• Asian Pacific Journal of Cancer Prevention
• /
• v.13 no.7
• /
• pp.3073-3076
• /
• 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
• /
• v.14 no.12
• /
• pp.7537-7542
• /
• 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
• /
• v.34 no.3
• /
• pp.725-734
• /
• 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
• /
• v.28 no.3
• /
• pp.135-139
• /
• 2005

This study was carried out to find the allelopathic effect of volatile materials released from Eupatorium rugosum. The GC method was employed for analysis of volatile materials from E. rugosum and 49 chemical substances were identified such as $\beta$-caryophyllene, $\alpha$-terpinenol, chamazulene, bornyl acetate, $\alpha$-pinene, etc. including unidentified three chemicals. Germination test in Phaseolus radiatus was done to find the inhibition effect of volatile materials using some chemicals which were proved to be important component or much amounts ones in E. rugosum. It was strongly inhibited by linalool and terpinen-4-ol. Seedling elongation and radicle growth of that were proportionally inhibited by the concentration of the essential oil, especially $\alpha$-pinene and bornyl acetate. Biomass of receptor plant was slightly decreased more than 58 ${\mu}l$ of the extract in case of $\alpha$-pinene, while it was decreased more than 19 ${\mu}l$ of that in bornyl acetate but it was shown non-significant. From the above results, it was found that volatile materials from E. rugosum showed a allelopathic effect and also $\alpha$-pinene, bornyl acetate, linalool and terpinen-4-ol used in bioassay were some of major allelochemicals in germination inhibition and especially linalool and terpinen-4-ol are prominent effect on growth inhibition of other plant.

• Journal of the Korean Society of Food Culture
• /
• v.4 no.4
• /
• pp.417-424
• /
• 1989

The volatile constituents of Mugwort seeds were extracted by simultaneous steam distillation-extraction apparatus, and analyzed by combined GC and GC-MS. Of the 73 compounds identified from Mugwort seed extract, the main volatile compounds were campher (14.242%), borneol(12.812%), 1.8-cineol(6.437%) and terpinen-4-ol(1.185%) comprising about 35%. Effect of the volatile constituents (champher, borneol, 1.8-cineol, terpinen-4-ol and essential oil) on the growth of Microorganism (B. subtilis, E. coli, S. cerevisiae, L. mesenteroides, L. Plantarum, A. oryzae). Of the volatile compounds had a antibiological effect, terpinen-4-ol was the most effective in volatile compound.

• Biomedical Science Letters
• /
• v.30 no.1
• /
• pp.32-35
• /
• 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.

• The Korea Journal of Herbology
• /
• v.22 no.4
• /
• pp.271-277
• /
• 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
• /
• v.45 no.2
• /
• pp.101-107
• /
• 2002

The essential oils isolated from leaves, flowers, stems, and fruits of Vitex rotundifolia by steam distillation and extraction (SDE) method were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 76 components detected by GC, 42 components were identified positively by GC-MS and GC co-injection with authentic standards, and 34 components were identified tentatively by mass spectral data only. They included 16 monoterpene hydrocarbons, 30 oxygenated hydrocarbons, 10 sesquiterpene hydrocarbons, 8 oxygenated sesquiterpenes, 3 diterpenes, and 9 miscellaneous components. The major components in the oil from the leaves were ${\alpha}-pinene$ (30.25%), 1,8-cineole (19.89%), sabinene (9.56%), ${\alpha}-terpineol$ (7.94%), ${\beta}-pinene$ (5.69%), and terpinen-4-ol (2.37%), and those in the flower oil were ${\alpha}-pinene$ (25.47%), 1,8-cineole (7.69%), manoyl oxide (6.21%), ${\beta}-pinene$ (4.20%), ${\alpha}-te.pineol$ (3.76%), and sabinene (2.78%). The major components in the oil from the stems were ${\alpha}-pinene$ (13.24%), ${\alpha}-terpineol$ (10.64%), 1,8-cineole (4.40%), manoyl oxide (4.02%), ${\beta}-pinene$ (2.39%), and terpinen-4-ol (2.21%) while those in the oil from the fruits were ${\alpha}-pinene$ (20.24%), 1,8-cineole (11.47%), ${\beta}P-pinene$ (9.79%), ${\alpha}-terpineol$ (7.08%), sabinene (3.68%), and limonene (2.77%). The percentage composition of monoterpenes in the oils from the leaves and the fruits were higher than in those from the flowers and the stems, whereas the oil from the flowers and the stems were characterized by a large content of sesquiterpenes, diterpenes and other unknown high molecular weight components.

• Korean Journal of Pharmacognosy
• /
• v.11 no.1
• /
• pp.1-6
• /
• 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
• /
• v.37 no.6
• /
• pp.585-599
• /
• 2009

This study was carried out to investigate the antifungal activity of the water soluble essential oil against Trichoderma spp. Water soluble essential oils from Pinus densiflora and Chamaecyparis obtusa were obtained from GAP (Gas assisted process) extraction apparatus. When the water soluble essential oil was treated, the growth of the conidial germination was maximum under the cultivation condition at $25^{\circ}C$ and in the culture medium adjusted to pH 5.0. The yield of water soluble essential oil was 3.9% and 3.7% in P. densiflora and C. obtusa, respectively. 24 and 15 kinds of compounds were identified in water soluble essential oils of P. densiflora and C. obtusa, respectively. The major components in the essential oil of P. densiflora were $\alpha$-Terpineol acetate and Terpinen-4-ol and those of C. obtusa were Terpinen-4-ol and $\alpha$-Terpineol. Antifungal activity was the best in the 5000 ppm of P. densiflora against Trichoderma harzianum and in 5000 ppm of C. obtusa against Trichoderma atroviride.