Anti-inflammatory activity of verbascoside- and isoverbascoside-rich Lamiales medicinal plants.

Verbascoside and isoverbascoside are two active phenylethanoid glycosides mainly found in plants of the order Lamiales. This study analyzes the verbascoside and isoverbascoside levels and the total phenolic contents in the water and ethanolic extracts of 20 medicinal plants of the order Lamiales commonly used in Thailand. The related bioactivities, including the antioxidant activity via the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reduction activity potential assays and anti-tyrosinase and -inflammatory activities via the cyclooxygenase and nitric oxide assays are also investigated.

Correction: Analysis of canthin-6-one alkaloids derived from spp. by micellar liquid chromatography and conventional high-performance liquid chromatography: a comparative evaluation.

[This corrects the article DOI: 10.1039/D2RA07034K.].

Analysis of canthin-6-one alkaloids derived from spp. by micellar liquid chromatography and conventional high-performance liquid chromatography: a comparative evaluation.

Extracts of Jack (EL) and Pierre (EH) contain numerous bioactive compounds and varying matrices that are challenging to separate using chromatographic techniques. Herein, micellar liquid chromatography (MLC) was used to analyze canthin-6-one alkaloids contained in these extracts, and the achieved performance was compared with that of a conventional high-performance liquid chromatography (HPLC) method. The optimal mobile phase of MLC corresponded to 15 : 85 (v/v) acetonitrile : water (pH 3) containing 110 mM sodium dodecyl sulfate and 10 mM NaHPO.

Evaluating the Efficacy of Quassinoids from and against Common Cold Human Coronavirus OC43 and SARS-CoV-2 Using In-Cell Enzyme-Linked Immunosorbent Assay.

Coronavirus disease-2019 (COVID-19), caused by severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) infection, has become a pandemic and public health crisis. SARS-CoV-2 and the seasonal common cold coronavirus (HCoV-OC43) belong to the beta genus of human coronaviruses (HCoVs). In-cell ELISA assays were performed using HCoV-OC43 and SARS-CoV-2 and evaluated the antiviral activity of herbal plants.

Phosphodiesterase-5 Inhibitory Activity of Canthin-6-One Alkaloids and the Roots of Eurycoma longifolia and Eurycoma harmandiana.

Eurycoma longifolia (EL) and Eurycoma harmandiana (EH) are natural medicinal plants belonging to the Simaroubaceae family, and are well-known for their ability to enhance male sexual performance. The present study investigated the phosphodiesterase-5 (PDE-5) inhibitory activity of intact roots of EL and EH. Additionally, canthin-6-one alkaloids, β-carboline alkaloids, and quassinoids were also screened for PDE-5 inhibitory activity.

HPLC-UV-Based Simultaneous Determination of Canthin-6-One Alkaloids, Quassinoids, and Scopoletin: The Active Ingredients in Eurycoma Longifolia Jack and Eurycoma Harmandiana Pierre, and Their Anti-Inflammatory Activities.

Background: Quassinoids and canthin-6-one alkaloids are bioactive markers of Eurycoma longifolia (EL) and E. harmandiana (EH) and have been commercially utilized to treat inflammation and male infertility.

Objectives: This study aims to reveal the contents of bioactive compounds and compare anti-inflammatory activities of these two species.

Phenylethanoid and flavone glycosides from Ruellia tuberosa L.

A new phenylethanoid glycoside, isocassifolioside (8), and two new flavone glycosides, hispidulin 7-O-α-L-rhamnopyranosyl-(1'″ → 2″)-O-β-D-glucuronopyranoside (11) and pectolinaringenin 7-O-α-L-rhamnopyranosyl-(1'″ → 2″)-O-β-D-glucuronopyranoside (12) were isolated from the aerial portions of Ruellia tuberosa L., together with verbascoside (1), isoverbascoside (2), nuomioside (3), isonuomioside (4), forsythoside B (5), paucifloside (6), cassifolioside (7), hispidulin 7-O-β-D-glucuronopyranoside (9) and comanthoside B (10). The structure elucidations were based on analyses of chemical and spectroscopic data including 1D- and 2D-NMR.

Unprecedented furan-2-carbonyl C-glycosides and phenolic diglycosides from Scleropyrum pentandrum.

Five unprecedented furan-2-carbonyl C-glycosides, scleropentasides A-E, and two phenolic diglycosides, 4-hydroxy-3-methoxybenzyl 4-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside and 2,6-dimethoxy-p-hydroquinone 1-O-β-D-xylopyranosyl-(1→6)-β-d-glucopyranoside, were isolated from leaves and twigs of Scleropyrum pentandrum together with potalioside B, luteolin 6-C-β-D-glucopyranoside (isoorientin), apigenin 8-C-β-D-glucopyranoside (vitexin), apigenin 6,8-di-C-β-D-glucopyranoside (vicenin-2), apigenin 6-C-α-L-arabinopyranosyl-8-C-β-D-glucopyranoside (isoschaftoside), apigenin 6-C-β-D-glucopyranosyl-8-C-β-D-xylopyranoside, adenosine and l-tryptophan. Structure elucidations of these compounds were based on analyses of chemical and spectroscopic data, including 1D and 2D NMR. In addition, the isolated compounds were evaluated for their radical scavenging activities using both DPPH and ORAC assays.

3-Hydroxydihydrobenzofuran glucosides from Gnaphalium polycaulon.

A new 3-hydroxydihydrobenzofuran glucoside, gnaphaliol 9-O-β-D-glucopyranoside (2), was isolated from the aerial parts of Gnaphalium polycaulon together with 1-{(2R*,3S*-3-(β-D-glucopyranosyloxy)-2,3-dihydro-2-[1-(hydroxyl methyl)vinyl]-1-benzofuran-5-yl}-ethanone or gnaphaliol 3-O-β-D-glucopyranoside (1), (Z)-3-hexenyl O-β-D-glucopyranoside (3) and adenosine (4). The absolute configurations at C-2 and C-3 positions of compound 1 were determined to be 2R and 3R. The structures of these compounds were elucidated on the basis of their physical and spectroscopic data.

Unusual glycosides of pyrrole alkaloid and 4'-hydroxyphenylethanamide from leaves of Moringa oleifera.

Glycosides of pyrrole alkaloid (pyrrolemarumine 4″-O-α-L-rhamnopyranoside) and 4'-hydroxyphenylethanamide (marumosides A and B) were isolated from leaves of Moringa oleifera along with eight known compounds; niazirin, methyl 4-(α-L-rhamnopyranosyloxy)benzylcarbamate, benzyl β-D-glucopyranoside, benzyl β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside, kaempferol 3-O-β-D-glucopyranoside, quercetin 3-O-β-D-glucopyranoside, adenosine and L-tryptophan. Structure elucidations were based on analyses of chemical and spectroscopic data including 1D- and 2D-NMR.

Acanmontanoside, a new phenylethanoid diglycoside from Acanthus montanus.

A new phenylethanoid glycoside acylated with syringic acid, namely acanmontanoside, was isolated from the aerial portions of Acanthus montanus (Nees). T. Anderson, along with decaffeoylverbascoside, verbascoside, isoverbascoside, leucosceptoside A, (2R)-2-O-ß-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (HBOA-Glc), (2R)-2-O-ß-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA-Glc), (3R)-1-octen-3-ol-3-O-ß-D-xylopyranosyl-(1→6)-O-ß-D-glucopyranoside and ebracteatoside B.

L-(-)-(N-trans-cinnamoyl)-arginine, an acylamino acid from Glinus oppositifolius (L.) Aug. DC.

An amino acid derivative, L-(-)-(N-trans-cinnamoyl)-arginine, was isolated from the whole plant of Glinus oppositifolius (L.) Aug. DC.

Antioxidant, antibacterial and antigiardial activities of Walsura robusta Roxb.

Walsura robusta Roxb. (Family: Meliaceae) is a well-known multi-purpose medicinal plant, and has been employed for a wide range of disease conditions without documented scientific data. In the current study, four pure isolated compounds, 3,4,5-trimethoxyphenyl beta-D-glucopyranoside (1), turpinionoside A (2), (+)-lyoniresinol 3alpha-O-beta-D-glucopyranoside (3) and (-)-lyoniresinol 3alpha-O-beta-D-glucopyranoside (4), were isolated from the leaves and twigs of W.

Evaluation of chikusetsusaponin IVa isolated from Alternanthera philoxeroides for its potency against viral replication.

Chikusetsusaponin IVa and calenduloside E were isolated from the whole plant of Alternanthera philoxeroides (Mart.) Griseb (Amaranthaceae) and evaluated for their antiviral activities. Chikusetsusaponin IVa showed antiviral activities against HSV-1, HSV-2, human cytomegalovirus, measles virus, and mumps virus with selectivity indices (CC (50)/IC (50)) of 29, 30, 73, 25, and 25, respectively.

Megastigmane and flavone glycosides from Strophioblachia fimbricalyx Boerl.

Three megastigmane glucosides, bridelionoside B, ampelopsisionoside and 3-hydroxy-5,6-epoxy-beta-ionol 9-O-beta-D-glucopyranoside, together with three flavone glycosides, apigenin 7-O-beta-D-glucopyranoside, isovitexin and spinosin, were isolated from the aerial portions of Strophioblachia fimbricalyx. The structure determinations were based on physical data and spectroscopic evidence.

Chemical constituents from Oldenlandia corymbosa L. of Thai origin.

From the whole plants of Oldenlandia corymbosa of Thai origin, ten compounds have been isolated and elucidated as geniposide, 6 alpha-hydroxygeniposide, scandoside methyl ester (6 beta-hydroxygeniposide), asperulosidic acid, deacetylasperuloside, asperuloside, 10-O-benzoylscandoside methyl ester, 10-O-p-hydroxybenzoylscandoside methyl ester, (+)-lyoniresinol-3 alpha-O-beta-glucopyranoside, and rutin. Their structures were determined on the basis of spectroscopic data.

Tricalysiosides P-U: Ent-kaurane glucosides and a labdane glucoside from leaves of Tricalysia dubia OHWI.

Further extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of Tricalysia dubia afforded five new ent-kaurane glucosides (4-8) and one new labdane glucoside (9), together with a known megastigmane glucoside, sammangaoside B (1), and monoterpene glucosides (2, 3). The structures of the new compounds were elucidated by analyses of one- and two-dimensional NMR spectroscopic data. The absolute configuration of the 9-position of sammangaoside B was revised to S and its total stereochemistry was established by the modified Mosher's method.

Megastigmane glucosides from Equisetum debile and E. diffusum.

A new megastigmane diglucoside, (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3,9-O-beta-D-diglucopyranoside (3), was isolated from the aerial portion of Equisetum debile along with macarangioside D (debiloside A), sammangaoside A, (6R,9S)-3-oxo-alpha-ionol 9-O-beta-D-glucopyranoside, debiloside B, kaempferol 3-O-sophoroside, kaempferol 3,7-O-beta-D-diglucopyranoside, kaempferol 3-O-sophoroside-7-O-beta-D-glucopyranoside, phenylethyl O-beta-D-glucopyranoside, (Z)-3-hexenyl O-beta-D-glucopyranoside, (7S,8R)-dehydrodiconiferyl 4-O-beta-D-glucopyranoside, and L-tryptophan. The absolute configuration at C-6 of the original structure of debilo-side A was revised to 6R-configuration, and was identical with macarangioside D (1). From the aerial portion of E.

Aromatic diglycosides from Cladogynos orientalis.

Two unusual aromatic diglycosides with galloyl substitution, 4''-O-galloyl-violutoside and 4''-O-galloyl-benzyl-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside, were isolated from the aerial portion of Cladogynos orientalis along with isovitexin, apigenin 6-C-(2''-O-galloyl)-beta-D-glucopyranoside, apigenin 8-C-(2''-O-galloyl)-beta-D-glucopyranoside, syringic acid beta-D-glucopyranoside, 3,4,5-trimethoxyphenyl beta-D-glucopyranoside, (6S,9R)-roseoside, and violutioside. The structural elucidations were based on analyses of chemical and spectroscopic data by including 1D and 2D NMR analyses.

Dolichandroside, a new phenolic triglycoside from Dolichandrone serrulata (DC.) Seem.

A new phenolic triglycoside, dolichandroside, was isolated from the branches of Dolichandrone serrulata together with decaffeoyl-verbascoside, verbascoside, isoverbascoside, markhamioside A, 2''-O-apiosylverbascoside, luteoside B and ixoside. The structure elucidations were based on analyses of spectroscopic data.

Lignan, phenolic and iridoid glycosides from Stereospermum cylindricum.

A lignan glycoside [(+)-cycloolivil 4'-O-beta-d-glucopyranoside], a phenolic glycoside [3,4-dimethoxyphenyl 1-O-beta-d-xylopyranosyl-(1-->6)-beta-d-glucopyranoside] and a iridoid glycoside (stereospermoside) were isolated from the leaves and branches of Stereospermum cylindricum, together with (+)-cycloolivil, (+)-cycloolivil 6-O-beta-d-glucopyranoside, (-)-olivil, (-)-olivil 4-O-beta-d-glucopyranoside, (-)-olivil 4'-O-beta-d-glucopyranoside, vanilloloside, decaffeoyl-verbascoside, isoverbascoside, 3,4,5-trimethoxyphenyl 1-O-beta-d-xylopyranosyl-(1-->6)-beta-d-glucopyranoside, ajugol, verminoside, and specioside. The structure elucidations were based on spectroscopic evidence.

Acetophenone diglycosides from Erythroxylum cambodianum.

Two new acetophenone diglycosides, erythroxylosides A and B, were isolated from the aerial portion of Erythroxylum cambodianum together with (+)-catechin, (-)-epicatechin, quercetin 3-O-rutinoside, (3S,5R,6R,7E,9S-megastigman-7-ene-3,5,6,9-tetrol 3-O-beta-D-glucopyranoside and citroside A. The structural elucidations were based on analyses of chemical and spectroscopic data.

A new iridoid diglycoside from Clerodendrum chinense.

A new iridoid diglucoside, 5-O-beta-glucopyranosyl-harpagide, has been isolated from the aerial part of Clerodendrum chinense together with three known iridoid glucosides and six known cyclohexylethanoids. Their structures have been determined by analyses of spectroscopic data.

Triterpenoidal glycosides from Justicia betonica.

dFrom the aerial portion of Justicia betonica L., four triterpenoidal glycosides (justiciosides A-D) were isolated. Their structures were established through chemical and NMR spectroscopic analyses as olean-12-ene-1beta,3beta,11alpha,28-tetraol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, olean-12-ene-1beta,3beta,11alpha,28-tetraol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, 11alpha-methoxy-olean-12-ene-1beta,3beta,28-triol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, 11alpha-methoxy-olean-12-ene-1beta,3beta,28-triol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, respectively.

Aliphatic alcohol and iridoid glycosides from Asystasia intrusa.

An aliphatic alcohol glycoside (asystoside) and an iridoid diglucoside (3'-O-beta-D-glucopyranosyl-catalpol) were isolated from the aerial part of Asystasia intrusa along with benzyl beta-D-glucopyranoside, zizybeoside I, (6S,9R)-roseoside, verbascoside, ehrenoside, 6beta-hydroxyantirrhide, angeloside, catalpol, ajugol, 6-deoxycatalpol, and scutellarioside II. The structural elucidations were based on analyses of physical and spectroscopic data.