Inhibiting activities of the secondary metabolites of Phlomis brunneogaleata against parasitic protozoa and plasmodial enoyl-ACP reductase, a crucial enzyme in fatty acid biosynthesis

Anti-plasmodial activity-guided fractionation of Phlomis brunneogaleata (Lamiaceae) led to the isolation of two new metabolites, the iridoid glycoside, brunneogaleatoside and a new pyrrolidinium derivative (2S,4R)-2-carboxy-4-(E)-p-coumaroyloxy-1,1-dimethylpyrrolidinium inner salt [(2S,4R)-1,1-dimethyl-4-(E)-p-coumaroyloxyproline inner salt]. Moreover, a known iridoid glycoside, ipolamiide, six known phenylethanoid glycosides, verbascoside, isoverbascoside, forsythoside B, echinacoside, glucopyranosyl-(1→Gi-6)-martynoside and integrifolioside B, two flavone glycosides, luteolin 7-O-β-D-glucopyranoside (10) and chrysoeriol 7-O-β-D-glucopyranoside (11), a lignan glycoside liriodendrin, an acetophenone glycoside 4-hydroxyacetophenone 4-O-(6′-O-β-D-apiofuranosyl)-β-D-glucopyranoside and three caffeic acid esters, chlorogenic acid, 3-O-caffeoylquinic acid methyl ester and 5-O-caffeoylshikimic acid were isolated. The structures of the pure compounds were elucidated by means of spectroscopic methods (UV, IR, MS, 1D and 2D NMR, [α]D) and X-ray crystallography. Compounds 10 and 11 were determined to be the major anti-malarial principles of the crude extract (IC50 values of 2.4 and 5.9 μg/mL, respectively). They also exhibited significant leishmanicidal activity (IC50 = 1.1 and 4.1 μg/mL, respectively). The inhibitory potential of the pure metabolites against plasmodial enoyl-ACP reductase (FabI), which is the key regulator of type II fatty acid synthases (FAS-II) in P. falciparum, was also assessed. Compound 10 showed promising FabI inhibiting effect (IC50 = 10 μg/mL) and appears to be the first anti-malarial natural product targeting FabI of P. falciparum

Secondary metabolites of Phlomis viscosa and their biological activities

Further phytochemical studies on the aerial parts of Phlomis viscosa (Lamiaceae) led to the isolation of 24 compounds: 3 iridoid glycosides, 10 phenylethanoid glycosides, a megastigmane glycoside and a hydroquinone glycoside, as well as 2 lignan glucosides and 7 neolignan glucosides, 1 of which is new (17b). Compound 17b was obtained as a minor component of an inseparable mixture (2:1) of 2 neolignan glucosides (17a/b), and characterized as 3',4-O-dimethylcedrusin 9-O-b -glucopyranoside. Full NMR data of the known 8-O-4' neolignan glucoside, erythro-1-(4-O-b-glucopyranosyl-3-methoxyphenyl)- 2-{2-methoxyl-4-[1-(E)-propene-3-ol]-phenoxyl}-propane-1,3-diol (18) are also reported. All isolated compounds were screened for cell growth inhibition versus 3 tumor cell lines (MCF7, NCI-H460, and SF-268) and several phenylethanoid glycosides were found to possess weak antitumoral activity. The phenylethanoid glycosides were also evaluated for their free radical (DPPH) scavenging, antibacterial and antifungal activities. The free radical (DPPH) scavenging activities of verbascoside (4), isoacteoside (5), forsythoside B (10), myricoside (13) and samioside (14) were found to be comparable to that of dl-a -tocopherol. Compounds 4, 5, 10 and 14 (MIC: 500 m g/mL) as well as Leucosceptoside A (8) and 13 (MIC:1000 m g/mL) showed very weak activity against Gram (+) bacteria

Secondary metabolites from Scutellaria albida L. ssp. velenovskyi (Rech. f.) Greuter & Burdet

Fourteen compounds (Fig.1) were isolated from the aerial parts of Scutellaria albida L. ssp. velenovskyi (Rech. f.) Greuter & Burdet, including four iridoids (1–4) catalpol, macfadienoside, mussaenosidic acid, albidoside; four flavonoids (5–8) hispidulin 7-Ο-β-D-glucuronide, scutellarin, xanthomicrol, eriodictyol; four phenylethanoid glycosides (9–12) verbascoside, leucosceptoside A, martynoside, 2-(3-hydroxy-4-methoxy-phenyl)-ethyl-1-Ο-β-D-glucopyranoside; the sugar ester 6′-β-D-glucopyranosyl-E-p-coumarate (13), as well as the acetogenic glucoside (Z)-3-hexenyl-1-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranoside (14). The structures of the isolates were established by means of NMR and HRMS spectral analyses. This is the first phytochemical study on S. velenovskyi and the first report of an acetogenic glycoside in the genus Scutellaria L. A chemical review on the isolated secondary metabolites in this study has been carried out. The chemotaxonomic value of the isolates is also discussed. Based on the literature data, the analysis revealed that the chemical profile of S. velenovskyi is close to that of the taxa belonging to the S. albida group. © 2019 Elsevier Lt

Two new triterpene and a new nortriterpene glycosides from Phlomis viscosa

The isolation and structure elucidation of two new oleanane-type triterpene glycosides, 29-(β-D-glucopyranosyloxy)-2α,3β,23-trihydroxyolean-12-en-28-oic acid (=(2α,3β,4α,29α)-29-(β-D-glucopyranosyloxy)-2,3,23-trihydroxyolean-12-en-28-oic acid; 1) and its C(20)-epimer, 30-(β-D-glucopyranosyloxy)-2α,3β,23-trihydroxyolean-12-en-28-oic acid (=(2α,3β,4α,29β)-29-β-D-glucopyranosyloxy)-2,3,23-trihydroxyolean-12-en-28-oic acid; 2), and a novel nortriterpene glycoside, (17S)-2α,18β,23-trihydroxy-3,19-dioxo-19(18[RIGHTWARDS ARROW]17)- abeo-28-norolean-12-en-25-oic acid β-D-glucopyranosyl ester (=(1R,2S,4aS,4bR,6aR,7R,9R,10aS,10bS)-3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11-tetradecahydro-1-hydroxy-7-(hydroxymethyl)-3′,4′,4a,4b,7-pentamethyl-2′,8- dioxospiro[chrysene-2(1H),1′-cyclopentane]-10a-carboxylic acid β-D-glucopyranosyl ester; 3) from Phlomis viscosa (Lamiaceae) are reported. The structures of the compounds were asigned by means of spectroscopic (IR, 1D- and 2D-NMR, and LC-ESI-MS) and chemical (acetylation) methods

Sugar Esters from Globularia Orientalis

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