Search

In the course of our continuing search for biologically active compounds from medicinal herbs, four undescribed terpenoids including one monoterpenoid glycoside, (1 R, 3S, 4S, 5 R)-(-)-1,8-epoxy-p-menthan-5-ethoxycarbonyl-3-O-β-D-glucopyranoside (1), one iridoid glycoside, 3′-O-β-D-glucopyranosyl-melampyroside (2), one sesquiterpene, 1-(2-methylbutanol)-2-pentyl-1,3-cyclohexadiene (3), and one triterpenoid, 28-nor-3β,18β-dihydroxyurs-12-ene (4), together with nine known terpenoids (5–13) were isolated from the dried aerial parts of Dracocephalum moldavica (Lamiaceae). Their chemical structures were elucidated by detailed spectroscopy (1 D and 2 D NMR), HRESIMS data analysis and acid hydrolysis. Among them, compounds 9 and 10 were isolated from the family Lamiaceae, compounds 5, 6 and 11–13 were identified from the genus Dracocephalum and compounds 7 and 8 were reported from the D. moldavica for the first time. The biological evaluation of anti-complementary activity revealed that some compounds, 4, 6 and 12 exhibited anti-complementary activity with CH50 and AP50 values ranging from 0.67–1.43 and 1.12–1.55 mM, respectively. [ABSTRACT FROM AUTHOR]

A new monoterpenoid glycoside (1 R, 2 R, 4S)-1,8-epoxy-p-menthan-2-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (1) and a new phenolic glycoside, cis-1-(3-hydroxy-4-methoxyphenyl)-2-butene-4-O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranoside (2) were isolated from the dried aerial parts of Dracocephalum moldavica, together with 12 known compounds. Compound 5 was isolated from the Lamiaceae family for the first time, compounds 3, 4, 6 and 8–12 were identified from the genus Dracocephalum for the first time and compounds 7 and 13–14 were reported from the D. moldavica for the first time. All the compounds were evaluated for anti-complementary activity against the classical and alternative pathways. Compounds 2–4, 8 and 11 showed anti-complementary activity to different extents, with CH50 and AP50 values ranging from 0.78–1.24 and 1.52–1.84 mM, respectively. The targets of compounds 2–4, 8 and 11 in complement activation cascade were identified as well. [ABSTRACT FROM AUTHOR]

Sanguisorba officinalis L. is a traditional herbal plant that belongs to the genus Sanguisorba and the family Rosaceae. Two new phenolic glycosides (1–2), ten known phenolics (3–12), and six known monoterpenoid glycosides (13–18) were isolated from the roots of S. officinalis using silica gel column and preparative middle pressure liquid chromatography (MPLC). The chemical structures were elucidated based on extensive spectroscopic experiments, including 1D and 2D NMR as well as HR-ESI-MS, and comparison with those reported in the literature. Compounds 3–5, and 13 were isolated from the Rosaceae family and compound 7 was obtained from the genus Sanguisorba for the first time. Additionally, all compounds were evaluated for their anti-complementary activities against the classical pathway. Furthermore, compounds 1, 5, 9, and 14 showed significant anti-complementary activities with the 50% haemolytic inhibition concentrations (CH50) values of 0.40 ± 0.03, 0.57 ± 0.01, 0.51 ± 0.07, and 0.53 ± 0.05 mM, respectively. [ABSTRACT FROM AUTHOR]

Two new flavonoids, (2S)-6,8-dimethyl-5,7,3′,4′-tetrahydroxyflavanone 4′-O-β-D-glucopyranoside (1) and quercetin 3-O-β-D-(6′′-p-methoxybenzoyl)-galactopyranoside (2), together with ten known flavonoids (3–12) were isolated from the leaves of Rhododendron dauricum L. The structures of the flavonoids were characterized from spectroscopic data (1D and 2D NMR and HR-ESI-MS). The isolated flavonoids were evaluated for their inhibitory effects on the production of tumour necrosis factor (TNF)-α in LPS-stimulated RAW 264.7 cells. Compound 11 exhibited inhibitory activity against TNF-α production with an IC50 value of 46.2 ± 1.2 µM. [ABSTRACT FROM AUTHOR]

A new pentacyclic triterpenoid, 3-oxo-urs-11,13(18)-dien-28-oic acid (1), along with twelve known triterpenoids, α-amyrin (2), 19α-hydroxy-α-amyrin (3), triptohypol E (4), uvaol (5), 2α,3α-dihydroxyurs-11-en-13β,28-olide (6), 3β-hydroxyurs-11-en-13β,28-olide (7), ursolic acid (8), asiatic acid (9), oleanolic acid (10), aegiceradienol (11), obtusalin (12) and betulinic acid (13) were isolated from the leaves of Rhododendron dauricum L. Their structures were established from spectroscopic data and comparison with reported values. Among them, compounds 3, 4, 6, 7 and 11 were isolated from the Ericaceae family for the first time. Compounds 2, 5, 9, 12 and 13 were obtained from R. dauricum for the first time. Additionally, compounds 6, 10 and 11 significantly inhibited the levels of NO in LPS-stimulated RAW 264.7 cells at 3 μM. [ABSTRACT FROM AUTHOR]

One new aryldihydronaphthalene-type lignan ( 1 ) together with eight known lignans ( 2-4, 7-11 ) as well as two caffeic-acid dimers ( 5, 6 ) were isolated from an ethanol extract of the whole plant of Corispermum mongolicum Iljin (Chenopodiaceae). The chemical structures of these compounds were determined from 1D and 2D NMR and HR-ESI-MS spectra, and results were compared with data from the literature. This study is the first demonstration of nine compounds ( 2 and 4 - 11 ) isolated from the Chenopodiaceae family, with one of these ( 3 ) from the genus Corispermum . Anti-inflammatory effects of the isolated compounds were evaluated in terms of inhibition of production of nitric oxide, tumour necrosis factor-α, and interleukin-6 in lipopolysaccharide-induced RAW 264.7 cells.