• Analytical Science and Technology
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• v.8 no.4
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• pp.901-906
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• 1995

Studies on the chemical constituents from a Korean wild mushroom, Phellinus ribis, were carried out. A triterpenoid, two peroxysterols, and a chlorobenzene compound were isolated from the hexane soluble fraction of the methanol extract of dried fruiting bodies of the basidomycetes. Those compounds identifed were 3-hydroxy-20(29)-lupen-28-oic acid (betulinic acid), 5,8-epidioxyergosta-6,22-dien-3-ol(ergosterol peroxide), 5,8-epidioxyergosta-6,9(11),22-trien-3-ol (dehydroperoxyergosterol), and 1,2,4,5-tetrachloro-3,6-dimethoxybenzene. Structural studies were carried out on molecular species of a ceramide and cerebroside isolated from the chloroform soluble fraction of the methanol extract. For ceramide, the major component fatty acids were a-hydroxy fatty acid isomers of $C_{22:00}{\sim}C_{25:00};$ the predominant long-chain bases were trihydroxy sphinganine of $C_{17}{\sim}C_{18}$. The structure of a cerebroside containing mono-sugar was assumed that the long-chain base was $C_{19:2}$ sphingadienine; the major fatty acids were $C_{16}{\sim}C_{15}$ ${\alpha}$-hydroxy fatty acid isomers.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.29 no.1
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• pp.27-44
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• 2003

전반적인 피부세포의 생리적 지능 자하로 인한 자연노화와 더불어, 여러 피부 스트레스 요인들이 다양하게 작용하여 발생하는 외인성노화를 방지하거나, 개선할 수 있는 항노화소재로서의 개발 가능성을 알아보기 위해, 예로부터 항염활성이 있다고 알려진 oleanolic acid(OA)를 포함한 ursolic acid(UA), betulin, betulinic acid(BA) 등의 triterpenoids가 어떻게 피부에서의 항노화 활성을 나타내는지를 알아보았다. 시험 결과, OA는 자외선에 의한 각질형성세포에서의 PGE$_2$ 생성과 섬유아세포(NHF)에 의한 matrix metalloproteinase-1(MMP-1) 분비를 억제하였다. 그리고, NHF의 procollagen 생성을 촉진하였으며, 이런 procollagen 생성촉진활성이 in vivo에서도 발현되는 것을 무모생쥐의 실험을 통해서 확인하였다. 또한 OA는 각질세포의 증식과 분화를 촉진하여 표피세포로 하여금 세라마이므와 필라그린 생성을 증가시키도록 하는 작용도 있음을 보여주었다. 더불어 실험한 UA, betulin, BA 들은 비록, betulin, BA의 경우 세포 독성이 다른 물질 들에 비해 높았고, UA가 각질세포의 분화를 오히려 억제하는 양상을 보이기는 했지만, 대부분의 기능은 OA와 유사하였다. 피부세포보호작용과 진피 기질물질에 대한 작용, 그리고, 표피의 장벽기능과 보습기능에 대해 시험한 본 연구는, 식물성분인 triterpenoids가 피부를 위한 항노화소재로서의 개발 가능성이 있음을 확인하는 계기가 되었고, 그 중에서도 OA가 보다 우수한 항노화 소재가 될 수 있음을 시사하고 있다.

• Natural Product Sciences
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• v.23 no.4
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• pp.258-264
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• 2017

This study analyzed the seeds of Zizyphus jujuba var. inermis commonly used as a remedy in traditional Chinese medicine, in order to determine its various biologically active compounds. Through process 3-pentadecylcatechol, ${\rho}$-menth-8-ene, and ${\gamma}$-bisabolene were isolated and identified for the first time which are urushiol, monoterpenoidal, and sesquiterpenoidal compounds, respectively. Also, found were another sesquiterpenoidal compounds, vomifoliol, and four steroidal compounds, ${\beta}$-sitosterol, stigmasterol, stigmasta-5,23-dien-$3{\beta}$-ol, and stigmast-4-en-3-one. In addition, fourteen triterpenoidal compounds were isolated and identified. These were lupeol, betulinic acid, betulinaldehyde, alphitolic acid, 3-O-cis-${\rho}$-coumaroyl-alphitolic acid, 3-O-trans-${\rho}$-coumaroyl-alphitolic acid, 2-O-cis-${\rho}$-coumaroyl-alphitolic acid, 2-O-trans-${\rho}$-coumaroyl-alphitolic acid, zizyberanalic acid, ceanothic acid, oleanolic acid, maslinic acid, 3-O-cis-${\rho}$-coumaroyl-maslinic acid, and 3-O-trans-${\rho}$-coumaroyl-maslinic acid. The structures were identified by comparing of the spectroscopic experiments, NMR and MS, and then compared that reported data, respectively. Three extracts of water, methanol, and chloroform from the seeds showed a weak anti-proliferative effect, anti-microbial activity, and anti-oxidant effect, respectively.

• Korean Journal of Pharmacognosy
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• v.37 no.3
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• pp.162-168
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• 2006

The isolation and identification of a new xanthone (6-0-palmitolyl-1,6-dihydroxy-5,7-dimethoxyxanthone) along with n-alkanols, fatty acids, 1,6-dihydroxy-5,7-dimethoxyxanthone, 1,7-dihydroxykanthone, betulinic acid, ${\beta}-sitosterol$, methyl 4-hydroxybenzoate, quercetin, and kaempferol from the aerial parts of Hypericum ascyron was reported. The structures were elucidated by spectroscopic methods, mainly NMR and mass spectrometry.

• Archives of Pharmacal Research
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• v.26 no.4
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• pp.275-278
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• 2003

A new acylglycosyl Sterol (4) was isolated from the MeOH extract of Quisqualis Fructus together with four known compounds. On the basis of spectroscopic data, their structures were elucidated as clerosterol (1), betulinic acid (2), methylursolate (3), 3-Ο-[6 -Ο-(8Z-octadecenoyl)-$\beta$-D-glucopyranosyl]-clerosterol (4) and $\alpha$-xylofuranosyluracil (5).

• Natural Product Sciences
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• v.18 no.3
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• pp.183-189
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• 2012

It is well known that inflammation is associated with neurodegenerative disorders, including Alzheimer' disease, Parkinson's disease and ischemia. Nitric oxide (NO), a pro-inflammatory mediator, is produced by inducible NO synthase (iNOS) in microglia as well as macrophages and appears to account for neurodegeneration. In this study, we aimed to isolate NO inhibitors from Pyrus pyrifolia by activity guided purification. As a result, we identified daucosterol and ${\beta}$-sitosterol, which have not been isolated from this plant before. This article also describes NO inhibitory activities of the methanol extract of Pyrus pyrifolia fruit and the isolated compounds from this, which are lupeol, betulin, betulinic acid, ${\beta}$-sitosterol and daucosterol, in LPS-activated RAW 264.7 and BV2 cell lines. Western blot analysis was performed to clarify the underlying mechanism of NO inhibition in the two cell lines.

• Bulletin of the Korean Chemical Society
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• v.34 no.9
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• pp.2675-2679
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• 2013

Activity-directed isolation of the methylene chloride fraction from the stems of Parthenocissus tricuspidata have led to the identification of two new compounds (1-2): 1-(2',3',5'-trihydroxyphenyl)-2-(4"-hydroxyphenyl)-ethane-1,2-(E)-epoxide (1, tricuspidatin A) and erythro-1-(3',5'-dihydroxyphenyl)-2-(4"-hydroxyphenyl)-ethane-1,2-diol (2, tricuspidatin B), together with four known compounds (3-6): ${\beta}$-sitosterol (3), nonacosan-1-ol (4), 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid hexacosyl ester (5) and betulinic acid (6). Their chemical structures were elucidated based on spectroscopic (IR, UV, MS, 1D and 2D NMR) and physicochemical analyses. Compounds 1 and 2 showed strong DNA topoisomerase II inhibitory activity at both concentrations of 20 and $100{\mu}M$. In addition, 3 exhibited strong cytotoxic activity against the HT-29 and HepG2 cancer cell lines, and 6 showed strong cytotoxicity against the HT-29 and MCF-7 ones.

• Korean Journal of Medicinal Crop Science
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• v.13 no.2
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• pp.85-90
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• 2005

Phytochemical study on the EtOAc fraction from a MeOH extract of the leaves of Alnus hirsuta Rupr. led to the isolation of nine compounds betulin (1), betulinic acid (2), hirsutanonol (3), hirsutenone (4), quercetin (5), avicularin (6), gallic acid (7), hyperin (8), and daucosterol (9). Among them, six compounds 1, 2, 57, and 9 are report from this plant for the first time. All isolated compounds were evaluated for their antioxidant activity using DPPH radical scavenging capacity and inhibition effect on mitochondrial lipid peroxidation. Six phenolic compounds 3-8 were found to have potent antioxidant activity. Of which, compounds 3, 4 and 5 showed significant free radical scavenging activity with the $IC_{50}$ values of $18.3\;{\pm}\;2.5,\;15.7\;{\pm}\;3.8\;and\;23.5\;{\pm}\;3.1\;{\mu}m$, respectively. In addition, the compounds 3-8 exhibited inhibition effect on the mitochondrial lipid peroxidation with the $IC_{50}$ values of $88.0\;{\pm}\;6.5,\;12.6\;{\pm}\;1.2,\;8.0 \;{\pm}\;1.1,\;58.5\;{\pm}\;4.3,\;173.6\;{\pm}\;15.2,\;and\;75.0\; {\pm}\; 6.7\;{\mu}m$, respectively.

• Natural Product Sciences
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• v.24 no.4
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• pp.219-224
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• 2018

During the screening for cytotoxic compounds from plants grown in Korea, Betula platyphylla (BP) showed potent activity against the adenocarcinomic human alveolar basal epithelial A549 cell line. To identify the cytotoxic components from BP, the $CH_2Cl_2$ fraction with the most significant cytotoxic effect was applied to the column chromatographies. Seven compounds were isolated: lupeol (1), betulinic acid (2), (-)-rhododendrol (3), platyphyllenone (4), platyphyllone (5), (-)-centrolobol (6), and oleanolic acid (7). Among them, three diarylheptanoids (4 - 6) exhibited cytotoxicity toward A549 cells. Especially, $50{\mu}M$ of 4 reduced A549 cell viability to $18.93{\pm}0.82%$ compared to control ($100.00{\pm}21.48%$). Lactate dehydrogenase (LDH) leakage and intracellular reactive oxygen species (ROS) production were also induced by $50{\mu}M$ 4. This is the first report on the cytotoxic effect of BP-derived diarylheptanoids 4-6 against A549 cells. The compound 4 may be useful for the development of early hit compounds for non-small cell lung carcinoma, but the consideration about selectivity of 4 is required since 4 also showed the cytotoxicity in the human normal lung epithelial BEAS-2B cell line.

• Archives of Pharmacal Research
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• v.27 no.2
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• pp.169-172
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• 2004

Activity-guided fractionation of the EtOAc-soluble extract of the stems of Couepia ulei, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa 1c1c7 mouse hepatoma cells led to the isolation of two active compounds, a new natural product, erythro-2,3-bis(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-o1 (1), and a known compound, evofolin-B (2), along with five inactive compounds all of known structure, viz., betulinic acid, oleanolic acid, pomolic acid, ($\pm$)-syringaresinol, and ursolic acid. These isolates were identified by analysis of physical and spectral data. Compounds 1 and 2 exhibited QR inducing activity, with observed CD (concentration required to double induction) values of 16.7 and 16.4 $\mu\textrm{M}$, respectively.