• Journal of Ginseng Research
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• v.33 no.3
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• pp.212-218
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• 2009

Triterpenoid saponins were synthesized in Panax ginseng C.A. Meyer via the isoprenoid pathway by cyclization of 2,3-oxidosqualene to give primarily oleanane (beta-amyrin) or dammarane triterpenoid skeletons. The triterpenoids are backbone and undergoes various modifications (oxidation, substitution and glycosylation), mediated by cytochrome P450 (CYP)-dependent monooxygenases, glycosyltransferase and other enzymes. This is likely to be due in part to the complexity of the molecules and the lack of pathway intermediates for biochemical studies. A cDNA clone encoding a putative CYP gene was isolated from flower bud of ginseng and transformed into the plant(Nicotiana tabacum cv. Xanthi) and confirmed by PCR analysis. The CYP gene (PgCYP) contained an open reading frame(ORF) encoding mature protein of 500 amino acids. The expression of PgCYP were investigated in transgenic tobacco by reverse transcriptase-polymerase chain reaction (RT-PCR).

• Journal of Ginseng Research
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• v.20 no.4
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• pp.389-415
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• 1996

Panax ginseng C.A. Meyer(Araliaceae) has been traditionally used as an expensive and precious medicine in oriental countries for more than 5, 000 years. Ginseng saponin isolated from the root of Panax ginseng have been regarded as the main effective components responsible for the pharmacological and biological activities. Such as antiaging effects. antidiabetic effects anticancer effects. Protection against physical and chemical stress. Analgesic and antipyretic effects. Effects on the central nervous system, tranquilizing action and others. Thirty kinds of ginsenosides have been so far isolated from ginseng saponin and their chemical structures have been elucidated since 1960's. Among which protopanaxadiol type is 19 kinds. protopanaxatriol type. 10 kinds and oleanane type, one. Since ginsenosides are generally labile under acidic conditions ordinary acid hydrolysis is always accompanied by many side reactions, such as epimerization. hydroxylation and cyclization of side chain of the sapogenins Especially. it is well known that C-20 glycosyl linkage of ginsenoside was hydrolysed on heating with acetic acid to give an equilibrated mixture of 20(S) and 20(R) epimers. And also, the chemical transformations of the secondary metabolites have appeared during the steaming process to prepare red ginseng. Indicating demalonylation of malonyl ginsenosides, elimination of glycosyl residue at C-20 and isomerization of hydroxyl configuration at C-20. But these studies have not provided a comprehensive picture in explaning how these ginsenosides showed val'iotas pharmacological activities of ginseng. Though some of them have been involved in the mechanism of pharmacological actions. Recently, non-saponin components have received a great deal of attention for their antioxidant, anticancer antidiabetic, immunomodulating. anticomplementary activities and so on. To meet the demand for such wide applications, studies on the non-saponin components play an important role in providing a good evidence of pharmacological and biol ogical activities. Among the non-saponin constituents of Korean ginseng, polyacetylenes, phenols. Sesquiterpenes, alkaloids. polysaccharides oligosaccharides, oligopeptides and aminoglycosides together with ginsenosides of terrestrial part are mainly described.

• Journal of the Korean Wood Science and Technology
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• v.24 no.1
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• pp.27-33
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• 1996

The aim of this research was to investigate the chemical components of C30 compounds, especially triterpenoids in Korean native mistletoes of Korthalsella japonicus Engler parasiting to Camellia japonica L., Viscum album var. coloratum (Kom.) Ohmi, to Quercus acutissima Carruth. and Loran-thus yadoriko Sieb. to Neolitsea sericea (BI.) Koidz. For the identification of triterpenoidal components, alkaline hydrolyzates of mistletoes meals were analyzed by TLC, GC, and GC/MS. The content of oleanolic acid and ursolic acid derivatives were highest in K. japonica. In V. album, there was no big difference between leaves and twigs in content. but oleanolic acid in leaves. and olean-12-en-$3{\beta}$-ol and lup-20(29)-en-3-one in twigs were prominent. Similiar to V. album in L. yadoriki there was no difference between leaves and twigs in content, and both olean-12-en-$3{\beta}$-ol, lup-20(29)-en-3-one and urs-12-en-$3{\beta}$-ol in leaves, lup-20(29)-en-3-one in twigs were abundant. Triterpenoids as olea-12-en-$3{\beta}$-ol, lupe-20(29)-en-3-one, 3-oxo-urs-12-en-24-oic acid, and $21{\beta}$-A'-neogam-macer-22(29)-en-3-ol acetate were common in all samples tested. whereas ursolic acid only in P. japonicus and ursenol in L. yadoriki were detected. And P. japonicus had the largest number of triterpenoids and showed the highest in biological activity. So it is noted that Korean mistletoes tested in the study had three types of triterpenoid, oleanane, lupane, and ursane, irrespective of hosts, sampling positions and species.

• Journal of Ginseng Research
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• v.38 no.3
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• pp.194-202
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• 2014

Background: Ginsenosides, the major ingredients of Panax ginseng, have been studied for many decades in Asian countries as a result of their wide range of pharmacological properties. The less polar ginsenosides, with one or two sugar residues, are not present in nature and are produced during manufacturing processes by methods such as heating, steaming, acid hydrolysis, and enzyme reactions. $^1H$-NMR and $^{13}C$-NMR spectroscopic data for the identification of the less polar ginsenosides are often unavailable or incomplete. Methods: We isolated 21 compounds, including 10 pairs of 20(S) and 20(R) less polar ginsenosides (1-20), and an oleanane-type triterpene (21) from a processed ginseng preparation and obtained complete $^1H$-NMR and $^{13}C$-NMR spectroscopic data for the following compounds, referred to as compounds 1-21 for rapid identification: 20(S)-ginsenosides Rh2 (1), 20(R)-Rh2 (2), 20(S)-Rg3 (3), 20(R)-Rg3 (4), 6'-O-acetyl-20(S)-Rh2 [20(S)-AcetylRh2] (5), 20(R)-AcetylRh2 (6), 25-hydroxy-20(S)-Rh2 (7), 25-hydroxy-20(S)-Rh2 (8), 20(S)-Rh1 (9), 20(R)-Rh1 (10), 20(S)-Rg2 (11), 20(R)-Rg2 (12), 25-hydroxy-20(S)-Rh1 (13), 25-hydroxy-20(R)-Rh1 (14), 20(S)-AcetylRg2 (15), 20(R)-AcetylRg2 (16), Rh4 (17), Rg5 (18), Rk1 (19), 25-hydroxy-Rh4 (20), and oleanolic acid 28-O-b-D-glucopyranoside (21).

• Journal of Ginseng Research
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• v.39 no.4
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• pp.365-370
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• 2015

Background: The beneficial effects of ginsenoside species have been well demonstrated in a number of studies. However, the function of ginsenoside Ro (GRo), an oleanane-type saponin, has not been sufficiently investigated. Thus, the aim of the present study was to investigate the anti-inflammatory effects of GRo in vitro using the Raw 264.7 mouse macrophage cell line treated with lipopolysaccharide (LPS), and to clarify the possible mechanism of GRo involving heme oxygenase-1 (HO-1), which itself plays a critical role in self-defense in the presence of inflammatory stress. Methods: Raw 264.7 cells were pretreated with GRo (up to $200{\mu}M$) for 1 h before treatment with 1 mg/mL LPS, and both cell viability and inflammatory markers involving HO-1 were evaluated. Results: GRo significantly increased cell viability in a dose dependent manner following treatment with LPS, and decreased levels of reactive oxygen species and nitric oxide. GRo decreased inflammatory cytokines such as nitric oxide synthase and cyclooxygenase-2 induced by LPS. Moreover, GRo increased the expression of HO-1 in a dose dependent manner. Cotreatment of GRo with tin protoporphyrin IX, a selective inhibitor of HO-1, not only inhibited upregulation of HO-1 induced by GRo, but also reversed the anti-inflammatory effect of GRo in LPS treated Raw 264.7 cells. Conclusion: GRo induces anti-inflammatory effects following treatment with LPS via upregulation of HO-1.

• Journal of Ginseng Research
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• v.43 no.1
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• pp.27-37
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• 2019

Background: The structural conversions in ginsenosides induced by steaming or heating or acidic condition could improve red ginseng bioactivities significantly. In this paper, the chemical transformations of red American ginseng from fresh Panax quinquefolium L. under steaming were investigated, and the possible mechanisms were discussed. Methods: A method with reversed-phase high-performance liquid chromatography coupled with linear ion trap mass spectrometry ($HPLC-MS^n$)-equipped electrospray ionization ion source was developed for structural analysis and quantitation of ginsenosides in dried and red American ginseng. Results: In total, 59 ginsenosides of protopanaxadiol, protopanaxatriol, oleanane, and ocotillol types were identified in American ginseng before and after steaming process by matching the molecular weight and/or comparing $MS^n$ fragmentation with that of standards and/or known published compounds, and some of them were determined to be disappeared or newly generated under different steaming time and temperature. The specific fragments of each aglycone-type ginsenosides were determined as well as aglycone hydrated and dehydrated ones. The mechanisms were deduced as hydrolysis, hydration, dehydration, and isomerization of neutral and acidic ginsenosides. Furthermore, the relative peak areas of detected compounds were calculated based on peak areas ratio. Conclusion: The multicomponent assessment of American ginseng was conducted by $HPLC-MS^n$. The result is expected to provide possibility for holistic evaluation of the processing procedures of red American ginseng and a scientific basis for the usage of American ginseng in prescription.

• Bulletin of the Korean Chemical Society
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• v.29 no.3
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• pp.615-619
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• 2008

Eight triterpenoids, six lanostanes 1-6, one lupenane 7, and one oleanane 8, were isolated by bioactivity-guided fractionation of the ethylacetate extract from roots of Glycine max (L.) Merr. All isolated compounds were examined for their inhibitory activities against human ACAT-1 (hACAT-1) and human ACAT-2 (hACAT-2). Among them, three triterpenoids showed potent hACAT inhibitory activities, (24R)-ethylcholest-5-ene-3,7-diol (1) and 3b -hydroxylup-20(29)-en-28-oic acid (7) exhibited more potent inhibitory activity against hACAT-1 (1: IC50 = 25.0 1.2 and 7: IC50 = 11.5 0.4 m M) than hACAT-2 (1: IC50 = 102.0 5.4 and 7: IC50 = 33.9 3.7 m M), respectively. Interestingly, 5a ,8a -epidioxy-24(R)-methylcholesta-6,22-diene-3b -ol (4) has proven to be a specific inhibitor against hACAT-1 (IC50 = 38.7 0.8 m M) compared to hACAT-2 (IC50 >200). In conclusion, this is the first study to demonstrate that triterpenoids of G. max have potent inhibitory activities against hACAT-1 and hACAT-2.

• Journal of Ginseng Research
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• v.45 no.2
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• pp.305-315
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• 2021

Background: Panax stipuleanatus represents a folk medicine for treatment of inflammation. However, lack of experimental data does not confirm its function. This article aims to investigate the analgesic and anti-inflammatory activities of triterpenoid saponins isolated from P. stipuleanatus. Methods: The chemical characterization of P. stipuleanatus allowed the identification and quantitation of two major compounds. Analgesic effects of triterpenoid saponins were evaluated in two models of thermal- and chemical-stimulated acute pain. Anti-inflammatory effects of triterpenoid saponins were also evaluated using four models of acetic acid-induced vascular permeability, xylene-induced ear edema, carrageenan-induced paw edema, and cotton pellet-induced granuloma in mice. Results: Two triterpenoid saponins of stipuleanosides R₁ (SP-R₁) and R₂ (SP-R₂) were isolated and identified from P. stipuleanatus. The results showed that SP-R₁ and SP-R₂ significantly increased the latency time to thermal pain in the hot plate test and reduced the writhing response in the acetic acid-induced writhing test. SP-R₁ and SP-R₂ caused a significant decrease in vascular permeability, ear edema, paw edema, and granuloma formation in inflammatory models. Further studies showed that the levels of inflammatory mediators, nitric oxide, malondialdehyde, tumor necrosis factor-α, and interleukin 6 in paw tissues were downregulated by SP-R₁ and SP-R₂. In addition, the rational harvest of three- to five-year-old P. stipuleanatus was preferable to obtain a higher level of triterpenoid saponins. SP-R₂ showed the highest content in P. stipuleanatus, which had potential as a chemical marker for quality control of P. stipuleanatus. Conclusion: This study provides important basic information about utilization of P. stipuleanatus resources for production of active triterpenoid saponins.