• Journal of Pharmaceutical Investigation
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• v.5 no.1
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• pp.23-27
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• 1975

Hederine, m. p. $256{\sim}257^{\circ}\;C_{41}H_{64}O_{11}\;{\cdot}\;2H_{2}O$ : $23-hydroxy-3{\beta}-({\beta}-{\alpha}-arabinosidor hamnoside)-olenana-12-ene-oique,$ was obtained from the cortex of Kalopanax pictum. Acid hydrolysis of hederine yielded hederagenin, arabinose and rhamnose. Hederagenin was identified by comparison of it's mixed melting point and IR spectra against authentic sample. Arabinose and rhamnose were identified by TLC against standards.

• Archives of Pharmacal Research
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• v.22 no.3
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• pp.313-316
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• 1999

Certain steroids and triterpenoids isolated from diverse plant families were known to posses anti-inflammatory activity. In the course of finding new anti-inflammatory natural products, some steroidal and triterpenoid saponins were isolated and evaluated for their anti-inflammatory activity using in vivo mouse ear edema test. At the oral dose of 100 mg/kg, several steroidal saponins and triterpenoid saponins such as hederagenin glycosides showed significant inhibition of ear edema (20∼37% inhibition), though less potent than indomethacin and hydrocortisone.

• Journal of Nutrition and Health
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• v.55 no.6
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• pp.617-629
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• 2022

Purpose: Osteoporosis is characterized by structural deterioration of the bone tissue because of the loss of osteoblastic activity or the increase in osteoclastic activity, resulting in bone fragility and an increased risk of fractures. Hederagenin (Hed) is a pentacyclic triterpenoid saponin isolated from Dipsaci Radix, the dried root of Dipsacus asper Wall. Dipsaci Radix has been used in Korean herbal medicine to treat bone fractures. In this study, we attempted to demonstrate the potential anti-osteoporotic effect of Hed by examining its effect on osteoblast differentiation in MC3T3-E1 cells. Methods: Osteoblastic MC3T3-E1 cells were cultured in 0, 1, and 10 ㎍/mL Hed for 3 and 7 days. The activity of alkaline phosphatase (ALP), bone nodule formation and level of expression of bone-related genes and proteins were measured in MC3T3-E1 cells exposed to Hed. The western blot test was used to detect the activation of the bone morphogenetic protein-2 (BMP2)/ Suppressor of Mothers against Decapentaplegic (SMAD)1 pathway. Results: Hed significantly increased the proliferation of MC3T3-E1 cells. Intracellular ALP activity was significantly increased in the 1 ㎍/mL Hed-treated group. Hed significantly increased the concentration of calcified nodules. Furthermore, Hed significantly upregulated the expression of genes and proteins associated with osteoblast proliferation and differentiation, such as Runt-related transcription factor 2 (Runx2), ALP, osteopontin (OPN), and type I procollagen (ProCOL1). Induction of osteoblast differentiation by Hed was associated with increased BMP2. In addition, Hed induced osteoblast differentiation by increasing the activity of SMAD1/5/8. These results suggest that Hed has the potential to prevent osteoporosis by promoting osteoblastogenesis in osteoblastic MC3T3-E1 cells via the modulation of the BMP2/SMAD1 pathway. Conclusion: The results presented in this study indicate that Hed isolated from Dipsaci Radix has the potential to be developed as a healthcare food and functional material possessing anti-osteoporosis effects.

• Proceedings of the PSK Conference
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• 2000.04a
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• pp.97.1-97.1
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• 2000

• Journal of the Korean Society of Food Culture
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• v.5 no.2
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• pp.243-251
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• 1990

We determined the structure of main saponin which extracted from the shoot of Aralia Elata. The results were as follows. 1. The main aglycons and suger of the total saponins of Nr2 sample were identified as oleanolic acid and hederagenin, and glucose, arabinose and rhamnose. A probable new aglycon was isolated and inferred as 1, 3-methylenedioxy-3-dehydroxyoleanolic acid. 2. One compound of Fh saponin (named as Elatoside $Fh_2$) which was obtained first in this species was elucidated as 3-O-$({\alpha}-L-arabinopyranosyl(1{\rightarrow}2)-{\beta}-D-gluco-pyranosyl)$-28-O-${\beta}-D-glucophyranosyl$ oleanolic acid on the basis of chemical and spectral evidence of IR, $^1H$, $^{13}C-NMR$ and MS.

• Natural Product Sciences
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• v.15 no.4
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• pp.250-255
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• 2009

Seven compounds including hederagenin 3-[(O-${\alpha}$-L-rhamnopyranosyl-($1{\rightarrow}2$)-${\alpha}$-L-arabinopyranosyl) (1), $3{\beta}$-[(O-${\alpha}$-L-rhamnopyranosyl-($1{\rightarrow}2$)-${\alpha}$-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid (2), caffeic acid methyl ester (3), ferulic acid (4), orebiusin A (5), latifonicinin C (6) and 5-(hydroxymethyl)-2-furfuraldehyde (7) were isolated from the ethyl acetate fraction of the roots of Pulsatilla koreana. Their chemical structures were established based on physicochemical and spectroscopic data analyses. All isolates were investigated for their cytotoxic activity against cancer cell lines. Among them, compound 1 showed inhibitory activity against A549, COLO 205, and L1210 cancer cell lines with $IC_{50}$ values of 15.8, 36.5, and 22.8 ${\mu}g$/mL, respectively.

• Korean Journal of Pharmacognosy
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• v.17 no.1
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• pp.78-84
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• 1986

Among the Araliaceae plants indigenous to Korea, those whose medicinal usage are comparatively high have been selected in this serial studies. Chiisanoside and acanthoside D were isolated and identified from the Acanthopanax chinensis leaves and root bark. Chiisanoside and acanthoside D have been found to have the lowering S-GPT, S-GOT value and BSP-retention rate and survival rate, anti-histaminic effect in the toxic state through the bio-pharmacological experiments. ${\alpha}-hederin$, hederagenin pentaglycoside were isolated both stem bark of Kalopanax pictum Nakai var. magnificum and Kalopanax pictum Nakai var. Max. respectively. Syringoside, acanthoside D were also isolated from the root bark of Acanthopanax koreanum. The biological activity of ginsenoside $Rb_1$, $Rg_1$, Re were examined. Ginsenoside $Rb_1$, $Rg_1$, Re promotes the antileaking effect in X-ray (Co 60) irradiated toxic state.

• Journal of Life Science
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• v.20 no.2
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• pp.281-291
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• 2010

We investigated the antioxidant effects of hederagenin 3-O-b-D-glucopyranosyl($1{\rightarrow}3$)-a-L-rhamnopyranosyl($1{\rightarrow}2$)-a-L-arabinopyranoside (HDL) isolated from root bark of Ulmus davidiana on the activity of enzymes related to reactive oxygen species (ROS) in human osteosarcoma U2OS cells. Cobalt chloride ($CoCl_2$), a transition metal, was used as an inducer of oxidative stress, generating hydrogen peroxide ($H_2O_2$) via increasing xanthine oxidase (XO) activity. The increased levels of $H_2O_2$, XO, ferritin, and ferritin iron by $CoCl_2$ were diminished effectively by co-treatment with HDL in U2OS cells. Furthermore, decreased levels of antioxidant enzymes such as superoxide dismutase (SOD), catalase (CAT) by $CoCl_2$ were highly increased by co-treatment with HDL in U2OS cells; however, the levels of glutathione peroxidase (GPx) did not change. The increased contents of TBARS related to lipid peroxidation were significantly reduced by HDL in U2OS cells. The concentration of GSH changed in a pattern that went against regulated TBARS by $CoCl_2$ and HDL. We examined the expression of p53, $p21^{CIP1/WAF1}$, and $p27^{KIP1}$ proteins related to oxidative stress and cell cycle regulation. As a result, the expression of $p27^{KIP1}$ modulated by $CoCl_2$ was not changed by HDL. However, the expression of p53 and $p21^{CIP1/WAF}$ increased by $CoCl_2$ was reduced by HDL in U2OS cells. Together with alteration of p53 and $p21^{CIP1/WAF1}$ proteins, the accumulated cells at G1 phase by $CoCl_2$ was decreased by HDL in U2OS cells. Our data suggests that HDL inhibits $CoCl_2$-generated ROS in U2OS cells, providing potentially new antioxidant compounds that are isolated from natural products.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.136-137
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• 2002

Lonicera japonica Thunb. is a twining shrub that has been used as an antidote and to treat urinary disorders, fever and headache. It has been known as an anti-inflammatory agent in Korea from ancient times and is used widely for treating upper-respiratory tract infections, diabetes mellitus and rheumatoid arthritis. In the previous research, we isolated several flavonoid derivatives from the EtOAc soluble fraction. (omitted)

• Korean Journal of Pharmacognosy
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• v.17 no.2
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• pp.178-183
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• 1986

It was our working hypothesis that introduction of 11-keto groups to 12-oleanene/ursene series of triterpenoids should endow them with corticoid-like activities, since pharmacological actions of glycyrrhetinic acid (GA) are known to be caused by inhibition on $corticoid-{\delta}^4-reductase$. 11-Keto-triterpenoids derived artificially in these studies, such as 11, 19-diketo-18, 19-secoursolic acid methyl ester(I), $11-keto-{\beta}-boswellic$ acid derivatives (IIa-IIc), 11-Keto-presenegenin dimethyl ester (III), II-keto-oleanolic acid derivatives (IVa-IVd) and 11-keto-hederagenin (V) possess the fundamental functions of ${\alpha},\;{\beta}-unsaturated$ ketone on C-11 and hydroxyl group on C-3, as like GA (VI). Additionally, they involve the carboxyl groups on rings A (II, III), D (I, III, IV, V) and E (VI), and the hydroxyl groups on rings A (III, V) and C (III). All the compounds competitively inhibited $corticoid-5{\beta}-reductase$, and the highest inhibitory potency appeared in I. All of them except $3,\;11-diketo-{\beta}-boswellic$ acid methyl ester (IIc) were more effective about five times to twice than GA. On carrageenin-induced edema test, compounds I and IVa-IVd showed anti-inflammatory activities, but III enhanced rather edema. Structure-activity relations were found in the aspects of hydrophilicity of ring A and hydrophobicity of rings C/D. The more they were hydrophilic in ring A and hydrophobic in rings C/D, the more they inhibited the enzyme. And the more they were hydrophobic in rings C/D, the more they exhibited antiiflammatory activities. However, the increased hydrophilicity in ring A resulted in increasing edema, probably due to a nonspecific inhibition on $aldosterone-5{\beta}-reductase$.