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Metabolite Profiling of Violet, White and Pink Flowers Revealing Flavonoids

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Metabolite Profiling of Violet, White and Pink Flowers Revealing Flavonoids J Biosci (2021)46:3 Ó Indian Academy of Sciences DOI: 10.1007/s12038-020-00125-3 (0123456789().,-volV)(0123456789().,-volV) Metabolite profiling of violet, white and pink flowers revealing flavonoids composition patterns in Rhododendron pulchrum Sweet 1 1 1 1 SHUZHEN WANG ,SHIYING HUANG ,JIE YANG ,ZHILIANG LI , 1 1 2 MINGJU ZHANG ,YUANPING FANG ,QIAOFENG YANG * and 1 WEIBIN JIN * 1Hubei Key Laboratory of Economic Forest Germplasm Improvement and Resources Comprehensive Utilization, Hubei Collaborative Innovation Center for the Characteristic Resources Exploitation of Dabie Mountains, Hubei Zhongke Research Institute of Industrial Technology, and College of Life Science, Huanggang Normal University, Huanggang 438000, Hubei Province, China 2College of Food and Bioengineering, Henan University of Animal Husbandry and Ecomomy, Zhengzhou 450000, Henan Province, China *Corresponding authors (Emails, [email protected]; [email protected]) MS received 17 June 2020; accepted 27 November 2020 Flower color is the major characteristics and critical breeding program for most Rhododendron species. However, little is known about their coloration mechanism and color inheritance. In this study, petal pigment constituents of three Rhododendron pulchrum Sweet cultivars with different colors were clarified based on LC- ESI-MS/MS method. Using a broad-targeted metabolomic approach, a total of 149 flavonoids and their glycosylated or methylated derivatives were identified, including 18 anthocyanins (Pg, Cy, Dp, Pn, Pt, and Mv) and 32 flavonols (mainly kaempferol 3-O-glycosides and quercetin 3-O-glycosides). Moreover, anthocyanins were mainly represented by anthocyanidin-3-O-glycosides (glucoside, rutinoside, galactoside, and di-glyco- sides). Flavone and C-glycosylated flavone were major second metabolites responsible for the difference among three different R. pulchrum cultivars. The accumulation of total flavonoids displayed a clear phenotypic variation: cultivars ‘zihe’ and ‘fenhe’ were clustered together, while ‘baihe’ was clustered alone in the HCA analysis. The composition and content of anthocyanins were more complex in colored flowers (‘zehe’ and ‘fenhe’) than in white flower (‘baihe’). This study further enhanced our understanding on the flavonoids profile of flower coloration and will provide biochemical basis for further genetic breeding in Rhododendron species. Keywords. Anthocyanin; flower color; genetic breeding; metabolomics; Rhododendron pulchrum Sweet 1. Introduction flavonoids, carotenoids, and betalains (Liu et al. 2016). Flavonoids, belonging to the class of phenyl- Flower color is one of the most important breeding propanoids, provide a wide range of colors ranging program objectives in ornamental plants (Liu et al. from pale-yellow to blue (Hang et al. 2011). Flavo- 2016). Many factors, such as pigment composition, pH, noids are widely distributed in many flowers, leaves, cell shape, and co-pigmentation, are related to petal seeds and fruits, which also possess healthy benefits, colors (Hang et al. 2011; Sinopoli et al. 2019). Among such as protecting against certain cancers and inflam- these factors, pigment composition is the most impor- matory disease (Sinopoli et al. 2019; Herna´ndez et al. tant, as quality trait of flower color is largely deter- 2009). Depending on their structures, flavonoids could mined by metabolic composition, especially be classified into six types, including chalcones, fla- Electronic supplementary material: The online version of this article (https://doi.org/10.1007/s12038-020-00125-3) contains supplementary material, which is available to authorized users. http://www.ias.ac.in/jbiosci 3 Page 2 of 10 Shuzhen Wang et al. vones, flavonols, flavanones, flavan-3-ols, and antho- identified in Rhododendron species (Park et al. 2018; cyanins (Veitch and Grayer 2011; Dong et al. 2014; Du et al. 2018). The red petals contain 2–4 major Tanaka et al. 2008). anthocyanins, as cyanidin 3-galactoside and cyanidin Anthocyanins biosynthesis is an important part of 3-arabinoside are common to Rhododendron simsii flavonoid branch within the phenylpropanoid pathway with red flowers (Park et al. 2018). However, pigments (Aderson et al. 2015; Dong et al. 2019; Kim et al. composition in petals of azalea species is limited. 2017; Rothenberg et al. 2019; Wang et al. 2018a). As Metabolomics aims to analyze all metabolites in a anthocyanidin glycosides, anthocyanins play crucial biological sample comprehensively, and shows great roles in protecting plant against stress conditions, oxi- potential in elucidating plant metabolic processes. In dant damage, and infection by pathogens (Rothenberg this study, the pigment compositions of three R. pul- et al. 2019). In particular, six anthocyanidins are chrum cultivars with different colors were analyzed common in vascular plants, including pelargonidin using LC-ESI-MS/MS, aiming at clarifying the features (Pg), peonidin (Pn), petunidin (Pt), cyanidin (Cy), of pigment composition, as well as providing basis for malvidin (Mv), and delphinidin (Dp) (Zhang et al. genetic improvement of flower color in R. pulchrum 2014). Moreover, anthocyanins derivatives Dp, Pt, and and other Rhododendron species. Mv are source of violet and dark colors, whereas the derivatives Cy and Pg are main pigments in bright-red- color fruits (Cho et al. 2016). In particular, Mv 3-O- 2. Materials and methods arabinoside-5-O-glucosed and DP 3-O-arabinoside-5- O-glucosed play important roles in violet coloration 2.1 Plant materials (Park et al. 2018). Up to now, more than 635 antho- cyanins and 23 anthocyanidins have been well identi- R. pulchrum cultivars ‘fenhe’, ‘baihe’, and ‘zihe’ with fied in fruits, vegetables, and flowers (Castan˜eda et al. pink, white, and violet flowers were sampled from 2009). Huanggang Normal University Botanical Garden The genus Rhododendron, including approximately (30°1601200N, 114°3101200E, 200–248 m) (figure 1). 1000 species and most unique to China, was introduced Colors of R. pulchrum petals were evaluated according into Europe at the end of the 18th century (Popescu and to the Royal Horticultural Society Colour Kopp 2013; Wang et al. 2017). A great many of Chart (RHSCC) under natural light. For each specific Rhododendron species, such as R. simsii, R. molle, and color, petals were harvested randomly from six indi- R. fortunei, have valuable horticultural and medicinal viduals and pooled for each biological replicate. All values, in addition to the beautiful vegetative forms and samples were harvested on the same day, immediately bright-colored flowers (Wang et al. 2017). As most placed in liquid nitrogen and stored at -70°C until valuable and largest genera of woody plants, Rhodo- vacuum freeze-drying. dendron was first used as ornamental plants in Eng- land, and then developed in Belgium and Holland. In particular, various flower colors were observed in 2.2 Chemicals Rhododendron, such as red, red-purple, purple-violet, purple, purplish pink, white, yellow, and pink, which All the chemicals were of analytical reagent grade. show high aesthetic and economic values (Hang et al. HPLCt-grade methanol, acetonitrile, and acetic acid 2011). In addition, blotches, stripes, and even white were purchased from Merck Company (Germany). The margin were observed in petals of some Rhododendron water was doubly purified with a MilliQ ULTRA water species (Du et al. 2018; Mizuta et al. 2009). purification system (Millipore, Bedford, MA). Anthocyanin and flavonols, such as Cy, Dp, Mv and Authentic standards were brought from ANPEL their glycoside derivatives, are also major pigments in (Shanghai, China) and Sigma-Aldrich (USA). Stan- the genus Rhododendron, which have been isolated dards stock solutions were prepared in methanol or using paper chromatography, thin-layer chromatogra- methanol-dimethyl sulfoxide (DMSO, 50:50, v/v), and phy (TLC), and high-performance liquid chromatog- stored at -20°C in darkness. The internal standard was raphy (HPLC) (Sinopoli et al. 2019;Duet al. 2018). combined standard solutions of flavonoids, which were Moreover, their structures were elucidated by 1H-NMR prepared just before use by mixing individual stock spectroscopic (Sinopoli et al. 2019). Quercetin, myr- solutions and diluted with 70% aqueous methanol. icetin, mearnsetin, kaempferol, isorhamnetin, dios- Quality control samples (QC) were prepared from a metin and their glycoside derivatives all have been combined sample by mixing all sample extracts, then Metabolite profiling of Rhododendron pulchrum Sweet Page 3 of 10 3 Figure 1. R. pulchrum flower tissues sampled for metabolomics study of flavonoids: (A) cultivar ‘zihe’, violet flower; (B) cultivar ‘fenhe’, pink flower; (C) cultivar ‘baihe’, white flower. were divided into three equal parts (mix 1, mix 2, and 0 min, 5:95 V/V at 10.0 min, 5:95 V/V at 11.0 min, mix 3). During the experiments, QC were injected 95:5 V/V at 11.1 min, and 95:5 V/V at 15.0 min). The every five samples to assess the repeatability. effluent was alternatively connected to an ESI-triple quadrupole-linear ion trap (Q TRAP)-MS. The ESI source operation parameters were as follows: ion 2.3 Sample preparation, extraction, and LC-MS source, turbo spray; source temperature, 550°C; ion analysis spray voltage (IS) 5500 V; ion source gas I (GSI), 55 psi; gas II (GSII), 60 psi; curtain gas (CUR), 25.0 psi; The freeze-dried petals were ground using a mixer mill and the collision gas (CAD) was high. Instrument (MM 400, Retsch) with a zirconia beads for 1.5 min at tuning and mass calibration were performed with 10 30 Hz. Then,
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