Chemical constituents from fruits of Morinda citrifolia and their inhibitory effects on proliferation of synoviocytes in vitro / 中国中药杂志

The chemical constituents from the fruits of Morinda citrifolia were systematically explored by chromatographic fractionation methods including silica gel, octadecylsilyl(ODS) gel, Sephadex LH-20 gel, and preparative high performance liquid chromatography(pre-HPLC). The chemical structures of all isolated compounds were identified on the basis of their physicochemical properties, spectroscopic analyses, as well as the comparisons of their physicochemical and spectroscopic data with the reported data in literature. As a result, 22 isolated compounds from the 90% ethanol extract of the fruits of M. citrifolia were identified, which were moricitritone(1), 2'-deoxythymidine(2), cyclo-(L-Pro-L-Tyr)(3), methyl-5-hydroxy-2-pyridinecarboxylate(4), methyl pyroglutamate(5), bisbenzopyran(6), epipinoresinol(7), 3, 3'-bisdemethyl pinoresinol(8), 3, 3'-bisdemethyltanegool(9), trimesic acid(10), crypticin B(11), kojic acid(12), vanillic acid(13), protocatechoic acid(14), 5-hydroxymethyl furfural(15), blumenol A(16), 1-O-(9Z, 12Z-octadecadienoyl) glycerol(17), mucic acid dimethylester(18), methyl 2-O-β-D-glucopyranosylbenzoate(19), 2-phenylethyl-O-β-D-glucoside(20), scopoletin(21), and quercetin(22). Among them, compound 1 was a new pyrone derivative, compounds 2, 4-7, 10-12, and 17 were isolated from the plants belonging to Morinda genus for the first time, and compound 18 was obtained from M. citrifolia for the first time. Moreover, on the basis of testing the activities of all isolated compounds on inhibiting the proliferation of synovial fibroblasts in vitro by MTS assay, the anti-rheumatoid arthritis activities of all isolated compounds were initially evaluated. The results showed that compounds 1-6, 9, 19, and 20 exhibited remarkable anti-rheumatoid arthritis activities, which displayed the inhibitory effects on the proliferation of MH7A synovial fibroblast cells with the IC_(50) values in the range of(3.69±0.08) to(168.96±0.98) μmol·L~(-1).

Literature research and discussion of Chinese medicinal properties of Morinda citrifolia / 中国中药杂志

Noni is a dry and mature fruit of Morinda citrifolia, which is widely distributed in the islands in the southern Pacific Ocean and the Indochina Peninsula in Asia. It is edible and has been used as a natural medicine for thousands of years. At present, Noni has been legally introduced into China, but there is no clear standard of traditional Chinese medicine properties and clinical application of traditional Chinese medicine, which greatly limits the application of compatibility with traditional Chinese medicine in China. This article appllied our pioneering modern research technology of new herbal medicine outside of China, theoretically studied the traditional Chinese medicine properties of Noni, and scientifically guided the reasonable compatibility and application of Noni with traditional Chinese medicine. The Web of Science and PubMed databases were selected to access the literatures on Noni. The retrieval time was August 1, 2018, with Noni or Morinda citrifolia as the search term. A total of 862 articles were retrieved. By reading the titles and abstracts of the articles, in addition to repetitive and irrelevant literature, 251 scientific research literatures with reasonable design and high credibility were selected, including 25 clinical trials, 94 pharmacological experiments, and 51 chemical composition literatures. Through analysis of scientific research literatures, led by clinical experiments, supported by pharmacological experiments, combined with the research progress of chemical components, the medicinal properties were studied under the guidance of traditional Chinese medicine theory. The Chinese medicine property of Noni is flat, with acid and sweet flavor.The channel tropisms of Noni included kidney, liver and spleen. The function of Noni included tonifying kindey and liver, strengthening tendon and bone, yiqi yangyin. The clinical application of Noni is used for liver and kidney deficiency, waist and knee weakness, weak muscles and bones; Qi and Yin deficiency, tiredness and thirst. Taken as fruit pulp or dry powder, the equivalent of dried product is 1-4 g. Noni is also distributed in Taiwan, Hainan in China. Hainan, Yunnan have been cultivated and introduced. Give Noni a clear Chinese medicine property, and lay a theoretical foundation for the compatibility of Noni with traditional Chinese medicine, which can enrich the Chinese medicine resources and promote the development of Chinese medicine.

Chemical constituents from fermented Noni juice / 中国中药杂志

The present work was launched to study the chemical constituents from fermented Noni juice. Ten compounds were isolated by using silicagel,Sephadex LH-20 and pre-HPLC. The structures of these compounds were identified by 1D and 2D NMR. Their structures were established as norimester( 1),cyclo( R-Pro-S-Phe)( 2),cyclo-( L-Pro-L-Leu)( 3),trans-cyclo-( D-tryptophanyl-Ltyrosyl)( 4),cyclo( L-Trp-N-methyl-L-Ala-)( 5),4-allyl-2-hydroxyphenyl 1-O-β-D-apiosyl-( 1 → 6)-β-D-glucopyranoside( 6),2-methoxy-4-vinylphenyl β-D-apiofuranosyl-( 1→6)-β-D-glucopyranoside( 7),( +)-lirioresinol A( 8),( ±)-syringaresinol( 9),and2-formyl-1 H-pyrrole-1-butanoic acid( 10). All compounds were tested for their antibacterial activity and α-glucosidase inhibitory activity. Compound 1 was a new compound. All compounds were isolated from fermented Noni juice for the first time. Compound 1 showed significant inhibitory activity against α-glucosidase [IC50 value of( 4. 22±0. 03) μmol·L-1].

Análisis preliminar de los metabolitos secundarios de polvos mixtos de hojas de plantas medicinales / Preliminary analysis of secondary metabolites in mixed powders of leaves of medicinal plants

Introducción: el tamizaje fitoquímico de una planta brinda una percepción sobre los posibles beneficios medicinales; la literatura refiere información de esta determinación en las hojas deAnacardium occidentale L., Psidium guajava L., Morinda citrifolia L. y Moringa oleifera Lam. , no obstante, en cuanto al polvo mixto de sus hojas no se encontró información disponible. Objetivo: determinar los metabolitos secundarios mediante tamizaje fitoquímico a los polvos mixtos de hojas de A. occidentale, P. guajava, M. citrifolia y M. oleifera. Métodos: se recolectaron las hojas de las plantas en estudio, estas se deshidrataron a temperatura ambiente y artificial, seguidamente se trituraron a 1 mm de tamaño de partículas. Para la elaboración de las muestras se tomó el polvo seco obtenido de las hojas y se mezcló en cinco proporciones. Luego, se realizó el tamizaje fitoquímico a los extractos hidro-alchólicos obtenidos de las muestras. Resultados: el tamizaje fitoquímico de los polvos mixtos no detectó resinas, ni flavonoides, excepto en la muestra 4, que se observó este último metabolito. Las quinonas abundan en todas las muestras, excepto en el ensayo 1, que se detectó poca presencia. Además, las proporciones 1, 2 y 3 presentaron saponinas y los alcaloides se identificaron en las muestras 1, 4 y 5, así como, las coumarinas se observaron en las muestras con mayores proporciones de las plantas individuales. Los otros metabolitos secundarios se detectaron con baja presencia en todas las mezclas. Conclusiones: de acuerdo al análisis preliminar de los metabolitos secundarios de los polvos mixtos de hojas de P. guajava, A. occidentale, M. oleifera y M. citrifolia, se sugiere el estudio de estas mezclas medicinales como aditivo fitoquímico en las dietas de los animales, como primer estudio biológico(AU)

Introduction: Phytochemical screening of a plant provides insight into its potential medicinal uses. Phytochemical data about the leaves of Anacardium occidentale L., Psidium guajava L., Morinda citrifolia L. and Moringa oleifera Lam. may be found in the literature. However, no information was found about the mixed powder of these leaves. Objective: Perform phytochemical screening of mixed powders of leaves of A. occidentale, P. guajava, M. citrifolia and M. oleifera to determine their secondary metabolites. Methods: Leaves of the study plants were collected, dehydrated at ambient and room temperature and crushed to 1 mm particles. The study samples were formed by mixing the dry powder from the leaves at five proportions. Phytochemical screening was then conducted of the hydroalcoholic extracts obtained from the samples. Results: Phytochemical screening of the mixed powders did not detect any resins or flavonoids, except in sample 4, where the latter metabolite was found. Quinones are abundant in all samples, except for assay 1, where they were scant. Proportions 1, 2 and 3 contained saponins; alkaloids were identified in samples 1, 4 and 5; and coumarines were found in the samples with greater proportions of individual plants. The remaining secondary metabolites had a low presence in all the mixtures. Conclusions: Based on the preliminary analysis of secondary metabolites in mixed powders of leaves of P. guajava, A. occidentale, M. oleifera and M. citrifolia, it is suggested to study these medicinal mixtures as phytochemical additives in animal feed as a first biological study(AU)

Composição centesimal, compostos bioativos e atividade antioxidante de frutos de Morinda citrifolia Linn (noni) cultivados no Paraná / Proximate composition, bioactive compounds and antioxidant activity of fruits of Morinda citrifolia L. (noni) cultivated in Paraná, Brazil

O fruto de noni (Morinda citrifolia L.) é consumido há milênios na medicina popular polinésia devido aos benefícios nutricionais e terapêuticos. O consumo de noni em outros países, incluindo o Brasil, cresceu vertiginosamente nos últimos anos em decorrência das atividades biológicas atribuídas a ingestão do suco da fruta, principalmente pela propriedade anticâncer. Contudo, a composição química da planta, que está relacionada com suas propriedades biológicas, é determinada pelo seu local de origem, e por influência do clima e do solo onde é cultivada. Neste sentido, este trabalho teve como objetivo analisar a polpa extraída de frutos maduros de noni cultivados em Maringá-PR. A análise da polpa in natura apresentou 89,16% de umidade, 0,75% de cinzas, 2,10% de proteínas, 2,19% de lipídios e 5,81% de carboidratos. Dos compostos bioativos, foram analisados antocianinas (1,39 mg.100 g-1 polpa), flavonoides amarelos (13,01 mg.100 g-1 polpa), carotenóides (0,45 mg.100 g-1 polpa) e vitamina C (12,16 mg.100 g-1 polpa). Para fenólicos totais e atividade antioxidante foram preparados diferentes extratos, sendo que os maiores teores de fenólicos totais foram encontrados no extrato aquoso (1143,56 mg equivalente de ácido gálico (EAG).100 g-1), seguido do extrato etanólico (966,96 mg EAG.100 g-1), metanol/acetona (820,88 mg EAG.100 g-1) e metanólico (306,33 mg EAG.100 g-1). Os melhores resultados para antioxidantes, determinado pelo EC50 - concentração do extrato necessária para reduzir 50% do radical DPPH, foram encontrados nos extratos metanol/acetona (EC50 de 25,18 mg.mL-1) e metanólico (EC50 de 25,96 mg.mL-1). A atividade antioxidante dos frutos pode estar relacionada com o conteúdo de vitamina C, uma vez que os extratos com um menor conteúdo de fenóis totais foram aqueles que apresentaram menores valores de EC50.

The noni fruit (Morinda citrifolia L.) has been consumed for millennia in the Polynesian folk medicine because of its nutritional and therapeutic benefits. The consumption of the noni fruit in other countries, including Brazil, has increased in recent years because of the biological activities attributed to the ingestion of noni juice, especially the anticancer effect. However, the chemical composition of the plant, which is related to its biological properties, is determined by its geographical origin and is influenced by climate and soil. Therefore, this study aimed to analyze the pulp extracted from noni fruit grown in Maringá, state of Paraná, Brazil. The fresh pulp analysis showed 89.16% of moisture, 0.75% of ash, 2.10% of protein, 2.19% of fat and 5.81% of carbohydrates. The bioactive compounds analyzed were anthocyanins (1.39 mg.100 g-1 pulp), yellow flavonoids (13.01 mg.100 g-1 pulp), carotenoids (0.45 mg.100 g-1 pulp) and vitamin C (12.16 mg.100 g-1 pulp). For the analysis of total phenols and antioxidant activity, different extracts were prepared. The highest total phenolic contents were found in the aqueous extract (1143.56 mg EAG.100 g-1), followed by the ethanol extract (966.96 mg EAG.100 g-1), methanol/acetone extract (820.88 mg EAG.100 g-1) and methanol extract (306.33 mg EAG.100 g-1). The results for the antioxidant capacity were determined by the EC50, which is concentration of extract required to reduce 50% of the DPPH radical. The best results for the antioxidant capacity were found in the methanol/acetone extract (EC50 of 25.18 mg.mL-1) and in the methanol extract (EC50 of 25.96 mg.mL-1). The antioxidant activity of the fruit may be related to its vitamin C content, since the extracts with lower total phenolic content were those that had lower EC50 values.

Evaluation of antitumoral and antimicrobial activity of Morinda lcitrifolia L. grown in Southeast Brazil

PURPOSE: To evaluate the antitumor and antimicrobial activity of ethanolic extract of Morinda citrifolia L. fruit cultivated in southeastern Brazil. METHODS: Preparation ethanolic extract of the fruit of Morinda citrifolia L. Culture of melanoma cells B16-F10 for treatment with ethanolic extract of Morinda citrifolia L. fruit to determine cell viability by MTT and determination temporal effect of ethanolic extract fruit on the cell growth B16-F10 for 8 days. Evaluation of antimicrobial activity of ethanolic extract fruit against Staphylococcus aureus and Escherichia coli by determination of Minimum Inhibitory Concentration (MIC). RESULTS: The ethanolic extract of Morinda citrifolia L. fruit (10mg/mL) decreased cellular activity and inhibited 45% the rate of cell proliferation of B16-F10 melanoma treated during period studied. The ethanolic extract of Morinda citrifolia L. fruit demonstrated antimicrobial activity inhibiting the growth of both microorganisms studied. Staphylococcus aureus was less resistant to ethanolic extract of Morinda citrifolia L. fruit than Escherichia coli, 1 mg/mL and 10 mg/mL, respectively. CONCLUSION: What these results indicate that the ethanolic extract of the fruit of Morinda citrifolia L. showed antitumor activity with inhibition of viability and growth of B16-F10 cells and also showed antibacterial activity as induced inhibition of growth of Staphylococcus aureus and Escherichia coli. .

Efecto neurofarmacológico del zumo de Morinda citrifolia / Neuropharmacological properties of Morinda citrifolia juice

Morinda citrifolia Linn. (Rubiaceae) (Noni) is a plant, to which several therapeutic properties have assigned, but its neuropsicopharmacological effects have been poor studied. The aim of this work was to characterize the neuropharmacological properties of its juice, in male mice, by means of a battery of behavioral tests: Irwin test, exploratory behavior, barbiturate sleeping time and amphetamine-induced stereotypes. Doses of 450, 900 and 1800 mg/kg were administered, according to the juice dry weight. The results obtained from the different tests suggest the presence of non identified chemical compounds with sedative activity, specifically of neuroleptic type.

Morinda citrifolia Linn. (Rubiaceae) (Noni) es una planta que presenta diversas propiedades terapéuticas, pero sus efectos neuropsicofarmacológicos han sido poco estudiados. El objetivo del presente trabajo, fue caracterizar el perfil neurofarmacológico de su jugo, en ratones machos, por medio de una batería de pruebas de comportamiento: prueba de Irwin, conducta exploratoria, tiempo de sueño barbitúrico y estereotipias anfetamina-inducidas. Dosis de 450, 900 y 1800 mg/kg fueron administrada, de acuerdo con el peso de jugo seco. Los resultados obtenidos de las diferentes pruebas sugieren la presencia de compuestos químicos no identificados con actividad sedante, especialmente de tipo neuroléptica.

Total polyphenol content and antioxidant activity of commercial Noni (Morinda citrifolia L) juice and its components

The plant Morinda citrifolia L. (noni) has been the focus of many recent studies due to its potential effects on treatment and prevention of several diseases. However, there are few in vivo and in vitro studies concerning its composition and antioxidant capacity. The aim of the present study was to determine the total polyphenol content (TPC) and antioxidant capacity of a juice commercialized as noni juice, but containing grape, blueberry and noni fruits. Commercial noni juice was compared against its separate constituents of blueberry and grape juice. Folin-Ciocalteu and DPPH• methods were used to determine the concentration of total polyphenol content and antioxidant activity, respectively. Commercial noni juice presented higher values of TPC (91.90 mg of gallic acid/100 mL juice) and antioxidant activity (5.85 mmol/L) compared to its 5% diluted constituents. Concentrated blueberry juice presented higher TPC and antioxidant activity than the other juices analyzed. Considering that the blueberry and grape juices account for only 10% in the composition of commercial noni juice, it can be inferred that these two components contribute significantly to the antioxidant activity. Therefore, additional studies are necessary in order to elucidate the contribution of the noni juice as an antioxidant.

A planta Morinda citrifolia L. tem sido objeto de muitas pesquisas decorrente de seus efeitos benéficos no tratamento e prevenção de muitas doenças. No entanto, são escassos os estudos in vivo e in vitro sobre os compostos presentes e sua capacidade de atuar como antioxidante. Objetivou-se com este trabalho determinar o índice de polifenóis totais (IPT) e a capacidade antioxidante do suco de noni comercial, constituído de uva, mirtilo e a fruta do noni. O suco de noni comercial foi comparado com seus constituintes (mirtilo e suco de uva) separadamente. Os métodos Folin-Ciocalteu e DPPH• foram utilizados para determinar a concentração de polifenóis totais e capacidade antioxidante, respectivamente. O suco de noni apresentou valores superiores de IPT (91,90 mg ácido gálico/100 mL de suco) e atividade antioxidante (5,85 mmol/L) quando comparado aos seus constituintes diluídos a 5%. O suco de mirtilo, na sua forma concentrada, apresentou IPT e atividade antioxidante superior aos demais sucos. Considerando que os sucos de mirtilo e de uva representam apenas 10% na composição do suco de noni, pode-se inferir que estes dois constituintes contribuem de forma significativa para a atividade antioxidante. Assim, estudos adicionais são necessários para elucidar a contribuição do suco de noni como sequestrador de radicais livres.

Desarrollo de una tecnología para la obtención de extracto acuoso de hojas de Morinda citrifolia L (noni) / Development of a technology for obtaining an aqueous extract from Morinda citrifolia L. leaves

Morinda citrifolia L (noni) es una planta que ha cobrado gran interés en los últimos años por causa de múltiples propiedades medicinales atribuidas a sus frutos, raíz, corteza, semillas y, en particular, sus hojas que poseen actividad antiinflamatoria, astringente, antiséptica e hipoglucemiante. Las plantas medicinales y sus extractos bioactivos son incorporados cada vez más en la industria farmacéutica en la sustitución de las preparaciones artesanales, y así aumentar la calidad de los medicamentos de origen herbario...

Morinda citrifolia L (noni) is a plant that has aroused great interest in the last few years because of the many medicinal properties of its fruits, roots, bark, seeds and particularly its leaves that have antiinflammatory, astringent, antiseptic and hypoglucemic effects. Medicinal plants and their bioactive extracts are increasingly incorporated into the drug industry to replace traditionally-made preparations and to increase the quality of herbal medicines...

Determinación de características fisicoquímicas del extracto natural pasteurizado a base de Morinda citrifolia L / Determination of physicochemical characteristics of the natural pasteurized extract based on Morinda citrifolia L

El presente trabajo de investigación trata de determinar las propiedades fisicoquímicas del extracto natural pasteurizado a base de Morinda citrifolia L. Elabora un extracto natural pasteurizado a base de Morinda citrifolia L., se aplican los procedimientos adecuados para el procesamiento de la fruta, se determina las características organolépticas, densidad, pH, grados Brix e índice de acidez del extracto natural pasteurizado a base de noni y se compara las propiedades antes mencionadas del extracto pasteurizado con el no pasteurizado.