• 제목/요약/키워드: terpene alcohol

검색결과 25건 처리시간 0.022초

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

  • 김선홍;이수연;홍창영;장수경;이성숙;박미진;최인규
    • Journal of the Korean Wood Science and Technology
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    • 제41권3호
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    • pp.247-257
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    • 2013
  • 본 연구는 피부사상균 Epidermophyton floccosum, Trichophyton mentagrophytes, Trichophyton rubrum에 대한 일본잎갈나무 정유의 항진균 활성을 평가하고, 항진균 유효성분을 구명하고자 하였다. 또한 일본잎갈나무 정유에 노출된 피부사상균의 균사를 전자현미경으로 관찰하여 일본잎갈나무 정유의 항진균 효과를 균사의 형태학적 변화를 통하여 밝히고자 하였다. 일본잎갈나무 정유의 주성분은 (-)-bornyl acetate였으며, MIC는 모든 균에 대해 125 ppm을 나타냈다. 한천희석법을 통한 항진균 활성 평가에서는 모든 균에 대해 500 ppm 이상에서 100%의 활성, 100 ppm의 낮은 농도에서도 50% 이상의 활성을 나타냈다. SEM과 TEM을 통해 균사를 관찰한 결과, 일본잎갈나무 정유에 노출된 E. floccosum은 정상세포와 다른 균사 형태가 관찰되었다. 팡이실 모양의 격막을 갖고 있는 곧고 매끈한 표면의 정상세포와는 달리, 처리구에서는 균사 표면에 주름이 있었으며 균사가 터지거나 접히고 부풀어 오른 것, 세포소기관과 세포벽이 붕괴된 것도 관찰되었다. 분획을 통해 일본잎갈나무 정유의 항진균 유효성분을 확인한 결과, (-)-${\tau}$-muurolol, (+)-terpinen-4-ol, ${\alpha}$-terpineol, ${\alpha}$-cadinol 등의 terpene alcohol 화합물이었다.

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

  • 강귀환
    • Applied Biological Chemistry
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    • 제41권1호
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    • pp.84-88
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    • 1998
  • 밤꿀과 밤꽃 향기성분의 연관성을 조사코자 밤꿀은 용매추출과 수증기 증류법을 병행하여, 그리고 밤꽃은 수증기 증류법에 의해 향기성분을 분리한 다음 GC, GC-MS에 의해 확인 비교하였다. 밤꽃으로 부터 14종의 방향족 화합물, 13종의 탄화수소류, 7 종의 지방산류, 4종의 테르펜류, 12종의 함산소 탄화수소류, 7종의 기타 성분 등 64종의 성분이 확인되었고, 밤꿀로 부터는 7종의 방향족화합물, 16종의 탄화수소류, 12종의 지방산류, 1종의 테르펜류, 2종의 함산소 탄화수소류, 3종의 기타 성분 등 41종이 확인되었다. 밤꽃 향기의 주요성분으로는 전체 향기의 49.02%를 차지하고 있는 2-phenyl ethyl alcohol, 1-phenyl ethyl alcohol, benzyl alcohol 등이 주를 이루었고 밤꿀 향기의 특징적인 성분으로는 2-phenyl ethyl alcohol, benzyl alcohol, 1-phenyl ethyl alcohol, 1-(2-aminophenyl) ethanone 등이었다.

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

  • 정미숙;이미순
    • 한국식생활문화학회지
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    • 제18권1호
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    • pp.69-74
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    • 2003
  • 우리나라의 고유한 향신료로 활용되고 있는 소엽의 휘발성 향기성분 분석에 적합한 solid phase microextraction(SPME) fiber를 선정하기 위하여 carboxen/polydimethylsiloxane(CAR/PDMS)과 polydimethylsiloxane(PDMS)의 2종류 fiber를 이용하여 향을 추출한 후 GC/MS로 분석하였다. CAR/PDMS fber에 소엽의 향을 흡착시켜 분석한 결과, 39종의 성분이 확인되었으며, PDMS fiber를 이용하였을 때는 20가지의 향기성분이 확인되었다. 특히 PDMS fiber를 사용하였을 때 CAR/PDMS fber를 이용하였을 때 보다 perillaldehyde (40.50%), limonene (27.32%), E,E-,${\alpha}-famesene$ (10.22%) 및 ${\beta}-caryophyllene$ (8.02%)의 소엽의 주요 향기성분이 선택적으로 많이 확인되었다. 따라서 방향성 식용식물인 소엽의 향기를 SPME법으로 추출할 때는 PDMS fiber가 적합하다고 판단된다.

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

  • 이영숙;정은정;노정옥
    • 동아시아식생활학회지
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    • 제22권4호
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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.

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

  • 박선구;김성수;박준대;홍정선;김인규
    • 대한화학회지
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    • 제39권7호
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    • pp.559-563
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    • 1995
  • 인도네시아 Manado만의 Sulawesi에서 채집한 KB cancer cell line에 대해 in vitro로 활성을 갖는 해면 Luffariella sp.으로부터 Germacrene alcohol(1), Aaptamine(2) 및 Hexacyclic terpene(3)을 분리하였으며, 1에대한 spectral data는 문헌치와 비교${\cdot}$분석하여 수정하였다. 이들을 $^1H$, $^13C$ NMR, $^1H$ $^13C$(bond) Heteronuclear Multiple Quantum Coherence Spectroscopy(HMQC), $^1H$$^13C$(2 and 3 bond)Heteronuclear Multiple Bond Correlation Spectroscopy(HMBC), Electron Impact Mass Spectroscopy(EI ms), UV 및 IR에 의해 밝혔다.

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

  • 장희진;나도영;김옥찬;양광규
    • 한국식품과학회지
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    • 제21권6호
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    • pp.851-856
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    • 1989
  • 추출방법을 달리하여 얻은 육두구 정유에 대한 물리적 성질을 측정하고, GC와 GC/MS를 이용하여 분석하였다. 추출수율은 용매추출이 23%로 가장 많았고 SDE 추출, $CO_2$ 추출순이었다. 육두구유에 대한 물리적 성질과 GC분석결과에서 본 실험에 사용한 육두구는 East Indies type에 가까운 것을 확인할 수 있었고 각각 추출물의 분석결과로부터 sabinene은 3.6-14.1%, miristicin은 28.4-48.7% elemicin은 1.2-2.1%이 함유되어 있음을 알 수 있었다. 또 발암물질로 알려진 safrole은 SDE 추출에서 3.8%, 용매추출에서 3.6%, $CO_2$추출에서 5.6% 함유하고 있는 것으로 나타났다. SDE 추출이나 용매추출에서 확인된 camphene은 $CO_2$추출에서 확인할 수 없었고 monoterpene, terpene alcohol 계통의 화합물은 SDE 추출이나 용매 추출에 많았다. 방향족 화합물은 $CO_2$추출에서 많이 추출됨을 확인할 수 있었다.

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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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    • 제32권10호
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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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    • 제18권7호
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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.

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

  • 김윤제;이영근;최영환;김용철
    • 생명과학회지
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    • 제18권8호
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    • pp.1066-1071
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    • 2008
  • 오미자의 건조공정에 의한 휘발성 terpene류와 색의 변화를 조사하기 위하여, 건조조건을 $50^{\circ}C$$70^{\circ}C$의 열풍건조, $-70^{\circ}C$의 진공동결건조의 3종 건조방법으로 건조한 후 SDE 연속추출장치로 terpene류를 추출하여 GC/MS로 분석하고, 각 건조된 오미자를 마쇄한 분말의 색도를 Hunter colorimeter로 측정하였다. 생오미자의 GC/MS 분석 결과, 15종의 monoterpene류, 28종의 sesquiterpene류 및 7종의 terpene alcohol류가 확인되었으며, 또한 myrcene (56.97 ${\mu}g/g$)과 ${\gamma}-terpinene$ (58.49 ${\mu}g/g$)이 monoterpene류, ${\beta}-elemene$ (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 ${\mu}g/g$) 및 ${\alpha}$-ylangene (28.06 ${\mu}g/g$) 등이 sesquiterpene류, 그리고 T-muurolol (96.45 ${\mu}g/g$)과 terpinen-4-ol (46.02 ${\mu}g/g$)이 terpene alcohol류의 주성분이었다. 건조과정의 초기에 생오미자 terpene류의 절반 이상이 감소되었으며, 이후 건조기간의 경과에 따른 추가적 감소는 아주 적었다. 또한 총 terpene류의 절반 이상을 차지하는 sesquiterpene류의 함량은 진공동결건조에서는 소량 증가하다 6일 이후 감소하는 패턴을 보였다. 그리고 terpene alcohol류는 진공동결건조한 시료에서 그 함량이 비교적 많이 남았으나, 고온인 $70^{\circ}C$에서 열풍건조한 시료에서는 가장 적게 남아 있었다. 건조방법에 따른 L값은 동결건조, $50^{\circ}C$ 열풍건조, $70^{\circ}C$ 열풍건조 순서로 높았으며, a값 및 b값도 동결건조에서 가장 높았으며 $70^{\circ}C$ 열풍건조에서 가장 낮게 나타났다.

Sesquiterpenoids Bioconversion Analysis by Wood Rot Fungi

  • Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil
    • 한국균학회소식:학술대회논문집
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    • 한국균학회 2016년도 춘계학술대회 및 임시총회
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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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