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1.
Molecules ; 27(16)2022 Aug 14.
Artigo em Inglês | MEDLINE | ID: mdl-36014416

RESUMO

Comprehensive phytochemical examination from different perspectives using preparative and analytical chromatographic techniques combined with spectroscopic/spectrometric methods of the so-called "yellow twig" Nauclea orientalis (L.) L. (Rubiaceae) led to the identification of 13 tryptamine-derived (=monoterpene-indole) alkaloids. The identified alkaloids comprise strictosamide and four of its glucosidic derivatives, three oxindole derivatives, and five yellow-colored angustine-type aglycones. Qualitative and quantitative HPLC analyses showed the enrichment of strictosamide in all studied organs. Based on these results, we performed metabolomic analyses of monoterpene-indole alkaloids and made a 1H NMR in vitro monitoring of enzymatic deglucosylation of strictosamide. A comparison of the stability of strictosamide and its enantiomer vincoside lactam by theoretical calculations was also performed revealing a slightly higher stability of vincoside lactam. Additionally, we conducted two different anti-feedant assays of strictosamide using larvae of the polyphageous moth Spodoptera littoralis Boisduval. The obtained results indicate that generally two different biosynthetic pathways are most likely responsible for the overall alkaloid composition in this plant. Strictosamide is the key compound in the broader pathway and most likely the source of the identified angustine-type aglycones, which may contribute significantly to the yellow color of the wood. Its cross-organ accumulation makes it likely that strictosamide is not only important as a reservoir for the further biosynthesis, but also acts in the plants' defense strategy.


Assuntos
Alcaloides , Antineoplásicos , Rubiaceae , Alcaloides/química , Alcaloides Indólicos/química , Lactamas , Monoterpenos , Rubiaceae/química , Tailândia , Alcaloides de Vinca
2.
Molecules ; 27(16)2022 Aug 19.
Artigo em Inglês | MEDLINE | ID: mdl-36014541

RESUMO

Ophiorrhiza japonica Bl. is a traditional Chinese materia medica widely used to treat several diseases. Chemical and pharmacological studies on O. japonica have been carried out; however, neither of them has been fully explored. In this study, an array of compounds was isolated from the title plant, including a new anthraquinone, ophiorrhizaquinone A (1), three alkaloids 2-4 and seven other compounds 5-11 with diverse structural types. Additionally, compounds 2, 5, 7, 8, 10 and 11 were isolated from the genus of Ophiorrhiza for the first time. Antioxidant bioassays in vitro using DPPH and ABTS were performed, and the results showed that compound 3 exhibited modest antioxidant activity with IC50 values of 0.0321 mg/mL and 0.0319 mg/mL, respectively. An in silico study of PPARα agonistic activities of compounds 2 and 3 was conducted by molecular docking experiments, revealing that both of them occupied the active site of PPARα via hydrogen bonds and hydrophobic interactions effectively. This study enriched both the phytochemical and pharmacological profiles of O. japonica.


Assuntos
Antioxidantes , Rubiaceae , Antioxidantes/química , Simulação de Acoplamento Molecular , PPAR alfa , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Rubiaceae/química
3.
An Acad Bras Cienc ; 94(2): e20201975, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-35946644

RESUMO

Colleters are glandular structures related to young shoots protection. In several Angiosperm families, as in Rubiaceae colleters are taxonomically important. This study reports presence, location, morpho-anatomical structure, ontogeny and histochemistry of colleters in vegetative and reproductive organs in 6 species of Cephalanthus and 20 species representatives of the tribe Naucleeae. Primarily based on their color and their secretion color, they were classified into light (LC) and dark (DC) colleters. The LC are exclusive to the inner side of the stipule, while the DC are found in several vegetative and reproductive organs. Histochemical studies revealed that higher mucilage and phenol content in DC could explain the dark color secretion. Results were analyzed at genus, tribe and subtribe levels, evidencing the taxonomic relevance in the family. Finally, the presence of corolline colleters in angiosperm flowers was reviewed. It was confirmed that, besides Cephalanthus, they are only present in Adenoa (Passifloraceae) and Chamaecrista (Fabaceae). Therefore, structures described as colleters in Nerium (Apocynaceae) and Cuscuta (Cuscutaceae) corollas do not correspond to colleters. This proves that corolline colleter is a rare character in Angiosperms. To conclude we provide a record of presence/absence, type and distribution of corolline colleters in an Angiosperm phylogenetic tree.


Assuntos
Fabaceae , Magnoliopsida , Rubiaceae , Flores , Humanos , Filogenia
4.
J Nat Med ; 76(4): 865-872, 2022 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-35788957

RESUMO

Ophiorrhiza pumila is a medicinal plant that grows in subtropical forests and produces camptothecin (CPT). To determine an optimal harvest time of O. pumila in a plant factory with artificial light (PFAL), we investigated the CPT distribution in each organ and at the developmental stage and estimated the annual CPT production. For this study, the O. pumila plants were grown in controlled environments (16 h light period, photosynthetic photon flux density of 100 µmol m-2 s-1 under white light-emitting diode lamps, air temperature of 28 °C, relative humidity of 80%, and CO2 concentration of 1000 µmol mol-1). First, the stem, root, and seed pod had higher CPT contents than the leaves, flower, and ovary. The optimal harvest time of O. pumila in a PFAL was 63 days after transplanting (DAT), because the CPT content in the whole organs was the highest at the seed-ripening stage. Second, based on these results, the estimated annual CPT production of O. pumila cultivated in a PFAL was 380 mg m-2 y-1 (63 DAT). This value was 4.3 times greater than the annual CPT production by Camptotheca acuminata in a greenhouse. We concluded that the CPT production by O. pumila in a PFAL throughout the year has many advantages, although the demand for electrical energy was high compared to that of Camptotheca acuminata in a greenhouse.


Assuntos
Antineoplásicos Fitogênicos , Rubiaceae , Camptotecina , Folhas de Planta , Sementes
5.
Molecules ; 27(13)2022 Jun 23.
Artigo em Inglês | MEDLINE | ID: mdl-35807284

RESUMO

Cephalanthus tetrandrus (Roxb.) Ridsd. et Badh. F. (CT) belongs to the Rubiaceae family. Its dried leaves are widely used in traditional Chinese medicine to treat enteritis, dysentery, toothache, furuncles, swelling, traumatic injury, fracture, bleeding, and scalding. In order to further clarify the unknown chemical composition of CT, a rapid strategy based on UHPLC-Q-exactive orbitrap was established for this analysis using a Thermo Scientific Hypersil GOLDTM aQ (100 mm × 2.1 mm, 1.9 µm) chromatographic column. The mobile phase was 0.1% formic acid water-acetonitrile, with a flow rate of 0.3 mL/min and injection volume of 2 µL; for mass spectrometry, an ESI ion source in positive and negative ion monitoring modes was adopted. A total of 135 chemicals comprising 67 chlorogenic acid derivatives, 48 flavonoids, and 20 anthocyanin derivatives were identified by comparing the mass spectrum information with standard substances, public databases, and the literature, which were all discovered for the first time in this plant. This result broadly expands the chemical composition of CT, which will contribute to understanding of its effectiveness and enable quality control.


Assuntos
Medicamentos de Ervas Chinesas , Rubiaceae , Cromatografia Líquida de Alta Pressão/métodos , Medicamentos de Ervas Chinesas/química , Flavonoides/análise , Espectrometria de Massas/métodos
6.
J Nat Med ; 76(4): 748-755, 2022 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-35902551

RESUMO

Ophiorrhiza plants (Family Rubiaceae) are known to produce diverse monoterpenoid indole alkaloids including camptothecin with potent antitumor activity. This review contains a summary of recent chemical studies reported over the past 10 years regarding alkaloids (monoterpenoid indole and tetrahydroisoquinoline alkaloids, and cyclopeptide) in Ophiorrhiza plants. In addition, the alkaloid biosynthetic pathways based on their reported structures were proposed.


Assuntos
Alcaloides , Rubiaceae , Alcaloides/química , Vias Biossintéticas , Camptotecina/química , Camptotecina/metabolismo , Rubiaceae/química , Rubiaceae/metabolismo
7.
Fitoterapia ; 160: 105228, 2022 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-35667521

RESUMO

A pair of new diastereoisomers neolignans (1-2) and a new alkaloid (7) were isolated from the stems of Nauclea officinalis: naucleaoxyneolignoside A (1), naucleaoxyneolignoside B (2), (2S,3S)-javaniside (7), together with nine known compounds, 2S-3,3-di-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol (3), threo-1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol (4), nauclefine (5), angustidine (6), naucleoxoside A (8), naucleoxoside B (9), angustoline (10), (3S,19S)-3,14-dihydroangustoline (11), and (3S,19R)-3,14-dihydroangustoline (12).The structures of 1, 2 and 7 were elucidated by extensive spectroscopic methods and the known compounds were identified by comparison of their data with those reported in the literature. The absolution configurations of 1, 2, 7,11 and 12 were confirmed by the quantum chemical CD calculation method. Compounds 1-9 showed weak to moderate inhibitory activity on nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro with IC50 values comparable to that of dexamethasone. In addition, compounds 1-9 were evaluated for the antibacterial and cytotoxic effects, and the results revealed that these compounds showed no anti-bacterial activity, and compounds 3-6 showed modest cytotoxic activity.


Assuntos
Lignanas , Rubiaceae , Animais , Alcaloides Indólicos , Lignanas/farmacologia , Camundongos , Estrutura Molecular , Propano , Rubiaceae/química
8.
World J Gastroenterol ; 28(20): 2214-2226, 2022 May 28.
Artigo em Inglês | MEDLINE | ID: mdl-35721884

RESUMO

BACKGROUND: Direct acting antiviral (DAA) therapy has enabled hepatitis C virus infection to become curable, while histological changes remain uncontained. Few valid non-invasive methods can be confirmed for use in surveillance. Gadolinium-ethoxybenzyl-diethylenetriamine penta-acetic acid (Gd-EOB-DTPA) is a liver-specific magnetic resonance imaging (MRI) contrast, related to liver function in the hepatobiliary phase (HBP). Whether Gd-EOB-DTPA-enhanced MRI can be used in the diagnosis and follow up of hepatic fibrosis in patients with chronic hepatitis C (CHC) has not been investigated. AIM: To investigate the diagnostic and follow-up values of Gd-EOB-DTPA-enhanced MRI for hepatic histology in patients with CHC. METHODS: Patients with CHC were invited to undergo Gd-EOB-DTPA-enhanced MRI and liver biopsy before treatment, and those with paired qualified MRI and liver biopsy specimens were included. Transient elastography (TE) and blood tests were also arranged. Patients treated with DAAs who achieved 24-wk sustained virological response (SVR) underwent Gd-EOB-DTPA-enhanced MRI and liver biopsy again. The signal intensity (SI) of the liver and muscle were measured in the unenhanced phase (UEP) (SIUEP-liver, SIUEP-muscle) and HBP (SIHBP-liver, SIHBP-muscle) via MRI. The contrast enhancement index (CEI) was calculated as [(SIHBP-liver/SIHBP-muscle)]/[(SIUEP-liver/SIUEP-muscle)]. Liver stiffness measurement (LSM) was confirmed with TE. Serologic markers, aspartate aminotransferase-to-platelet ratio index (APRI) and Fibrosis-4 (FIB-4), were also calculated according to blood tests. The grade of inflammation and stage of fibrosis were evaluated with the modified histology activity index (mHAI) and Ishak fibrosis score, respectively. Fibrosis regression was defined as a ≥ 1-point decrease in the Ishak fibrosis score. The correlation between the CEI and liver pathology was evaluated. The diagnostic and follow-up values of the CEI, LSM, and serologic markers were compared. RESULTS: Thirty-nine patients with CHC were enrolled [average age, 42.3 ± 14.4 years; 20/39 (51.3%) male]. Twenty-one enrolled patients had eligible paired Gd-EOB-DTPA-enhanced MRI and liver tissues after achieving SVR. The mHAI median significantly decreased after SVR [baseline 6.0 (4.5-13.5) vs SVR 2.0 (1.5-5.5), Z = 3.322, P = 0.017], but the median stage of fibrosis did not notably change (P > 0.05). Sixty pairs of qualified MRI and liver tissue samples were available for use to analyze the relationship between the CEI and hepatic pathology. The CEI was negatively correlated with the mHAI (r = -0.56, P < 0.001) and Ishak score (r = -0.69, P < 0.001). Further stratified analysis showed that the value of the CEI decreased with the progression of the stage of fibrosis rather than with the grade of necroinflammation. For patients with Ishak score ≥ 5, the areas under receiver operating characteristics curve of the CEI, LSM, APRI, and FIB-4 were approximately at baseline, 0.87-0.93, and after achieving SVR, 0.83-0.91. The CEI cut-off value was stable (baseline 1.58 and SVR 1.59), but those of the APRI (from 1.05 to 0.24), FIB-4 (from 1.78 to 1.28), and LSM (from 10.8 kpa to 7.1 kpa) decreased dramatically. The APRI and FIB-4 cannot be used as diagnostic means for SVR in patients with Ishak score ≥ 3 (P > 0.05). Seven patients achieved fibrosis regression after achieving SVR. In these patients, the CEI median increased (from 1.71 to 1.83, Z = -1.981, P = 0.048) and those of the APRI (from 1.71 to 1.83, Z = -2.878, P = 0.004) and LSM (from 6.6 to 4.8, Z = -2.366, P = 0.018) decreased. However, in patients without fibrosis regression, the medians of the APRI, FIB-4, and LSM also changed significantly (P < 0.05). CONCLUSION: Gd-EOB-DTPA-enhanced MRI has good diagnostic value for staging fibrosis in patients with CHC. It can be used for fibrotic-change monitoring post SVR in patients with CHC treated with DAAs.


Assuntos
Hepatite C Crônica , Rubiaceae , Ácido Acético , Adulto , Antivirais/uso terapêutico , Biomarcadores , Meios de Contraste , Feminino , Gadolínio/uso terapêutico , Gadolínio DTPA , Hepatite C Crônica/complicações , Hepatite C Crônica/diagnóstico por imagem , Hepatite C Crônica/tratamento farmacológico , Humanos , Fígado/diagnóstico por imagem , Fígado/patologia , Cirrose Hepática/diagnóstico por imagem , Cirrose Hepática/tratamento farmacológico , Imageamento por Ressonância Magnética/métodos , Masculino , Pessoa de Meia-Idade , Poliaminas , Estudos Retrospectivos
9.
Biomed Res Int ; 2022: 7856305, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-35757466

RESUMO

The use of natural products for medicinal purposes is becoming more and more common nowadays, as evidenced by the presence in plants of secondary metabolites with different potentials such as antioxidant and antibacterial properties. We evaluated in this work the antimicrobial activities of the extracts and some isolated compounds from the seeds of Psychotria succulenta Hiern. (Rubiaceae), a Cameroonian medicinal plant traditionally used to cure microbial infections. The ethanol extract was prepared by maceration and extracted with ethyl acetate and n-butanol. The EtOAc (m = 168 g) and n-BuOH (m = 20 g) extracts were further fractionated by silica gel column chromatography to isolation of compounds. Their structures were elucidated by spectroscopic analysis and by comparison with published data. The antibacterial activity of extracts and compounds was assessed by evaluating the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) against pathogenic bacteria. Thirteen compounds including four alkaloids (veprisine (1), naucleofficine III (2), vepridimerine B (3), and vepridimerine C (4)), three triterpenes (barbinervic acid (5), 3-O-α-L-rhamnopyranosyl quinovic acid (6), and oleanolic acid (7)), one steroid (ß-sitosterol-3-O-ß-D-glucopyranoside (8)), four phenolic compounds (scopoletin (9), gallic acid (10), quercetin-3-O-ß-D-glucopyranoside (11), and kaempferol 3-O-α-L-rhamnopyranoside-7-O-α-L-rhamnopyranoside (12)), and one iridoid (borreriagenin (13)) were isolated from the EtOAc and n-BuOH extracts. These compounds were identified by 1D and 2D NMR combined analysis as well as by melting point comparison. The EtOH, EtOAc, and n-BuOH extracts exhibited significant antibacterial activities (MIC = 32-128 µg/mL; MBC = 64-256 µg/mL) against Staphylococcus aureus (Gram-positive bacterium), Pseudomonas aeruginosa, Escherichia coli, and Klebsiella pneumonia (Gram-negative bacteria). Among the isolated compounds, scopoletin (9) showed a moderate activity against Klebsiella pneumoniae with MIC and MBC values of 16 µg/mL and 32 µg/mL, respectively. It appears that, chemotaxonomically, some of the isolated compounds have already been obtained from the genus Psychotria but to the best of our knowledge, this is the first report on the phytochemical investigation of P. succulenta. Although many other studies need to be achieved, our results support the use of P. succulenta in traditional medicine to cure infectious diseases particularly those caused by the tested bacteria.


Assuntos
Psychotria , Rubiaceae , Antibacterianos/química , Bactérias , Testes de Sensibilidade Microbiana , Extratos Vegetais/química , Escopoletina
10.
Biomed Res Int ; 2022: 7569848, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-35769665

RESUMO

Background: Diarrheal diseases are a major cause of morbidity and mortality throughout the world and particularly in developing countries. Nauclea diderrichii is a plant used in traditional medicine in the treatment of anemia, fever, gastric ulcer, malaria, abdominal pain, skin infections, and diarrhea. The present work is aimed at evaluating the antisecretory and spasmolytic activities of aqueous and ethanolic stem bark extracts of Nauclea diderrichii in Wistar rats. Methods: The effect of aqueous and ethanolic extracts of Nauclea diderrichii was tested at doses of 100, 200, and 300 mg/kg on castor oil-induced secretory diarrhea, misoprostol-induced fluid accumulation, and the effect of pretreatment with yohimbine and glibenclamide. They were also tested on normal motility and castor oil- and carbachol-induced hypermotility. Results: The results showed that the aqueous and ethanolic extracts of Nauclea diderrichii significantly (p < 0.001) inhibited castor oil-induced secretory diarrhea at all the doses. Both extracts significantly (p < 0.001) inhibit fluid accumulation induced by misoprostol. The pretreatment with glibenclamide reduced the antidiarrheal activity of aqueous extract of Nauclea diderrichii. The pretreatment with yohimbine did not alter the effect of the aqueous extract of Nauclea diderrichii. On intestine transit as on castor oil- and carbachol-induced motility, the aqueous and ethanolic extracts at doses of 100 and 200 mg/kg reduced significantly (p < 0.05, p < 0.01, and p < 0.001) the travelled distance by charcoal and peristaltic index. Conclusions: The study demonstrated that the aqueous and ethanolic extracts of Nauclea diderrichii possess antisecretory and antispasmolytic properties hence its use in traditional medicine against diarrhea.


Assuntos
Misoprostol , Rubiaceae , Animais , Antidiarreicos/farmacologia , Carbacol/efeitos adversos , Óleo de Rícino/efeitos adversos , Diarreia/induzido quimicamente , Diarreia/tratamento farmacológico , Etanol , Glibureto , Parassimpatolíticos/uso terapêutico , Casca de Planta , Extratos Vegetais/uso terapêutico , Ratos , Ratos Wistar , Ioimbina/efeitos adversos
11.
J Ethnopharmacol ; 296: 115464, 2022 Oct 05.
Artigo em Inglês | MEDLINE | ID: mdl-35714880

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Remijia ferruginea DC. (Rubiaceae) (syn. Cinchona ferruginea A.St.-Hil.) is used in traditional medicine for the treatment of wounds, fever and malaria. AIM: This study investigated in vitro the proliferative and antioxidant effects of hydroalcoholic extract of leaves of R. ferruginea (HERF) and in vivo the healing effect of ointment based on HERF. MATERIALS AND METHODS: The plant extract was characterized by liquid chromatography/mass spectrometry. Cell proliferation assays and in vitro antioxidant activity were performed. In in vivo assays, wound contraction ax was evaluated, as well as histological analyzes such as cellularity, proportion of blood vessels and collagen type I and III index. In addition, analyzes of the antioxidant enzymes SOD, CAT and GST were performed. RESULTS: Our results showed in the chromatographic analysis that catechin, rutin and quercetin were the main phenolic compounds in the plant extract and may be responsible for the antioxidant and proliferative effects (p < 0.05). In addition, these compounds were found in higher concentration in leaves collected in spring. The ointment containing HERF was able to modulate tissue morphology, increasing cell proliferation, blood vessels, being able to stimulate the production of collagen fibers type I and III, (p < 0.05) contributing to scar tissue maturation and resistance. CONCLUSION: Our findings indicated that the three doses of HERF tested (1%, 3% and 5%) can modulate the skin repair process, but the best effects were observed after exposure to the highest dose.


Assuntos
Antioxidantes , Rubiaceae , Animais , Antioxidantes/uso terapêutico , Pomadas/farmacologia , Extratos Vegetais/uso terapêutico , Folhas de Planta/química , Ratos , Ratos Wistar
12.
Chem Biodivers ; 19(6): e202200001, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35578975

RESUMO

Plant insect interactions are governed by various factors. Nectar availability and floral nectar composition play a significant role in deciding the pollinator pool that visits a particular plant species. This study investigates nectar sugar composition and volume from three endemic species from Western Ghats of India viz. Canthium dicoccum (Gaertn.) Teijsm. & Binn., Ligustrum perrottetii A. DC., and Wendlandia thyrsoidea (Roth) Steud., in their natural habitats. Our results demonstrate intraspecific variation in nectar sugar composition in these endemic plant species. Fructose, mannose and glucose sugars were found in the nectar of all three species. In addition to these three, arabinose was found in Ligustrum and sucrose in Canthium. Nectar volume showed variations in bagged and unbagged conditions. The highest average nectar quantity was found in Canthium (1.27 µl/flower), followed by Ligustrum (0. 31 µl/flower), and Wendlandia (0.14 µl/flower). Floral visitor diversity with a specific emphasis on butterflies showed the highest number of visitors on Ligustrum i. e., 42 out of 45 total butterfly species across all three plant species. This is the first report of standing nectar crop and nectar-sugar composition data compiled for these plant species.


Assuntos
Borboletas , Rubiaceae , Animais , Biodiversidade , Carboidratos , Néctar de Plantas , Plantas , Açúcares
13.
Appl Microbiol Biotechnol ; 106(11): 3851-3877, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35596786

RESUMO

Camptothecin (CPT) is a monoterpenoid-alkaloid, an anticancer compound from plant. Ever since its discovery in 1996 from the bark of Camptotheca acuminata, various researches have been conducted for enhancing its production. CPT has also been reported in several other species belonging to the plant families Icacinaceae, Rubiaceae, Apocynaceae, Nyssaceae, Betulaceae, Violaceae, Meliaceae, and Gelseminaceae. Out of these, Ophiorrhiza sp. (Rubiaceae) is the next possible candidate for sustainable CPT production after C. acuminata and Nothapodytes nimoonia. Various biotechnological-studies have been conducted on Ophiorrhiza sp. for searching the elite species and the most optimal strategies for CPT production. The genus Ophiorrhiza has been used as medicines for antiviral, antifungal, antimalarial, and anticancer activities. Phytochemical analysis has revealed the presence of alkaloids, flavonoids, triterpenes, and CPT from the plant. Because of the presence of CPT and its herbaceous habit, Ophiorrhiza sp. has now become a hot topic in research area. Currently, for mass production of the elite spp., tissue culture techniques have been implemented. In the past decades, several researchers have contributed on the diversity assessment, phytochemical analysis, mass production, and in vitro production of CPT in Ophiorrhiza sp. In this paper, we review the on the biotechnological strategies, optimal culture medium, micropropagation of Ophiorrhiza sp., effect of PGR on shoot formation, rhizogenesis, callus formation, and enhanced production of CPT for commercial use. KEY POINTS: • Latest literature on in vitro propagation of Ophiorrhiza sp. • Biotechnological production of camptothecin and related compounds • Optimization, elicitation, and transgenic studies in Ophiorrhiza sp.


Assuntos
Alcaloides , Antineoplásicos Fitogênicos , Camptotheca , Magnoliopsida , Rubiaceae , Biotecnologia , Camptotecina/análise
14.
Molecules ; 27(10)2022 May 22.
Artigo em Inglês | MEDLINE | ID: mdl-35630810

RESUMO

Three new polycyclic phenol derivatives, 2-acetyl-4-hydroxy-6H-furo [2,3-g]chromen-6-one (1), 2-(1',2'-dihydroxypropan-2'-yl)-4-hydroxy-6H-furo [2,3-g][1]benzopyran-6-one (2) and 3,8,10-trihydroxy-4,9-dimethoxy-6H-benzo[c]chromen-6-one (8), along with seven known ones (3-7, 9 and 10) were isolated for the first time from the leaves of Spermacoce latifolia. Their structures were determined by spectroscopic analysis and comparison with literature-reported data. These compounds were tested for their in vitro antibacterial activity against four Gram-(+) bacteria: Staphyloccocus aureus (SA), methicillin-resistant Staphylococcus aureus (MRSA), Bacillus cereus (BC), Bacillus subtilis (BS), and the Gram-(-) bacterium Escherichia coli. Compounds 1, 2, 5 and 8 showed antibacterial activity toward SA, BC and BS with MIC values ranging from 7.8 to 62.5 µg/mL, but they were inactive to MRSA. Compound 4 not only showed the best antibacterial activity against SA, BC and BS, but it further displayed significant antibacterial activity against MRSA (MIC 1.95 µg/mL) even stronger than vancomycin (MIC 3.9 µg/mL). No compounds showed inhibitory activity toward E. coli. Further bioassay indicated that compounds 1, 4, 5, 6, 8 and 9 showed in vitro α-glucosidase inhibitory activity, among which compound 9 displayed the best α-glucosidase inhibitory activity with IC50 value (0.026 mM) about 15-fold stronger than the reference compound acarbose (IC50 0.408 mM). These results suggested that compounds 4, 8 and 9 were potentially highly valuable compounds worthy of consideration to be further developed as an effective anti-MRSA agent or effective α-glucosidase inhibitors, respectively. In addition, the obtained data also supported that S. latifolia was rich in structurally diverse bioactive compounds worthy of further investigation, at least in searching for potential antibiotics and α-glucosidase inhibitors.


Assuntos
Antibacterianos , Inibidores de Glicosídeo Hidrolases , Fenóis , Rubiaceae , Antibacterianos/química , Antibacterianos/farmacologia , Bacillus cereus , Bacillus subtilis , Escherichia coli , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Staphylococcus aureus Resistente à Meticilina , Testes de Sensibilidade Microbiana , Fenóis/química , Fenóis/farmacologia , Folhas de Planta/química , Rubiaceae/química , alfa-Glucosidases/farmacologia
15.
Food Chem Toxicol ; 163: 113003, 2022 May.
Artigo em Inglês | MEDLINE | ID: mdl-35413384

RESUMO

Morinda officinalis has diverse pharmacological effects and has the potential to be used as functional food and medicine. Fermentation is traditionally used to process Morinda officinalis. However, the toxicological profile of fermented Morinda officinalis (FMO) is not reported. In the present study, the toxicological characteristics of FMO were assessed for the first time. FMO did not show any genotoxicity based on the Ames test, mammalian erythrocyte micronucleus test, and mouse primary spermatocyte chromosome aberration test. FMO administered by gavage in mice and rats at a dose of 20 g/kg BW did not induce death or toxicity based on acute study, indicating that FMO could be regarded as non-toxic at the tested dose. In the 90-day subchronic toxicity study, rats fed with FMO at the maximum dose of 8 g/kg BW did not affect mortalities, BW, food consumption, organ weights, hematology, serum biochemistry, or urinalysis. The no observed adverse effect level of FMO in both sexes was not less than 8 g/kg BW/day based on subchronic toxicity. The obtained results support the safe use of FMO as functional food and medicine.


Assuntos
Morinda , Rubiaceae , Animais , Mamíferos , Camundongos , Morinda/toxicidade , Testes de Mutagenicidade/métodos , Nível de Efeito Adverso não Observado , Extratos Vegetais , Ratos , Ratos Sprague-Dawley , Testes de Toxicidade Aguda/métodos , Testes de Toxicidade Subcrônica/métodos
16.
Rapid Commun Mass Spectrom ; 36(13): e9317, 2022 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-35445460

RESUMO

RATIONALE: Due to the special geographical location and climate of China, there are large differences in the chemical composition and content of Paederia scandens (PS) from different origins, which will have a large impact on its efficacy. METHODS: An efficient quality control method for PS was established by combining ultra-high-performance liquid chromatography (UPLC) and electrospray ionization mass spectrometry analyses. First, a UPLC-quadrupole time-of-flight mass spectrometry system was employed to identify the chemical composition of PS from seven different origins. Then, the chemical variation in 73 batches of PS samples was subsequently investigated by quantitation of four marker compounds. RESULTS: A total of 15 common compounds were identified in the samples of PS from seven origins. And four of the marker compounds were chosen based on VIP values to characterize the differences between PS samples of different origins. The linearity ranged between 0.005 and 2.500 mg/mL; the correlation coefficients (r2 ) ranged from 0.999 to 1; the limits of detection ranged from 0.013 to 0.033 µg/mL; and the relative standard deviations for repeatability, precisions, and stabilities were below 0.2%, 1.6%, and 0.6%, respectively. CONCLUSION: The results show that the method can be effective and comprehensive in evaluating the quality of PS from different origins. And this comprehensive strategy proved to be a powerful technique used to differentiate between different geographical herbs.


Assuntos
Medicamentos de Ervas Chinesas , Rubiaceae , Cromatografia Líquida de Alta Pressão/métodos , Medicamentos de Ervas Chinesas/química , Espectrometria de Massas por Ionização por Electrospray/métodos , Espectrometria de Massas em Tandem/métodos
17.
J Nat Prod ; 85(4): 1029-1038, 2022 04 22.
Artigo em Inglês | MEDLINE | ID: mdl-35412828

RESUMO

Seven new naphthoquinone diglycosides (1-7), three new anthraquinones (8-10), and eight known analogues were obtained from the aerial parts of Mitracarpus hirtus collected from West Africa in a bioassay-guided phytochemical investigation. All isolated compounds were elucidated by comparison with the literature and interpretation of spectroscopic data, and the absolute configurations of the new naphthoquinone diglycosides (1-10) were confirmed by chemical methods and ECD calculations. Notably, compound 1 was found to be the first naphthoquinone diglycoside containing carboxylic acid and isopentenyl side chains isolated from a species in the genus Mitracarpus. Compounds 6-18 showed antibacterial activity against multiple Helicobacter pylori strains with MIC values ranging from 0.0625 to 64 µg/mL. Particularly, 1-hydroxybenzoisochromanquinone (17) and benzo[g]isoquinoline-5,10-dione (18), with MIC values of 0.0625 and 0.125 µg/mL, displayed 32-512-fold higher potencies than a positive control, metronidazole. Compound 18 also demonstrated high antibiofilm activity and killed biofilm-encased Helicobacter pylori cells more effectively than metronidazole.


Assuntos
Helicobacter pylori , Naftoquinonas , Rubiaceae , Antibacterianos/farmacologia , Benzoquinonas , Metronidazol/farmacologia , Testes de Sensibilidade Microbiana , Naftoquinonas/farmacologia , Componentes Aéreos da Planta
18.
BMC Genomics ; 23(1): 256, 2022 Apr 03.
Artigo em Inglês | MEDLINE | ID: mdl-35366818

RESUMO

BACKGROUND: Ophiorrhiza pumila (Rubiaceae) is capable of producing camptothecin (CPT), one monoterpene indole alkaloid extensively employed in the treatment of multiple cancers. Transcription factors (TFs) GATA are a group of transcription regulators involved in plant development and metabolism, and show the feature of binding to the GATA motif within the promoters of target genes. However, GATA TFs have not been characterized in O. pumila. RESULT: In this study, a total of 18 GATA genes classified into four subfamilies were identified, which randomly distributed on 11 chromosomes of O. pumila. Synteny analysis of GATA genes between O. pumila and other plant species such as Arabidopsis thaliana, Oryza sativa, Glycine max, Solanum lycopersicum, Vitis vinifera, and Catharanthus roseus genomes were analyzed. Tissue expression pattern revealed that OpGATA1 and OpGATA18 were found to be correlated with ASA, MK, CPR and GPPS, which were highly expressed in leaves. OpGATA7, showed high expression in roots as most of the CPT biosynthetic pathway genes did, suggesting that these OpGATAs may be potential candidates regulating CPT biosynthesis in O. pumila. CONCLUSIONS: In this study, we systematically analyzed the OpGATA TFs, and provided insights into the involvement of OpGATA TFs from O. pumila in CPT biosynthesis.


Assuntos
Camptotecina , Rubiaceae , Vias Biossintéticas , Raízes de Plantas/genética , Rubiaceae/genética , Rubiaceae/metabolismo , Fatores de Transcrição/genética , Fatores de Transcrição/metabolismo
19.
Biomed Pharmacother ; 149: 112833, 2022 May.
Artigo em Inglês | MEDLINE | ID: mdl-35316751

RESUMO

The present study evaluated the antidiabetic activities of the 70% ethanol stem bark extract of Aidia genipiflora (AGB) and one of its constituents, oleanonic acid in streptozotocin (40 mg/kg)-induced diabetic rats. In vitro assays of glucose uptake and inhibition of carbohydrate metabolizing enzymes were then used to investigate their mechanism(s) of hypoglycaemic action. In silico evaluation of the pharmacokinetic and toxicity properties of the compound was also carried out. Administration of AGB (100-400 mg/kg) and oleanonic acid (15 - 60 mg/kg) resulted in significant reductions (p < 0.001) in the blood glucose and considerable decrease (p < 0.05) in the elevated lipid parameters of the diabetic animals. AGB activity at 200 and 400 mg/kg; and oleanonic acid at 60 mg/kg were comparable to glibenclamide (5 mg/kg). The extract and its isolate strongly inhibited α-glucosidase and α-amylase activity with IC50 values of (10.48 ± 1.39 µg/mL and 14.51 ± 1.26 µg/mL) and (36.52 ± 1.95 µM and 105.84 ± 1.08 µM) respectively. The glucose uptake assays showed that AGB and oleanonic acid exerted both insulin-dependent and independent promotional effect of glucose transport into the periphery by upregulating the expression of PI3K and PPARγ transcripts with a concomitant increase in GLUT-4 transcripts. Although oleanonic acid was predicted to be teratogenic, it was found to be generally non-lethal with favourable pharmacokinetics properties making it suitable for further studies. The study has shown that the stem bark of A. genipiflora is a source of new hypoglycaemic agents and that oleanonic acid possesses hypoglycaemic and anti-hyperlipidaemic activities.


Assuntos
Diabetes Mellitus Experimental , Rubiaceae , Animais , Glicemia/metabolismo , Hipoglicemiantes/efeitos adversos , Extratos Vegetais/efeitos adversos , Ratos , Estreptozocina/efeitos adversos , Triterpenos , alfa-Amilases
20.
Chem Phys Lipids ; 245: 105202, 2022 07.
Artigo em Inglês | MEDLINE | ID: mdl-35337796

RESUMO

The use of deuterium-incorporated bioactive compounds is an efficient method for tracing their metabolic fate and for quantitative analysis by mass spectrometry without complicated HPLC separation even if their amounts are extremely small. Plant sphingolipids and their metabolites, which have C4, 8-olefins on a common backbone as a sphingoid base, show unique and fascinating bioactivities compared to those of sphingolipids in mammals. However, the functional and metabolic mechanisms of exogenous plant sphingolipids have not been elucidated due to the difficulty in distinguishing exogenous sphingolipids from endogenous sphingolipids having the same polarity and same molecular weight by mass spectrometric analysis. Their roles might be elucidated by the use of deuterated probes with original biological and physicochemical properties. In this study, we designed (2S,3R,4E,8Z)-2-aminooctadeca-4,8-diene-17,17,18,18,18-d5-1,3-diol (penta-deuterium-labeled 4E, 8Z-sphingadienine) as a tracer for exogenous metabolic studies. In addition, the sphingadienine was confirmed to be metabolized in HEK293 cells and showed distinct peaks in mass spectrometric analysis.


Assuntos
Rubiaceae , Esfingolipídeos , Animais , Deutério , Etanolaminas , Células HEK293 , Humanos , Mamíferos/metabolismo , Rubiaceae/metabolismo , Esfingolipídeos/química
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