• Natural Product Sciences
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• v.20 no.4
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• pp.290-295
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• 2014

The triterpenoids contained in four Rubus species (Rosaceae) were quantitatively analyzed using HPLC to select plants with large quantities of niga-ichigoside $F_1$. Unripe fruits, ripe fruits, and leaves were extracted to estimate the quantity of niga-ichigoside $F_1$, together with Rubus-specific $19{\alpha}$-hydroxyursane-type triterpenoids, euscaphic acid, tormentic acid, and kaji-ichigoside $F_1$, and a dimeric triterpenoid coreanoside $F_1$. Niga-ichigoside $F_1$ was most abundant in the leaves of R. crataegifolius (23.4 mg/g dry weight). The amount of triterpenoid in the black, ripe fruits of R. coreanus was lower than the unripe fruits of the same plant. On the other hand, the ripe fruits of three plants, R. crataegifolius, R. parvifolius and R. pungens var. oldhami, which are reddish, contained higher or similar level of triterpenoids than their unripe fruits. In addition, the concentration of niga-ichigoside $F_1$ in the ripe fruit of R. crataegifolius was 20.5 mg/g, suggesting that the fruits could be used as a functional food. Methyl gallate and ellagic acid were used as quantitative indices of total tannin. Methyl gallate levels were higher in ripe fruits than unripe fruits in R. crataegifolius, R. pungens var. oldhami, and R. parvifolius. In R. crataegifolius, the quantity of methyl gallate was 30.5 mg/g in ripe fruit, but 1.19 mg/g in unripe fruit.

• Natural Product Sciences
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• v.14 no.4
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• pp.260-264
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• 2008

To find the antidiabetic activity of the tripterpenoid-rich fractions of Rubus coreanus (TRF-cor) and R. crataegifolius (TRF-cra) leaves or its main component niga-ichigoside $F_1$ (Niga-$F_1$), anti-hyperglycemic and antihyperlipidemic effects were investigated in the diabetic rat model induced by streptozotocin (STZ). Treatments of rats with 200 mg/kg of the TRF-cor, TRF-cra (each, p.o.) or 20 mg/kg of Niga-$F_1$ significantly inhibited the increase of blood glucose concentration about 44.8%, 28.7% or 20.6%, respectively, in the diabetic rats. In addition, treatments with those fractions inhibited the increase of serum concentrations of triglyceride, total cholesterol or LDL-cholesterol caused by STZ. The inhibitory rate on atherogenic index (AI) values of the TRFcor (200 mg/kg), TRF-cra (200 mg/kg) or Niga-$F_1$ (20 mg/kg)-treated groups were decreased about 55.7%, 36.3% or 22.6%, respectively, comparable to STZ-treated group. In the oral glucose tolerance test, treatment of TRF-cor or TRF-cra inhibited the increase of blood glucose concentration in the STZ-induced rats. Administration of 20 mg/kg of Niga-$F_1$ (p.o.) also exhibited similar effects with the effects of both TRFs at 200 mg/kg dose (p.o.). These results support that the triterpenoids, in particular Niga-$F_1$, are contributed to the antidiabetic effects of R. coreanus or R. crataegifolius.

• Korean Journal of Pharmacognosy
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• v.38 no.2 s.149
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• pp.187-191
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• 2007

The extraction yield of the methanolic extracts and 19${\alpha}$-hydroxyursane-type triterpenoid (19${\alpha}$-HUT) fraction were investigated in the unripe and ripe fruits and the leaves of the four Rubus plants (Rubus coreanus, R. crataegifolius, R. phoenicolasius, R. pungens var. oldhami) to develop the biomaterial 19${\alpha}$-HUT mixture as functional foods. Thin layer chromatogaphy-Densitometer (TLC-DM) was used to analyze the individual quantity of 19${\alpha}$-HUTs using standard compounds (euscaphic acid, tormentic acid, 23-hydroxytormentic acid, kaji-ichigoside F$_1$, rosamultin, niga-ichigoside F$_1$). The content of methanolic extract of the fruits were higher in the ripe stage than in the unripe stage whereas the content of 19${\alpha}$-HUT mixture varied with each Rubus species. The Rubus plants containing the highest amount of 19${\alpha}$-HUTs in the leaves were R. coreanus, R. phoenicolasius and R. pungens var. oldhami while only R. cratagefolius showed the highest content in the ripe fruits. The mean of total genin content of 19${\alpha}$-HUTs was 0.94 mg/g; that of the glycosides was 0.60 mg/g. The genin quantity was found in the order of 23-hydroxytormentic acid> euscaphic acid> tormentic acid; the glycoside was observed in the order of niga-ichig-oside F$_1$> kaji-ichigoside F$_1$> rosmaultin, by which the biosynthetic pathway of 23-hydroxytormentic acid and its glucoside niga-ichigoside F$_1$ via the intermediates tormentic acid and/or rosamultin was presumed. It is also suggested that the ripe fruits of R. crataegifolius will be desirable to use as functional foods rather than unripe fruits.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.197.4-198
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• 2003

As an attempt to search for bioactive natural constituents exerting antinociceptive and antiinflammatory activities, we examined the potency of the extract of R. coreanus fruits by the activity-guided fractionation. The EtOAc- and BuOH fraction and those alkaline hydrolysates showed significant antinociceptive effects as assessed by writhing-, hot plate- and tail flicks tests in mice and rats as well as antiinflammatory effect in rats with carrageenan-induced edema. BuOH extract was subjected to column chromatography to obtain a large amount of niga-ichigoside F$_1$ (1, 23-hydroxytormentic acid 28-O-glc), which was again hydrolyzed in NaOH solution to yield an aglycone 23-hydroxytormentic acid (1a). (omitted)

• Natural Product Sciences
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• v.21 no.1
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• pp.14-19
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• 2015

Several $19{\alpha}$-hydroxyursane-type triterpenoids and hydrolysable tannins have beneficial effects on human health. Rubus crataegifolius (Rosaceae) has the cleft simple leaf whereas R. parvifolius has pinnate compound leaves. This research was aimed to find the variation in the contents of the triterpenoids and tannins between the infected versus uninfected leaves of R. coreanus and R. parvifolius and between young versus mature leaves. Triterpenoids and tannins were quantitatively analyzed by HPLC. Six triterpenoids including tormentic acid, euscaphic acid, 23-hydroxytormentic acid, coreanoside $F_1$, kaji-ichigoside $F_1$ and niga-ichigoside $F_1$ were used for standard compounds. Gallotannins and ellagitannins were quantitatively evaluated using the indicatives of methyl gallate and ellagic acid. The infected leaves of R. crataegifolius contained higher levels of triterpenoids and tannin than the uninfected leaves; however, lower quantity of total tannin was observed in the mature leaves than in the young leaves. Although the pinnate compound leaves of R. parvifolius exhibited similar tendency of those compositional variation with R. crataegifolius each other, its contents of triterpenoids do not considerably vary. Variation of the contents of triterpenoids and tannins were particularly distinct in R. crataegifolius by growth and infection.

• Natural Product Sciences
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• v.13 no.1
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• pp.33-39
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• 2007

Eleven polyhydroxyursane triterpenoids (PHUTs) were tested to determine their cytoprotective, immunosuppressive and anti-inflammatory effects. To compare the bioactivities of $19{\alpha}$-hydroxyursane-type triterpenoids {23-hydroxytormentic acid (6), its methyl ester (7), tormentic acid (8), niga-ichigoside $F_1$ (9),euscaphic acid (10) and kaji-ichigoside $F_1$ (11)} of the Rosaceae crude drugs (Rubi Fructus and Rosa rugosae Radix) with PHUTs possessing no $19{\alpha}-hydroxyl$ of Centella asiatica (Umbelliferae), the four PHUTs, asiaticoside (1), madecassoside (2), asiatic acid (3), and madecassic acid (4) were isolated from C. asiatica and 23-hydroxyursolic acid (5) from Cussonia bancoensis. Cytoprotective effects were assessed by measuring cell viabilities against cisplatin-induced cytotoxocity in $LLC-PK_1$, cells (proximal tubule, pig kidney) to determine whether these agents have protective effects against nephrotoxicity caused by cisplatin. The inhibitory effect of 11 PHUTS on nitric oxide (NO) and prostaglandin $E_2\;(PGE_2)$ were evaluated by measuring nitrite accumulation in lipopolysaccharide (LPS)-induced macrophage RAW 264.7 cells, and their anti-inflammatory effects were tested in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema model. Six MHUTs (compounds 1, 2, 4, 6, 10, and 11) exhibited higher cell viabilities during cisplatin-induced cytotoxicity testing even at a concentration of $200\;{\mu}g/ml$ than cisplatin only-treated group, suggesting that ese compounds have the potentcytoprotective efffcts. Compounds 1 and 3 of the C. asiatica and niga-ichigoside $F_1$ exhibited no inhibitory effect on NO and/or $PGE_2$ production whereas other PHUTs produced mild to significant NO and/or $PGE_2$ production.The four compounds (2, 5, 9, and 10) potently inhibited mouse ear edema induced by TPA whereas two compounds (1 and 3) had no activity in this test. These results suggest that many PHUTs are potentchemopreventives. Structure-activity relationship (SAR) was also discussed in each assay with regard to the significant role of OHs at the position of 2, 3, 6, 19, and 23 and to the glycoside linkage at the 28-carboxyl.

• Proceedings of the Korean Society of Applied Pharmacology
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• 2003.11a
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• pp.97-97
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• 2003

This study is investigated the effect of Rubus coreanus MIQ. against nephrotoxicity induced by cisplatin in rat. We examined the potency of the extract of R. coreanus fruits by the activity-guided fractionation. The EtOAc- and BuOH fraction, niga-ichigoside F$_1$and 23-hydroxytormentic acid showed significant protective effects as lipid peroxidation in renal tissue and was was not affect the activity of xanthine oxidase and aldehyde oxidase by cisplatin-induced nephrotoxicity. The concentration of glutathione in renal tissue was decreased by cisplatin-induced nephrotoxicity, but was improved by pretreatment of R. coreanus compounds especially in butanol, ethylacetate fraction and 23-hydroxytormentic acid.

• Natural Product Sciences
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• v.13 no.2
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• pp.152-159
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• 2007

To demonstrate anti-hyperlipidemic activity of the 19${\alpha}$-hydroxyursane-type triterpenoid (19${\alpha}$-HUT)-rich fraction, this fraction was prepared from the extract of Rubus crataegifolius leaves. This fraction was found to have anti-hyperlipidemic effect in a high fat diet-induced rat model from the observation of reduction of abdominal fat pad weights, atherogenic index and hypercholesterolemia at 30 and 60 mg/kg (p.o.) The 19${\alpha}$-HUT fraction was subjected to SiO$_2$, ODS, and/or Sephadex LH-20 column chromatography to yield a new triterpenoid (1) called pomolic acid ester along with nine known triterpenoids which are all 19${\alpha}$-HUTs: euscaphic acid (2), tormentic acid (3), 23-hydroxytormentic acid (4), kaji-ichigoside F$_1$ (5), rosamultin (6), niga-ichigosides F$_1$ (7) and F$_2$ (8), suavissimoside F$_1$ (9) and coreanoside F$_1$ (10). The structure of compound 1 was established as 28-O-formyl-3,19-dihydroxyurs-12-en-28-oic acid on the basis of 2D-NMR spectroscopic data and mass spectrum. Compound 1 was isolated for the first time from natural sources.