• Title/Summary/Keyword: Long-chain phenol

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Cashew Nut Oil: Extraction, Chromatographic and Rheological Characterisation.

  • Vincent Okechuwku ANIDIOBU;Chioma Oluchi ANIDIOBU
    • The Korean Journal of Food & Health Convergence
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    • v.9 no.4
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    • pp.11-18
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    • 2023
  • Oil was extracted from cashew nuts. The physicochemical parameters of the oil were determined. A chromatographic assay of the oil was carried out using Gas Chromatography-Mass Spectrometry. Seventeen compounds were detected: Phenol, Phenol 2-methyl-, Cyclohexene 4, 4-dimethyl-, m-Fluoro-2-diazoacetophenone 4-dimethyl-, Tetradecanoic acid, Phenol 4-octyl-, n-Hexadecanoic acid. Others are 9, 12-Octadecadienoic acid (Z, Z) - methyl ester, Hexadecanoic acid methyl ester, Methyl stearate, Dodecanoic acid methyl ester, 9, 12, 15-Octadecatrienoic acid methyl ester, 9, 12, 15-Octadecatrienoic acid (Z, Z, Z)-, Oleic acid, Octadecanoic acid, Tetracosanoic acid and 9-Octadecenoic acid methyl ester. Among the components are omega three and omega six essential free fatty acids. The rheological profiling and flow properties of cashew nut oil were determined using a Programmable Rheometer. Cashew nut oil exhibits slight dilatant behaviour at the low end of shear rate. The long chain and high molecular weight of its constituents controlled its rheology. Long-chained 9-Octadecenoic acid methyl ester, 9, 12-Octadecadienoic acid (Z, Z) - methyl ester, Tetracosanoic acid and methyl stearate, coupled with their high molecular weights are responsible for the shear thickening effect observed. Two models, Carreau-Yasuda and Ostwald-de Waele Power Law were employed to fit the rheological data. The Carreau-Yasuda model followed well the data.

Islation of Long-Chain Phenols from Ginkgo biloba L. and Their Bio-Activer Principles (은행나무 고분자(高分子) 페놀성(性) 화합물(化合物)의 단리(單離) 및 생리활성(生理活性) 원칙(原則))

  • Kim, Young-Kyoon
    • Journal of the Korean Wood Science and Technology
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    • v.21 no.3
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    • pp.82-86
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    • 1993
  • 은행나무 추출물의 생리활성에 대한 실험결과, 그 추출물이 GAG release에 의한 IL-1의 억제효과(87%)를 나타냄을 관찰하였다. 그 추출물을 chromatography로 분리한후 분광학적 분석을 이용하여 그 함유물질들이 anarchardic acid 및 그와 유사한 페놀성 물질임을 밝혔다. 각 성분에 대하여 활성효과를 다시 실험한 결과, 주성분인 IIIb와 IIIc는 활성효과를 보이지 않았으며, 단지, 소량물질인 Va와 Vb만이 중간 정도의 효과(각각 43과 55%)를 나타내었다. 이 결과에 의하면, 은행나무의 추출성분이 IL-1의 억제효과를 분명히 나타내나, 그 효과가 주성분에 기인하는 것이 아님을 보여 주었다.

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Analysis of Mitochondrial DNA in Patients with Essential Tremor (본태성 수전증 환자의 미토콘드리아 DNA 분석)

  • Lee, Uhn;Yoo, Young Mi;Yoo, Chan Jong
    • Journal of Korean Neurosurgical Society
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    • v.29 no.2
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    • pp.188-195
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    • 2000
  • Objective : Essential tremor(ET) is the most common movement disorder, however, there has been little agreement in the neurologic literature regarding diagnostic criteria for ET. Familial ET is an autosomal dominant disorder presenting as an isolated postural tremor. The main feature of ET is postural tremor of the arms with later involvement of the head, voice, or legs. In previous studies, it was reported that ET susceptibility was inherited in an autosomal dominant inheritance. As previous results, it would suggest that ET might be associated with defect of mitochondrial or nuclear DNA. Recent studies are focusing on molecular genetic detection of movement disorders, such as essential tremor and restless legs syndrome. Moreover, authors have analysed mitochondrial DNA(mtDNA) from the blood cell of positive control(PC) and ET patients via long and accurate polymerase chain reaction(LA PCR). Materials & Methods : Blood samples were collected from PC and 9 ET patients. Total DNA was extracted twice with phenol followed by chloroform : isoamylalcohol. For the analysis of mtDNA, LA PCR was performed by mitochondrial specific primers. Results : With this technique, deletions of large quantities were detected within several regions of mtDNA in ET patients except for D-loop and CO I regions. Conclusion : The authors believe that ET is a genentic disorder with deficiency of mitochondrial DNA multicomplexes and mitochondiral dysfunction could be one of major causative factors of ET. Mitochondrial dysfunction may play an important role in the pathogenesis and possibility of disease progression among familial group with ET patients.

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The Analysis of Mitochondrial DNA in the Patients with Essential Tremor and Parkinson's Disease (본태성 수전증과 파킨슨병 환자에서 미토콘드리아 DNA 비교 분석)

  • Kim, Rae Sang;Yoo, Chan Jong;Lee, Sang-Gu;Kim, Woo-Kyung;Han, Ki-Soo;Kim, Young-Bo;Park, Cheol-Wan;Lee, Uhn
    • Journal of Korean Neurosurgical Society
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    • v.29 no.11
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    • pp.1415-1420
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    • 2000
  • Essential tremor(ET) is the most common movement disorder however there has been little agreement in the neurologic literature regarding diagnostic criteria for ET. Familial ET is an autosomal dominant disorder presenting as an isolated postural tremor. The main feature of ET is postural tremor of the arms with later involvement of the head, voice, or legs. In previous studies, it was reported that ET susceptibility was inherited in an autosomal dominant inheritance. As with previous results, it would suggest that ET might be associated with defect of mitochondrial or nuclear DNA. Recent studies are focusing molecular genetic detection of movement disorders, such as essential tremor and restless legs syndrome. Parkinson's disease(PD) is a neurodegenerative disease involving mainly the loss of dopaminergic neurons in substantia nigra by several factors. The cause of dopaminergic cell death is unknown. Recently, it has been suggested that Parkinson's disease many result from mitochondrial dysfunction. The authors have analysed mitochondrial DNA(mtDNA) from the blood cell of PD and ET patients via long and accurate polymerase chain reaction(LA PCR). Blood samples were collected from 9 PD and 9 ET patients. Total DNA was extracted twice with phenol followed by chloroform : isoamylalcohol. For the analysis of mtDNA, LA PCR was performed by mitochondrial specific primers. With LA PCR, 1/3 16s rRNA~1/3 ATPase 6/8 and COI~3/4 ND5 regions were observed in different patterns. But, in the COI~1/3 ATPase 6/8 region, the data of PCR were observed in same pattern. This study supports the data that ET and PD are genentic disorders with deficiency of mitochondrial DNA multicomplexes.

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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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