• Title/Summary/Keyword: terpene alcohol

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Evaluation on Anti-Dermatophyte Effect of Larix (kaempferi) Essential Oil on the Morphological Changes of Eermatophyte Fungal Hyphae (피부사상균 균사의 형태학적 변화를 통한 일본잎갈나무 정유의 항진균 활성 효과 구명)

  • Kim, Seon-Hong;Lee, Su-Yeon;Hong, Chang-Young;Jang, Soo-Kyeong;Lee, Sung Suk;Park, Mi-Jin;Choi, In-Gyu
    • Journal of the Korean Wood Science and Technology
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    • v.41 no.3
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    • pp.247-257
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    • 2013
  • This study was to investigate the antifungal activity of Larix kaempferi essential oil against dermatophytes, Epidermophyton floccosum, Trichophyton mentagrophytes and Trichophyton rubrum. The active components of L. kaempferi against dermatophytes were determined (characterized by GC-MS), and the morphological changes of the dermatophytes exposed to the L. kaempferi essential oil were observed by electron microscope. Main component of L. kaempferi essential oil was (-)-bornyl acetate. In antifungal activity tests, MIC of L. kaempferi crude oil was 125 ppm on every fungi and 100% (agar dilution method) at more than 500 ppm. By using SEM and TEM, the fungal morphology of E. floccosum exposed to the L. kaempferi essential oil was different from that of normal hyphal morphology. Hyphae exposed to the L. kaempferi essential oil was damaged with distorted and collapsed surfaces. In addition, there were destruction and disorganization of organelles in cytoplasm and collapse of cell membrane. Active antifungal components from L. kaempferi essential oil were identified as terpene alcohol compounds like (-)-${\tau}$-muurolol, (+)-terpinen-4-ol, ${\alpha}$-terpineol, and ${\alpha}$-cadinol.

Volatile Flavor Components of Chestnut Honey Produced in Korea (한국산 밤꿀의 휘발성 향기성분)

  • Kang, Kui-Hwan
    • Applied Biological Chemistry
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    • v.41 no.1
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    • pp.84-88
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    • 1998
  • Composition of volatile flavor components of chestnut flower sand honey were investigated by GC and GC-MS. A total of 64 components including 14 aromatic compounds, 13 hydrocarbons, 7 fatty acids, 4 terpenes, 12 oxygenated hydrocarbons, and 7 misellaneous compounds and a total 41 components including 7 aromatic compounds, 16 hydrocarbons, 12 fatty acids, 1 terpene, 2 oxygenated hydrocarbons, and 3 misellaneous compounds were identified from total volatile concentrates of chestnut flower and honey respectively. The main components of flower volatile were 2-phenyl ethyl alcohol, 1-phenyl ethyl alcohol and benzyl alcohol which comprise 49.02% of this volatiles The main components of flower volatile were 2-phenyl ethyl alcohol, 1-phenyl ethyl alcohol and benzyl alcohol which comprise 49.02% of this volatiles. Aromatic compounds such as 2-phenyl ethyl alcohol, benzyl alcohol, 1-phenyl ethyl alcohol, 1-(2-aminophenyl) ethanone act as major contributor to the characteristic honey-like flavor of chestnut honey.

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Analysis of Volatile Compounds in Perilla frutescens var. acuta by Solid Phase Microextraction (SPME에 의한 소엽의 향기성분 분석)

  • Chung, Mi-Sook;Lee, Mie-Soon
    • Journal of the Korean Society of Food Culture
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    • v.18 no.1
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    • pp.69-74
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    • 2003
  • This study was conducted to find the appropriate fiber for extraction of volatile compounds from Perilla frutescens var. acuta. by solid phase microextraction (SPME). Two SPME fiber, carboxen/polydimethylsiloxane (CAR/PDMS) and polydimethylsiloxane (PDMS) were used to determine the selectivity of the fibers to the different flavor compounds present in the Perilla frutescens var. acuta. Thirty-nine compounds were identified in the volatile compounds extracted by CAR/PDMS fiber, including 6 aldehyde, 1 alcohol, 10 hydrocarbons, 17 terpene hydrocarbons, 2 ketones and 3 benzenes. In PDMS fiber, 3 aldehydes, 2 alcohols, 13 terpene hydrocarbons and 2 miscellaneouses were identified. Perillaldehyde was found to be major volatile flavor component of fresh Perilla frutescens var. acuta. Perillaldehyde and terpene hydrocarbons were more identified in PDMS fiber. These results suggested that the selectivity of PDMS fiber was better than that of CAR/PDMS fiber in Perilla frutescens var. acuta..

Study on Sensory Properties and Volatile Flavor Compounds of Kimchi Added with Backryeoncho (Opuntia ficus-indica var. saboten) Extracts (백련초 추출물 첨가 김치의 관능적 특성 및 휘발성 성분에 대한 연구)

  • Lee, Young-Sook;Jeong, Eun-Jeong;Rho, Jeong-Ok
    • Journal of the East Asian Society of Dietary Life
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    • v.22 no.4
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    • pp.506-513
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    • 2012
  • This principal objective of this study was to evaluate the sensory properties and flavor compounds of Kimchi prepared with different levels (0.0%, 0.4%, 0.8%, and 1.2%) of Backryeoncho extracts (BE). At high levels of BE, Kimchi showed increased level of crispness and flavor, and also jeotgal odor decreased in the sensory evaluation. Addition of 0.8 % BE resulted in the highest scores for color, taste, and overall acceptance of Kimchi. Therefore, addition of 0.8 % BE appears to be an acceptable approach to enhance the quality of Kimchi without reducing acceptability. As a result of flavor compound analysis, a total of 24 volatile flavor compound, including 11 S-containing compounds, 6 terpenes, 1 acid, 1 ester, 1 alcohol, 2 miscellaneous compounds, 2 thiocyanates, etc., were detected by GC/MS. The major volatile compounds were s-containing compounds and terpene hydrocarbon, and especially terpene of sabinene was newly detected in Kimchi with added BE. Levels of 2-vinyl-[4H]-1,3-dithin derived from garlic flavor as a sulfide-containing compound along with diallyl trisulfide derived from green onion flavor were reduced in Kimchi with added 0.8% BE. Most sulfide-containing compounds were reduced in Kimchi with added BE, whereas most terpenes detected in control Kimchi were not detected.

A Study on the Chemical Constituents from Marine Sponge Luffariella sp. (해면 Luffariella sp.의 화학적 성분 연구)

  • Park, Sun Ku;Kim, Sung Soo;Park, Jun Dae;Hong, Jung Sun;Kim, In Kyu
    • Journal of the Korean Chemical Society
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    • v.39 no.7
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    • pp.559-563
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    • 1995
  • The three metabolites, Germacrene alcohol(1), Aaptamine(2) and Hexacyclic terpene(3) were isolated from Marine Sponge Luffariella sp., collected in October 1992, Manado Bay, Sulawesi in Indonesia showed in vitro activity against KB cancer cell line, and structure assignment for 1 was corrected by comparison of their spectral data with the literature $values^1$. Their structure were elucidated by $^1H$, $^13C$ NMR, $^1H$ $^13C$(1 bond) Heteronuclear Multiple Quantum Coherence Spectroscopy$(HMQC)^2$, $^1H$ $^13C$(2 and 3 bond) Heteronuclear Multiple Bond Correlation Spectroscopy$(HMBC)^3$, Electron Impact Mass Spectroscopy(EI ms), Ultra-violet Spectroscopy(UV) and Infrared Spectroscopy(IR).

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Studies on the Some Physical and Chemical Characteristics of Nutmeg Oil by Different Extraction Methods (추출방법에 따른 Nutmeg Oil의 물리적, 화학적 성질에 관한 연구)

  • Jang, Hee-Jin;Ra, Do-Young;Kim, Ok-Chan;Yang, Kwang-Kyu
    • Korean Journal of Food Science and Technology
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    • v.21 no.6
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    • pp.851-856
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    • 1989
  • The physical properties of essential oil of nutmeg extracted in different methods (SDE, Solvent, $CO_2$) were investigated and also the components of essential oil were analyzed using G.C. and G.C./ Mass. Solvent extraction yield was 23% and was higher than those of SDE extraction and $CO_2$ extraction. From the analysis result and physical properties of nutmeg oil, it was conformed that the nutmeg used In this experiment was similar to East Indies type. The content of sabinene was 3.6-14.1%, 28.4-48.7% for myristicin, 1.2-2.1% for elemicin, and 3.6-5.6% for safrole. The camphene was identified in SDE extracts but not in $CO_2$ extracts. The volatile components of SDE extracts and solvent extracts contained large amount of monoterpene and terpene alcohol but $CO_2$ extracts aminly contained aromatic compounds.

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Effects of Probiotic Fermented Fruit Juice-Based Biotransformation by Lactic Acid Bacteria and Saccharomyces boulardii CNCM I-745 on Anti-Salmonella and Antioxidative Properties

  • Laosee, Wanida;Kantachote, Duangporn;Chansuwan, Worrapanit;Sirinupong, Nualpun
    • Journal of Microbiology and Biotechnology
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    • v.32 no.10
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    • pp.1315-1324
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    • 2022
  • Fermentation is an effective process for providing various beneficial effects in functional beverages. Lactic acid bacteria and yeast fermentation-based biotransformation contribute to enhancement of nutritional value and digestibility, including lactose intolerance reduction and control of infections. In this study, the probiotic fermented fruit juice (PFJ) was produced by Lactobacillus plantarum TISTR 1465, Lactobacillus salivarius TISTR 1112, and Saccharomyces boulardii CNCM I-745 while mixed fruit juice (MFJ) was used as the basic medium for microorganism growth. The potential function, the anti-salmonella activity of PFJ, was found to be effective at 250 mg/ml of MIC and 500 mg/ml of MBC. Biofilm inhibition was performed using the PFJ samples and showed at least 70% reduction in cell attachment at the MIC concentration of Salmonella Typhi DMST 22842. The antioxidant activities of PFJ were determined and the results revealed that FSB.25 exhibited 78.40 ± 0.51 mM TE/ml by FRAP assay, while FPSB.25 exhibited 3.44 ± 0.10 mM TE/ml by DPPH assay. The volatile compounds of PFJ were characterized by GC-MS, which identified alcohol, aldehyde, acid, ester, ketone, phenol, and terpene. The most abundant organic acid and alcohol detected in PFJ were acetic acid and 2-phenylethanol, and the most represented terpene was β-damascenone. The sensory attributes showed scores higher than 7 on a 9-point hedonic scale for the FPB.25, illustrating that it was well accepted by panelists. Taken together, our results showed that PFJ could meet current consumer demand regarding natural and functional, fruit-based fermented beverages.

Cloning and Functional Characterization of the Germacradienol Synthase (spterp13) from Streptomyces peucetius ATCC 27952

  • Ghimire, Gopal Prasad;Oh, Tae-Jin;Lee, Hei-Chan;Kim, Byung-Gee;Sohng, Jae-Kyung
    • Journal of Microbiology and Biotechnology
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    • v.18 no.7
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    • pp.1216-1220
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    • 2008
  • Sequence analysis of the metabolically rich genome of Streptomyces peucetius ATCC 27952 revealed a 2,199 bp sesquiterpene alcohol (germacradienol) synthase-encoding gene from the germacradienol synthase/terpene cyclase gene cluster. The gene was named spterp13, and its putative function is as a germacradienol synthase/terpene cyclase. The amino acid sequence of Spterp13 shows 66% identity with SAV2163 (GeoA) from S. avermitilis MA4680 and 65% identity with SCO6073 from S. coelicolor A3(2), which produces germacradienol/geosmin. The full-length recombinant protein was heterologously expressed as a his-tagged fusion protein in Escherichia coli, purified, and shown to catalyze the $Mg^{2+}$-dependent conversion of farnesyl diphosphate to the germacradienol, which was verified by gas chromatography/mass spectrometry.

Effects of Drying Conditions on the Profile of Volatile Terpenoid and Colour of Schizandra Fruit(Schizandra Chinensis fructus) (건조 조건이 오미자의 휘발성 terpene류 및 색도에 미치는 영향)

  • Kim, Yun-Je;Lee, Young-Guen;Choi, Young-Whan;Kim, Yong-Chul
    • Journal of Life Science
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    • v.18 no.8
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    • pp.1066-1071
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    • 2008
  • Schizandra fruit (Schizandra chinensis fructus) were dried by three processes, $50^{\circ}C$ (50HAD), $70^{\circ}C$ hot air (70HAD) and freeze drying process (FRD). Terpenoid were collected by SDE(Simultaneous Steam Distillation-Extraction) and followed by GC-MSD analysis. Also colour profile of each dried samples were measured by Hunter colorimeter. From fresh schizandra fruit, were detected 15 kinds of monoterpene, 28 kinds of sesquiterpene and 7 kinds of terpene alcohol. Myrcene(56.97 ${\mu}g/g$) and ${\gamma}$-terpinene(58.49 ${\mu}g/g$) were the major monoterpenes, ${\beta}$-elemene(120.16 ${\mu}g/g$), ${\alpha}$-bergamotene (103.45 ${\mu}g/g$), ${\gamma}$-selinene (75.97 ${\mu}g/g$), ${\beta}$-cubebene(66.69 ${\mu}g/g$), aristolene (51.25 ${\mu}g/g$) and ${\alpha}$-ylangene(28.06 ${\mu}g/g$) were the sesquiterpenes, and T-muurolol (96.45 ${\mu}g/g$) and terpinen-4-ol(46.02 ${\mu}g/g$) were the terpene alcohols. The dried samples lost more than half of terpenoid content of fresh schizandra fruit during early stage of drying process, and then the level of terpenoid content was not significantly changed. The content of sesquiterpenes appeared to increase until 6 day of FRD. The amount of residual terpene alcohols contained in schizandra fruit dried by FRD was more than those remained after drying by other processes, and schizandra fruit dried by 70HAD exhibited the least residual terpene alcohols. Brightness parameter $L^{\ast}$ decreased with the rise in the level of drying temperature, to which redness parameter $a^{\ast}$ and yellowness $b^{\ast}$ appeared to be similar.

Sesquiterpenoids Bioconversion Analysis by Wood Rot Fungi

  • Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil
    • 한국균학회소식:학술대회논문집
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    • 2016.05a
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    • pp.19-20
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    • 2016
  • Sesquiterpenoids are defined as $C_{15}$ compounds derived from farnesyl pyrophosphate (FPP), and their complex structures are found in the tissue of many diverse plants (Degenhardt et al. 2009). FPP's long chain length and additional double bond enables its conversion to a huge range of mono-, di-, and tri-cyclic structures. A number of cyclic sesquiterpenes with alcohol, aldehyde, and ketone derivatives have key biological and medicinal properties (Fraga 1999). Fungi, such as the wood-rotting Polyporus brumalis, are excellent sources of pharmaceutically interesting natural products such as sesquiterpenoids. In this study, we investigated the biosynthesis of P. brumalis sesquiterpenoids on modified medium. Fungal suspensions of 11 white rot species were inoculated in modified medium containing $C_6H_{12}O_6$, $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ for 20 days. Cultivation was stopped by solvent extraction via separation of the mycelium. The metabolites were identified as follows: propionic acid (1), mevalonic acid lactone (2), ${\beta}$-eudesmane (3), and ${\beta}$-eudesmol (4), respectively (Figure 1). The main peaks of ${\beta}$-eudesmane and ${\beta}$-eudesmol, which were indicative of sesquiterpene structures, were consistently detected for 5, 7, 12, and 15 days These results demonstrated the existence of terpene metabolism in the mycelium of P. brumalis. Polyporus spp. are known to generate flavor components such as methyl 2,4-dihydroxy-3,6-dimethyl benzoate; 2-hydroxy-4-methoxy-6-methyl benzoic acid; 3-hydroxy-5-methyl phenol; and 3-methoxy-2,5-dimethyl phenol in submerged cultures (Hoffmann and Esser 1978). Drimanes of sesquiterpenes were reported as metabolites from P. arcularius and shown to exhibit antimicrobial activity against Gram-positive bacteria such as Staphylococcus aureus (Fleck et al. 1996). The main metabolites of P. brumalis, ${\beta}$-Eudesmol and ${\beta}$-eudesmane, were categorized as eudesmane-type sesquiterpene structures. The eudesmane skeleton could be biosynthesized from FPP-derived IPP, and approximately 1,000 structures have been identified in plants as essential oils. The biosynthesis of eudesmol from P. brumalis may thus be an important tool for the production of useful natural compounds as presumed from its identified potent bioactivity in plants. Essential oils comprising eudesmane-type sesquiterpenoids have been previously and extensively researched (Wu et al. 2006). ${\beta}$-Eudesmol is a well-known and important eudesmane alcohol with an anticholinergic effect in the vascular endothelium (Tsuneki et al. 2005). Additionally, recent studies demonstrated that ${\beta}$-eudesmol acts as a channel blocker for nicotinic acetylcholine receptors at the neuromuscular junction, and it can inhibit angiogenesis in vitro and in vivo by blocking the mitogen-activated protein kinase (MAPK) signaling pathway (Seo et al. 2011). Variation of nutrients was conducted to determine an optimum condition for the biosynthesis of sesquiterpenes by P. brumalis. Genes encoding terpene synthases, which are crucial to the terpene synthesis pathway, generally respond to environmental factors such as pH, temperature, and available nutrients (Hoffmeister and Keller 2007, Yu and Keller 2005). Calvo et al. described the effect of major nutrients, carbon and nitrogen, on the synthesis of secondary metabolites (Calvo et al. 2002). P. brumalis did not prefer to synthesize sesquiterpenes under all growth conditions. Results of differences in metabolites observed in P. brumalis grown in PDB and modified medium highlighted the potential effect inorganic sources such as $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ on sesquiterpene synthesis. ${\beta}$-eudesmol was apparent during cultivation except for when P. brumalis was grown on $MgSO_4$-free medium. These results demonstrated that $MgSO_4$ can specifically control the biosynthesis of ${\beta}$-eudesmol. Magnesium has been reported as a cofactor that binds to sesquiterpene synthase (Agger et al. 2008). Specifically, the $Mg^{2+}$ ions bind to two conserved metal-binding motifs. These metal ions complex to the substrate pyrophosphate, thereby promoting the ionization of the leaving groups of FPP and resulting in the generation of a highly reactive allylic cation. Effect of magnesium source on the sesquiterpene biosynthesis was also identified via analysis of the concentration of total carbohydrates. Our current study offered further insight that fungal sesquiterpene biosynthesis can be controlled by nutrients. To profile the metabolites of P. brumalis, the cultures were extracted based on the growth curve. Despite metabolites produced during mycelia growth, there was difficulty in detecting significant changes in metabolite production, especially those at low concentrations. These compounds may be of interest in understanding their synthetic mechanisms in P. brumalis. The synthesis of terpene compounds began during the growth phase at day 9. Sesquiterpene synthesis occurred after growth was complete. At day 9, drimenol, farnesol, and mevalonic lactone (or mevalonic acid lactone) were identified. Mevalonic acid lactone is the precursor of the mevalonic pathway, and particularly, it is a precursor for a number of biologically important lipids, including cholesterol hormones (Buckley et al. 2002). Farnesol is the precursor of sesquiterpenoids. Drimenol compounds, bi-cyclic-sesquiterpene alcohols, can be synthesized from trans-trans farnesol via cyclization and rearrangement (Polovinka et al. 1994). They have also been identified in the basidiomycota Lentinus lepideus as secondary metabolites. After 12 days in the growth phase, ${\beta}$-elemene caryophyllene, ${\delta}$-cadiene, and eudesmane were detected with ${\beta}$-eudesmol. The data showed the synthesis of sesquiterpene hydrocarbons with bi-cyclic structures. These compounds can be synthesized from FPP by cyclization. Cyclic terpenoids are synthesized through the formation of a carbon skeleton from linear precursors by terpene cyclase, which is followed by chemical modification by oxidation, reduction, methylation, etc. Sesquiterpene cyclase is a key branch-point enzyme that catalyzes the complex intermolecular cyclization of the linear prenyl diphosphate into cyclic hydrocarbons (Toyomasu et al. 2007). After 20 days in stationary phase, the oxygenated structures eudesmol, elemol, and caryophyllene oxide were detected. Thus, after growth, sesquiterpenes were identified. Per these results, we showed that terpene metabolism in wood-rotting fungi occurs in the stationary phase. We also showed that such metabolism can be controlled by magnesium supplementation in the growth medium. In conclusion, we identified P. brumalis as a wood-rotting fungus that can produce sesquiterpenes. To mechanistically understand eudesmane-type sesquiterpene biosynthesis in P. brumalis, further research into the genes regulating the dynamics of such biosynthesis is warranted.

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