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Jasmonates promote enhanced production of bioactive caffeoylquinic acid derivative in Eclipta prostrata (L.) L. hairy roots.

ABSTRACT: Eclipta prostrata (L.) L. is widely used in traditional medicine for treatment of hepatitis, poisoning from snake bites and viral infections. Pharmacological studies confirmed its antioxidant, anti-inflammatory and anticancer activities. The efficacy of E. prostrata (L.) L. extracts has been correlated to phenylpropanoids such as flavonoids, coumestans and caffeoylquinic acid derivatives. In this work, the production of wedelolactone, demethylwedelolactone and 3,5-di-O-caffeoylquinic acid (3,5-diCQA) in hairy root cultures of E. prostrata (L.) L. C19 clone was increased after addition of eliciting agents jasmonic acid (JA) or methyl jasmonate (MeJA) at multiple concentrations. Cultures elicited with 100 μM of JA saw a 5.2 fold increase in wedelolactone (from 0.72 to 3.72 mg/g d.w.), a 1.6 fold increase in demethylwedelolactone (from 5.54 to 9.04 mg/g d.w.) and a 2.47 fold increase in 3,5-diCQA (from 18.08 to 44.71 mg/g d.w.). Obtained data validate the potential of E. prostrata (L.) L. hairy root cultures as a production system of wedelolactone, demethylwedelolactone and especially 3,5-diCQA, which has recently been reported to possess activity against coronavirus disease (Covid-19) by in silico computational studies.

Supplementary information

The online version contains supplementary material available at 10.1007/s11240-021-02201-4.

SUBMITTER: Maciel G

PROVIDER: S-EPMC8606271 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Biosynthetic studies through feeding experiments in <i>Eclipta prostrata</i> (L.) L. hairy roots.

Project description:Eclipta prostrata (L.) L. is a medicinal plant of the Asteraceae family, and several extracts and isolated compounds of E. prostrata (L.) L. showed a wide range of biological activities such as antimicrobial, anticancer, hepatoprotective, neuroprotective, hair growth promoting activities, and more recently against covid-19. Eclipta prostrata (L.) L. hairy roots produce wedelolactone (WL), demethylwedelolactone (DWL) and 3,5-di-O-caffeoylquinic acid (3,5-diCQA), and there is no data in literature regarding biosynthetic pathways are involved. To verify the biosynthetic route, feeding experiments were carried out using sodium [2-13C]acetate, [3-13C]dl-phenylalanine, and 13C-labeled compounds (WL, DWL and 3,5-diCQA) were detected by ultra-high-performance liquid chromatography-quadrupole time of flight mass spectrometry (HPLC-QTOF-MS). Analysis showed that the metabolic pathways operative of coumestans (WL and DWL) are derived from acetate and shikimate pathways, while that the phenylpropanoid (3,5-diCQA) biosynthesis is exclusively from shikimate pathway.Supplementary informationThe online version contains supplementary material available at 10.1007/s11240-022-02342-0.

| S-EPMC9288585 | biostudies-literature

Eclipta prostrata

Project description:Eclipta prostrata overview

| PRJNA643331 | ENA

The complete chloroplast genome of <i>Eclipta prostrata</i> L. (Asteraceae).

Project description:Eclipta prostrata is an herbal medicinal plant belonging to the Asteraceae family. In this study, complete chloroplast genome sequence of the E. prostrata was characterized by de novo assembly using whole genome sequence data. The genome of E. prostrata was 151,757 bp in length, which was composed of large single copy region of 83,285 bp, small single copy region of 18,346 bp and a pair of inverted repeat regions of 25,063 bp. The genome harboured 80 protein coding sequences, 30 tRNA genes and 4 rRNA genes. We confirmed close taxonomic relationship between E. prostrata and Helianthus annuus through phylogenetic analysis with chloroplast protein-coding genes.

| S-EPMC7799467 | biostudies-literature

Eclipta prostrata cultivar:wild

Project description:Tissue specific de novo transcriptome sequencing of Eclipta prostrata

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Eclipta prostrata cultivar:Wild

Project description:Tissue specific de nove transcriptome sequencing of Eclipta prostrata (L.) L. for deciphering wedelolactone biosynthetic pathways.

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Qualitative and quantitative analysis of Eclipta prostrata L. by LC/MS.

Project description:Eclipta prostrata L. is one of the Chinese medicinal tonics which are usually used for treating loose teeth, dizziness, tinnitus, hemoptysis, hematuria, and uterine bleeding. However, quality control of this herbal medicine has been not satisfactory. This study reported its qualitative and quantitative analyses based on LC/MS method. UHPLC-DAD-Q-TOF-MS fingerprinting and MS fragmentation cleavage pathway were investigated for qualitative analysis. Furthermore, a method for simultaneous quantitative determination of nine compounds, luteolin 7-O-β-D-glucopyranoside, ecliptasaponin C, luteolin, eclalbasaponin IV, apigenin, ecliptasaponin A, echinocystic acid 28-O-β-D-glucopyranoside, echinocystic acid, and 3-oxo-16α-hydroxy-olean-12-en-28-oic acid in E. prostrata, was established. The method was validated for samples of E. prostrata from different habitats. The results showed good linear correlation, precision, accuracy, and repeatability that could be used for contents determination of the nine compounds in E. prostrata from different habitats.

| S-EPMC4312610 | biostudies-other

Potent antioxidative and UVB protective effect of water extract of Eclipta prostrata L.

Project description:Oxidative stress, including Ultraviolet (UV) irradiation-induced skin damage, is involved in numerous diseases. This study demonstrates that water extract of Eclipta prostrata L. (WEP) has a potent effect in scavenging 1,1-diphenyl-2-picrylhydrazyl (DPPH), superoxide radicals, and chelating ferrous ion, exhibiting IC50 values of 0.23 mg/mL, 0.48 mg/mL, and 1.25 mg/mL, respectively. The WEP total phenol content was 176.45 mg gallic acid equivalents (GAE)/g sample. Chlorogenic acid, a component of the plant's active ingredients, was determined by HPLC and antioxidative assay. However, no caffeic acid, stigmasterol, or wedelolactone was present in WEP. WEP absorbs both UVA and UVB irradiation, and furthermore, the extract shows a dose-dependent response in the protection of HaCaT human keratinocytes and mouse fibroblasts 3T3 cells against UVB-induced cytotoxicity, which may result from a synergistic effect between chlorogenic acid and other active components present in WEP.

| S-EPMC3934447 | biostudies-other

Eclipta prostrata promotes the induction of anagen, sustains the anagen phase through regulation of FGF-7 and FGF-5.

Project description:ContextEclipta prostrata L. (Asteraceae) (EP) has been widely used for the treatment of skin disease in Asian traditional medicine.ObjectiveThis study investigates the potency of EP in promoting hair growth in vivo and in vitro.Materials and methodsC57BL/6N mice were divided into four groups (n = 4) as follows: control (topical treatment of normal saline), topical 3% minoxidil to the dorsal skin of mice for 14 days, and low (1 mg/day) and high (10 mg/day) doses of EP orally administered once a day for 14 days. Dorsal hairs of C57BL/6N mice were depilated to synchronize anagen induction. Hair growth activity was evaluated by gross and microscopic observations. Sections of dorsal skin were stained with haematoxylin and eosin. We also treated the various concentrations of EP (5, 10 and 50 μg/mL) for 24 h on the human dermal papilla cells (HDPs) and examined the effects of EP on the expression of FGF-7 and mTOR signalling.ResultsEP enhanced the induction of anagen in the dorsal skin of mice, characterized by the appearance of inner root sheath along with hair shaft, the emergence of hair shaft through the epidermis. EP increased the expression of FGF-7, while decreased the level of FGF-5 in C57/BL6 mice. EP also increased the expression of FGF-7, activated the mTOR signalling in HDPs.Discussion and conclusionsThese results suggest that EP has a potency to enhance the growth of hair follicle, promoting hair growth through regulation of FGF-7 and FGF-5.

| S-EPMC6374973 | biostudies-literature

A Cytotoxic and Anti-inflammatory Campesterol Derivative from Genetically Transformed Hairy Roots of Lopezia racemosa Cav. (Onagraceae).

Project description:The genetically transformed hairy root line LRT 7.31 obtained by infecting leaf explants of Lopezia racemosa Cav with the Agrobacterium rhizogenes strain ATCC15834/pTDT, was evaluated to identify the anti-inflammatory and cytotoxic compounds reported previously for the wild plant. After several subcultures of the LRT 7.31 line, the bio-guided fractionation of the dichloromethane-methanol (1:1) extract obtained from dry biomass afforded a fraction that showed important in vivo anti-inflammatory, and in vitro cytotoxic activities. Chemical separation of the active fraction allowed us to identify the triterpenes ursolic (1) and oleanolic (2) acids, and (23R)-2α,3β,23,28-tetrahydroxy-14,15-dehydrocampesterol (3) as the anti-inflammatory principles of the active fraction. A new molecule 3 was characterized by spectroscopic analysis of its tetraacetate derivative 3a. This compound was not described in previous reports of callus cultures, in vitro germinated seedlings and wild plant extracts of whole L. racemosa plants. The anti-inflammatory and cytotoxic activities displayed by the fraction are associated to the presence of compounds 1-3. The present study reports the obtaining of the transformed hairy roots, the bioguided isolation of the new molecule 3, and its structure characterization.

| S-EPMC6155711 | biostudies-literature

Characterization of Shikonin Derivative Secretion in Lithospermum erythrorhizon Hairy Roots as a Model of Lipid-Soluble Metabolite Secretion from Plants.

Project description:Shikonin derivatives are specialized lipophilic metabolites, secreted in abundant amounts from the root epidermal cells of Lithospermum erythrorhizon. Because they have anti-microbial activities, these compounds, which are derivatives of red naphthoquinone, are thought to serve as a chemical barrier for plant roots. The mechanism by which they are secreted from cells is, however, largely unknown. The shikonin production system in L. erythrorhizon is an excellent model for studying the mechanism by which lipophilic compounds are secreted from plant cells, because of the abundant amounts of these compounds produced by L. erythrorhizon, the 0 to 100% inducibility of their production, the light-specific inhibition of production, and the visibility of these products as red pigments. To date, many factors regulating shikonin biosynthesis have been identified, but no mechanism that regulates shikonin secretion without inhibiting biosynthesis has been detected. This study showed that inhibitors of membrane traffic strongly inhibit shikonin secretion without inhibiting shikonin production, suggesting that the secretion of shikonin derivatives into the apoplast utilizes pathways common to the ADP-ribosylation factor/guanine nucleotide exchange factor (ARF/GEF) system and actin filament polymerization, at least in part. These findings provide clues about the machinery involved in secreting lipid-soluble metabolites from cells.

| S-EPMC4961010 | biostudies-literature

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