Phytoecdysteroids from <i>Ajuga macrosperma</i> var. <i>breviflora</i> Roots

Castro, Amaya; Coll, Josep Pujol i; Tandrón, Yudelsy A.; Pant, A.K.; Mathela, C. S.

doi:10.1021/np800131f

Cited by 38 publications

(26 citation statements)

References 14 publications

(16 reference statements)

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“…1). 3,34 For the ecdysteroid extraction, a previously optimized protocol 38 was followed with some modications. 34 In brief, powdered plant material ($500 mg) was extracted rst with 10 ml of methanol (MeOH) two times and then the residue was extracted again with 85% MeOH and both fractions (100% MeOH and 85% MeOH) were mixed and dried.…”

Section: Extraction Of Ecdysteroidsmentioning

confidence: 99%

Effect of pRi T-DNA genes and elicitation on morphology and phytoecdysteroid biosynthesis in Ajuga bracteosa hairy roots

et al. 2017

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The medicinal plant Ajuga bracteosa is a rich source of biologically active and metabolism-enhancing phytoecdysteroids. Transgenic hairy roots from A. bracteosa were obtained by infection with Agrobacterium rhizogenes strains A4, LBA-9402 and ARqua1. The 59 selectively established and rolCpositive hairy root lines increased in size up to 6.6-fold (L42) after one month of in vitro culturing and produced a phytoecdysteroid content ranging from 69.3 to 4449 mg g À1 (L3 and A2, respectively). The clones of these transgenic roots were maintained for successive subcultures on hormone-free medium to obtain a stabilized morphology. Hairy roots displayed four different morphologies: typical hairy root (THR) (59%), callus-like (CM) (17%), thick (TK) (14%) and thin (TN) (10%). The growth rate of the transgenic hairy root lines varied according to their morphology, with CM showing the highest rate (3.93-fold per month). However, THR exhibited the highest phytoecdysteroid content (1538.5 mg g À1 ). Considering the hairy root morphology in relation to the pRi TR-DNA genes, 100% of the hairy root lines harbored the mas1 and ags genes and 90% of CM lines the aux1 gene. Strikingly, the clones with TK morphology were all positive for the TL-and TR-DNA genes. In contrast, 0% of TN clones harbored the aux1 and ags genes, and only 16.7% the mas1 gene. All CM and TK hairy roots were positive for the ags gene, while mas1 was present in all hairy root types except TN. As expected, all the root lines considered in this work were positive for the rol C gene. Eleven hairy root lines displaying a high growth rate and phytoecdysteroid content were elicited with methyl jasmonate (MeJ) and coronatine (Cor). MeJ doubled the phytoecdysteroid content after 14 days of elicitation (8356 mg g À1 in L2) compared with unelicited control hairy roots, and in in vitro-grown untransformed roots the increase was 5.6-fold. a Growth capacity of transgenic clones of different root lines expressed as (harvested FW/inoculum FW) aer 28 days of culture in hormone-free half strength MS medium. Each value is the average of 3 replicates. THR: typical hairy root, CM: callus like morphology, TK: hairy root with thick morphology, TN: hairy root with thin morphology, PE: phytoecdysteroid content.47948 | RSC Adv., 2017, 7, 47945-47953This journal is Fig. 3 HPLC chromatographs showing the elution of phytoecdysteroids. (a) Standard ecdysteroids (100 mg ml À1 of each standard), (b) phytoecdysteroid elution pattern in one of the hairy root extract.This journal is

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Section: Extraction Of Ecdysteroidsmentioning

confidence: 99%

Effect of pRi T-DNA genes and elicitation on morphology and phytoecdysteroid biosynthesis in Ajuga bracteosa hairy roots

et al. 2017

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“…Characteristic components of these genera are neoclerodane diterpenoids, 4,5 representative of an important chemical class with a variety of demonstrated biological activities including cytotoxic, analgesic, and antimicrobial activities. 6–9 The roots of J. columba , T. capillipes , and T. sagittata containing columbin ( 1 ) have been used in folk medicine as analgesic and antipyretic agents. 2 Tinospora sagittata , which is in the Pharmacopeia of the People’s Republic of China , demonstrates anti-inflammatory, analgesic, antibacterial, antiulcer, antitumor, and antistress effects, 10–13 and its roots have been used in traditional medicine to ease sore throats, stop diarrhea, and treat upper respiratory tract infections.…”

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confidence: 99%

Semisynthesis and Kappa-Opioid Receptor Activity of Derivatives of Columbin, a Furanolactone Diterpene

et al. 2017

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Columbin (1) is a furanolactone diterpene isolated from the roots of Jateorhiza and Tinospora species. These species generally grow in Asia and Africa and have been used in folk medicine for their apparent analgesic and antipyretic activities. Columbin (1) is of particular interest due to its structural similarity to the known kappa opioid receptor (KOR) agonist salvinorin A. Given that the KOR is of interest in the study of many serious diseases, such as anxiety, depression, and drug addiction, obtaining natural or semisynthetic molecules with KOR activity recently has gained much interest. For this reason, in the present study, derivatives of 1 were designed and synthesized using known structure-activity relationships of salvinorin A at KORs. The structures of the columbin analogues prepared were elucidated by NMR spectroscopy and mass spectroscopy and their KOR activity was investigated in vitro by inhibition of forskolin-induced cAMP accumulation. Slight improvements in KOR activity were observed in columbin derivatives over their parent compound. However, despite the structural similarities to salvinorin A, neither columbin (1) nor its derivatives were potent KOR ligands. This work represents not only the first evaluation of columbin (1) at the KOR but also one of the first works to explore synthetic strategies that are tolerated on the columbin core.

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“…Similarly, larvae of the greenhouse whitefly ( Trialeurodes vaporariorum ) exhibited 100% mortality when fed on Ajuga reptans plants. High levels of the three major phytoecdysteroids, 20-hydroxyecdysone (ecdysterone), makisterone A and cyasterone, have been found in several plants, including Ajuga [ 4 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ], quinoa and spinach [ 4 , 27 ]. An extract of 20-hydroxyecdysone and cyasterone from Ajuga iva L. showed high activity against Oligonychus perseae [ 28 , 29 ]; a dose of 5 μg/mL of pure extracted A. iva ecdysterone significantly reduced fecundity, fertility and survival of this pest, while commercial 20-hydroxyecdysone at the same dose had lesser effects [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

“…Clerodanes (diterpenoids) are a large group of C20 terpene compounds derived from geranylgeranyl diphosphate and biosynthesized through the deoxyxylulose phosphate pathway in the cytoplasm, mostly in the leaves and stems of the Lamiaceae and Asteraceae families [ 31 ]. Clerodin was originally isolated from Clerodendrum infortunatum (Lamiaceae), and has potential as a natural pesticide due to its insect repellent activities [ 20 , 32 , 33 , 34 ]. Koul [ 33 ] showed that the most active compounds, dihydroclerodin and clerodin hemiacetal from Caryopteris divaricata , exhibit 100% antifeedant activity at 50 ppm.…”

Section: Introductionmentioning

confidence: 99%

Activity of Ajuga iva Extracts Against the African Cotton Leafworm Spodoptera littoralis

Taha-Salaime

Lebedev

Abo-Nassar

et al. 2020

Insects

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Control of the crop pest African cotton leafworm, Spodoptera littoralis (Boisduval), by chemical insecticides has led to serious resistance problems. Ajuga plants contain phytoecdysteroids (arthropod steroid hormone analogs regulating metamorphosis) and clerodanes (diterpenoids exhibiting antifeedant activity). We analyzed these compounds in leaf extracts of the Israeli Ajuga iva L. by liquid chromatography time-of-flight mass spectrometry (LC-TOF-MS) and thin-layer chromatography (TLC), and their efficiency at reducing S.littoralis fitness. First and third instars of S. littoralis were fed castor bean leaves (Ricinus communis) smeared with an aqueous suspension of dried methanolic crude extract of A. iva phytoecdysteroids and clerodanes. Mortality, larval weight gain, relative growth rate and survival were compared to feeding on control leaves. We used ‘4’,6-diamidino-2-phenylindole (DAPI, a fluorescent stain) and phalloidin staining to localize A. iva crude leaf extract activity in the insect gut. Ajuga iva crude leaf extract (50, 100 and 250 µg/µL) significantly increased mortality of first-instar S. littoralis (36%, 70%, and 87%, respectively) compared to controls (6%). Third-instar larval weight gain decreased significantly (by 52%, 44% and 30%, respectively), as did relative growth rate (−0.05 g/g per day compared to the relevant controls), ultimately resulting in few survivors. Crude leaf extract (250 µg/µL) reduced gut size, with relocation of nuclei and abnormal actin-filament organization. Ajug iva extract has potential for alternative, environmentally safe insect-pest control.

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Phytoecdysteroids from Ajuga macrosperma var. breviflora Roots

Cited by 38 publications

References 14 publications

Effect of pRi T-DNA genes and elicitation on morphology and phytoecdysteroid biosynthesis in Ajuga bracteosa hairy roots

Effect of pRi T-DNA genes and elicitation on morphology and phytoecdysteroid biosynthesis in Ajuga bracteosa hairy roots

Semisynthesis and Kappa-Opioid Receptor Activity of Derivatives of Columbin, a Furanolactone Diterpene

Activity of Ajuga iva Extracts Against the African Cotton Leafworm Spodoptera littoralis

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