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1.
Sci Rep ; 14(1): 5112, 2024 03 01.
Article in English | MEDLINE | ID: mdl-38429360

ABSTRACT

Calophyllum soulattri Burm.f. is traditionally used to treat skin infections and reduce rheumatic pain, yet genetic and genomic studies are still limited. Here, we present the first complete mitochondrial genome of C. soulattri. It is 378,262 bp long with 43.97% GC content, containing 55 genes (30 protein-coding, 5 rRNA, and 20 tRNA). Repeat analysis of the mitochondrial genome revealed 194 SSRs, mostly mononucleotides, and 266 pairs of dispersed repeats ( ≥ 30 bp) that were predominantly palindromic. There were 23 homologous fragments found between the mitochondrial and plastome genomes. We also predicted 345 C-to-U RNA editing sites from 30 protein-coding genes (PCGs) of the C. soulatrii mitochondrial genome. These RNA editing events created the start codon of nad1 and the stop codon of ccmFc. Most PCGs of the C. soulattri mitochondrial genome underwent negative selection, but atp4 and ccmB experienced positive selection. Phylogenetic analyses showed C. soulattri is a sister taxon of Garcinia mangostana. This study has shed light on C. soulattri's evolution and Malpighiales' phylogeny. As the first complete mitochondrial genome in Calophyllaceae, it can be used as a reference genome for other medicinal plant species within the family for future genetic studies.


Subject(s)
Calophyllum , Genome, Mitochondrial , Malpighiales , Genome, Mitochondrial/genetics , Phylogeny , Codon, Initiator , Codon, Terminator
2.
Sci Rep ; 14(1): 4867, 2024 02 28.
Article in English | MEDLINE | ID: mdl-38418841

ABSTRACT

Baccaurea ramiflora Lour., an evergreen tree of the Baccaurea genus of the Phyllanthaceae family, is primarily distributed in South Asia, Southeast Asia, and southern China, including southern Yunnan Province. It is a wild or semi-cultivated tree species with ornamental, edible, and medicinal value, exhibiting significant development potential. In this study, we present the whole-genome sequencing of B. ramiflora, employing a combination of PacBio SMRT and Illumina HiSeq 2500 sequencing techniques. The assembled genome size was 975.8 Mb, with a contig N50 of 509.33 kb and the longest contig measuring 7.74 Mb. The genome comprises approximately 73.47% highly repetitive sequences, of which 52.1% are long terminal repeat-retrotransposon sequences. A total of 29,172 protein-coding genes were predicted, of which 25,980 (89.06%) have been annotated, Additionally, 3452 non-coding RNAs were identified. Comparative genomic analysis revealed a close relationship between B. ramiflora and the Euphorbiaceae family, with both being sister groups that diverged approximately 59.9 million years ago. During the evolutionary process, B. ramiflora exhibited positive selection in 278 candidate genes. Synonymous substitution rate and collinearity analysis demonstrated that B. ramiflora underwent a single ancient genome-wide triploidization event, without recent genome-wide duplication events. This high-quality B. ramiflora genome provides a valuable resource for basic research and tree improvement programs focusing on the Phyllanthaceae family.


Subject(s)
Genome, Plant , Malpighiales , China , Repetitive Sequences, Nucleic Acid , Evolution, Molecular , Phylogeny
3.
Chem Biodivers ; 21(3): e202301960, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38196022

ABSTRACT

The fixed oil from the inner mesocarp of Caryocar coriaceum Wittm. is used in the Chapada do Araripe region of Brazil for the treatment of genitourinary candidiasis. This study aimed to evaluate the chemical composition, antifungal activity, reduction of fungal virulence, and the preliminary toxicity of the fixed oil from the inner mesocarp of C. coriaceum tested against three Candida yeasts. The oil was characterized by gas chromatography (GC-MS and GC-FID). Antifungal activity was assessed using the serial microdilution method. Additionally, the potential of the oil as an enhancer of fluconazole action was tested at sub-inhibitory concentrations (MIC/8). The mechanism of action of C. coriaceum fixed oil was determined by evaluating the inhibition of morphological transition in Candida spp. The chemical composition of the fixed oil of C. coriaceum comprised both unsaturated and saturated fatty acids. Oleic (61 %) and palmitic (33 %) acids were the major constituents. Regarding its anti-Candida activity, the oil inhibited the growth of C. albicans (IC50 : 371 µg/mL) and C. tropicalis (IC50 : 830 µg/mL). Furthermore, the oil reversed the antifungal resistance of C. albicans and C. tropicalis, restoring the susceptibility to fluconazole and reducing their IC50 from 12.33 µg/mL and 362 µg/mL to 0.22 µg/mL and 13.93 µg/mL, respectively. The fixed oil of C. coriaceum completely inhibited the morphological transition of C. albicans and C. tropicalis at a concentration of 512 µg/mL, but exhibited limited low antifungal potential against C. krusei. The observed antifungal activity may be attributed to the overproduction of reactive oxygen species. Additionally, the oil showed no toxic effect on the Drosophila melanogaster in vivo model. The fixed oil from the inner mesocarp of C. coriaceum emerge as a strong candidate for the development of new pharmaceutical formulations to treat infections caused by Candida spp.


Subject(s)
Fluconazole , Malpighiales , Animals , Fluconazole/pharmacology , Candida , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Drosophila melanogaster , Plant Oils/pharmacology , Plant Oils/chemistry , Candida albicans , Microbial Sensitivity Tests
4.
Fitoterapia ; 173: 105826, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38219842

ABSTRACT

Five undescribed lignans, cleiseberharnins A-D (1-4), cleiseberharside A (5) were isolated from the fruits of Cleistanthus eberhartii (Phyllanthaceae), together with six known aryltetralin lignans, cleistantoxin (6), picroburseranin (7), neocleistantoxin (8), 7-hydroxypicropolygamain (9), cleisindoside D (10), and cleisindoside A (11). Their structures and relative configurations were established by analysis of HRESIMS and NMR data, and quantum chemical calculations of JH,H coupling constants. The absolute configurations of 1-5 were determined by analysis of their experimental CD spectra and comparison with calculated electronic circular dichroism (ECD) spectra. All compounds (1-11) were evaluated for their cytotoxicity against KB, MCF-7, HepG-2, and Lu-1 human cancer cell lines. Among the tested compounds, compounds 6 and 7 showed strong activity against KB, MCF7, HepG2 and Lu-1 cell lines with IC50 values in the range of 0.02-0.62 µM. Compound 1 showed activity against three cancer cell lines KB, HepG2, and Lu-1 with IC50 values of 6.98, 7.61 and 11.75 µM, respectively. Compound 2 exhibited a selective inhibition with moderate cytotoxicity against Lu-1 with IC50 value of 15.30 µM. Compounds 4, 5 and 9 showed moderate activity against the three cancer cell lines with IC50 values in the range of 8.73-19.70 µM.


Subject(s)
Antineoplastic Agents, Phytogenic , Antineoplastic Agents , Lignans , Malpighiales , Humans , Cell Line, Tumor , Fruit/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Molecular Structure , Lignans/pharmacology , Lignans/chemistry
5.
J Med Food ; 27(2): 145-153, 2024 Feb.
Article in English | MEDLINE | ID: mdl-38079198

ABSTRACT

Pequi is a native and popular fruit in Cerrado biome. The internal yellow-orange mesocarp is the edible fraction of the fruit, but its shell (peel and external mesocarp), which comprises 80% of the fruit, is not used by the agro-industry during fruit processing. There is a growing interest in the reduction of food loss and waste because of environmental, economic, and social impacts. So this study evaluated the chemical composition, antioxidant capacity, and in vitro prebiotic activity of pequi shell flour. Pequi shell flour was obtained from the lyophilization and milling of pequi shell. The content of dietary fibers, oligosaccharides, sugars, organic acids, total phenolics and tannins, polyphenol profile, and antioxidant capacity was determined in pequi shell flour. In addition, its prebiotic activity was evaluated on growth and metabolism of probiotics Lactobacillus and Bifidobacterium strains. Pequi shell flour has a high content of dietary fibers (47.92 g/100 g), soluble fibers (18.65 g/100 g), raffinose (2.39 g/100 g), and phenolic compounds (14,062.40 mg gallic acid equivalents/100 g). For the first time, the polyphenols epigallocatechin gallate, epicatechin, and procyanidin B2 were identified in this by-product. Pequi shell flour promoted greater growth of Lacticaseibacillus casei L-26 (at 24-48 h) and Bifidobacterium animalis subsp. lactis BB-12, as well as higher prebiotic activity scores than fructooligosaccharides (standard prebiotic). Pequi shell flour is rich in prebiotic compounds and has a high antioxidant and prebiotic potential. The promising results encourage its use as an ingredient with antioxidant and potential prebiotic properties to elaborate new functional foods and nutraceuticals.


Subject(s)
Food Ingredients , Malpighiales , Antioxidants , Lactobacillus , Bifidobacterium , Dietary Fiber
6.
Braz. j. biol ; 84: e253598, 2024. tab, graf
Article in English | LILACS, VETINDEX | ID: biblio-1355857

ABSTRACT

Abstract Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae) trees are widely distributed throughout the Cerrado ecosystem. The fruits of C. brasiliense trees are used by humans for food and as the main income source in many communities. C. brasiliense conservation is seriously threatened due to habitat loss caused by the land-use change. Sucking insects constitute an important ecological driver that potentially impact C. brasiliense survival in degraded environments. In addition, insects sampling methodologies for application in studies related to the conservation of C. brasiliense are poorly developed. In this study, sucking insects (Hemiptera) and their predators were recorded in three vertical strata of Caryocar brasiliense canopies. The distribution of sucking species showed vertical stratification along the canopy structure of C. brasiliense. The basal part of the canopy had the highest numbers of sucking insects Aphis gossypii (Glover 1877) (Hemiptera: Aphididae) and Bemisia tabaci (Genn. 1889) (Hemiptera: Aleyrodidae), and their predators Chrysoperla sp. (Neuroptera: Chrysopidae), spiders (Araneae), and Zelus armillatus (Lep. & Servi., 1825) (Hemiptera: Reduviidae). Predators' distribution follows the resource availability and preferred C. brasiliense tree parts with a higher abundance of prey.


Resumo Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae) é amplamente distribuído por todo o ecossistema de cerrado. Os frutos de C. brasiliense são utilizados na alimentação humana e constitui uma importante fonte de renda para muitas comunidades. A perda de habitat provocada pelas mudanças de uso da terra coloca em risco a conservação de C. brasiliense. Insetos sugadores constituem um importante fator ecológico que, potencialmente, afeta o fitness de C. brasiliense em ambientes degradados. Além disso, as metodologias de amostragem de insetos para aplicação em estudos relacionados à conservação de C. brasiliense são pouco desenvolvidas. Neste estudo, o número de insetos sugadores (Hemiptera) e seus predadores foram avaliados em três estratos verticais do dossel de C. brasiliense. A distribuição das espécies sugadoras apresentou estratificação vertical ao longo da estrutura do dossel. O estrato basal do dossel apresentou o maior número de insetos sugadores Aphis gossypii (Glover 1877) (Hemiptera: Aphididae) e Bemisia tabaci (Genn. 1889) (Hemiptera: Aleyrodidae), e seus predadores Chrysoperla sp. (Neuroptera: Chrysopidae), aranhas (Araneae) e Zelus armillatus (Lep. & Servi., 1825) (Hemiptera: Reduviidae). Os predadores distribuíram-se de acordo com a disponibilidade de recursos, ocorrendo em maior número nas partes do dossel com maior abundância de suas presas.


Subject(s)
Humans , Animals , Aphids , Malpighiales , Trees , Ecosystem , Insecta
7.
Braz. j. biol ; 84: e253215, 2024. tab
Article in English | LILACS, VETINDEX | ID: biblio-1360216

ABSTRACT

Frequencies, magnitudes, and distributions of occurrence can affect the events. The problem can be worse or the solution better if greater frequencies and magnitudes are presented with aggregated distribution in the production system. Indices, hence, are used to assist in decision-making on certain issues. The system formed by Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae), a typical and economically important Brazilian Cerrado tree species, and its several arthropods are adequate to evaluate a new index. This study aimed to test an index to identify the loss and solution sources and their importance in the system's loss or income gain. The index is: Percentage of Importance Indice [...] separated the loss sources [e.g., Edessa rufomarginata De Geer, 1773 (Hemiptera: Pentatomidae) on fruits = 41.90%)] on the percentage of reduction of fruit production (e.g., 0.13%), calculated the attention level (e.g., 0.10/fruit), with a total lost production of 1.35% (≈ 307 total lost fruits). The % I.I. also separated the solution sources [e.g., Zelus armillatus (Lep. and Servi., 1825) (Hemiptera: Reduviidae) = 55.48%), the non-attention level (e.g., Z. armillatus: 0.394 for E. rufomarginata on fruit), with total income gain of 0.56% (≈ 128 total saved fruits) on the natural system (e.g., C. brasiliense trees). This index can calculate losses or the effectiveness of the solutions monetarily. Here I test the % I.I., an index that can detect the key loss and solution sources on the system, which can be applied in some knowledge areas.


Frequências, magnitudes e distribuição de ocorrência pode afetar os eventos. O problema pode ser pior ou a solução melhor se maiores frequências e magnitudes forem apresentadas com distribuição agregada no sistema de produção. Índices, então, são usados para assistir na decisão de certas questões. O sistema formado pelo Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae), uma espécie arbórea típica e economicamente importante do Cerrado brasileiro, e seus diversos artrópodes são adequados para avaliar um novo índice. A motivação deste trabalho foi testar um índice capaz de identificar as fontes de perda e de soluções, e suas importâncias em termos de perdas ou ganhos no sistema. O índice é: percentagem de importância [...] separou as fontes de perda [ex., Edessa rufomarginata De Geer, 1773 (Hemiptera: Pentatomidae) em frutos = 41,90%)] na percentagem de redução na produção de frutos (ex., 0,13%), calculando o nível de atenção (ex., 0,10/fruto), com um total de perda de produção de 1,35% (≈ 307 frutos totais perdidos). O % I.I. também separou as fontes de solução [ex., Zelus armillatus (Lep. and Servi., 1825) (Hemiptera: Reduviidae) = 55,48%)], o nível de não atenção (ex., Z. armillatus: 0,394 para E. rufomarginata em fruto), com total de ganho de 0,56% (≈ 128 total de frutos salvos) no sistema natural (ex., árvores de C. brasiliense). Esse índice pode calcular essas perdas ou a eficácia das soluções monetariamente. Aqui eu testo o % I.I., um índice capaz de detectar fatores chaves de perda e de soluções no sistema, capaz de ser aplicado em algumas áreas do conhecimento.


Subject(s)
Arthropods , Brazil , Grassland , Economics , Malpighiales
8.
J Insect Sci ; 23(5)2023 Sep 01.
Article in English | MEDLINE | ID: mdl-37656822

ABSTRACT

Myrmecophytes have mutualistic relationships with symbiotic ants. Although myrmecophytic Macaranga (Malpighiales: Euphorbiaceae) species are well protected by aggressive Crematogaster (Hymenoptera: Formicidae) ants, some bug species occur on the myrmecophytes. To clarify the associations of these bugs with the plants and the ants, we studied the food habits of 3 bug species, Pilophorus lambirensis Nakatani et Komatsu, 2013 (Hemiptera: Miridae: Phylinae), Phylinae sp. 1, and Arbela sp. 1 (Hemiptera: Nabidae). We conducted field observations in a Bornean rainforest. First, we located these bugs and studied their behavioral responses to the ants on Macaranga species; we then conducted stable isotope analyses. All bugs avoided direct contact with ants, but they occurred only on trees with active ants. Pilophorus lambirensis and Phylinae sp. 1 were most commonly observed on the apical parts of host trees, whereas Arbela sp. 1 was mainly in areas distant from the apical parts where ants were sparse. The stable isotope ratios indicated that Phylinae sp. 1 fed on food bodies, which are nutrient-rich spherical bodies produced by Macaranga trees on the apical parts for ants. Although the main diet of the other 2 species remains unclear, nitrogen isotopic signatures demonstrated that P. lambirensis is herbivorous, whereas Arbela sp. 1 is carnivorous. However, the distant location from ants and its isotopic signatures indicated that Arbela sp. 1 rarely fed on the ants. At least 2 mirid bug species might obtain enemy-free space in addition to the food provided by the myrmecophytes.


Subject(s)
Ants , Euphorbiaceae , Heteroptera , Malpighiales , Animals , Herbivory , Predatory Behavior
9.
Molecules ; 28(16)2023 Aug 21.
Article in English | MEDLINE | ID: mdl-37630417

ABSTRACT

The dichloromethane extract of the roots of Bridelia balansae Tutcher (Phyllanthaceae) was found to show potential anticancer activity against HCT116 colorectal cancer cell. Our bioassay-guided phytochemical investigation of the roots of B. balansae led to the identification of 14 compounds including seven lignans (1-7), three phenylbenzene derivatives (8-10), two flavanone (11-12), and two triterpenoids (13-14). Among them, 4'-demethyl-4-deoxypodophyllotoxin (1) is the first aryltetralin lignan compound identified from this plant species. In addition, the stereochemistry of 1 was validated by X-ray crystallography for the first time, and its distinguished cytotoxic effect on HCT116 cells with an IC50 value at 20 nM was induced via an apoptosis induction mechanism. Compound 1 could also significantly decrease the migration rate of HCT116 cells, indicating its potential application against cancer metastasis. The western blot analysis showed that 1 has the potential to inhibit cell proliferation and metastasis. Treatment of 1 resulted in the downregulation of matrix metalloproteinases 2 (MMP2) and p-Akt, while p21 was upregulated. Collectively, the present study on the phytochemical and biological profile of B. balansae has determined the plant as a useful source to produce promising anticancer lead compounds.


Subject(s)
Lignans , Malpighiales , Biological Assay , Blotting, Western , Cell Death , Cell Proliferation , Lignans/pharmacology
10.
Fitoterapia ; 170: 105627, 2023 Oct.
Article in English | MEDLINE | ID: mdl-37517558

ABSTRACT

Two new 30-norfriedelane triterpenoids namely glaucalactone C (1) and glaucanoic acid (2) along with sixteen known compounds (3-18) have been isolated from the methanolic extracts of the stem bark and fruits of Caloncoba glauca (P.Beauv.) Gilg (Achariaceae). The structures of all the isolated compounds have been established with the aid of their extensive spectroscopic analyses (1D and 2D-NMR) as well as mass spectrometry. Six compounds (1-5, 9) were screened for antiplasmodial activity against two strains P. falciparum Dd2 and P. falciparum 3D7. The results showed that glaucanoic acid (2) was the most active one with IC50 values of (3.5 ± 0.1 µg/mL) and (4.6 ± 0.7 µg/mL) against PfDd2 and Pf3D7, respectively, while glaucalactone C (1) moderately inhibited PfDd2 (9.4 ± 0.1 µg/mL) and weakly Pf3D7 (15.9 ± 2.3 µg/mL). The molecular docking analyses of the isolated compounds showed that compounds 1-4 and 9-11 are potential drug targets and were further supported by their ADMET studies that revealed welwitschiilactones B and C (4 and 5) as well as ß-sitosterol (10) as the most qualified compounds to be safe as drugs. The results indicate that C. glauca is an important source of good candidates in new antiplasmodial drug development.


Subject(s)
Antimalarials , Malpighiales , Antimalarials/pharmacology , Antimalarials/chemistry , Plant Extracts/chemistry , Fruit , Molecular Docking Simulation , Plant Bark/chemistry , Molecular Structure , Plasmodium falciparum , Structure-Activity Relationship
11.
An Acad Bras Cienc ; 95(2): e20201550, 2023.
Article in English | MEDLINE | ID: mdl-37436198

ABSTRACT

This study aimed to develop and evaluate bread with the use of pulp and flours of pequi, in partial replacement of water and wheat flour, to develop a bakery product with good technological, nutritional and sensorial qualities. The pequi husk and pulp flours were obtained by means of a thermal pre-treatment, oven drying and standardization of the dry material. Whereas, the bread formulation was defined through the baker's formulation. Besides, the dehydration process caused significant changes (p<0.05) in the L* value and chromaticity (C*), mainly of the flours (husk and pequi pulp), such changes are due to non-enzymatic oxidative processes and pigment degradation, especially carotenoids. The effect of the substitution of ingredients (wheat flour and water) by husk and pulp flours and pequi pulp contributed to the increase in lipid, crude fiber, nitrogen-free extract and energy value content. However, the substitution promoted changes in the attributes of color and textural properties, such as increased hardness, chewiness and cohesiveness. Nevertheless, all formulations showed good sensory acceptance and thus, pequi sweet breads can be implemented in school meals for contributing and meeting the nutritional recommendations established by the School Feeding Brazilian Program (PNAE).


Subject(s)
Fruit , Malpighiales , Fruit/chemistry , Flour/analysis , Bread/analysis , Triticum
12.
J Nat Prod ; 86(6): 1606-1614, 2023 06 23.
Article in English | MEDLINE | ID: mdl-37307145

ABSTRACT

Chemical investigation of the twigs of Cleistanthus sumatranus (Phyllanthaceae) led to the isolation of 10 undescribed lignans, sumatranins A-J (1-10). Compounds 1-4 are unprecedented furopyran lignans characterized by a unique 2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromene heterotricyclic framework. Compounds 9 and 10 are rare 9'-nor-dibenzylbutane lignans. Structures were established based on analyses of spectroscopic data, X-ray crystallographic data, and experimental ECD spectra. Immunosuppressive assays revealed compounds 3 and 9 displayed moderate inhibitory effects with good selectivity indexes against LPS-induced B lymphocyte proliferation.


Subject(s)
Lignans , Malpighiales , Lignans/pharmacology , Lignans/chemistry , Molecular Structure
13.
An Acad Bras Cienc ; 95(1): e20220128, 2023.
Article in English | MEDLINE | ID: mdl-37075351

ABSTRACT

The dwarf pequi tree, Caryocar brasiliense subsp. intermedium, is extremely restricted to ecological niches in the Cerrado biome. Thus, understanding the conditioning factors of the micro-endemism of this sub-species through its spatial distribution and the physical-chemical attributes of the soil was the objective of this research. The research was carried out in a fragment of rupestrian field. The area was divided into quadrants in which the number of pequi trees was quantified and the physicochemical characteristics of the soil were determined. The modeling of semivariograms was performed using semivariances, and ordinary kriging was used for spatial interpolation of variables with spatial dependence. The number of pequi trees, the altitude, the remaining phosphorus and the humidity showed a strong degree of spatial dependence, unlike the pH, the calcium and the magnesium, all of which had a pure nugget effect. The other variables showed a moderate degree of spatial dependence. The greater availability of bases (SB > 0.1 cmolc dm-3) and phosphorus (> 1.05 mg dm-3), the reduced percentage of moisture (< 5%) and low potential acidity (< 4.0 cmolc dm-3) were the factors positively related to the establishment and development of the dwarf pequi tree in the area.


Subject(s)
Malpighiales , Trees , Ecosystem , Soil , Humidity
14.
Zootaxa ; 5257(1): 131-142, 2023 Mar 24.
Article in English | MEDLINE | ID: mdl-37044616

ABSTRACT

Torrenticolid mites (Hydrachnidiae, Acari) are presented from Yintiaoling National Nature Reserve, China. Torrenticola multiserrater Gu & Guo sp. nov., and T. pseudoalargada Gu & Guo sp. nov. are described and illustrated as new to science; T. siamis Pesic & Smit, 2009 and T. nipponica (Enami, 1940) are reported as new records for Chongqing's fauna. Meanwhile, this is the first report of Torrenticolidae from Chongqing, China.


Subject(s)
Malpighiales , Mites , Animals , China
15.
Molecules ; 28(2)2023 Jan 04.
Article in English | MEDLINE | ID: mdl-36677570

ABSTRACT

Glochidpurnoids A and B (1 and 2), two new coumaroyl or feruloyl oleananes, along with 17 known triterpenoids (3-19) were obtained from the stems and twigs of Glochidion puberum. Their structures were elucidated by extensive spectroscopic data analyses, chemical methods, and single crystal X-ray diffraction. All compounds were screened for cytotoxicity against the colorectal cancer cell line HCT-116, and 2, 3, 5, 6, 11, and 17 showed remarkable inhibitory activities (IC50: 0.80-2.99 µM), being more active than the positive control 5-fluorouracil (5-FU). The mechanistic study of 2, the most potent compound, showed that it could induce endoplasmic reticulum (ER) stress-mediated apoptosis and improve the sensitivity of HCT-116 cells to 5-FU.


Subject(s)
Colorectal Neoplasms , Malpighiales , Humans , Apoptosis , Fluorouracil/pharmacology , Cell Line, Tumor , Colorectal Neoplasms/drug therapy , Colorectal Neoplasms/metabolism , Endoplasmic Reticulum Stress
16.
Nat Prod Res ; 37(3): 468-477, 2023 Feb.
Article in English | MEDLINE | ID: mdl-34570603

ABSTRACT

Phytochemical investigation of the methanolic extract of the trunk bark of Caloncoba welwitschii (Oliv.) Gilg (Achariaceae) led to the isolation of four new compounds, including three new 30-norfriedelane triterpenes, welwitschiilactones D-F (1-3), one new friedelane triterpene, welwitschioic acid (4) as well as ten known compounds: stigmastane-3,6-dione (7), a mixture of ß-sitosterol and stigmasterol (6a and 6b), a mixture of ß-sitosterol and stigmasterol glucoside (11a and 11b), (2S,3S,4R,5R)-N-(1,3,4,5-tetrahydroxyndecan-2-yl)tetradecanamide (10), 1-O-ß-D-glucopyranosyl-(2S,3R,8E)-2-[(2'R)-2-hydroxylpalmitoylamino]-8-octadecene-1,3-diol (12), 3ß,21ß-dihydroxy-27-oxo-30-nor-(D:A)-friedo-olean-20(29))en-27,19α-lactone (8), 21ß-hydroxy-3,27-dioxo-30-nor-(D:A)-friedo-olean-20(29)-en-27,19α-lactone (9) and 2ß,21ß-dihydroxy-27-oxo-30-nor-(D:A)-friedo-olean-20(29)-en-27,19α-lactone (5). The structures of all the isolated compounds were determined by extensive spectroscopic analyses (1D and 2D NMR as well as ESI-MS). The relative configuration of the 20-oxymethine in 1 as well as that of 19-oxymethine in 2 and 3 has been established using the NOESY spectrum. In an experiment, a sample of welwitschiilactone C (5) was chemically modified through reduction reaction to give a new hemi-synthetic derivative namely 2ß,3ß,21ß-trihydroxy-30-nor-(D:A)-friedo-olean-20(29)-en-27,19α-lactone (5a).


Subject(s)
Malpighiales , Triterpenes , Plant Bark/chemistry , Triterpenes/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure
17.
J Ethnopharmacol ; 304: 116044, 2023 Mar 25.
Article in English | MEDLINE | ID: mdl-36528212

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: Sauropus androgynus L. Merr. (Euphorbiaceae) commonly known as "multigreen" and "multivitamin" is consumed as a vegetable and used in traditional medicine to relieve fever. AIM OF THE STUDY: This in vitro study is aimed to explore the activities of the lipophilic fraction of the leaves of S. androgynus (LFSA) against dengue (DENV), chikungunya (CHIKV) viruses and malaria (P. falciparum strain 3D7) parasite. MATERIALS AND METHODS: The LFSA was analyzed by using GC-FID and GC-MS. The antiviral activity of LFSA was studied using the Vero CCL-81 cell line. The cytotoxicity assay was performed using 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT). Focus forming unit (FFU), cell-based immunofluorescence (IFA) assays, and quantitative RT-PCR, were used to determine and confirm antiviral activity against DENV and CHIKV. The antiparasitic activity of LFSA was carried out against P. falciparum strain 3D7 grown in fresh O+ human erythrocytes culture. RESULTS: Twelve compounds were identified in LFSA using GC/MS. The most abundant compound was squalene (36.9%), followed by vitamin E (12.5%) and linolenic acid (10.2%). Significant reduction in DENV titre was observed under pre- and post-infection treatment conditions at a concentration of 31.25 µg/ml, but no anti-malarial and anti-CHIKV activity was observed. The Autodock-Vina-based in-silico docking study revealed that ß-sitosterol could form a strong interaction with the DENV E glycoprotein. CONCLUSION: Our findings suggest that LFSA can inhibit DENV infection and might act as a potent prophylactic/therapeutic agent against DENV-2. In-silico results suggested that ß-sitosterol may block the viral entry by inhibiting the fusion process.


Subject(s)
Chikungunya Fever , Chikungunya virus , Dengue Virus , Dengue , Malpighiales , Humans , Dengue/drug therapy , Chikungunya Fever/drug therapy , Antiviral Agents/pharmacology , Antiviral Agents/therapeutic use
18.
Int J Mol Sci ; 25(1)2023 Dec 25.
Article in English | MEDLINE | ID: mdl-38203470

ABSTRACT

Sauropus androgynus (S. androgynus) (2n = 4x = 52) is one of the most popular functional leafy vegetables in South and Southeast Asia. With its rich nutritional and pharmaceutical values, it has traditionally had widespread use for dietary and herbal purposes. Here, the genome of S. androgynus was sequenced and assembled, revealing a genome size of 1.55 Gb with 26 pseudo-chromosomes. Phylogenetic analysis traced back the divergence of Sauropus from Phyllanthus to approximately 29.67 million years ago (Mya). Genome analysis revealed that S. androgynus polyploidized around 20.51 Mya and shared a γ event about 132.95 Mya. Gene function analysis suggested that the expansion of pathways related to phloem development, lignin biosynthesis, and photosynthesis tended to result in the morphological differences among species within the Phyllanthaceae family, characterized by varying ploidy levels. The high accumulation of ascorbic acid in S. androgynus was attributed to the high expression of genes associated with the L-galactose pathway and recycling pathway. Moreover, the expanded gene families of S. androgynus exhibited multiple biochemical pathways associated with its comprehensive pharmacological activity, geographic adaptation and distinctive pleasurable flavor. Altogether, our findings represent a crucial genomic asset for S. androgynus, casting light on the intricate ploidy within the Phyllanthaceae family.


Subject(s)
Malpighiales , Polyploidy , Phylogeny , Ploidies , Ascorbic Acid
19.
Molecules ; 27(24)2022 Dec 17.
Article in English | MEDLINE | ID: mdl-36558144

ABSTRACT

This study aimed to establish the phytochemical profile of Glochidion velutinum and its cytotoxic activity against prostate cancer (PC-3) and breast cancer (MCF-7) cell lines. The phytochemical composition of G. velutinum leaf extract and its fractions was established with the help of total phenolic and flavonoid contents and LC-MS/MS-based metabolomics analysis. The crude methanolic extract and its fractions were studied for pharmacological activity against PC-3 and MCF-7 cell lines using the MTT assay. The total phenolic content of the crude extract and its fractions ranged from 44 to 859 µg GAE/mg of sample whereas total flavonoid contents ranged from 20 to 315 µg QE/mg of sample. A total of forty-eight compounds were tentatively dereplicated in the extract and its fractions. These phytochemicals included benzoic acid derivatives, flavans, flavones, O-methylated flavonoids, flavonoid O- and C-glycosides, pyranocoumarins, hydrolysable tannins, carbohydrate conjugates, fatty acids, coumarin glycosides, monoterpenoids, diterpenoids, and terpene glycosides. The crude extract (IC50 = 89 µg/mL), the chloroform fraction (IC50 = 27 µg/mL), and the water fraction (IC50 = 36 µg/mL) were found to be active against the PC-3 cell line. However, the crude extract (IC50 = 431 µg/mL), the chloroform fraction (IC50 = 222 µg/mL), and the ethyl acetate fraction (IC50 = 226 µg/mL) have shown prominent activity against breast cancer cells. Moreover, G. velutinum extract and its fractions presented negligible toxicity to normal macrophages at the maximum tested dose (600 µg/mL). Among the compounds identified through LC-MS/MS-based metabolomics analysis, epigallocatechin gallate, ellagic acid, isovitexin, and rutin were reported to have anticancer activity against both prostate and breast cancer cell lines and might be responsible for the cytotoxic activities of G. velutinum extract and its bioactive fractions.


Subject(s)
Breast Neoplasms , Malpighiales , Humans , Female , Plant Extracts/pharmacology , Plant Extracts/chemistry , Chromatography, Liquid , Antioxidants/chemistry , Chloroform , Tandem Mass Spectrometry , MCF-7 Cells , Breast Neoplasms/metabolism , Flavonoids/pharmacology , Flavonoids/analysis , Phytochemicals/pharmacology , Phytochemicals/analysis , Glycosides
20.
Planta ; 256(6): 109, 2022 Nov 09.
Article in English | MEDLINE | ID: mdl-36350413

ABSTRACT

MAIN CONCLUSION: We report the genome assembly of P. cochinchinensis, as the first high-quality chromosome-level genome of Phyllanthaceae which is rich in medicinal plants. Phyllanthus cochinchinensis, a member of the Phyllanthaceae, is one of the famous medicinal plants in South China. Here, we report a de novo chromosome-level genome assembly for P. cochinchinensis using a combination of Nanopore and Illumina sequencing technologies. In total, the assembled genome consists of 284.88 Mb genomic sequences with a contig N50 of 10.32 Mb, representing ~ 95.49% of the estimated genome size. By applying Hi-C data, 13 pseudochromosomes of P. cochinchinensis were constructed, covering ~ 99.87% of the assembled sequences. The genome is annotated with 59.12% repetitive sequences and 20,836 protein-coding genes. Whole-genome duplication of P. cochinchinensis is likely shared with Ricinus communis as well as Vitis vinifera. Homologous genes within the flavonoid pathway for P. cochinchinensis were identified and copy numbers and expression level of related genes revealed potential critical genes involved in flavonoid biosynthesis. This study provides the first whole-genome sequence for the Phyllanthaceae, confirms the evolutionary status of Phyllanthus from the genomic level, and provides foundations for accelerating functional genomic research of species from Phyllanthus.


Subject(s)
Malpighiales , Phyllanthus , Molecular Sequence Annotation , Phyllanthus/genetics , Phylogeny , Chromosomes
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