Triterpenoids from the fruits and leaves of the blackberry (<i>Rubus allegheniensis</i>) and their inhibitory activities on foam cell formation in human monocyte-derived macrophage

<div><p>From the methanol extract of the fruits of the blackberry (<i>Rubus allegheniensis</i> Port.), four triterpenoids – pomolic acid (<b>1</b>), tormentic acid (<b>2</b>), euscaphic acid (<b>3</b>) and 1β-hydroxyeuscaphic acid (<b>4</b>) – were isolated, while six triterpenoids – <b>2</b>, <b>3</b>, myrianthic acid (<b>5</b>), ziyu glycoside II (<b>6</b>), sericic acid (<b>7</b>) and 19-hydroxy-2,3-secours-12-ene-2,3,28-trioic acid 3-methyl ester (<b>8</b>) – were obtained from the methanol extract of the leaves of this plant. Their structures were determined on the basis of spectral data. Compounds <b>1</b>–<b>8</b> were examined for their inhibitory activities on foam cell formation in human monocyte-derived macrophages induced by acetylated low-density lipoproteins at a 50 μM concentration. Among the tested compounds, <b>1</b> showed the strongest activity, with the inhibitory effect being 90%. The inhibitory activities of <b>2</b>–<b>8</b> were evaluated to be 30%, 32%, 33%, 4%, 48%, 4% and 24%, respectively. Further, the structure–activity relationship of these compounds was investigated.</p></div

A new hemiterpene glycoside from the ripe tomatoes

<div><p></p><p></p>A new hemiterpene glycoside (<b>1</b>) was isolated from ripe tomatoes (the fruit of <i>Lycopersicon esculentum</i>, Solanaceae) along with eight known compounds. The chemical structure of <b>1</b> was determined to be 2-methylbutan-1-ol β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside, based on spectroscopic data as well as chemical evidence. In addition, the radical-scavenging activities of the isolated compounds on the free radical of 1,1-diphenyl-2-picrylhydrazyl were examined. Among the tested compounds, tryptophan, 4-<i>O</i>-β-d-glucopyranosyl caffeic acid and dihydro-<i>p</i>-coumaryl alcohol γ-<i>O</i>-β-d-glucopyranoside demonstrated 42.0%, 50.1% and 76.0% scavenging activities, respectively, at a concentration of 0.5 mM.<p></p></div

A new triterpenoid glycoside from the leaves and stems of <i>Duranta repens</i>

<div><p>A new triterpenoid glycoside (<b>1</b>) was isolated from the methanol extract of the leaves and stems of <i>Duranta repens</i> L. (Verbenaceae) along with 14 known compounds consisting of eight triterpenoids, four iridoids, one phenylethanoid glycoside and one flavonoid. The chemical structure of <b>1</b> was determined to be bayogenin 3-<i>O</i>-[β-D-glucopyranoside]-28-<i>O</i>-[α-L-rhamnopyranosyl-(1→5)-<i>O</i>-β-D-apiofuranosyl-(1→4)-<i>O</i>-α-L-rhamnopyranosyl-(1→2)-<i>O</i>-α-L-arabinopyranosyl] ester, based on spectroscopic data. In addition, the inhibitory effects of the isolates on lipoxygenase activity were examined. Among them, acteoside and apigenin resulted in 94 ± 3.6% and 82 ± 4.7% inhibition, respectively, at 0.5 mM.</p></div

A new triterpenoid glycoside from the leaves and stems of <i>Duranta repens</i>

<div><p>A new triterpenoid glycoside (<b>1</b>) was isolated from the methanol extract of the leaves and stems of <i>Duranta repens</i> L. (Verbenaceae) along with 14 known compounds consisting of eight triterpenoids, four iridoids, one phenylethanoid glycoside and one flavonoid. The chemical structure of <b>1</b> was determined to be bayogenin 3-<i>O</i>-[β-D-glucopyranoside]-28-<i>O</i>-[α-L-rhamnopyranosyl-(1→5)-<i>O</i>-β-D-apiofuranosyl-(1→4)-<i>O</i>-α-L-rhamnopyranosyl-(1→2)-<i>O</i>-α-L-arabinopyranosyl] ester, based on spectroscopic data. In addition, the inhibitory effects of the isolates on lipoxygenase activity were examined. Among them, acteoside and apigenin resulted in 94 ± 3.6% and 82 ± 4.7% inhibition, respectively, at 0.5 mM.</p></div

Tomatidine, a Tomato Sapogenol, Ameliorates Hyperlipidemia and Atherosclerosis in ApoE-Deficient Mice by Inhibiting Acyl-CoA:cholesterol Acyl-transferase (ACAT)

It was previously revealed that esculeoside A, a new glycoalkaloid, and esculeogenin A, a new aglycon of esculeoside A, contained in ripe tomato ameliorate atherosclerosis in apoE-deficent mice. This study examined whether tomatidine, the aglycone of tomatine, which is a major tomato glycoalkaloid, also shows similar inhibitory effects on cholesterol ester (CE) accumulation in human monocyte-derived macrophages (HMDM) and atherogenesis in apoE-deficient mice. Tomatidine significantly inhibited the CE accumulation induced by acetylated LDL in HMDM in a dose-dependent manner. Tomatidine also inhibited CE formation in Chinese hamster ovary cells overexpressing acyl-CoA:cholesterol acyl-transferase (ACAT)-1 or ACAT-2, suggesting that tomatidine suppresses both ACAT-1 and ACAT-2 activities. Furthermore, the oral administration of tomatidine to apoE-deficient mice significantly reduced levels of serum cholesterol, LDL-cholesterol, and areas of atherosclerotic lesions. The study provides the first evidence that tomatidine significantly suppresses the activity of ACAT and leads to reduction of atherogenesis

A new resin glycoside from <i>Calystegia soldanella</i> and its antiviral activity towards herpes

<p>A new resin glycoside, named calysolin XVIII (<b>1</b>), was isolated from the leaves, stems and roots of <i>Calystegia soldanella</i> Roem. et Schult. (Convolvulaceae). The structure of <b>1</b> was defined as 11<i>S</i>-jalapinolic acid 11-<i>O</i>-β-d-glucopyranosyl-(1 → 3)-<i>O</i>-(2-<i>O</i>-2<i>S</i>-methylbutyryl,4-<i>O</i>-3-hydroxy-2-methylenebutyryl)-α-l-rhamnopyranosyl-(1 → 2)-[<i>O</i>-β-d-glucopyranosyl-(1 → 6)-<i>O</i>-(34-di-<i>O</i>-2<i>S</i>-methylbutyryl)-β-d-glucopyranosyl-(1 → 3)]-<i>O</i>-β-d-glucopyranosyl-(1 → 2)-β-d-quinovopyranoside, intramolecular 1,2″′″′-ester on the basis of spectroscopic data. Compound <b>1</b> is the first known resin glycoside to feature 3-hydroxy-2-methylenebutyric acid as a component organic acid. In addition, <b>1</b> demonstrated an antiviral activity against herpes simplex virus type 1, with an IC₅₀ value 2.3 μM.</p

Tomatidine, a Tomato Sapogenol, Ameliorates Hyperlipidemia and Atherosclerosis in ApoE-Deficient Mice by Inhibiting Acyl-CoA:cholesterol Acyl-transferase (ACAT)

It was previously revealed that esculeoside A, a new glycoalkaloid, and esculeogenin A, a new aglycon of esculeoside A, contained in ripe tomato ameliorate atherosclerosis in apoE-deficent mice. This study examined whether tomatidine, the aglycone of tomatine, which is a major tomato glycoalkaloid, also shows similar inhibitory effects on cholesterol ester (CE) accumulation in human monocyte-derived macrophages (HMDM) and atherogenesis in apoE-deficient mice. Tomatidine significantly inhibited the CE accumulation induced by acetylated LDL in HMDM in a dose-dependent manner. Tomatidine also inhibited CE formation in Chinese hamster ovary cells overexpressing acyl-CoA:cholesterol acyl-transferase (ACAT)-1 or ACAT-2, suggesting that tomatidine suppresses both ACAT-1 and ACAT-2 activities. Furthermore, the oral administration of tomatidine to apoE-deficient mice significantly reduced levels of serum cholesterol, LDL-cholesterol, and areas of atherosclerotic lesions. The study provides the first evidence that tomatidine significantly suppresses the activity of ACAT and leads to reduction of atherogenesis

Two new resin glycosides, muricatins XII and XIII, from the seeds of <i>Ipomoea muricata</i>

Two new resin glycosides, muricatins XII (1) and XIII (2), were isolated from the crude resin glycoside fraction of the seeds of Ipomoea muricata (L.) Jacq. (Convolvulaceae), along with three known ones, muricatins V (3), VI (4), and IX (5). Compounds 1 and 2 contained new glycosidic acids, muricatic acids E (1a) and F (2a), respectively. The structures of these compounds were determined using data obtained from spectroscopy measurements and chemical evidence. The results suggested that 1 and 2 have macrolactone structures (jalapins). Furthermore, the cytotoxic activity of the crude resin glycoside fraction and 3–5 against HL-60 human promyelocytic leukaemia cells was evaluated. All tested samples demonstrated cytotoxic activities.</p

Two new triterpenoids from the seeds of blackberry (<i>Rubus fructicosus</i>)

<p>Two new ursane-type triterpenoids (<b>1</b>, <b>2</b>) attached to isopropylidenedioxy group were isolated from the seeds of blackberry (<i>Rubus fructicosus</i> L., Rosaceae) along with two known ursane-type triterpenoids, 2,3-<i>O</i>-isopropylidenyl-2α,3α,19α-trihydroxyurs-12-en-28-oic acid (<b>3</b>) and 1β-hydroxyeuscaphic acid (<b>4</b>). The chemical structures of <b>1</b> and <b>2</b> were determined to be 2,3-<i>O</i>-isopropylidene-1β,2β,3β,19α-tetrahydroxyurs-12-en-28-oic acid and 1,2-<i>O</i>-isopropylidene-1β,2α,3α,19α-tetrahydroxyurs-12-en-28-oic acid, respectively, based on spectroscopic data. Additionally, their cytotoxic activity towards HL-60 human leukaemia cells was evaluated. Among them, <b>3</b> demonstrated a clear cytotoxic activity with 72.8 μM of IC₅₀ value.</p