Composition and location of phytoecdysteroids in Ajuga reptans in vivo and in vitro cultures

Tomás, Jaime Prohens; Camps, Francisco; Claveria, Elisabet; Coll, Josep Pujol i; Melé, Enric; Messeguer, Joaquima

doi:10.1016/0031-9422(92)83112-c

Cited by 47 publications

(20 citation statements)

References 18 publications

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“…In later callus cultivation studies, the yield of 20E was increased from 0.1% to 0.2% and turkesterone decreased from 0.032% to 0.004% when treated with an 8 mM dose of the mutagen N-nitroso-N-methylurea (Zakirova et al 2000;Zakirova and Yakubova 2002). Although callus cultures of a related plant, Ajuga reptans, did not produce phytoecdysteroids, hairy roots transformed with Agrobacterium rhizogenes accumulated 20E up to 0.12% on a dry weight basis; 4 times higher than the content of the plant's roots in vivo (Tomas et al 1992;Matsumoto and Tanaka 1991). Hairy root cultures have not been reported in A. turkestanica.…”

Section: Introductionmentioning

confidence: 93%

In vitro production of metabolism-enhancing phytoecdysteroids from Ajuga turkestanica

Cheng

Yousef

Grace

et al. 2008

Plant Cell Tiss Organ Cult

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In order to develop a sustainable source of metabolism-enhancing phytoecdysteroids, cell suspension and hairy root cultures were established from shoot cultures of wild-harvested Ajuga turkestanica, a medicinal plant indigenous to Uzbekistan. Precursors of phytoecdysteroids (acetate, mevalonic acid cholesterol) or methyl jasmonate (an elicitor) were added to subculture media to increase phytoecdysteroid accumulation. In cell suspension cultures, 20-hydroxyecdysone (20E) content increased 3-or 2-fold with the addition of 125 or 250 lM methyl jasmonate, respectively, compared to unelicited cultures. Precursor addition, however, did not provoke phytoecdysteroid accumulation. In hairy root cultures, addition of sodium acetate, mevalonic acid, and methyl jasmonate, but not cholesterol, increased phytoecdysteroid content compared to unelicited cultures. Hairy root cultures treated with 150 mg l -1 sodium acetate, or 15 or 150 mg l -1 mevalonic acid, increased 20E content approximately 2-fold to 19.9, 20.4 or 21.7 lg mg -1 , respectively, compared to control (10.5 lg mg -1 ). Older hairy root cultures, extracted after the seventh subculture cycle, also showed increases in 20E content (24.8 lg mg -1 ), turkesterone (0.9 lg mg -1 ) and cyasterone (8.1 lg mg -1 ) compared to control cultures maintained for a shorter duration of four subculture cycles. Doses of 10 or 20 lg ml -1 hairy root extract increased protein synthesis by 25.7% or 31.1%, respectively, in a C2C12 mouse skeletal cell line. These results suggest that sustainable production of metabolically active phytoecdysteroid can be achieved through hairy root culture systems. Keywords 20-Hydroxyecdysone Á Cell suspension culture Á Cyasterone Á Hairy root Á Methyl jasmonate Á Mevalonic acid Á Turkesterone Abbreviations 20E 20-Hydroxyecdysone CC Column chromatography CD 3 OD Deuterated methanol DAD Diode array detector DMEM Dulbecco's modified eagle's media DPM Decays per minute DW Dry weight ESI-MS Electrospray ionization-mass spectroscopy FW Fresh weight HPLC High performance liquid chromatography Electronic supplementary material The online version of this article (

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Section: Introductionmentioning

confidence: 93%

In vitro production of metabolism-enhancing phytoecdysteroids from Ajuga turkestanica

Cheng

Yousef

Grace

et al. 2008

Plant Cell Tiss Organ Cult

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“…However, the occurrence of steroidal lactones is not completely restricted to Solanaceae, whereas these compounds have also been found in soft coral from Minabea sp. [3], and in plants such as Tacca plantaginea [4] and T. chantrieri [5] (Taccaceae), Cassia siamea (Leguminosae) [6], Ajuga parviflora [7], A. reptans [8], and A. bracteosa (Lamiaceae) [9], and Eucalyptus globulus (Myrtaceae) [10].…”

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confidence: 99%

Withanolides from Aureliana fasciculata var. fasciculata

Almeida-Lafetá

Ferreira

Emerenciano

et al. 2010

Helvetica Chimica Acta

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In the first phytochemical study of the Aureliana genus (Solanaceae), two new withanolides, 1 and 2, together with two known sterols, were isolated from the MeOH extract of the leaves of Aureliana fasciculata var. fasciculata. The structures were established as (4S,22R)-16a-acetoxy-5b,6b-epoxy-4b,17a-dihydroxy-1-oxowitha-2,24-dienolide (aurelianolide A) and (4S,22R)-16a-acetoxy-4b,17a-dihydroxy-1-oxowitha-2,5,24-trienolide (aurelianolide B). The new compounds possessed the unusual 16a,17a-dioxygenated group and were fully characterized by spectroscopic techniques, including 1 H-and Introduction. -The withasteroids comprise a group of naturally occurring C 28 -steroids characterized by an unaltered or a modified ergostane skeleton with a lactone or potential lactone ring in the C 9 side chain [1]. The most abundant type is designated usually as withanolide, and these compounds possess an a,b-unsaturated d-lactone ring in the side chain of the molecule. These steroid derivatives are frequently polyoxygenated, and biogenetic transformations can produce highly modified structures, both in the steroid nucleus and in the side chain, such as physalins, withaphysalins, acnistins, withanolides, ixocarpalactones, and perulactones [2]. To date, over 400 withasteroids have been reported which are restricted in distribution to the plant family Solanaceae occurring primarily in ca. 20 genera [1] [2]. However, the occurrence of steroidal lactones is not completely restricted to Solanaceae, whereas these compounds have also been found in soft coral from Minabea sp.

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“…It is to be expected that different portions of the plant of each species would differ somewhat both quantitatively and qualitatively in the levels and profiles of ecdysteroids present. Thus, marked differences are often observed between the ecdysteroid levels and profiles of over-and underground portions of the same species (e.g., in Ajuga reptans, Tomás et al, 1992; and Cyanotis longifolia, see Crouzet et al, pages, this issue). Ecdysteroid levels in Silene species also vary between plant parts and fluctuate during development (Zibareva and Yeryomina, 1996;Zibareva, 2000).…”

Section: Discussionmentioning

confidence: 96%

The phytoecdysteroid profiles of 7 species of Silene (Caryophyllaceae)

Zibareva

Yeriomina

Munkhjargal

et al. 2009

Arch Insect Biochem Physiol

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The phytoecdysteroid profiles of extracts of aerial parts of flowering plants of 7 ecdysteroid-containing species in the genus Silene (Caryophyllaceae; S. fridvaldszkyana Hampe, S. gigantea L., S. graminifolia Otth, S. mellifera Boiss. & Reuter, S. repens Patr., S. schmuckeri Wettst., and S. sendtneri Boiss.) have been examined and identified by HPLC and, in the case of two new compounds, by mass spectrometry and NMR. S. frivaldszkyana was found to contain predominantly 20-hydroxyecdysone (20E), with smaller amounts of 2-deoxyecdysone (2dE), 2-deoxy-20-hydroxyecdysone (2d20E), polypodine B (polB), integristerone A (IntA), 26-hydroxypolypodine B (26polB), and 20,26-dihydroxyecdysone (20,26E). Additionally, a new minor ecdysteroid, 26-hydroxyintegristerone A, has been identified from this species. S. gigantea contains 3 major ecdysteroids (2dE, 2d20E, and 20E) and much smaller amounts of intA and 2-deoxy-20-hydroxyecdysone 25-beta-D-glucoside, which is a new ecdysteroid. Ecdysteroids in the other 5 species have been identified by co-chromatography with reference compounds on RP- and NP-HPLC systems. There is considerable variability with regard to ecdysteroid profiles within the genus Silene. The chemotaxonomic value of ecdysteroid profiles within the genus Silene is discussed.

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Composition and location of phytoecdysteroids in Ajuga reptans in vivo and in vitro cultures

Cited by 47 publications

References 18 publications

In vitro production of metabolism-enhancing phytoecdysteroids from Ajuga turkestanica

In vitro production of metabolism-enhancing phytoecdysteroids from Ajuga turkestanica

Withanolides from Aureliana fasciculata var. fasciculata

The phytoecdysteroid profiles of 7 species of Silene (Caryophyllaceae)

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