• Asian Pacific Journal of Cancer Prevention
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• 제13권7호
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• pp.3073-3076
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• 2012

Terpinen-4-ol is a terpene found in the rhizome of Plai (Zingiber montanum (Koenig) Link ex Dietr.). In this study apoptogenic activity and mechanisms of cell death induced by terpinen-4-ol were investigated in the human leukemic MOLT-4 cell line. Terpinen-4-ol exhibited cytotoxicity in MOLT-4 cells, with characteristic morphological features of apoptosis by Wright's staining. The mode of cell death was confirmed to be apoptosis by flow cytometric analysis after staining with annexin V-FITC and propidium iodide. A sub-G1 peak in DNA histograms of cell cycle assays was observed. Terpinen-4-ol induced-MOLT-4 cell apoptosis mediated through an intrinsic pathway involving the loss of mitochondrial transmembrane potential (MTP) and release of cytochrome c into the cytosol. In addition, terpinen-4-ol also induced apoptosis via an extrinsic pathway by caspase-8 activation resulting in the cleavage of cytosolic Bid. Truncated-Bid (tBid) translocated to mitochondria and activated the mitochondrial pathway in conjunction with down-regulation of Bcl-2 protein expression. Caspase-3 activity also increased. In conclusion, terpinen-4-ol can induce human leukemic MOLT-4 cell apoptosis via both intrinsic and extrinsic pathways.

• Asian Pacific Journal of Cancer Prevention
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• 제14권12호
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• pp.7537-7542
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• 2013

Background: Terpinen-4-ol, a monoterpene, is found as the main component of essential oil extracts from many plants. In this study apoptotic and autophagic types of cell death induced by terpinen-4-ol and associated mechanisms were investigated in human leukemic HL-60 cells. Materials and Methods: The cytotoxicity of human leukemic U937 and HL-60 cells was determined by MTT assay. Cytochrome c release, expression of Bax, Bcl-2, Bcl-xl and cleaved Bid were determined by Western blotting. Cell morphology was examined under a transmission electron microscope. LC3-I/II, ATG5 and Beclin-1 levels were detected by immunoblotting. Results: Terpinen-4-ol exhibited cytotoxicity to human leukemic HL-60 but not U937 cells. The apoptotic response to terpinen-4-ol in HL-60 cells was due to induction of cytochrome c release from mitochondria and cleavage of Bid protein after the stimulation of caspase-8. There was a slightly decrease of Bcl-xl protein level. The characteristic cell morphology of autophagic cell death was demonstrated with multiple autophagosomes in the cytoplasm. At the molecular level, the results from Western blot analysis showed that terpinen-4-ol significantly induced accumulation of LC3-I/II, ATG5 and Beclin-1, regulatory proteins required for autophagy in mammalian cells. Conclusions: Terpinen-4-ol induced-human leukemic HL-60 cell death was via both autophagy and apoptosis.

• Journal of Microbiology and Biotechnology
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• 제34권3호
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• pp.725-734
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• 2024

CYP102A1 from Bacillus megaterium is an important enzyme in biotechnology, because engineered CYP102A1 enzymes can react with diverse substrates and produce human cytochrome P450-like metabolites. Therefore, CYP102A1 can be applied to drug metabolite production. Terpinen-4-ol is a cyclic monoterpene and the primary component of essential tea tree oil. Terpinen-4-ol was known for therapeutic effects, including antibacterial, antifungal, antiviral, and anti-inflammatory. Because terpenes are natural compounds, examining novel terpenes and investigating the therapeutic effects of terpenes represent responses to social demands for eco-friendly compounds. In this study, we investigated the catalytic activity of engineered CYP102A1 on terpinen-4-ol. Among CYP102A1 mutants tested here, the R47L/F81I/F87V/E143G/L188Q/N213S/E267V mutant showed the highest activity to terpinen-4-ol. Two major metabolites of terpinen-4-ol were generated by engineered CYP102A1. Characterization of major metabolites was confirmed by liquid chromatography-mass spectrometry (LC-MS), gas chromatography-MS, and nuclear magnetic resonance spectroscopy (NMR). Based on the LC-MS results, the difference in mass-to-charge ratio of an ion (m/z) between terpinen-4-ol and its major metabolites was 16. One major metabolite was defined as 1,4-dihydroxyp-menth-2-ene by NMR. Given these results, we speculate that another major metabolite is also a mono-hydroxylated product. Taken together, we suggest that CYP102A1 can be applied to make novel terpene derivatives.

• The Korean Journal of Ecology
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• 제28권3호
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• pp.135-139
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• 2005

서양등골나물의 휘발성 추출물에 포함된 terpenoid 화합물을 분리, 동정하였고, 주요 물질 4종에 대한 종자발아와 유식물 생장을 조사하였다. 서양등골나물 정유에 포함된 화합물의 수는 $\beta$-caryophyllene, $\alpha$-terpinenol, chamazulene, bornyl acetate, $\alpha$-pinene등 총 49종이었으며, 그 중 3종은 미확인되었다. 서양등골나물의 정유로부터 분리 확인한 휘발성 화학물질 중 다량 함유되어 있거나 중요한 성분으로 판명된 $\alpha$-pinene, bornyl acetate, linalool 및 terpinen-4-ol 등 4종의 물질에 대한 녹두의 발아 억제 효과를 조사하였다. linalool과 terpinen-4-ol에 의해서는 녹두의 종자가 전혀 발아하지 못하여 발아 억제효과가 매우 큰 것으로 보인다. 정유 내 화합물에 의한 녹두 유식물의 초기 생장 결과, $\alpha$-pinene과 bornyl acetate에 대한 묘조와 유근의 생장은 농도에 따라 점점 억제되었고, linalool과 terpinen-4-ol에 대해서는 실험구에서 생장 반응이 나타나지 않을 만큼 강하게 억제반응이 나타났다. 생체량에 있어서 $\alpha$-pinene의 경우 58 ${\mu}l$ 이상에서 유의한 영향을 미치고 있었으며, bornyl acetate의 경우에는 19 ${\mu}l$ 이상에서 감소하는 것으로 나타났으나 그 이후에는 통계적으로 유의한 차이를 나타내지는 않았다. 위의 결과를 종합해 볼 때, 정유 내에 포함된 서양등골나물의 알레로 화합물 중 생물검정에 사용된 $\alpha$-pinene, bornyl acetate, linalool과 terpinen-4-ol은 식물의 발아 억제 효과를 나타내는 주요한 물질 중 하나로 생각되며, 특히 linalool과 terpinen-4-ol은 다른 식물의 생장을 감소시키는 데 탁월한 효과가 있음을 알 수 있었다.

• 한국식생활문화학회지
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• 제4권4호
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• pp.417-424
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• 1989

한방과 식품분야에서 널리 이용되고 있는 쑥의 특성 중 항미생물 효과에 대한 연구를 하였다. 쑥씨에서 분리한 정유를 GC, GC-MS로 분석한 결과 77종의 휘발성 물질이 동정되었고 그 중에서 가장 많이 존재하는 것은 campher(14.242%), borneol(12.812%), 1.8-cineol(6.437%), terpinen-4-ol(1.185%) 등으로 전체 정유성분의 약 35%를 차지했다. 이들 4종과 Mugwort seed extract(essential oil)를 가지고 대표적인 식품 미생물인 S. cerevisiae, L. mesenteroides, L. plantarum, A. oryzae와 B. subtilis 그리고 식품오염 정도의 지표 미생물인 E. coli 등의 생육에 미치는 항미생물 효과를 측정한 결과 terpinen-4-ol이 가장 효과가 커 1000ppm 정도로 미생물의 생육을 거의 억제시켰으나 cineol, essential oil은 효과가 그다지 크지 않은 반면에 borneol과 campher는 항미생물 효과가 미약했다.

• 대한의생명과학회지
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• 제30권1호
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• pp.32-35
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• 2024

In vitro antimicrobial activities of hot water extracts of Chamaecyparis obtuse, for methicillin-resistant Staphylococcus aureus (MRSA) was compared to commonly used conventional antimicrobial agents. All MRSA was susceptible to linezolid or vancomycin, but also to erythromycin. MIC range and MIC₉₀ to erythromycin, clindamycin, levofloxacin, tetracycline for MRSA were each 4 ㎍/mL, 2 ~ >128 ㎍/mL, ≤0.06 ~ >128 ㎍/mL, 0.25 ~ >128 ㎍/mL, 0.25~64 ㎍/mL and 4 ㎍/mL, .128 ㎍/mL, >128 ㎍/mL, >128 ㎍/mL, 64 ㎍/mL. The hot water extracts of leaf of C. obtuse had the lowest MIC range, MIC₅₀, and MIC₉₀ (0.125 µL/mL) for the MRSA tested, and it was possible more potent than various conventional antimicrobial agents. Screen antibacterial drug candidate with high antibacterial activity such as derivatives of C. obtuse leaf extract such as terpinen-4-ol or using combined therapy with commercialized antibacterial agents will likely be helpful in treating refractory MRSA infections.

• 대한본초학회지
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• 제22권4호
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• pp.271-277
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• 2007

Objective : The content of essential oils from Ssajuari and Sajabalssuk was analyzed based on storage period. A total of eight samples old Ssajuari (harvested in 2000, 2001, 2002, 2003, and 2004), fresh Ssajuari (harvested in 2004), old Sajabalssuk (harvested in 2002), and fresh Sajabalssuk (harvested in 2004) was analyzed. Methods : The analysis of the content of essential oils from Ssajuari and Sajabalssuk was conducted by GC/MS. Results : The main essential oils of Ssajuari were ${\beta}$-thujone and 1.8-cineole. The ${\alpha},{\beta}$-thujone and 1,8-cineole were increased but the caryophyllene oxide was decreased. in accordance with storage period. The main essential oils of fresh Sajabalssuk were trans-${\beta}$-caryophyllene, terpinen-4-ol. The main essential oils of old Sajabalssuk was ${\beta}$-thujone and 1,8-cineole like Ssajuari. But 1,8-cineole was higher than that of Ssajuari samlpes. Conclusion : All samples had trans-sabinene hydrate, 1,8-cineole, terpinen-4-ol and caryophyllene oxide. According to stored year, ${\beta}$-thujone, ${\alpha}$-thujone were increased but terpinen-4-ol, caryophyllene oxide were decreased.

• Applied Biological Chemistry
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• 제45권2호
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• pp.101-107
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• 2002

순비기나무의 잎, 꽃, 줄기 및 열매로부터 수증기 증류법으로 정유를 분리한 다음 GC-MS 및 GC를 이용한 표준품과 머무름 시간의 비교에 의해 76종의 성분을 동정하였다. 동정된 성분은 monoterpene hydrocarbons 16종, oxygenated monoterpenes 30종, sesquiterpene hydrocarbons 10종, oxygenated sesquiterpenes 8종, diterpenes 3종, 기타 성분 9종으로서, 특히 ${\alpha}-pinene$, ${\beta}-pinene$, sabinene, 1,8-cineole, terpinen-4-ol, ${\alpha}-terpineol$등의 monoterpene류가 주요 구성성분들이었다. 부위별 주요 구성성분으로서 잎에서는 ${\alpha}-pinene$ (30.25%) > 1,8-cineole (19.89%) > sabinene (9.56%) > ${\alpha}-ternineol$ (7.94%) > ${\beta}-pinene$ (5.69%) > terpinen-4-ol (2.37%), 꽃에서는 ${\alpha}-pinene$ (25.47%) > 1,8-cineole (7.69%) > manoyl oxide(6.21%) > ${\beta}-pinene$ (4.20%) > ${\alpha}-terpineol$ (3.76%) >sabinene (2.78%), 줄기에서는 ${\alpha}-pinene$ (13.24%)>${\alpha}-terpineol$ (10.64%)>1,8-cineole (4.40%)>manoyl oxide (4.02%) > ${\beta}-pinene$ (2.39%) > terninen-4-ol (2.21%), 그리고 열매에서는 ${\alpha}-pinene$ (20.24%) > 1,8-cineole (11.47%) > ${\beta}-pinene$ (9.79%) > u-terpineol (7.08%) > sabinene (3.68%) limonene (2.77%)의 순서로 조성비율이 높았다. 전반적으로 순비기나무의 잎과 열매에서 분리한 정유에서는 monoterpene류의 조성비율이 높았으나 꽃과 줄기에서는 잎이나 열매에 비해 sesquitepene류, diterpene류 이외에도 구조를 동정하지 못하였으나 diterpene류 일 것으로 예상되는 분자량이 비교적 큰 성분들의 조성비율이 높았다.

• 생약학회지
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• 제11권1호
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• pp.1-6
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• 1980

By means of prefractionation on a silicagel column and combination of GC-Mass spectrometry, the essential oil constituents of Thymus magnus Nakai were analysed. Ten terpenoid compounds, ${\gamma}-terpinene$, ${\alpha}-pinene$, ${\beta}-caryophyllene$, ${\beta}-bisabolene$, pcymene, 4-isopropyltropolone, thymol, carvacrol, terpinen-4-ol and Borneol, were identified by referring to the spectrums of their authentic specimens.

• Journal of the Korean Wood Science and Technology
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• 제37권6호
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• pp.585-599
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• 2009

본 연구는 수목으로부터 분리된 수용성 정유를 이용하여 버섯에 병해를 일으키는 푸른곰팡이병의 원인 미생물인 Trichoderma에 대한 항균활성을 확인하고자 시도되었다. 소나무(Pinus densiflora)와 편백나무(Chamaecyparis obtusa) 잎으로부터 GAP (Gas assisted process)을 이용하여 수용성 정유를 획득하였다. 버섯의 푸른 곰팡이병을 발생시키는 Trichoderma spp. 곰팡이 5종은 $25^{\circ}C$에서 균사생장이 가장 높았으며, pH 5.0의 배지조건에서 가장 양호한 균사 생장을 나타내었다. 소나무와 편백나무 잎의 수용성 정유는 3.9% 및 3.7%의 수율을 나타내었다. 소나무와 편백나무 잎 정유의 화학적 조성은 동일 화합물이 많았으며, 동일 화합물로는 $\alpha$-Terpineol acetate, Terpinen-4-ol 및 $\alpha$-Terpineol이 확인되었다. 소나무 잎의 수용성 정유는 5000 ppm 농도에서 Trichoderma harzianum에 대하여 가장 높은 항균활성을 나타냈으며, 편백나무 잎의 수용성 정유 또한 5000 ppm 농도에서 Trichoderma atroviride에 대하여 가장 높은 항균활성을 나타내었다.