• Natural Product Sciences
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• v.6 no.2
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• pp.102-105
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• 2000

Chemical investigation of the hot hexane extract of the stem bark of Gordonia dassanayakei afforded a new oleanane triterpenoid, $11{\alpha},13{\beta}-dihydroxyolean-3,12-dione$ (1) and two other oleanane triterpenoids, $3{\beta}-acetoxy-11{\alpha},13{\beta}-dihydroxyolean-12-one\;(2)\;and\;3{\beta},11{\alpha}-diacetoxy-13{\beta}-hydroxyolean-12-one\;(3)\;and\;a\;hopane\;6{\alpha},22-diol$ (4), which are new to the plant.

• Journal of Ginseng Research
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• v.37 no.1
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• pp.74-79
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• 2013

In continuation of our research to find biological components from Panax stipuleanatus, four oleanane-type triterpenes (12 to 15) were isolated successively. Fifteen oleanane-type saponins (1 to 15) were evaluated for nuclear factor (NF)-${\kappa}B$ activity using a luciferase reporter gene assay in HepG2 cells. Compounds 6 to 11 inhibited NF-${\kappa}B$, with $IC_{50}$ values between 3.1 to 18.9 ${\mu}M$. The effects on inducible nitric oxide synthase and cyclooxygenase-2 by compounds 8, 10, and 11 were also examined using reverse transcription-polymerase chain reaction. Three compounds (8, 10, and 11) inhibited NF-${\kappa}B$ activity by reducing the concentration of inflammatory factors in HepG2 cells.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.371.3-372
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• 2002

We have reported cytotoxicities based on several types of sugar linkage in saponins in addition to antitumor and antiinflammatory effects. In order to find further structure-activity relationship on the cytotoxicity of saponins. we intended to isolate oleanane disaccharides Irom the saponin-containing extract of Akebia Quinata (Lardizabalaceae). (omitted)

• Archives of Pharmacal Research
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• v.28 no.5
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• pp.546-549
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• 2005

A new oleanane-triterpene, 3${\beta}$-acetoxy-11${\alpha}$-benzoyloxy-13${\beta}$-hydroxyolean-1 2-one (1), was isolated along with a known quinone-methide triterpene, pristimerin (2), from the root bark of Siphonodon celastrinneus Griff., a Thai medicinal plant of the family Celastraceae. Their structures were determined based on spectroscopic analysis.

• Natural Product Sciences
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• v.4 no.4
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• pp.253-256
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• 1998

Chemical investigation of hot hexane extract of the stem bark of Gordonia ceylanica afforded a new triterpenoid, $3{\beta}-acetoxy-28-hydroxyolean-12-ene$ (1) and three other oleanane triterpenoids, $3{\beta}-hydroxyolean-12-ene$ (2), $3{\beta}-acetoxyolean-12-ene$ (3), and $3{\beta}-acetoxyolean-12-en-11-one$ (4) which are new to the species. Structure of compound 1 was suggested by $^1H\;NMR,\;^{13}C\;NMR$ and MS spectral data and confirmed by converting to previously reported compound, erythrodiol diacetate (5). Structures of 2, 3 and 4 were established by comparison of the spectral data with the previously reported compounds. Further the acid hydrolysate of 4 was identical with $3{\beta}-hydroxyolean-12-en-11-one$ (6).

• Bulletin of the Korean Chemical Society
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• v.31 no.10
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• pp.2786-2790
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• 2010

Three new oleanane-type triterpene saponins (1, 2 and 3) were isolated from aerial parts of Gladiolus gandavensis, along with two known compounds (4 and 5). Their structures were elucidated as 29-O-($\beta$-D-glucopyranosyl)-$2{\beta}$,$3{\beta}$-dihydroxyolean-12-en-28-oicacid(1), 3-O-($\beta$-D-xylopyranosyl)-29-O-($\beta$-D-glucopyranosyl)-12-en-28-oic acid (2), and $2{\beta}$,$3{\beta}$,29-trihydroxyolean-12-en-28-oic acid 28-O-[$\beta$-D-glucopyranosyl($1{\rightarrow}2$)-($\alpha$-L-rhamnopyranosyl($1{\rightarrow}6$))-$\beta$-D-glucopyranosyl] ester (3), by spectroscopic methods, and by comparison with known analogues. These oleanane-type triterpene saponins glycosidated at C-29 were not obtained frequently.

• Biomolecules & Therapeutics
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• v.22 no.4
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• pp.334-340
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• 2014

In this study, 23 oleanane-type triterpenoid saponins were isolated from a methanol extract of the roots of Pulsatilla koreana. The NF-${\kappa}B$ inhibitory activity of the isolated compounds was measured in $TNF{\alpha}$-treated HepG2 cells using a luciferase reporter system. Compounds 19-23 inhibited $TNF{\alpha}$-stimulated NF-${\kappa}B$ activation in a dose-dependent manner, with $IC_{50}$ values ranging from $0.75-8.30{\mu}M$. Compounds 19 and 20 also inhibited the $TNF{\alpha}$-induced expression of iNOS and ICAM-1 mRNA. Moreover, effect of the isolated compounds on PPARs transcriptional activity was assessed. Compounds 7-11 and 19-23 activated PPARs the transcriptional activity significantly in a dose-dependent manner, with $EC_{50}$ values ranging from $0.9-10.8{\mu}M$. These results suggest the presence of potent anti-inflammatory components in P. koreana, and will facilitate the development of novel anti-inflammatory agents.

• Analytical Science and Technology
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• v.34 no.4
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• pp.172-179
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• 2021

Oleanane-type triterpenoids exist as secondary metabolites in various plants. In particular, soyasaponin, an oleanane-type triterpenoid, is abundant in the hypocotyl of soybean, one of the most widely cultivated crops in the world. Depending on their chemical structure, soyasaponins are categorized as group A saponins or group DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) saponins. The different soyasaponin chemical structures present different health functionalities and taste characteristics. However, conventional phenotype screening of soybean requires a substantial amount of time for functionality of soyasaponins. Therefore, we attempted to use liquid chromatography with a photodiode array detector and tandem mass spectrometry (LC-PDA/MS/MS) for accurately predicting the phenotype and chemical structure of soyasaponins in the hypocotyl of five common soybean natural mutants. In this method, the aglycones (soyasapogenol A [SS-A] and soyasapogenol B [SS-B]) were detected after acid hydrolysis. These results indicated that the base peak and fragmentation differ depending on the chemical structure of soyasaponin with aglycone. Thus, a fragmentation database can help predict the chemical structure of soyasaponins in soyfoods and plants.

• Natural Product Sciences
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• v.19 no.2
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• pp.150-154
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• 2013

A new oleanane-type triterpenoid saponin together with six known saponins were isolated from the roots of Pulsatilla cernua. Their structures were elucidated on the basis of spectroscopic data, including 2D NMR spectra and chemical evidence. Compounds 1 and 6 are reported from this genus for the first time.

• Natural Product Sciences
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• v.20 no.4
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• pp.281-284
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• 2014

In this study, twenty-one oleanane-type triterpenoid saponins were isolated from a methanol extract of the roots of Pulsatilla koreana. Antagonistic activities were measured in these compounds by the aequorin based cellular functional assay system for the corticotropin releasing factor receptor (CRF1). Of them, compounds 7 - 10 showed the highest degree of CRF1 inhibition further at the concentration of $10{\mu}M$. Moreover, by the analysis based on the structure-activity relationship of isolated saponins, a sugar chain at C-3 and a carboxyl group at C-28, as well as a methyl group at C-23 seems to be key functional elements. To our knowledge, this is the first report on CRF1 inhibition of saponins from P. koreana.