Enhanced Production of Resveratrol, Piceatannol, Arachidin-1, and Arachidin-3 in Hairy Root Cultures of Peanut Co-treated with Methyl Jasmonate and Cyclodextrin

Yang, Tingting; Fang, Lingling; Nopo-Olazabal, Cesar; Condori, Jose; Ñopo-Olazabal, Luis; Balmaceda, Catalina; Medina-Bolívar, Fabricio

doi:10.1021/jf5050266

Cited by 64 publications

(55 citation statements)

References 48 publications

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“…When CD is not added in the hairy root cultures, only limited amounts of resveratrol and stilbenoids are detected in the medium. These observations were reported previously when peanut hairy roots were treated with NaOAc, H 2 O 2 , or MeJA alone as elicitors (Yang et al, 2015a). Importantly, when resveratrol was added in nonelicited peanut hairy root cultures, 47% and 97% reductions of the initial resveratrol concentration in the culture medium were observed after 0.5 and 1 h of coincubation, respectively (Yang et al, 2015a).…”

Section: Metabolism Of Prenylated Stilbenoids In Peanut Hairy Root Cusupporting

confidence: 83%

“…As expected for peanut phytoalexins, nonprenylated and prenylated stilbenoids were only present in the peanut hairy root cultures after elicitor treatment (Medina-Bolivar et al, 2007;Yang et al, 2015a). To study the metabolic origin of the prenyl moiety of the prenylated stilbenoids, mevastatin or clomazone was added to 9-d peanut hairy root cultures cotreated with 100 mM MeJA and 9 g L 21 CD.…”

Section: Effects Of Metabolic Inhibitors On the Yield Of Prenylated Smentioning

confidence: 74%

“…S6). Based on previous observations regarding the loss of resveratrol accumulation in medium of nonelicited peanut hairy root cultures (Yang et al, 2015a), we speculated that resveratrol could be metabolized by one or multiple enzymatic mechanisms in peanut hairy roots.…”

Section: Degradation Of Exogenous Resveratrol In Peanut Hairy Rootsmentioning

confidence: 94%

“…Our previous work had indicated that hairy roots of peanut have the capability to produce and secrete resveratrol (3,5,49-trihydroxy-stilbene), piceatannol (3,5,39,49-tetrahydroxy-stilbene), and their prenylated analogs, arachidin-3 and arachidin-1, in the medium upon cotreatment with MeJA and CD as elicitors (Yang et al, 2015a). In this study, we have identified arachidin-2 in the ethyl acetate extract of the culture medium by comparing with the HPLC retention time, characteristic UV spectrum (l max = 323 nm; Fig.…”

Section: Purification and Structural Identification Of A New Prenylatmentioning

confidence: 99%

“…In order to elucidate the biosynthesis of peanut prenylated stilbenoids, we established hairy root cultures of peanut (Condori et al, 2010) and recently demonstrated that a sustainable production of the prenylated stilbenoids arachidin-1 and arachidin-3 can be achieved upon cotreatment of these cultures with methyl jasmonate (MeJA) and cyclodextrin (CD; Yang et al, 2015a). In this study, we took advantage of this bioproduction system and identified arachidin-2 and a new prenylated stilbenoid, named arachidin-5, as the prenylated products of the hairy root microsomal fraction using resveratrol and piceatannol as substrates, respectively.…”

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confidence: 99%

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A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway

et al. 2016

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Prenylated stilbenoids synthesized in some legumes exhibit plant pathogen defense properties and pharmacological activities with potential benefits to human health. Despite their importance, the biosynthetic pathways of these compounds remain to be elucidated. Peanut (Arachis hypogaea) hairy root cultures produce a diverse array of prenylated stilbenoids upon treatment with elicitors. Using metabolic inhibitors of the plastidic and cytosolic isoprenoid biosynthetic pathways, we demonstrated that the prenyl moiety on the prenylated stilbenoids derives from a plastidic pathway. We further characterized, to our knowledge for the first time, a membrane-bound stilbenoid-specific prenyltransferase activity from the microsomal fraction of peanut hairy roots. This microsomal fraction-derived resveratrol 4-dimethylallyl transferase utilizes 3,3-dimethylallyl pyrophosphate as a prenyl donor and prenylates resveratrol to form arachidin-2. It also prenylates pinosylvin to chiricanine A and piceatannol to arachidin-5, a prenylated stilbenoid identified, to our knowledge, for the first time in this study. This prenyltransferase exhibits strict substrate specificity for stilbenoids and does not prenylate flavanone, flavone, or isoflavone backbones, even though it shares several common features with flavonoid-specific prenyltransferases.

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Section: Metabolism Of Prenylated Stilbenoids In Peanut Hairy Root Cusupporting

confidence: 83%

Section: Effects Of Metabolic Inhibitors On the Yield Of Prenylated Smentioning

confidence: 74%

Section: Degradation Of Exogenous Resveratrol In Peanut Hairy Rootsmentioning

confidence: 94%

Section: Purification and Structural Identification Of A New Prenylatmentioning

confidence: 99%

mentioning

confidence: 99%

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A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway

et al. 2016

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Regioselective Hydroxylation of Stilbenes by Engineered Cytochrome P450 from Thermobifida fusca YX

et al. 2017

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Since the past decades, the plant stilbenoid resveratrol has gained significant attention of the general public as well as the research community due to its versatile medicinal properties. Apart from resveratrol, there is also an increasing interest in other plant stilbenoids because of their different potential biological activities. In order to meet the increasing demand for stilbenoids, alternative and sustainable approaches for their production are needed. We identified the cytochrome P450 monooxygenase 154E1 from Thermobifida fusca YX (CYP154E1) which enables the synthesis of (E)‐4,4′‐dihydroxystilbene via direct double hydroxylation of (E)‐stilbene. The construction of a triple mutant led to a more than six‐fold increased catalytic efficiency compared to the wild type enzyme. CYP154E1 and variants thereof accepted not only (E)‐stilbene but also possessed remarkable activity towards ortho‐ and meta‐substituted hydroxystilbenes leading to resveratrol, (E)‐2,4′‐dihydroxystilbene, (E)‐2,4′,5‐trihydroxystilbene and (E)‐3,4′‐dihydroxystilbene. The combination of protein engineering and the use of methyl‐β‐cyclodextrin as substrate solubilizing agent resulted in product titers of up to 4.2 g L−1 and enzyme total turnover numbers (TTN) of up to 20,000.magnified image

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Elicitation: A biotechnological tool for enhanced production of secondary metabolites in hairy root cultures

Halder

Sarkar

Jha

2019

Engineering in Life Sciences

237

116

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Elicitation is a possible aid to overcome various difficulties associated with the large‐scale production of most commercially important bioactive secondary metabolites from wild and cultivated plants, undifferentiated or differentiated cultures. Secondary metabolite accumulation in vitro or their efflux in culture medium has been elicited in the undifferentiated or differentiated tissue cultures of several plant species by the application of a low concentration of biotic and abiotic elicitors in the last three decades. Hairy root cultures are preferred for the application of elicitation due to their genetic and biosynthetic stability, high growth rate in growth regulator‐free media, and production consistence in response to elicitor treatment. Elicitors act as signal, recognized by elicitor‐specific receptors on the plant cell membrane and stimulate defense responses during elicitation resulting in increased synthesis and accumulation of secondary metabolites. Optimization of various parameters, such as elicitor type, concentration, duration of exposure, and treatment schedule is essential for the effectiveness of the elicitation strategies. Combined application of different elicitors, integration of precursor feeding, or replenishment of medium or in situ product recovery from the roots/liquid medium with the elicitor treatment have showed improved accumulation of secondary metabolites due to their synergistic effect. This is a comprehensive review about the progress in the elicitation approach to hairy root cultures from 2010 to 2019 and the information provided is valuable and will be of interest for scientists working in this area of plant biotechnology.

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Enhanced Production of Resveratrol, Piceatannol, Arachidin-1, and Arachidin-3 in Hairy Root Cultures of Peanut Co-treated with Methyl Jasmonate and Cyclodextrin

Cited by 64 publications

References 48 publications

A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway

A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway

Regioselective Hydroxylation of Stilbenes by Engineered Cytochrome P450 from Thermobifida fusca YX

Elicitation: A biotechnological tool for enhanced production of secondary metabolites in hairy root cultures

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