The flow rate was 0.8 mL/min. The data were analyzed with the ChemStation program var. 09 (Agilent Technologies, Waldbronn, Germany). HPLC–PDA–MS analysis: The isolated compounds were analyzed using a Shimadzu HPLC–PDA–MS system consisting of a CBM20A system controller, two LC-20AD pumps, a DGU-20A3 degasser, a SIL-20A autosampler, a SPD-M20A UV–VIS photodiode array detector, and a Shimadzu LCMS-2020 mass detector. The compounds were eluted and analyzed on a Shim-park XR-ODS 75 × 3.0 mm i.d. thermostatically controlled (36°C) column (2.2 µm particle size) at a flow rate of 0.3 mL/min. A 1% solution of aqueous acetic acid (A) and acetonitrile containing 1% acetic acid (B) were used for gradient elution as follows: 10–100% B (10 min), 100% B (2 min) and 100–10% B (2 min), with an injection volume of 2 µL. The MS settings were as follows: electrospray ionization (ESI), negative and positive ion modes, 150–800 m/z scans, N2 drying gas (10 L/min), nebulizer gas flow (1.5 L/min), interface voltage (3.5 kV) and detector voltage (1.2 kV). Acknowledgments - This work was supported by the Russian Foundation for Basic Research (grant 11-04-00770) and the Program of the Presidium of the Russian Academy of Sciences "Basic Research for Medicine" (grant 12-I-P5-04).

Table 2: Effect of phenylalanine on growth and polyphenol content (% DW) in the I. pseudacorus Ip-ISO callus line. Phenylalanine (mM) 0 0.1 1.0

Fresh biomass, g 2.06 ± 0.12 1.96 ± 0.10 1.86 ± 0.18

Dry biomass, g 0.18 0.19 0.18

1 0.10 ± 0.01 0.09 ± 0.02 0.22 ± 0.04

2 0.05 ± 0.01 0.07 ± 0.02 0.06 ± 0.01

3 0.04 ± 0.01 0.04 ± 0.01 0.06 ± 0.01

4 0. 19± 0.03 0.18 ± 0.05 0.30 ± 0.05

5 0.03 ± 0.006 0.03 ± 0.009 0.04 ± 0.007

Total 0.40 0.41 0.69

Calli were cultivated for 30 days. Inoculum biomass was 0.2 g. The data (mean  SE) were obtained from 4 independent experiments with 3 replicates each.

References [1] [2]

[3]

[4]

[5]

Mabberley DJ. (1997) The Plant Book. Cambridge University Press, Cambridge, UK. (a) Fedoreyev SA, Inyushkina YV, Bulgakov VP, Veselova MV, Tchernoded GK, Gerasimenko AV, Zhuravlev YN. (2012) Production of allantoin, rabdosiin and rosmarinic acid in callus cultures of the sea coastal plant Mertensia maritima (Boraginaceae). Plant Cell, Tissue and Organ Culture, 110, 183-188; (b) Fedoreyev SA, Bulgakov VP, Grishchenko OV, Veselova MV, Krivoschekova OE, Kulesh NI, Denisenko VA, Tchernoded GK, Zhuravlev YN. (2008) Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr.et Maxim. Journal of Agricultural and Food Chemistry, 56, 7023-7031; (c) Bulgakov VP, Inyushkina YV, Fedoreyev SA. (2012) Rosmarinic acid and its derivatives: biotechnology and applications. Critical Reviews in Biotechnology, 32, 203-217. (a) Bulgakov VP, Shkryl YN, Veremeichik GN. (2010) Engineering high yields of secondary metabolites in Rubia cell cultures through transformation with rol genes. Methods in Molecular Biology, 643, 229-242; (b) Tang S, Okashah RA, Cordonnier-Pratt MM, Pratt LH, Johnson VE, Taylor CA, Arnold ML, Knapp SJ. (2009) EST and EST-SSR marker resources for Iris. BMC Plant Biology, 9, 72-83; (c) Hanawa F, Tahara S, Mizutani J. (1991) Isoflavonoids produced by Iris pseudacorus leaves treated with cupric chloride. Phytochemistry, 30, 157-163. (a) Ritzdorf I, Bartels M, Kerp B, Kasel T, Klonowski S, Marner FJ. (1999) Identification of 10-desoxyiridal as an intermediate in the biosynthesis of iridals. Phytochemistry, 50, 995–1003; (b) Kurkin VA, Lamrini M, Klochkov SG. (2008) Lavandoside from Lavandula spica flowers.Chemistry of Natural Compounds, 44, 169-170; (c) Salama O, Chaudhuri RK, Sticher O. (1981) A lignan glycoside from Euphrasia rostkoviana. Phytochemistry, 20, 2603-2604; (d) Yuen MSM, Xue F, Mak TCW, Wong HNC. (1998) On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton. Tetrahedron, 54, 12429-12444; (e) Yang YI, Lee KT, Park HJ, Kim TJ, Choi YS, Shih IeM, Choi JH. (2012) Tectorigenin sensitizes paclitaxel-resistant human ovarian cancer cells through down regulation of the Akt and NFκB pathway. Carcinogenesis, 33, 2488-2498. (a) Jiang CP, Ding H, Shi DH, Wang YR, Li EG, Wu JH. (2012) Pro-apoptotic effects of tectorigenin on human hepatocellular carcinoma HepG2 cells. World Journal of Gastroenterology, 18, 1753-1764; (b) Mischenko NP, Fedoreyev SA, Glazunov VP, Tchernoded GK, Bulgakov VP, Zhuravlev YN. (1999) Anthraquinone production by callus cultures of Rubia cordifolia. Fitoterapia, 70, 552-557.

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Natural Product Communications 2013 Volume 8, Number 10 Contents Original Paper Guaiol - A Naturally Occurring Insecticidal Sesquiterpene Tao Liu, Chun-Juan Wang, Hui-Qin Xie and Qing Mu 3-Oxoabolene and 1-Oxocurcuphenol, Aromatic Bisabolanes from the Sponge Myrmekioderma sp. Afsaneh Yegdaneh, Sumaitt Putchakarn, Supreeya Yuenyongsawad, Alireza Ghannadi and Anuchit Plubrukarn Acanthoic Acid Inhibits Melanogenesis through Tyrosinase Down-regulation and Melanogenic Gene Expression in B16 Melanoma Cells Weon-Jong Yoon, Young-Min Ham, Hun Seok Yoon, Wook-Jae Lee, Nam Ho Lee and Chang-Gu Hyun Cembranoids from the Cultured Soft Coral Sinularia gibberosa Hsiu-Fen Lin, Huey-Jen Su, Nai-Lun Lee and Jui-Hsin Su Major Constituents of Boswellia carteri Resin Exhibit Cyclooxygenase Enzyme Inhibition and Antiproliferative Activity Sami I. Ali, Chuan-Rui Zhang, Amal A. Mohamed, Farouk K. EL-Baz, Ahmad K. Hegazy, Maimona A. Kord and Muraleedharan G. Nair Cucurbitane-type Triterpenes from Citrullus lanatus (Watermelon) Seeds Takashi Kikuchi, Rina Okada, Yu Harada, Kenji Ikushima, Takahiro Yamakawa, Takeshi Yamada and Reiko Tanaka A New Taraxerol Derivative from the Roots of Microcos tomentosa Sutin Kaennakam, Jirapast Sichaem, Suttira Khumkratok, Pongpun Siripong and Santi Tip-pyang Two New Triterpenoids from Gelsemium elegans and Aglaia odorata Bing Liu, Lin Yang, You-Kai Xu, Shang-Gao Liao, Huai-Rong Luo and Zhi Na Inhibition of Tumor Cells Multidrug Resistance by Cucumarioside A2-2, Frondoside А and their Complexes with Cholesterol Ekaterina S. Menchinskaya, Dmitry L. Aminin, Sergey A. Avilov, Aleksandra S. Silchenko, Pelageya V. Andryjashchenko, Vladimir I. Kalinin and Valentin A. Stonik Anticholinesterase and Antioxidant Activities of Fucoxanthin Purified from the Microalga Phaeodactylum tricornutum Arthitaya Kawee-ai, Ampin Kuntiya and Sang Moo Kim Impact of Ploidy Change on Secondary Metabolites and Photochemical Efficiency in Solanum bulbocastanum Immacolata Caruso, Fabrizio Dal Piaz, Nicola Malafronte, Nunziatina De Tommasi, Riccardo Aversano, Cristian Wulff Zottele, Maria-Teresa Scarano and Domenico Carputo Alkaloids from an Endophytic Streptomyces sp. YIM66017 Hao Zhou, Yabin Yang, Jucheng Zhang, Tianfeng Peng, Lixing Zhao, Lihua Xu and Zhongtao Ding Novel Decaturin Alkaloids from the Marine-Derived Fungus Penicillium oxalicum Pei-le Wang, Dan-yi Li, Lei-rui Xie, Xin Wu, Hui-ming Hua and Zhan-lin Li Monanchomycalin C, a New Pentacyclic Guanidine Alkaloid from the Far-Eastern Marine Sponge Monanchora pulchra Ksenya M. Tabakmakher, Vladimir A. Denisenko, Alla G. Guzii, Pavel S. Dmitrenok, Sergey A. Dyshlovoy, Hyi-Seung Lee and Tatyana N. Makarieva Antiinflammatory and Antioxidant Flavonoids from Helichrysum kraussii and H. odoratissimum Flowers Percival B. Legoale, Mahlori J. Mashimbye and Teunis van Ree Antiproliferative Effect of Flavonoids from the Halophyte Vitex rotundifolia on Human Cancer Cells You Ah Kim, Hojun Kim and Youngwan Seo Identification of a Xanthine Oxidase-inhibitory Component from Sophora flavescens using NMR-based Metabolomics Ryuichiro Suzuki, Yuka Hasuike, Moeka Hirabayashi, Tatsuo Fukuda, Yoshihito Okada and Yoshiaki Shirataki Flavone C-Glycosides from Lychnis senno and their Antioxidative Activity Hari Prasad Devkota, Kumiko Fukusako, Koji Ishiguro and Shoji Yahara Anti-oxidative and DNA Protecting Effects of Flavonoids-rich Scutellaria lateriflora Madhukar Lohani, Manuj Ahuja, Manal A Buabeid, Dean Schwartz, Dennis Shannon, Vishnu Suppiramaniam, Barbara Kemppainen and Muralikrishnan Dhanasekaran Polyphenolic Сompounds from Сallus Сultures of Iris pseudacorus Darya V. Tarbeeva, Sergey A. Fedoreyev, Marina V. Veselova, Anatoliy I. Kalinovskiy, Ludmila D. Seletskaya, Tamara I. Mazurok and Victor P. Bulgakov Pterocarpans from the Root Bark of Aeschynomene fascicularis Edgar Caamal-Fuentes, Rosa Moo-Puc, Luis W. Torres-Tapia and Sergio R. Peraza-Sanchez Cytotoxic Constituents of Pachyrhizus tuberosus from Peruvian Amazon Olga Leuner, Jaroslav Havlik, Milos Budesinsky, Vladimir Vrkoslav, Jessica Chu, Tracey D. Bradshaw, Jana Hummelova, Petra Miksatkova, Oldrich Lapcik, Irena Valterova and Ladislav Kokoska (+)-Rumphiin and Polyalthurea, New Compounds from the Stems of Polyalthia rumphii Tian-Shan Wang, You-Ping Luo, Jing Wang, Meng-Xiong He, Ming-Guo Zhong, Ying Li and Xiao-Ping Song Citriquinones A and B, New Benzoquinones from Penicillium citrinum P. K. Vinitha Ranji, S. Chandrani Wijeyaratne, K. Hector Jayawardana and G. M. Kamal B. Gunaherath Potent Microbial and Tyrosinase Inhibitors from Stem Bark of Bauhinia rufescens (Fabaceae) Aminu Muhammad and Hasnah Mohd Sirat Continued inside backcover

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