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1.
Chem Biodivers ; : e202401679, 2024 Aug 13.
Artículo en Inglés | MEDLINE | ID: mdl-39136410

RESUMEN

Phytochemical study on the methanol extract of the stems of Tinospora crispa (L.) Hook.f. & Thomson led to the isolation of thirteen compounds including three undescribed cis-clerodane-type furanoditerpenoids (1-3) and ten known ones (4-13). Their chemical structures were determined by IR, HR-ESI-MS, 1D-, and 2D-NMR spectra. Compounds 2-4, 6 and 8 inhibited moderately NO production in LPS activated RAW 264.7 cells with the IC50 values of 83.5, 57.6, 75.3, 78.1, and 74.7 µM, respectively.

2.
Chem Biodivers ; 21(9): e202400896, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-39140809

RESUMEN

This study investigates Symplocos cochinchinensis (Lour.) S. Moore leaves and stems, commonly known as Symplocos, a plant indigenous to Asia renowned for its traditional use in holistic medicine. A comprehensive phytochemical analysis of S. cochinchinensis led to the isolation of two new lignans, namely symplolignans A and B (1 and 2) along with eleven known lignan glucosides: nortrachelogenin 4-O-ß-D-glucopyranoside (3), nortracheloside (4), matairesinol 4-O-ß-D-glucopyranoside (5), lariciresinol 4'-O-ß-D-glucopyranoside (6), balanophonin 4-O-ß-D-glucopyranoside (7), dehydrodiconiferyl alcohol 4-O-ß-D-glucopyranoside (8), dehydrodiconiferyl alcohol γ'-O-ß-D-glucopyranoside (9), 3-(ß-D-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofura (10), and pinoresinol 4'-O-ß-D-glucopyranoside (11). Their chemical structures were elucidated using 1D- and 2D-NMR, mass spectrometry, and their spectroscopic data were compared with those reported in literatures. Furthermore, all compounds were evaluated for their hepatoprotective effects using the Resazurin reduction assay in HepG2 hepatocellular carcinoma cells. Compounds 1, 5, 7, and 8 exhibited notable hepatoprotective efficacy, with cell viability ranging from 105.0±2.6 to 109.2±3.3 at a concentration of 10 µM. This research highlights the therapeutic potential of these compounds and enhanced to the understanding of lignans and neolignans in liver cell proliferation.


Asunto(s)
Glicósidos , Lignanos , Hojas de la Planta , Tallos de la Planta , Lignanos/farmacología , Lignanos/aislamiento & purificación , Lignanos/química , Humanos , Hojas de la Planta/química , Glicósidos/química , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Tallos de la Planta/química , Células Hep G2 , Supervivencia Celular/efectos de los fármacos , Sustancias Protectoras/farmacología , Sustancias Protectoras/química , Sustancias Protectoras/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Estructura Molecular , Conformación Molecular
3.
Chem Biodivers ; : e202401608, 2024 Aug 26.
Artículo en Inglés | MEDLINE | ID: mdl-39185684

RESUMEN

Phytochemical study on the methanol extract of the leaves of Phyllanthus reticulatus led to the isolation of two new compounds, phyllanretiosides A (1) and B (2) together with ten known ones (3-12). Their chemical structures were determined by HR-ESI-MS, NMR, and ECD spectra in comparison with the literature. Three ellagitannins, phyllanretioside A (1), corilagin (3), and phyllanthusiin C (4) inhibited lipopolysaccharide(LPS)-induced nitric oxide production in RAW 264.7 cells with IC50 values of 63.2, 83.2, and 5.6 µM, respectively. In addition, compounds 1, 3, and 4 exhibited significantly antimicrobial activity (MICs: 16-128 µg/mL) towards some of seven microbial strains.

4.
RSC Adv ; 14(29): 20536-20542, 2024 Jun 27.
Artículo en Inglés | MEDLINE | ID: mdl-38952945

RESUMEN

Phytochemical studies on Aphanamixis plants have attracted considerable attention over the past few decades due to the structural diversities and significant biological activities of terpenoids produced by these plants. In the present study, five new acyclic diterpene lactone derivatives, aphanamixionolides A-E (1-5), and three known tirucallane-type triterpenes, namely, piscidinol A (6), hispidone (7), and bourjotinolone A (8), were isolated from the leaves of Aphanamixis polystachya. Their structures were elucidated by comprehensive analyses of HR-ESI-MS and NMR spectroscopic data and by comparison with those reported in the literature. Absolute configurations of the new compounds were determined by experimental and TD-DFT calculated ECD spectra. Compounds 1-8 inhibited NO production with IC50 values of 10.2-37.7 µM, which are comparable to positive control l-NMMA (IC50: 31.5 µM).

5.
Fitoterapia ; 177: 106056, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-38851515

RESUMEN

Four new acylated oleanane-type triterpene saponins, symplosaponins A-D (1-4) were successfully isolated from the leaves of Symplocos cochinchinensis (Lour.) S. Moore, alongside with five known compounds (5-9), 2-methoxy-4-prop-1-enylphenyl-1-O-ß-D-apiofuranosyl-(1 â†’ 6)-ß-D-glucopyranoside (5), and 1-[O-ß-d-xylopyranosyl-(1 â†’ 6)-O-ß-d-glucopyranosyl]-2,6-dimethoxy-4-propenyl-phenol (6), 6-O-p-coumaroylsucrose (7), arillatose B (8), and (-)-secoisolariciresinol-O-ß-D-glucopyranoside (9). The structures of these compounds were elucidated through spectroscopic methods, comparison with existing data, and chemical methods. Furthermore, all compounds were assessed for their impact on hepatocellular viability using the Resazurin reduction assay. These investigations aimed to explore the potential hepatoprotective properties of isolated compounds. As a result, 1-[O-ß-d-xylopyranosyl-(1 â†’ 6)-O-ß-d-glucopyranosyl]-2,6-dimethoxy-4-propenyl-phenol (6) and (-)-secoisolariciresinol-O-ß-D-glucopyranoside (9) demonstrated statistically significant hepatoprotective activity in a concentration-dependent manner.


Asunto(s)
Ácido Oleanólico , Fitoquímicos , Hojas de la Planta , Saponinas , Saponinas/farmacología , Saponinas/aislamiento & purificación , Saponinas/química , Estructura Molecular , Humanos , Hojas de la Planta/química , Ácido Oleanólico/farmacología , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/aislamiento & purificación , Ácido Oleanólico/química , Fitoquímicos/farmacología , Fitoquímicos/aislamiento & purificación , Animales , Células Hep G2 , Ratas , Sustancias Protectoras/farmacología , Sustancias Protectoras/aislamiento & purificación , Triterpenos/farmacología , Triterpenos/aislamiento & purificación , Triterpenos/química
6.
Chem Biodivers ; 21(8): e202401049, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38757233

RESUMEN

Four undescribed spirostan glycosides, (25S)-5α-spirostan- 12-one-2α,3ß-diol-3-O-ß-D-glucopyranosyl-(1→4)-ß-D-galactopyranoside (1), (25S)-5α-spirostan-12-one-2α,3ß-diol-3-O-ß-D-galatopyranosyl-(1→2)-ß-D-glucopyranosyl- (1→4)-ß-D-galactopyranoside (2), (25S)-5α-spirostan-12-one-2α,3ß-diol-3-O-ß-D-glucopyranosyl-(1→2)-[ß-D-glucopyranosyl-(1→3)]-ß-D-glucopyranosyl-(1→4)-ß-D-galactopyranoside (3), and hecogenin 3-O-ß-D-glucopyranosyl-(1→3)-[ß-D-xylopyranosyl-(1→2)]-ß-D-glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-ß-D-galactopyranoside (4), together with eleven known compounds (5-15) were isolated from the branches and leaves of Tribulus terrestris. Their chemical structures were established through spectroscopic methods, including HR-ESI-MS, 1D-, and 2D-NMR spectra. Preliminary biological evaluation on NO production inhibitory activity in LPS activated RAW 264.7 cells showed that compounds 1-3, 5, and 6 had significant inhibitory effects with IC50 values ranging from 2.4 to 18.3 µM, compared to that of the positive control compound, dexamethazone (IC50 13.6 µM).


Asunto(s)
Glicósidos , Lipopolisacáridos , Óxido Nítrico , Hojas de la Planta , Espirostanos , Tribulus , Ratones , Animales , Células RAW 264.7 , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Tribulus/química , Hojas de la Planta/química , Glicósidos/química , Glicósidos/farmacología , Glicósidos/aislamiento & purificación , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Espirostanos/química , Espirostanos/aislamiento & purificación , Espirostanos/farmacología , Tallos de la Planta/química , Relación Estructura-Actividad
7.
Chem Biodivers ; 21(8): e202401118, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38790139

RESUMEN

Phytochemical study on the methanol extract of the stem barks of Aphanamixis polystachya led to the isolation of four previously undescribed (1-4) and ten known compounds (5-14). Their chemical structures were elucidated to be 11-methoxysawaranospiroride C (1), 6α,9S,10,13-tetrahydroxymegastigmane-3-one (2), 11-hydroxyaphanamixin B (3), (2Z,6E,13E)-2,6,13-triene-11,15-dihydroxyphytanic acid (4), cinnacasside D (5), cinnacasside E (6), vilsonol F (7), (3S,5R,6S,7E,9R)-3,5,6,9-tetrahydroxy-7-en-megastigmane (8), (3S,5R,6R,7E,9R)-3,6,9,10-tetrahydroxy-7-en-megastigmane (9), citroside A (10), threo-1-(3,4,5-trimethoxyphenyl)-1,2,3-propanetriol (11), 3,4,5-trimethoxyphenyl-1-O-ß-D-glucopyranoside (12), p-coumaric acid (13), ferulic acid (14) by HR-ESI-MS, ECD, 1D-, and 2D-NMR spectra. Compounds 1, 3, 4, and 9 showed NO production inhibitory activity in LPS activated RAW 264.7 cells with IC50 values of 42.0, 67.9, 20.5, and 78.6 µM, respectively, while the remaining compounds were inactive with IC50 values over 100 µM.


Asunto(s)
Lipopolisacáridos , Óxido Nítrico , Corteza de la Planta , Ratones , Células RAW 264.7 , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Animales , Corteza de la Planta/química , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Óxido Nítrico/metabolismo , Tallos de la Planta/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Extractos Vegetales/aislamiento & purificación , Estructura Molecular , Relación Estructura-Actividad
8.
Chem Biodivers ; 21(7): e202400708, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38590273

RESUMEN

In this study, four undescribed bibenzyl derivatives (1-4), together with seven known compounds (5-11) were isolated from the aerial parts of Dendrobium officinale. Their chemical structures were determined to be (7'S,8'S) -9''-acetyldendrocandin U (1), (7'S,8'S) -4'-methoxydendrocandin T (2), (7'R,8'S) -dendrocandin B (3), (1S,2R) -5'''-methoxydendrofindlaphenol C (4) by analyzing of the spectroscopic data including HR-ESI-MS, 1D-, and 2D-NMR spectra. The absolute configurations of compounds 1-4 were determined by the electronic circular dichroism (ECD) spectra. Compounds 1-3, 5, 10 and 11 inhibited α-glucosidase with the IC50 values ranging from 56.3 to 165.3 µM, compounds 1-3, 5, 7-10 inhibited α-amylase with the IC50 values ranging from 65.2 to 177.6 µM.


Asunto(s)
Dendrobium , Inhibidores de Glicósido Hidrolasas , Componentes Aéreos de las Plantas , alfa-Amilasas , alfa-Glucosidasas , Dendrobium/química , alfa-Amilasas/antagonistas & inhibidores , alfa-Amilasas/metabolismo , alfa-Glucosidasas/metabolismo , Inhibidores de Glicósido Hidrolasas/farmacología , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Componentes Aéreos de las Plantas/química , Estilbenos/química , Estilbenos/farmacología , Estilbenos/aislamiento & purificación , Relación Estructura-Actividad , Estructura Molecular , Conformación Molecular
9.
RSC Adv ; 14(17): 12147-12157, 2024 Apr 10.
Artículo en Inglés | MEDLINE | ID: mdl-38628471

RESUMEN

In this study, seven new pentacyclic triterpene glycosides, named dendrocinaosides A-G (1-7), and six known ones (8-13) were isolated from the whole plants of Dendrobium officinale. Their structures were determined by analyses of HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1-4, 8, and 9 potentially inhibited α-glucosidase and α-amylase activities with the IC50 values ranging from 31.3 ± 2.2 to 42.4 ± 2.5 µM for anti α-glucosidase and from 36.5 ± 1.8 to 56.4 ± 2.0 µM for anti α-amylase activities, respectively, which were lower than that of the positive control, acarbose, showing IC50 values of 47.1 ± 1.4 µM for anti α-glucosidase and 145.7 ± 2.2 µM for anti α-amylase.

10.
J Nat Med ; 78(3): 741-752, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38573418

RESUMEN

In this study, nine triterpene glycosides including seven previously undescribed compounds (1-7), were isolated from leaves of Cryptolepis buchananii R.Br. ex Roem. and Schult. using various chromatographic methods. The chemical structures of the compounds were elucidated to be 3-O-ß-D-glucopyranosyl-(1 → 6)-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (1), 3-O-ß-D-glucopyranosyl-(1 → 2)-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (2), 3-O-ß-D-glucopyranosyl-(1 → 2)-ß-D-glucopyranosyluncargenin C 28-O-ß-D-glucopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (3), 3-O-ß-D-glucopyranosyl-(1 → 2)-ß-D-glucopyranosylhederagenin 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (4), 3-O-ß-D-glucopyranosylarjunolic acid 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (5), 3-O-ß-D-glucopyranosyl-(1 → 2)-ß- D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (6), 3-O-ß-D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (7), asiatic acid 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (8), and 3-O-ß-D-glucopyranosylasiatic acid 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (9), through infrared, high-resolution electrospray ionization mass spectrometry, one- and two-dimensional nuclear magnetic resonance spectral analyses. The isolates inhibited nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells, with half-maximal inhibitory concentration (IC50) values of 18.8-58.5 µM, compared to the positive control compound, dexamethasone, which exhibited an IC50 of 14.1 µM.


Asunto(s)
Glicósidos , Óxido Nítrico , Hojas de la Planta , Triterpenos , Triterpenos/química , Triterpenos/farmacología , Triterpenos/aislamiento & purificación , Óxido Nítrico/metabolismo , Glicósidos/química , Glicósidos/farmacología , Glicósidos/aislamiento & purificación , Ratones , Animales , Estructura Molecular , Hojas de la Planta/química , Células RAW 264.7 , Extractos Vegetales/química , Extractos Vegetales/farmacología
11.
Fitoterapia ; 175: 105903, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38479620

RESUMEN

A phytochemical study of the aerial parts of Piper mutabile C. DC. revealed seven undescribed compounds [two (2-7')-neolignans and five polyoxygenated cyclohexene glycosides] and six known propenylcatechol derivatives. The chemical structures of the isolated compounds were elucidated by extensive HR-ESI-MS and NMR analyses, as well as comparison with the literature. The absolute configurations of the (2-7')-neolignans were confirmed by GIAO 13C NMR calculations with a sorted training set strategy and TD-DFT calculation ECD spectra. The (2-7')-neolignans and polyoxygenated cyclohexene glycosides are unusual in natural sources. Undescribed neolignans 1 and 2 inhibited NO production in RAW 264.7 cells, with respective IC50 values of 14.4 and 9.5 µM.


Asunto(s)
Ciclohexenos , Glicósidos , Lignanos , Óxido Nítrico , Fitoquímicos , Piper , Componentes Aéreos de las Plantas , Óxido Nítrico/biosíntesis , Óxido Nítrico/metabolismo , Óxido Nítrico/antagonistas & inhibidores , Células RAW 264.7 , Ratones , Piper/química , Estructura Molecular , Componentes Aéreos de las Plantas/química , Animales , Fitoquímicos/farmacología , Fitoquímicos/aislamiento & purificación , Lignanos/farmacología , Lignanos/aislamiento & purificación , Lignanos/química , Glicósidos/farmacología , Glicósidos/aislamiento & purificación , Glicósidos/química , Ciclohexenos/farmacología , Ciclohexenos/aislamiento & purificación , China
12.
Chem Biodivers ; 20(12): e202301660, 2023 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-37957128

RESUMEN

Chemical study on marine sponge-derivated fungus Aspergillus nidulans resulted in the isolation of seven depsidones (1-7) and two macrocyclic peptides (8 and 9). Their chemical structures were elucidated by extensive analyses of HRESIMS and NMR spectral data, as well as comparison with the literature. Compound 1 was an undescribed depsidone. All compounds exhibited significant antimicrobial activity (MICs: 2-128 µg/mL) towards at least one of seven microbial strains, including Bacillus cereus, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica, and Candida albicans. Of these, chlorinated depsidones (1-3, and 5) displayed potential antimicrobial activity. Nidulin (2) possessed good activity against tested strains except for S. enterica with MIC values in range of 2-16 µg/mL. Interestingly, undescribed depsidone 1 was selectively bioactive on the Gram-positive bacteria (MICs: 2-4 µg/mL) and yeast (MIC: 8 µg/mL) but inactivity on the Gram-negative bacteria (MICs: >256 µg/mL). Macrocyclic peptides, 8 and 9, displayed modest activity against E. faecalis strain with MIC values of 32 and 128 µg/mL, respectively.


Asunto(s)
Antiinfecciosos , Aspergillus nidulans , Poríferos , Animales , Antibacterianos/farmacología , Antibacterianos/química , Antiinfecciosos/química , Pruebas de Sensibilidad Microbiana , Péptidos/farmacología
13.
Chem Biodivers ; 20(12): e202301683, 2023 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-38012075

RESUMEN

From the methanol extract of the Cryptolepis buchananii fruits, four undescribed pentacyclic triterpenene glycosides (1-4) and five known pentacyclic triterpenenes (5-9) were isolated. Their structures were determined to be uncargenin C 28-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucopyranosyl ester (1), 3-O-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucopyranosyl ester (2), 3-O-ß-D-glucopyranosyl-(1→6)-ß-D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucopyranosyl ester (3), 3-O-ß-D-glucopyranosyl-(1→2)-ß-D-glucopyranosylasiatic acid 28-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucopyranosyl ester (4), asiatic acid (5), 2α,3ß,23-trihydroxyoleana-11,13(18)-dien-28-oic acid (6), arjunolic acid (7), 6ß-hydroxyarjunolic acid (8), and actinidic acid (9) based on analyses of their HR-ESI-MS, 1D and 2D NMR spectra. All the isolates showed significantly NO production inhibition in LPS-activated RAW264.7 cells with the IC50 values ranging from 18.79 to 37.57 µM, compared to that of the positive control compound, dexamethasone, which showed IC50 value of 14.05 µM.


Asunto(s)
Saponinas , Triterpenos , Cryptolepis , Ésteres , Frutas , Glicósidos/farmacología , Glicósidos/química , Lipopolisacáridos/farmacología , Triterpenos Pentacíclicos/farmacología , Saponinas/química , Triterpenos/farmacología , Triterpenos/química
14.
Chem Biodivers ; 20(9): e202301037, 2023 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-37529975

RESUMEN

Four undescribed phenolic glycosides including three stilbene derivatives (1 and 3) and sodium salt of 3 (2), and a chalcone glycoside (4), together with thirteen known compounds (5-17) were isolated from the leaves of Syzygium attopeuense (Gagnep.) Merr. & L.M.Perry. Their chemical structures were elucidated to be (Z)-gaylussacin (1), 6''-O-galloylgaylussacin sodium salt (2), 6''-O-galloylgaylussacin (3), 4'-O-[ß-D-glucopyranosyl-(1→6)-glucopyranosyl]oxy-2'-hydroxy-6'-methoxydihydrochalcone (4), gaylussacin (5), pinosilvin 3-O-ß-D-glucopyranoside (6), myricetin-3-O-(2''-O-galloyl)-α-L-rhamnopyranoside (7), myricetin-3-O-(3''-O-galloyl)-α-L-rhamnopyranoside (8), myricetin-3-O-α-L-rhamnopyranoside (9), quercitrin (10), myricetin-3-O-ß-D-glucopyranoside (11), myricetin-3-O-ß-D-galactopyranoside (12), quercetin 3-O-α-L-arabinopyranoside (13), myricetin-3-O-2''-O-galloyl)-α-L-arabinopyranoside (14), (+)-gallocatechin (15), (-)-epigallocatechin (16), and 3,3',4'-trimethoxyellagic acid 4-O-ß-D-glucopyranoside (17) by the analysis of HR-ESI-MS, 1D and 2D NMR spectra in comparison with the previously reported data. Compounds 1-3, 5, and 6 significant inhibition of NO production in LPS-activated RAW264.7 cells, with IC50 values ranging from 18.37±1.38 to 35.12±2.53 µM, compared to a positive control (dexamethasone) with an IC50 value of 15.37±1.42 µM.


Asunto(s)
Glicósidos , Syzygium , Glicósidos/farmacología , Glicósidos/química , Óxido Nítrico , Fenoles/farmacología , Sodio , Estructura Molecular
15.
Fitoterapia ; 169: 105609, 2023 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-37453701

RESUMEN

Five new flavonoid C-glycosides named desmodinosides A-E (1-5) and one known compound, apigenin 6-C-ß-d-xylopyranosyl-2''-O-ß-D-glucopyranoside (6) have been isolated from the methanol extract of the aerial parts of Desmodium heterocarpon var. stigosum. These compounds were determined by 1D and 2D-NMR and HR-MS spectroscopies. The methanol extract of this plant, in particular, demonstrated hepatoprotection and antifungal inhibition. This extract has a remarkable hepatoprotection and activity-dose response with an EC50 of 43.07 µg/mL. The hepatoprotective effect on human liver hepatoma cells (HepG2) of the isolated flavonoid C-glycosides 1-6 was observed. Desmodinosides A-C (1-3) were found to exhibit moderate hepatoprotective activity on HepG2 cells. Of these, compound 2 showed the best hepatoprotective activity with an EC50 value of 74.12 µg/mL. While compounds 1 and 3 displayed EC50 values of 271.21 and 211.99 µg/mL, respectively. Quercetin, a positive control, also caused an EC50 value of 36.42 µg/mL. In addition to having hepatoprotective effect, the methanol extract had an inhibitory effect on the growth of oomycete; it inhibited Phytophthora infestans with IC50 of 13.3 µg/mL and IC90 of 78.7 µg/mL. The oomycete inhibition was directly attributed to compounds 5 and 6, which significantly inhibited P. infestans with IC50 values of 27.4 and 24.7 µg/mL, respectively. Both 5 and 6 and methanol extract were active against P. infestanse in a dose-dependent manner. Our study demonstrated for the first time the new flavonoid C-glycosides from D. heterocarpon var. stigosum and their novel pharmacological properties. The study findings also suggest the plant extract and its metabolites could be used as a new botanical source of bioactive compounds.


Asunto(s)
Antifúngicos , Flavonoides , Humanos , Antifúngicos/farmacología , Metanol , Estructura Molecular , Glicósidos , Extractos Vegetales/química
16.
Chem Biodivers ; 20(8): e202300853, 2023 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-37409765

RESUMEN

A chemical study of the methanol extract of the aerial parts of Achyranthes aspera led to the isolation of four new flavonoid C-glycosides (1-4) along with eight known analogs (5-12). Their structures were elucidated by a combination of spectroscopic data analysis, HR-ESI-MS, 1D and 2D NMR spectra. All the isolates were evaluated their NO production inhibitory activity in LPS-activated RAW264.7 cells. Compounds 2, 4, and 8-11 showed significant inhibition with IC50 values ranging from 25.06 to 45.25 µM, compared to that of the positive control compound, L-NMMA, IC50 value of 32.24 µM, whereas the remaining compounds were weak inhibitory activity with IC50 values over 100 µM. This is the first report of 7 from Amaranthaceae family, and 11 from the genus Achyranthes.


Asunto(s)
Achyranthes , Flavonoides , Flavonoides/farmacología , Flavonoides/química , Achyranthes/química , Óxido Nítrico , Extractos Vegetales/farmacología , Extractos Vegetales/química , Glicósidos/farmacología , Glicósidos/química , Estructura Molecular
17.
Chem Biodivers ; 20(8): e202300731, 2023 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-37344361

RESUMEN

Four undescribed compounds (1-4) named pelliolatifolias A-D together with seven known compounds trans-clovamide (5), N-trans-caffeoyl-4-hydroxyphenylalanine methyl ester (6), N-trans-caffeoyl-3,4-dihydroxyphenylalanine methyl ester (7), luteolin 4'-O-ß-D-glucopyrannoside (8), cis-syringin (9), trans-syringin (10), and citroside A (11) have been isolated from the methanol extract of the Pellionia latifolia leaves. Their chemical structures were elucidated based on extensive analyses of HR-ESI-MS, 1D and 2D NMR, and CD spectra. Compounds 1-7, 9 and 10 showed moderate inhibition of NO production in LPS-activated RAW264.7 cells with their IC50 values ranging from 39.27 to 75.42 µM, compared to that of the positive control compound, dexamethasone, IC50 value of 14.20 µM.


Asunto(s)
Óxido Nítrico , Fenilpropionatos , Ésteres , Glucósidos , Estructura Molecular
18.
Chem Biodivers ; 20(8): e202300785, 2023 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-37344399

RESUMEN

Phytochemical investigation on the aerial parts of Elsholtzia blanda Benth. afforded four new oleuropeic acid derivatives (1-4), named as elsholblanosides A-D, respectively, together with 11 known compounds (5-15). Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR, and ECD spectra. Compounds 1-4 and 14 showed moderate NO production inhibition in LPS-activated RAW264.7 cells with their IC50 values ranging from 23.2 to 86.33 µM, compared to that of the positive control compound, dexamethasone, IC50 value of 16.9 µM.


Asunto(s)
Ácidos Ciclohexanocarboxílicos , Lamiaceae , Animales , Ratones , Lipopolisacáridos/farmacología , Lamiaceae/química , Células RAW 264.7 , Estructura Molecular
19.
J Nat Med ; 77(4): 964-971, 2023 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-37358723

RESUMEN

Three undescribed triterpene glycosides syzybullosides A-C (1-3) along with fourteen known compounds were isolated from the leaves of Syzygium bullockii (Hance) Merr.& L.M. Perry, including six triterpene glycosides (1-6), four phenolics (7-9, 17), four megastigmanes (10-13), and three flavonoids (14-16). The structures of 1-17 were elucidated by extensive spectroscopic analysis, including IR, HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1-10 and 12-17 inhibited nitric oxide (NO) production in lipopolysaccharide activated RAW264.7 cells with IC50 values ranging from 1.30 to 13.70 µM, lower than that of the positive control compound, L-NMMA (IC50 = 33.8 µM).


Asunto(s)
Syzygium , Triterpenos , Estructura Molecular , Óxido Nítrico , Glicósidos/farmacología , Glicósidos/química , Triterpenos/farmacología , Triterpenos/química
20.
J Nat Med ; 77(4): 928-938, 2023 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-37294499

RESUMEN

Plants of the Schisandra genus are commonly used in folk medicinal remedies. Some Schisandra species and their lignans have been reported to improve muscle strength. In the present study, four new lignans, named schisacaulins A-D, together with three previously described compounds ananonin B, alismoxide, and pregomisin were isolated from the leaves of S. cauliflora. Their chemical structures were determined by extensive analyses of HR-ESI-MS, NMR, and ECD spectra. Schisacaulin D and alismoxide significantly stimulated skeletal muscle cell proliferation by increasing the number of fused myotubes and expression of myosin heavy chain (MyHC) which may be good candidates for the treatment of sarcopenia.


Asunto(s)
Lignanos , Schisandra , Schisandra/química , Lignanos/química , Hojas de la Planta/química , Proliferación Celular , Músculo Esquelético
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