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1.
Molecules ; 27(22)2022 Nov 10.
Artigo em Inglês | MEDLINE | ID: mdl-36431834

RESUMO

The genus Eremophila (family Scrophulariaceae) consists of approximately 200 species that are widely distributed in the semi-arid and arid regions of Australia. Multiple Eremophila spp. are used as traditional medicines by the First Australians in the areas in which they grow. They are used for their antibacterial, antifungal, antiviral, antioxidant, anti-diabetic, anti-inflammatory, and cardiac properties. Many species of this genus are beneficial against several diseases and ailments. The antibacterial properties of the genus have been relatively well studied, with several important compounds identified and their mechanisms studied. In particular, Eremophila spp. are rich in terpenoids, and the antimicrobial bioactivities of many of these compounds have already been confirmed. The therapeutic properties of Eremophila spp. preparations and purified compounds have received substantially less attention, and much study is required to validate the traditional uses and to highlight species that warrant further investigation as drug leads. The aim of this study is to review and summarise the research into the medicinal properties, therapeutic mechanisms, and phytochemistry of Eremophila spp., with the aim of focussing future studies into the therapeutic potential of this important genus.


Assuntos
Scrophulariaceae , Humanos , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Extratos Vegetais/química , Austrália , Medicina Tradicional , Antibacterianos/farmacologia , Antibacterianos/uso terapêutico
2.
Genes (Basel) ; 13(10)2022 Sep 21.
Artigo em Inglês | MEDLINE | ID: mdl-36292576

RESUMO

The Scrophularia incisa complex is a group of closely related desert and steppe subshrubs that includes S. incisa, S. kiriloviana and S. dentata, which are the only S. sect. Caninae components found in Northwest China. Based on earlier molecular evidence, the species boundaries and phylogenetic relationships within this complex remain poorly resolved. Here, we characterized seven complete chloroplast genomes encompassing the representatives of the three taxa in the complex and one closely related species, S. integrifolia, as well as three other species of Scrophularia. Comparative genomic analyses indicated that the genomic structure, gene order and content were highly conserved among these eleven plastomes. Highly variable plastid regions and simple sequence repeats (SSRs) were identified. The robust and consistent phylogenetic relationships of the S. incisa complex were firstly constructed based on a total of 26 plastid genomes from Scrophulariaceae. Within the monophyletic complex, a S. kiriloviana individual from Pamirs Plateau was identified as the earliest diverging clade, followed by S. dentata from Tibet, while the remaining individuals of S. kiriloviana from the Tianshan Mountains and S. incisa from Qinghai-Gansu were clustered into sister clades. Our results evidently demonstrate the capability of plastid genomes to improve phylogenetic resolution and species delimitation, particularly among closely related species, and will promote the understanding of plastome evolution in Scrophularia.


Assuntos
Genoma de Cloroplastos , Scrophularia , Scrophulariaceae , Humanos , Filogenia , Scrophularia/genética , Scrophulariaceae/genética , Evolução Molecular
3.
Zootaxa ; 5182(4): 389-398, 2022 Sep 07.
Artigo em Inglês | MEDLINE | ID: mdl-36095678

RESUMO

The Manulea tienmushanica (Daniel, 1954) species group is established, characterised and reviewed. Two new species are described: Manulea (M.) salweena sp. n. (China: Yunnan), and Manulea (M.) diaforetica sp. n. (China: Yunnan). Two new combinations are established: Manulea (M.) tienmushanica (Daniel, 1954), comb. n. and Manulea (M.) nigripuncta (Fang, 2000), comb. n. Adults, male and female genitalia are illustrated.


Assuntos
Mariposas , Scrophulariaceae , Animais , China , Feminino , Masculino
4.
Phytochemistry ; 203: 113408, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36063865

RESUMO

The plant genus Eremophila is endemic to Australia and widespread in arid regions. Root bark extract of Eremophila longifolia (R.Br.) F.Muell. (Scrophulariaceae) was investigated by LC-PDA-HRMS, and dereplication suggested the presence of a series of diterpenoids. Using a combination of preparative- and analytical-scale HPLC separation as well as extensive 1D and 2D NMR analysis, the structures of 12 hitherto unreported serrulatane diterpenoids, eremolongine A-L, were established. These structures included serrulatanes with unusual side chain modifications to form hitherto unseen skeletons with, e.g., cyclopentane, oxepane, and bicyclic hexahydro-1H-cyclopenta[c]furan moieties. Serrulatane diterpenoids in Eremophila have recently been shown to originate from a common biosynthetic precursor with conserved stereochemical configuration, and this was used for tentative assignment of the relative and absolute configuration of the isolated compounds. Triple high-resolution α-glucosidase/α-amylase/PTP1B inhibition profiling demonstrated that several of the eremolongines had weak inhibitory activity towards targets important for management of type 2 diabetes.


Assuntos
Diabetes Mellitus Tipo 2 , Diterpenos , Scrophulariaceae , Ciclopentanos , Diterpenos/farmacologia , Furanos/química , Casca de Planta , Extratos Vegetais/química , Scrophulariaceae/química , alfa-Amilases , alfa-Glucosidases
5.
BMC Genomics ; 23(1): 566, 2022 Aug 08.
Artigo em Inglês | MEDLINE | ID: mdl-35941527

RESUMO

BACKGROUND: The genus Verbascum L. (Scrophulariaceae) is distributed in Africa, Europe, and parts of Asia, with the Mediterranean having the most species variety. Several researchers have already worked on the phylogenetic and taxonomic analysis of Verbascum by using ITS data and chloroplast genome fragments and have produced different conclusions. The taxonomy and phylogenetic relationships of this genus are unclear. RESULTS: The complete plastomes (cp) lengths for V. chaixii, V. songaricum, V. phoeniceum, V. blattaria, V. sinaiticum, V. thapsus, and V. brevipedicellatum ranged from 153,014 to 153,481 bp. The cp coded 114 unique genes comprising of 80 protein-coding genes, four ribosomal RNA (rRNA), and 30 tRNA genes. We detected variations in the repeat structures, gene expansion on the inverted repeat, and single copy (IR/SC) boundary regions. The substitution rate analysis indicated that some genes were under purifying selection pressure. Phylogenetic analysis supported the sister relationship of (Lentibulariaceae + Acanthaceae + Bignoniaceae + Verbenaceae + Pedaliaceae) and (Lamiaceae + Phyrymaceae + Orobanchaceae + Paulowniaceae + Mazaceae) in Lamiales. Within Scrophulariaceae, Verbascum was sister to Scrophularia, while Buddleja formed a monophyletic clade from (Scrophularia + Verbascum) with high bootstrap support values. The relationship of the nine species within Verbascum was highly supported. CONCLUSION: Based on the phylogenetic results, we proposed to reinstate the species status of V. brevipedicellatum (Engl.) Hub.-Mor. Additionally, three genera (Mazus, Lancea, and Dodartia) placed in the Phyrymaceae family formed a separate clade within Lamiaceae. The classification of the three genera was supported by previous studies. Thus, the current study also suggests the circumscription of these genera as documented previously to be reinstated. The divergence time of Lamiales was approximated to be 86.28 million years ago (Ma) (95% highest posterior density (HPD), 85.12-89.91 Ma). The complete plastomes sequence data of the Verbascum species will be important for understanding the Verbascum phylogenetic relationships and evolution in order Lamiales.


Assuntos
Genoma de Cloroplastos , Lamiales , Scrophulariaceae , Verbascum , Genômica , Lamiales/genética , Filogenia , Scrophulariaceae/genética , Verbascum/genética
6.
Plant J ; 111(4): 936-953, 2022 08.
Artigo em Inglês | MEDLINE | ID: mdl-35696314

RESUMO

In a cross-continental research initiative, including researchers working in Australia and Denmark, and based on joint external funding by a 3-year grant from the Novo Nordisk Foundation, we have used DNA sequencing, extensive chemical profiling and molecular networking analyses across the entire Eremophila genus to provide new knowledge on the presence of natural products and their bioactivities using polypharmocological screens. Sesquiterpenoids, diterpenoids and dimers of branched-chain fatty acids with previously unknown chemical structures were identified. The collection of plant material from the Eremophila genus was carried out according to a 'bioprospecting agreement' with the Government of Western Australia. We recognize that several Eremophila species hold immense cultural significance to Australia's First Peoples. In spite of our best intentions to ensure that new knowledge gained about the genus Eremophila and any potential future benefits are shared in an equitable manner, in accordance with the Nagoya Protocol, we encounter serious dilemmas and potential conflicts in making benefit sharing with Australia's First Peoples a reality.


Assuntos
Diterpenos , Scrophulariaceae , Austrália
7.
Phytochemistry ; 196: 113072, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-34973506

RESUMO

Eremophila (Scrophulariaceae) is a genus of Australian desert plants, which have been used by Australian Aboriginal people for various medicinal purposes. Crude extracts of the leaf resin of Eremophila glabra (R.Br.) Ostenf. showed α-glucosidase and protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC50 values of 19.3 ± 1.2 µg/mL and 11.8 ± 2.1 µg/mL, respectively. Dual α-glucosidase/PTP1B high-resolution inhibition profiling combined with HPLC-PDA-HRMS and NMR were used to isolate and identify the compounds providing these activities. This resulted in isolation of seven undescribed serrulatane diterpenoids, eremoglabrane A-G, together with nine previously identified serrulatane diterpenoids and flavonoids. Three of the serrulatane diterpenoids showed PTP1B inhibitory activities with IC50 values from 63.8 ± 5.8 µM to 104.5 ± 25.9 µM.


Assuntos
Diterpenos , Scrophulariaceae , Austrália , Diterpenos/química , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Extratos Vegetais/química , Folhas de Planta/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Scrophulariaceae/química
8.
Molecules ; 26(17)2021 Sep 05.
Artigo em Inglês | MEDLINE | ID: mdl-34500824

RESUMO

Osteoarthritis (OA) is a complex disease, source of pain and disability that affects millions of people worldwide. OA etiology is complex, multifactorial and joint-specific, with genetic, biological and biomechanical components. Recently, several studies have suggested a potential adjuvant role for natural extracts on OA progression, in terms of moderating chondrocyte inflammation and following cartilage injury, thus resulting in an overall improvement of joint pain. In this study, we first analyzed the phenylethanoid glycosides profile and the total amount of polyphenols present in a leaf aqueous extract of Verbascum thapsus L. We then investigated the anti-inflammatory and anti-osteoarthritic bioactive potential of the extract in murine monocyte/macrophage-like cells (RAW 264.7) and in human chondrocyte cells (HC), by gene expression analysis of specifics inflammatory cytokines, pro-inflammatory enzymes and metalloproteases. Six phenylethanoid glycosides were identified and the total phenolic content was 124.0 ± 0.7 mg gallic acid equivalent (GAE)/g of extract. The biological investigation showed that the extract is able to significantly decrease most of the cellular inflammatory markers, compared to both control cells and cells treated with Harpagophytum procumbens (Burch.) DC. ex Meisn, used as a positive control. Verbascum thapsus leaf aqueous extract has the potential to moderate the inflammatory response, representing an innovative possible approach for the inflammatory joint disease treatment.


Assuntos
Anti-Inflamatórios/química , Compostos Fitoquímicos/química , Scrophulariaceae/química , Anti-Inflamatórios/uso terapêutico , Humanos , Inflamação/tratamento farmacológico , Osteoartrite/tratamento farmacológico , Osteoartrite/metabolismo , Compostos Fitoquímicos/uso terapêutico , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico
9.
Phytochemistry ; 190: 112887, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34339980

RESUMO

Chemical studies of the aerial parts of the Australian desert plant Eremophila microtheca afforded the targeted and known diterpenoid scaffolds, 3,7,8-trihydroxyserrulat-14-en-19-oic acid and 3-acetoxy-7,8-dihydroxyserrulat-14-en-19-oic acid. The most abundant serrulatane scaffold was converted to the poly-methyl derivatives, 3-hydroxy-7,8-dimethoxyserrulat-14-en-19-oic acid methyl ester and 3,7,8-trimethoxyserrulat-14-en-19-oic acid methyl ester using simple and rapid methylation conditions consisting of DMSO, NaOH and MeI at room temperature. Subsequently a 12-membered amide library was synthesised by reacting the methylated scaffolds with a diverse series of commercial primary amines. The chemical structures of the 12 undescribed semi-synthetic analogues were fully characterised following 1D/2D NMR, MS, UV, ECD and [α]D data analyses. All compounds were evaluated for their anthelmintic, anti-microbial and anti-viral activities. While none of the compounds significantly inhibited motility or development of the exsheathed third-stage larvae (xL3s) of a pathogenic ruminant parasite, Haemonchus contortus, the tri-methylated analogue induced a skinny phenotype in fourth-stage larvae (L4s) after seven days of treatment (IC50 = 14 µM). Anti-bacterial and anti-fungal activities were not observed at concentrations up to 20 µM. Activity against HIV latency reversal was tested in inducible, chronically-infected cells, with the tri-methylated analogue being the most active (EC50 = 38 µM).


Assuntos
Anti-Helmínticos , Diterpenos , Scrophulariaceae , Austrália , Diterpenos/farmacologia , Descoberta de Drogas
10.
Plant Cell Physiol ; 62(8): 1335-1354, 2021 Nov 10.
Artigo em Inglês | MEDLINE | ID: mdl-34223624

RESUMO

Shoot regeneration involves reprogramming of somatic cells and de novo organization of shoot apical meristems (SAMs). In the best-studied model system of shoot regeneration using Arabidopsis, regeneration is mediated by the auxin-responsive pluripotent callus formation from pericycle or pericycle-like tissues according to the lateral root development pathway. In contrast, shoot regeneration can be induced directly from fully differentiated epidermal cells of stem explants of Torenia fournieri (Torenia), without intervening the callus mass formation in culture with cytokinin; yet, its molecular mechanisms remain unaddressed. Here, we characterized this direct shoot regeneration by cytological observation and transcriptome analyses. The results showed that the gene expression profile rapidly changes upon culture to acquire a mixed signature of multiple organs/tissues, possibly associated with epidermal reprogramming. Comparison of transcriptomes between three different callus-inducing cultures (callus induction by auxin, callus induction by wounding and protoplast culture) of Arabidopsis and the Torenia stem culture identified genes upregulated in all the four culture systems as candidates of common factors of cell reprogramming. These initial changes proceeded independently of cytokinin, followed by cytokinin-dependent, transcriptional activations of nucleolar development and cell cycle. Later, SAM regulatory genes became highly expressed, leading to SAM organization in the foci of proliferating cells in the epidermal layer. Our findings revealed three distinct phases with different transcriptomic and regulatory features during direct shoot regeneration from the epidermis in Torenia, which provides a basis for further investigation of shoot regeneration in this unique culture system.


Assuntos
Diferenciação Celular/genética , Meristema/crescimento & desenvolvimento , Epiderme Vegetal/crescimento & desenvolvimento , Epiderme Vegetal/genética , Brotos de Planta/crescimento & desenvolvimento , Scrophulariaceae/crescimento & desenvolvimento , Scrophulariaceae/genética , Perfilação da Expressão Gênica , Meristema/genética , Brotos de Planta/genética
11.
Zhongguo Zhong Yao Za Zhi ; 46(9): 2207-2214, 2021 May.
Artigo em Chinês | MEDLINE | ID: mdl-34047122

RESUMO

By establishing the preparation process of Scrophulariaceae Radix reference extract(SRRE) and calibrating it, we discussed its feasibility as a substitute for single reference substance in the quality control of Scrophulariae Radix. The SRREs were prepared by solvent extraction method and chromatographic separation technology, and then calibrated with the reference substances of harpagide, angoroside C and harpagoside. The HPLC content determination method of Scrophulariae Radixl was established with SRREs of the known content and the reference substances of harpagide, angoroside C and harpagoside respectively as the control ones. Then the content of three components in Scrophulariae Radix was determined, and the t-test method was used to compare the results of the two methods. With SRRE as references, harpagide, angoroside C and harpagoside were in a good linear relationship(r≥0.999 8) within each range, and the average recovery rate was 98.55% to 100.6%. The t-test results showed that the P values of two determination methods were 0.493, 0.155 and 0.171 for harpagide, angoroside C and harpagoside respectively, indicating no significant diffe-rence between the two methods of content determination. The SRRE can be used as a substitute for the reference in the quality control of Scrophulariaceae Radix. The SRRE can replace the corresponding reference substance for the quality control of Scrophulariae Radix. The results of this study provide new methods and new ideas for the quality evaluation of Scrophulariae Radix, and provide a scientific basis for the application of reference extracts in the quality research of traditional Chinese medicine.


Assuntos
Medicamentos de Ervas Chinesas , Scrophularia , Scrophulariaceae , Cromatografia Líquida de Alta Pressão , Controle de Qualidade
12.
Food Chem Toxicol ; 147: 111899, 2021 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-33279675

RESUMO

Pesticides are used to control and combat insects and pests in the agricultural sector, households, and public health programs. The frequent and disorderly use of these pesticides may lead to variety of undesired effects. Therefore, natural products have many advantages over to synthetic compounds to be used as insecticides. The goal of this study was to find natural products with insecticidal potential against Musca domestica and Mythimna separata. To achieve this goal, we developed predictive QSAR models using MuDRA, PLS, and RF approaches and performed virtual screening of 117 natural products. As a result of QSAR modeling, we formulated the recommendations regarding physico-chemical characteristics for promising compounds active against Musca domestica and Mythimna separata. Homology models were successfully built for both species and molecular docking of QSAR hits vs known insecticides allowed us to prioritize twenty-two compounds against Musca domestica and six against Mythimna separata. Our results suggest that pimarane diterpenes, abietanes diterpenes, dimeric diterpenes and scopadulane diterpenes obtained from aerial parts of species of the genus Calceolaria (Calceolariaceae: Scrophulariaceae) can be considered as potential insecticidal.


Assuntos
Dípteros/efeitos dos fármacos , Diterpenos/química , Diterpenos/farmacologia , Inseticidas/farmacologia , Animais , Desenho de Fármacos , Moscas Domésticas/efeitos dos fármacos , Modelos Biológicos , Estrutura Molecular , Relação Quantitativa Estrutura-Atividade , Scrophulariaceae/química , Sensibilidade e Especificidade
13.
Eur J Med Chem ; 209: 112563, 2021 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-33038797

RESUMO

Phenylethanoid glycosides (PhGs) are compounds made of phenylethyl alcohol, caffeic acid and glycosyl moieties. The first published references about phenylethanoid glycosides concerned the isolation of echinacoside from Echinaceu ungustifolia (Asteraceae) in 1950 and verbascoside from Verbascum sinuatum (Scrophulariaceae) in 1963. Over the past 60 years, many compounds with these structural characteristics have been isolated from natural sources, and most of these compounds possess significant bioactivities, including antibacterial, antitumor, antiviral, anti-inflammatory, neuro-protective, antioxidant, hepatoprotective, and immunomodulatory activities, among others. In this review, we will summarize the phenylethanoid glycosides described in recent papers and list all the compounds that have been isolated over the past few decades. We will also attempt to present and assess recent studies about the separation, extraction, determination, and pharmacological activity of the excellent natural components, phenylethanoid glycosides.


Assuntos
Glicosídeos/química , Glicosídeos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Asteraceae/química , Descoberta de Drogas , Humanos , Álcool Feniletílico/química , Álcool Feniletílico/farmacologia , Plantas/química , Scrophulariaceae/química
14.
Microsc Res Tech ; 84(3): 521-530, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-32990330

RESUMO

The family Scrophulariaceae consists of taxonomically complex genera and species. The delimitation of the taxa within this family is always challenging. In this paper, we studied leaf epidermis anatomical characteristics and its taxonomic significance of four species belonging to four genera of the family Scrophulariaceae collected from northern Pakistan. The species were examined under light and scanning electron microscopes (LM and SEM). Qualitative and quantitative foliar epidermal anatomical features were examined for both adaxial and abaxial surfaces. Qualitative characters like epidermal cell shape, epidermal cell cover, anticlinal wall, trichomes type, stomata type and stomata position were examined. Quantitative characters like the length and width of leaf epidermis, stomata, stomatal pore, subsidiary cell and trichomes for both adaxial and abaxial surfaces were studied and measured. Stomatal index within the species and between the species was found to be different on adaxial and abaxial surfaces. Diacytic stomata and glandular trichomes on epidermis were only found in Anticharis glandulosa while rest of the taxa has anomocytic type stomata and dendroid trichomes on both surfaces. Based on the micromorphological characters, we did principal component analysis (PCA), and cluster analysis for the species delimitation and identification. A taxonomic key has been provided to delimit and identify the studied taxa based on foliar epidermal characters. The aim of the present research was to elucidate the micromorphological characters to distinguish the studied taxa for taxonomic purposes.


Assuntos
Epiderme Vegetal , Scrophulariaceae , Epiderme , Microscopia Eletrônica de Varredura , Paquistão , Folhas de Planta , Estômatos de Plantas
15.
Zootaxa ; 4789(2): zootaxa.4789.2.2, 2020 Jun 09.
Artigo em Inglês | MEDLINE | ID: mdl-33056432

RESUMO

Hoverflies (Diptera: Syrphidae) of the genus Microdon Meigen have larvae that live in ant nests where they are predatory on ant larvae. Reflecting the exceptional challenges of this very specialized lifestyle, Microdon eggs, larvae and puparia are highly distinctive in their morphology. Detailed descriptions of these immature stages is, however, lacking for all but a very few species, and much of this has been limited through the sole use of light microscopes. Here, using Scanning Electron Microscopy (SEM), we present detailed, comparative descriptions of the immature stages of three European Microdon species: M. analis, M. devius and M. myrmicae. Given that many adult Microdon species are very similar to each other in their outward appearance, we demonstrate that the morphology of their immature stages can improve our understanding of the phylogeny of the genus. We also discuss how particular adaptations of the immature morphology may allow their myrmecophilous life within ant nests. In this paper new diagnostic features are also presented to distinguish M. myrmicae from its sibling species M. mutabilis-the two are morphologically indistinguishable as adults.


Assuntos
Dípteros , Scrophulariaceae , Adaptação Fisiológica , Animais , Larva , Microscopia Eletrônica de Varredura
16.
Plant J ; 104(3): 693-705, 2020 11.
Artigo em Inglês | MEDLINE | ID: mdl-32777127

RESUMO

Serrulatane diterpenoids are natural products found in plants from a subset of genera within the figwort family (Scrophulariaceae). Many of these compounds have been characterized as having anti-microbial properties and share a common diterpene backbone. One example, leubethanol from Texas sage (Leucophyllum frutescens) has demonstrated activity against multi-drug-resistant tuberculosis. Leubethanol is the only serrulatane diterpenoid identified from this genus; however, a range of such compounds have been found throughout the closely related Eremophila genus. Despite their potential therapeutic relevance, the biosynthesis of serrulatane diterpenoids has not been previously reported. Here we leverage the simple product profile and high accumulation of leubethanol in the roots of L. frutescens and compare tissue-specific transcriptomes with existing data from Eremophila serrulata to decipher the biosynthesis of leubethanol. A short-chain cis-prenyl transferase (LfCPT1) first produces the rare diterpene precursor nerylneryl diphosphate, which is cyclized by an unusual plastidial terpene synthase (LfTPS1) into the characteristic serrulatane diterpene backbone. Final conversion to leubethanol is catalyzed by a cytochrome P450 (CYP71D616) of the CYP71 clan. This pathway documents the presence of a short-chain cis-prenyl diphosphate synthase, previously only found in Solanaceae, which is likely involved in the biosynthesis of other known diterpene backbones in Eremophila. LfTPS1 represents neofunctionalization of a compartment-switching terpene synthase accepting a novel substrate in the plastid. Biosynthetic access to leubethanol will enable pathway discovery to more complex serrulatane diterpenoids which share this common starting structure and provide a platform for the production and diversification of this class of promising anti-microbial therapeutics in heterologous systems.


Assuntos
Diterpenos/metabolismo , Scrophulariaceae/metabolismo , Alquil e Aril Transferases/metabolismo , Sistema Enzimático do Citocromo P-450/genética , Sistema Enzimático do Citocromo P-450/metabolismo , Eremophila (Planta)/genética , Escherichia coli/genética , Neopreno/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Raízes de Plantas/metabolismo , Plantas Geneticamente Modificadas , Fosfatos de Poli-Isoprenil/metabolismo , Scrophulariaceae/genética , Tabaco/genética , Tabaco/metabolismo , Transferases/genética , Transferases/metabolismo
17.
J Nat Prod ; 83(5): 1424-1431, 2020 05 22.
Artigo em Inglês | MEDLINE | ID: mdl-32239935

RESUMO

Eight furofuranone lignans with an endo,endo relationship between the oxygen atoms, an exo,exo relationship between the aryl groups, and a chair,chair conformation (1-4 and 6-9), in addition to the α-amino acid (3S)-hydroxy-3',4'-dimethoxy-L-phenylalanine (5), veratric acid (10), and ß-sitosterol (11), were isolated from the powdered and defatted air-dried aerial parts of Leucophyllum ambiguum. Four of these lignans, ciquitins A-D, 1-4, were isolated for the first time as natural products. The structures of these compounds were established based on their spectrometric/spectroscopic data. Additionally, single-crystal X-ray crystallography confirmed the structure of ciquitin A (1), and derivatization with (9S)-naproxen and X-ray diffraction crystallography data established its absolute configuration. Ciquitins A (1) and B (2) possess a 9-hydroxy group; this chemical characteristic grants these species conformational isomerism not seen in the other six lignans. The conformers of 1 and 2 are distinguishable via their 1H and 13C NMR spectroscopic data. This is the first report of this phenomenon, and hence, a complete assignment of the signals in both spectra of each conformer for each compound is presented. Compounds 1-9 were found to exhibit potent inhibitory activity in the 1.0 × 10-3 to 2.2 µM range against acetylcholinesterase, an enzyme directly involved in the etiology of Alzheimer's disease and senile dementia. Thus, these natural products are promising agents that are potentially useful for the treatment of neurological degeneration.


Assuntos
Lignanas/química , Lignanas/farmacologia , Componentes Aéreos da Planta/química , Scrophulariaceae/química , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Cristalografia por Raios X , Espectroscopia de Ressonância Magnética , Conformação Molecular , Estrutura Molecular , Difração de Raios X
18.
J Nat Prod ; 83(5): 1598-1610, 2020 05 22.
Artigo em Inglês | MEDLINE | ID: mdl-32255628

RESUMO

Ten new branched-chain fatty acid (BCFA) dimers with a substituted cyclohexene structure, five new monomers, and two known monomers, (2E,4Z,6E)-5-(acetoxymethyl)tetradeca-2,4,6-trienoic acid and its 5-hydroxymethyl analogue, were identified in the leaf extract of Eremophila oppositifolia subsp. angustifolia using a combination of HPLC-PDA-HRMS-SPE-NMR analysis and semipreparative-scale HPLC. The dimers could be classified as three types of Diels-Alder reaction products formed between monomers at two different sites of unsaturation of the dienophile. Two of the monomers represent potential biosynthetic intermediates of branched-chain fatty acids. Several compounds were found by high-resolution bioactivity profiling to inhibit PTP1B and were purified subsequently by semipreparative-scale HPLC. The dimers were generally more potent than the monomers with IC50 values ranging from 2 to 66 µM, compared to 38-484 µM for the monomers. The ten fatty acid dimers represent both a novel class of compounds and a novel class of PTP1B inhibitors.


Assuntos
Hipoglicemiantes/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/química , Scrophulariaceae/química , Cromatografia Líquida de Alta Pressão , Ácidos Graxos , Inibidores de Glicosídeo Hidrolases/química , Hipoglicemiantes/metabolismo , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Extração em Fase Sólida , alfa-Glucosidases/metabolismo
19.
J Ethnopharmacol ; 250: 112493, 2020 Mar 25.
Artigo em Inglês | MEDLINE | ID: mdl-31863859

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Lindernia crustacea (L.) F.Muell. (Scrophulariaceae) was selected for phytochemical investigation owing to its traditional use against human herpes virus infection and its anti-Epstein-Barr virus (EBV) effect. AIMS OF THE STUDY: The present study focused on the phytochemical investigation of L. crustacea including the isolation and structure determination of its biologically active compounds. Compounds with anti-EBV effects were also investigated. MATERIALS AND METHODS: The EtOH extract of L. crustacea was subsequently partitioned using different solvents. The EtOAc fraction was subjected to several chromatographic methods to obtain pure compounds. The structures of all isolates were established by spectroscopic analysis and compared with previously reported physical data. The anti-EBV effect was evaluated in an EBV-containing Burkitt's lymphoma cell line (P3HR1) to study the expression of EBV lytic proteins. RESULTS: Thirty-three compounds, including one diterpene (1), four anthraquinones (2-5), two ionones (6 and 7), fourteen phenylpropanoid glycosides (8-21), five flavonoids (22-26), one lignan glycoside (27), one phenethyl alcohol glycoside (28), one phenylpropene glycoside (29), one glucosyl glycerol derivative (30), one furanone (31), and two cinnamic acid derivatives (32 and 33), were isolated from the ethanolic extract of the plant. All isolated compounds were obtained for the first time from Lindernia sp. The evaluation of the anti-EBV activity of L. crustacea crude extract, partitioned fractions, and constituents was performed for the first time. Phytol (1), aloe-emodin (2), byzantionoside B (7), a mixture of trans-martynoside (8) and cis-martynoside (9), a mixture of trans-isomartynoside (10) and cis-isomartynoside (11), luteolin-7-O-ß-D-glucopyranoside (24), and apigenin-7-O-[ß-D-apiofuranosyl (1→6)-ß-D-glucopyranoside] (25) exhibited significant inhibitory effects on the EBV lytic cycle at 20 µg/mL in the immunoblot analysis. On the other hand, (6R,7E,9R)-3-oxo-α-ionol-ß-D-glucopyranoside (6) and a mixture of trans-dolichandroside A (12) and cis-dolichandroside A (13) showed moderate anti-EBV activity at 20 µg/mL. CONCLUSIONS: L. crustacea and its active isolates could be developed as potential candidates against EBV. Our findings provide scientific evidence for the traditional use of L. crustacea for its antiviral effects.


Assuntos
Antivirais/farmacologia , Herpesvirus Humano 4/efeitos dos fármacos , Extratos Vegetais/farmacologia , Scrophulariaceae/química , Antivirais/isolamento & purificação , Linfoma de Burkitt/virologia , Linhagem Celular , Humanos , Proteínas Imediatamente Precoces/genética , Transativadores/genética
20.
Phytochemistry ; 166: 112054, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31284174

RESUMO

Eremophila bignoniiflora is a shrub distributed throughout inland northern and eastern Australia, and it has been used in several medicinal applications by some Australian Aboriginal people. In our continued search for anti-diabetic constituents from natural resources, the crude ethyl acetate extract of E. bignoniiflora was found to have protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity with an IC50 value of 23.9 ±â€¯1.9 µg/mL. High-resolution PTP1B inhibition profiling combined with HRMS and NMR were subsequently used to investigate the individual compounds responsible for the observed bioactivity of the crude extract. This led to identification of five undescribed 2(5H)-furanone sesquiterpenes, together with 13 flavonoids and phenolic compounds. Dose-response curves of the isolated compounds revealed that two 2(5H)-furanone sesquiterpene cinnamates and three flavonoids exhibited moderate PTP1B inhibitory activity with IC50 values from 41.4 ±â€¯1.4 to 154.5 ±â€¯8.9 µM.


Assuntos
Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Furanos/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Scrophulariaceae/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia
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