• Title/Summary/Keyword: $\beta$-Amyrin

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Constituents from the Non-Polar Fraction of Artemisia apiacea

  • Lee, Sanghyun;Kim, Kyoung-Soon;Shim, Sang-Hee;Park, You-Mie;Kim, Bak-Kwang
    • Archives of Pharmacal Research
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    • v.26 no.11
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    • pp.902-905
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    • 2003
  • Five compounds of terpenoids and coumarins were isolated from the non-polar fraction of Artemisia apiacea by open column chromatography. Their structures were elucidated as $\alpha$-amyrin (1), $\beta$-amyrin (2), $\beta$-sitosterol (3), 5,6,7-trimethoxycoumarin (4) and 6-methoxy-7,8-methylenedioxycoumarin (5) by chemical and spectroscopic analysis. This is the first report of the isolation of $\alpha$-amyrin, $\beta$-amyrin, 5,6,7-trimethoxycoumarin and 6-methoxy-7,8-methylene-dioxycoumarin from this plant.

β-Amyrin Ameliorates Alzheimer's Disease-Like Aberrant Synaptic Plasticity in the Mouse Hippocampus

  • Park, Hye Jin;Kwon, Huiyoung;Lee, Ji Hye;Cho, Eunbi;Lee, Young Choon;Moon, Minho;Jun, Mira;Kim, Dong Hyun;Jung, Ji Wook
    • Biomolecules & Therapeutics
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    • v.28 no.1
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    • pp.74-82
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    • 2020
  • Alzheimer's disease (AD) is a progressive and most frequently diagnosed neurodegenerative disorder. However, there is still no drug preventing the progress of this disorder. β-Amyrin, an ingredient of the surface wax of tomato fruit and dandelion coffee, is previously reported to ameliorate memory impairment induced by cholinergic dysfunction. Therefore, we tested whether β-amyrin can prevent AD-like pathology. β-Amyrin blocked amyloid β (Aβ)-induced long-term potentiation (LTP) impairment in the hippocampal slices. Moreover, β-amyrin improved Aβ-induced suppression of phosphatidylinositol-3-kinase (PI3K)/Akt signaling. LY294002, a PI3K inhibitor, blocked the effect of β-amyrin on Aβ-induced LTP impairment. In in vivo experiments, we observed that β-amyrin ameliorated object recognition memory deficit in Aβ-injected AD mice model. Moreover, neurogenesis impairments induced by Aβ was improved by β-amyrin treatment. Taken together, β-amyrin might be a good candidate of treatment or supplement for AD patients.

Molecular Cloning and Characterization of Wound-inducible Beta-amyrin Synthase from Soybean (콩으로부터 상처 유도 beta-amyrin synthase 유전자의 동정 및 발현분석)

  • Park, Seong-Whan;Lee, Jai-Heon
    • Journal of Plant Biotechnology
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    • v.29 no.2
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    • pp.79-84
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    • 2002
  • Suppression subtractive hybridization (SSH) was used to isolate wound-induced cDNAs from wounded soybean. One of wound-induced cDNA, gmwi33 showed high homology with genes encoding $\beta$-amyrin synthase. The full length cDNA of gmwi33, designated GmAMS1, is 2416 bp long and contains an open reading frame consisted of 739 amino acids. GmAMS1 protein showed 89% identity with licorice GgbAS1 and 86% identity with pea OSCPSY. In 5 day-old, dark-grown seedlings, the expression of GmAMS1 was most strongly induced by light and weakly induced by methyl jasmonate and by low temperature. However, GmAMS1 was not induced by elicitor or UV-B treatment. Such expression pattern might be closely related with the oxygen-radical scavenging activity of soyasaponin.

Development of Biologically Active Compounds from Edible Plant Sources -XIII. Isolation of Triterpenoids from the Flower of Erigeron annuus L.- (식용 식물자원으로부터 활성물질의 탐색 -XIII. 개망초(Erigeron annuus L.) 꽃으로부터 triterpenoid의 분리-)

  • Kim, Dong-Hyun;Jung, Sung-Je;Bang, Myun-Ho;Chung, In-Sik;Kim, Sung-Hoon;Kwon, Byoung-Mog;Kim, Dae-Keun;Park, Mi-Hyun;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.47 no.4
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    • pp.422-425
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    • 2004
  • The flower of Erigeron annuus L. was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$, successively. From the EtOAc fraction, three compounds were isolated through the repeated silica gel, ODS column and high performance liquid chromatographies. From the result of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as ${\alpha}-amyrenone,\;{\alpha}-amyrin\;and\;{\beta}-amyrin$. These three compounds were isolated for the first time from the flower of Erigeron annuus L.

Antibacterial Mode of Action of β-Amyrin Promotes Apoptosis-Like Death in Escherichia coli by Producing Reactive Oxygen Species

  • Giyeol Han;Dong Gun Lee
    • Journal of Microbiology and Biotechnology
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    • v.32 no.12
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    • pp.1547-1552
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    • 2022
  • β-Amyrin is a pentacyclic triterpene widely distributed in leaves and stems worldwide. The ability of β-amyrin to induce the production of reactive oxygen species (ROS) in microorganisms suggests its potential as an antimicrobial agent. Thus, this study aimed to elucidate the antibacterial mode of action of β-amyrin. We treated Escherichia coli cells with β-amyrin and found that it triggered ROS accumulation. Excessive stress caused by ROS, particularly hydroxyl radicals, induces glutathione (GSH) dysfunction. GSH protects cells from oxidative and osmotic stresses; thus, its dysfunction leads to membrane depolarization. The resultant change in membrane potential leads to the release of apoptotic proteins, such as caspases. The activated caspases-like protein promotes the cleavage of DNA into single strands, which is a hallmark of apoptosis-like death in bacteria. Apoptotic cells usually undergo events such as DNA fragmentation and phosphatidylserine exposure, differentiating them from necrotic cells, and the cells treated with β-amyrin in this study were positive for annexin V and negative for propidium iodide, indicating apoptosis-like death. In conclusion, our findings suggest that the antibacterial mode of action of β-amyrin involves the induction of ROS, which resulted in apoptosis-like death in E. coli.

Chlorosmaridione; A Novel Chlorinated Diterpene Quinone Methide from Rosemarinus officinalis L.

  • El-Lakany, Abdalla M.
    • Natural Product Sciences
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    • v.10 no.2
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    • pp.59-62
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    • 2004
  • A novel chlorinated diterpene quinone methide; chlorosmaridione (7-chloro-11-hydroxy-abeita-7,9(11),13-triene-6,12-diode) was isolated from petroleum ether extract of the stems of Rosemarinus officinalis L. growing in Egypt. In addition, ${\beta}-sitosterol$, stigmasterol, lupeol acetate, ${\alpha}-amyrin,\;{\beta}-amyrin$, lupeol, acetyloleanolic acid, acetylursolic acid taxodione, horminone, and cryptotanshinone were also identified. Chemical structures of the isolated compounds have been elucidated on the bases of physical, chemical, and spectral data including IR, UV, MS, 1D-and 2D-NMR spectra.

Triterpenoids and Flavonoids Isolated from the Leaves of Alnus firma (사방오리 잎의 Triterpenoid 및 Flavonoid 화합물)

  • Yu, Young-Beob;Nakamura, Norio;Miyashiro, Hirotsugu;Hattori, Masao;Park, Jong-Cheol
    • Korean Journal of Pharmacognosy
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    • v.38 no.1
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    • pp.76-83
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    • 2007
  • In this study, three triterpenoids, two steroids and nine flavonoids were isolated from the leaves of Alnus firma Sieb. et Zucc. On the basis of spectroscopic evidences, the structures of these compounds were established as ${\beta}$-amyrin acetate, ${\beta}$-amyrin, ${\beta}$-sitosterol, alnustic acid methyl ester, ${\beta}$-sitosterol glucoside, pinocembrin, alnustinol, quercetin, quercetin-3-O-${\alpha}$-L-arabinofuranoside, quercetin-3-O-${\alpha}$-L -rhamnopyranoside, quercetin-3-O-${\beta}$-D-glucopyranoside, myricetin-3-O-${\beta}$-D-galac-topyranoside, (+)-catechin and (-)-epicatechin.

Triterpenoid constituents of the Herbs of Lactuca raddeana (산씀바귀의 Triterpenoid 성분조성)

  • Park, Hee-Juhn;Yun, Sei-Young;Kwak, Tae-Soon;Choi, Jae-Sue;Park, Jong-Hee
    • Korean Journal of Medicinal Crop Science
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    • v.3 no.2
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    • pp.151-155
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    • 1995
  • Chromatographic separation of Laduca raddeana extract afforded a mixture of fatty acyl triterpene, triterpene acetates and primary long chain alcohol. The kind of triterpene moieties in these two triter­penoids was six, i.e., ${\beta}-amyrin,\;{\alpha}-amyrin$, lupeol, pseudotaraxasterol, taraxasterol and germanicol on the basis of chemical and spectroscopic methods. The acyl moieties in the corresponding acyl mixture were characterized as acetates, myristate, palmitate, stearate and arachidate. And a mixture of primary long chain alcohol were composed of teracosanol and hexacosanol.

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Development of Biologically Active Compounds from Edible Plant Sources-XVII. Chemical Constituents from the Aerial Parts of Artemisia princeps PAMPANINI (Sajuarissuk) (식용식물자원으로부터 활성물질의 탐색-XVII. 싸주아리쑥(Artemisia princeps PAMPANINI, Sajuarissuk) 지상부의 화학성분)

  • Yoo, Jong-Su;Bang, Myun-Ho;Ahn, Eun-Mi;Song, Myoung-Chong;Chung, Hae-Gon;Jeong, Tae-Sook;Lee, Kyung-Tae;Choi, Myung-Sook;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.50 no.1
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    • pp.53-56
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    • 2007
  • The aerial parts of Artemisia princeps PAMPANINI were extracted with 80% aqueous MeOH and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2$O, successively. From the EtOAc fraction, five compounds were isolated through the repeated silica gel and ODS column chromatog-raphies. They were determined as friedelin (1), ${\beta}$-amyrin (2), ${\beta}$-amyrin acetate (3), camphanediol (4) and hispidulin (5) on the basis of spectral data, respectively.