Serratula tinctoria L. (Dyer’s Savory): In Vitro Culture and the Production of Ecdysteroids and Other Secondary Metabolites

Corio‐Costet, Marie‐France; Chapuis, L.; Delbecque, Jean‐Paul

doi:10.1007/978-3-662-08618-6_23

Cited by 11 publications

(6 citation statements)

References 27 publications

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“…A second question of interest concerns the regulation of ecdysteroid production. It has been repeatedly observed that cell suspensions or callus cultures from ecdysteroid‐producing species produce at best very small amounts of ecdysteroids, while tissue and hairy‐root cultures produce much larger amounts [23,39–41]. This means that tissue organization is required for adequate productivity.…”

Section: Discussionmentioning

confidence: 99%

Biotransformations of putative phytoecdysteroid biosynthetic precursors in tissue cultures of Polypodium vulgare

Reixach

Lafont

Camps

et al. 1999

European Journal of Biochemistry

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Incubation of calli and prothalli of Polypodium vulgare with different tritium-labelled ecdysteroids has led to modification of some previous assumptions about the biosynthesis of ecdysteroids in plants. Thus,-hydroxyecdysone was transformed efficiently in both tissues into 20-hydroxyecdysone (20E), but no 25-deoxyecdysteroids such as pterosterone and inokosterone were formed. Likewise, incubation of 2-deoxyecdysone (2dE) produced exclusively ecdysone (E) and 20E, indicating a high 2-hydroxylase activity in both tissues, despite calli not producing phytoecdysteroids. This 2-hydroxylation was also evident in the transformation of 2,22-dideoxyecdysone (2,22dE) into 22-deoxyecdysone (22dE). Different ecdysteroids that do not occur in P. vulgare were formed in the incubation of 3-dehydro-2,22,25-trideoxyecdysone (3D2,22,25dE) by 3a-reduction and 3b-reduction and 25-hydroxylation processes. The fact that 22,25-dideoxyecdysone and 22dE were the only 2-hydroxylated products formed in this case suggests that only compounds bearing a 3b-hydroxyl group are substrates for the 2-hydroxylase. Surprisingly, 22-hydroxylation was never observed with either 2,22dE or 3D2,22,25dE, raising the possibility that it could occur at an early step in the biosynthetic pathway. In this respect, labelled 22R-hydroxycholesterol was efficiently converted into E and 20E, whereas 22S-hydroxycholesterol was not transformed into ecdysteroids, because of its unsuitable configuration at C22. Finally, the conversion of 25-hydroxycholesterol into E and 20E was greatly enhanced after thermal treatment of prothalli which induces the release of previously stored ecdysteroids. Thus, P. vulgare prothalli and calli appear to be particularly suitable models for the study of ecdysteroid biosynthesis and its regulation in plants.Keywords: 20-hydroxyecdysone; fern; hydroxycholesterol derivatives; in vitro cultures; induction.Many plant species produce C 27 ±C 29 ecdysteroids of a wide structural diversity [1±5]. These analogues of insect molting hormone (20-hydroxyecdysone, 20E) are secondary metabolites which are expected to provide some protection to plants against non-adapted phytophagous insect species [6]. Although the presence of such compounds in plants was demonstrated more than 30 years ago, little has been learnt since about their biosynthetic pathway(s), and whether it operates in a sequence that is similar to or different from that in Arthropods is not known.In vivo and in vitro labelling experiments have established that these compounds are biosynthesized from mevalonate via C 27 , C 28 and C 29 phytosterols. Cholesterol has been proved to be the intermediate in the biosynthesis of C 27 phytoecdysteroids in Taxus baccata [7]. In biosynthetic studies with Ajuga reptans roots transformed with Agrobacterium rhizhogenes, 24-methylcholesterol and 24-ethylcholesterol have been proposed as intermediates for the biosynthesis of C 28 and C 29 ecdysteroids, respectively [8]. Adler & Grebenok [9] proposed lathosterol (5a-cholest-7-en-3b-ol) as the logical ...

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Section: Discussionmentioning

confidence: 99%

Biotransformations of putative phytoecdysteroid biosynthetic precursors in tissue cultures of Polypodium vulgare

Reixach

Lafont

Camps

et al. 1999

European Journal of Biochemistry

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“…Supplementation of cultures of this species transformed by Agrobacterium rhizogenes (with a characteristic hairy root phenotype) with the synthetic auxin 2,4-dichlorophenoxy acetic acid (2,4-D) had dosedependent negative effects on their PE contents. Growth of the hairy roots slowed on media containing 0.05-0.5 mg/l of 2,4-D, and addition of 1 mg/l stopped their growth entirely due to tissue necrosis (Corio-Costet et al 1996). Reductions in EC concentrations in hairy roots of another plant species (the European herbaceous plant Ajuga reptans) have also been observed following addition of 0.1 mg/l of natural auxin (indole-3-acetic acid, IAA) to the cultivation medium, despite increases in the roots' growth rate due to increases in the number of root apical meristems (Uozumi et al 1995).…”

Section: Auxinsmentioning

confidence: 98%

Plant ecdysteroids: plant sterols with intriguing distributions, biological effects and relations to plant hormones

Tarkowská

Strnad

2016

Planta

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The present review summarises current knowledge of phytoecdysteroids' biosynthesis, distribution within plants, biological importance and relations to plant hormones. Plant ecdysteroids (phytoecdysteroids) are natural polyhydroxylated compounds that have a four-ringed skeleton, usually composed of either 27 carbon atoms or 28-29 carbon atoms (biosynthetically derived from cholesterol or other plant sterols, respectively). Their physiological roles in plants have not yet been confirmed and their occurrence is not universal. Nevertheless, they are present at high concentrations in various plant species, including commonly consumed vegetables, and have a broad spectrum of pharmacological and medicinal properties in mammals, including hepatoprotective and hypoglycaemic effects, and anabolic effects on skeletal muscle, without androgenic side-effects. Furthermore, phytoecdysteroids can enhance stress resistance by promoting vitality and enhancing physical performance; thus, they are considered adaptogens. This review summarises current knowledge of phytoecdysteroids' biosynthesis, distribution within plants, biological importance and relations to plant hormones.

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“…() also isolated the sterols cholesterol, lathosterol and 2‐methylene‐cholesterol from the roots and hypothesised that these may have a role in the biogenesis of ecdysteroids. Corio‐Costet, Chapuis & Delbecque () isolated both free and esterified 4,4‐Dimethylsterols, 4‐Methylsterols and 4‐Desmethylsterols.…”

Section: Structure and Physiologymentioning

confidence: 99%

“…The plant also contains significant concentrations of the phytoecdysteroids 20-hydroxecdysone, its 2-,3-, and 22-monoacetates, rubrosterone, poststerone, polypodine B (5b, 20dihydroxyecdystone), pterosterone (25-deoxy-20, 24-dihydroxyecdystone) and makisterone C (24-ethyl-20-hydroxyecdystone plus a range of minor compounds) (B athori, Szendrei & Herke 1986;B athori et al 1996Corio-Costet et al 1993;Corio-Costet, Chapuis & Delbecque 1994;Delbecque et al 1995;Rudel et al 1992). The roots contain the highest concentrations of phytoecdysteroids with up to 2% of dry mass (Rudel et al 1992).…”

Section: ( F ) B I O C H E M I C a L D A T Amentioning

confidence: 99%

Biological Flora of the British Isles: Serratula tinctoria

Jefferson

Walker

2017

Journal of Ecology

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Summary This account presents information on all aspects of the biology of Serratula tinctoria L. that are relevant to understanding its ecological characteristics and behaviour. The main topics are presented within the standard framework of the Biological Flora of the British Isles: distribution, habitat, communities, responses to biotic factors, responses to environment, structure and physiology, phenology, floral and seed characters, herbivores and disease, history and conservation. Serratula tinctoria is a gynodioecious perennial forb of open or semi‐shaded habitats including grassland, heath, mire, open woodland and scrub and their ecotones. It is found throughout most of England and Wales but it is very rare in Scotland and absent from Ireland. Serratula tinctoria is found in Europe as far north as southern Sweden and Norway. It is absent from much of the Boreal biogeographical zone, including most of Fennoscandia and northern Poland, Russia and the Baltic States, and from the lowland Mediterranean zone. Serratula tinctoria occurs on soils overlying a wide variety of superficial deposits and sedimentary, metamorphic and igneous rocks, including ultramafic rocks. The pH range of these soils is wide, ranging from acidic to moderately alkaline but with nutrient status classed as oligotrophic, or more rarely mesotrophic. In mire or fen habitats, it occurs in topogenous or soligenous situations with a similar soil water pH range. It is able to tolerate a wide spectrum of soil water‐table conditions, ranging from very dry to flooded. Serratula tinctoria is pollinated by various insects of the orders Hymenoptera, Diptera and Lepidoptera, particularly bumblebees, hoverflies and butterflies. It produces phytoecdysteroids, which mimic a hormone that regulates insect development. The seed has a feathery pappus for wind dispersal and establishment is primarily from seed. However, it has strong dispersal limitation with slow migration rates into restored grasslands of 1 m year−1. The species has a short‐term persistent seed bank. Seedling recruitment is enhanced by disturbance that creates bare ground, increasing light flux and lower cover of bryophytes and litter, and reduced by higher nutrient availability and lack of management. Formerly the source of a yellow dye, S. tinctoria has declined in Britain since at least the late 19th Century primarily due to a combination of drainage, ploughing and agricultural improvement and, conversely, lack of management by cutting and grazing in its grassland, heath and mire habitats. There is evidence that the decline slowed or stabilised between the late‐1980s and the mid‐2000s, in part due to the positive impact of conservation via statutory protection on designated sites and wider measures delivered through agri‐environment schemes.

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Serratula tinctoria L. (Dyer’s Savory): In Vitro Culture and the Production of Ecdysteroids and Other Secondary Metabolites

Cited by 11 publications

References 27 publications

Biotransformations of putative phytoecdysteroid biosynthetic precursors in tissue cultures of Polypodium vulgare

Biotransformations of putative phytoecdysteroid biosynthetic precursors in tissue cultures of Polypodium vulgare

Plant ecdysteroids: plant sterols with intriguing distributions, biological effects and relations to plant hormones

Biological Flora of the British Isles: Serratula tinctoria

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