Journal of Oleo Science
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Print ISSN : 1345-8957
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Volume 66 , Issue 8
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Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics (TEAC)
  • Mitsuo MIYAZAWA, Yoshinori ASAKAWA
    Volume 66 (2017) Issue 8 Pages 803
    Released: August 01, 2017
    JOURNALS FREE ACCESS
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  • Toshio Morikawa, Hisashi Matsuda, Masayuki Yoshikawa
    Volume 66 (2017) Issue 8 Pages 805-814
    Released: August 01, 2017
    [Advance publication] Released: April 04, 2017
    JOURNALS FREE ACCESS

    Frankincense and myrrh have been used as incense in religious and cultural ceremonies since the beginning of written history. Their common medicinal properties are used in the treatment for inflammatory conditions, some cancerous diseases, and wound healing. In the course of our characterization of the anti-inflammatory constituents from frankincense and myrrh, several terpenoid constituents were found to inhibit nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages. Here we review the structure of those terpenoid constituents from the gum resins of frankincense and myrrh and evaluate their anti-inflammatory effects by their nitric oxide production inhibitory activity.

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  • Shinobu Oda
    Volume 66 (2017) Issue 8 Pages 815-831
    Released: August 01, 2017
    JOURNALS FREE ACCESS

    Bioconversions such as enzymatic and microbial transformations are attractive alternatives to organic synthesis because of practical advantages such as resource conservation, energy efficiency, and environmentally harmonic properties. In addition, the production of secondary metabolites through microbial fermentation is also useful for manufacturing pharmaceuticals, agricultural chemicals, and aroma compounds. For microbial production of useful chemicals, the authors have developed three unique interfacial bioprocesses: a solid–liquid interface bioreactor (S/L-IBR), a liquid–liquid interface bioreactor (L/L-IBR), and an extractive liquid-surface immobilization (Ext-LSI) system. The S/L-IBR comprises a hydrophobic organic solvent (upper phase), a microbial film (middle phase), and a hydrophilic gel such as an agar plate (lower phase); the L/L-IBR and the Ext-LSI consist of a hydrophobic organic solvent (upper phase), a fungal mat with ballooned microspheres (middle phase), and a liquid medium (lower phase). All three systems have unique and practically important characteristics such as utilization of living cells, high concentration of lipophilic substrates/products in an organic phase, no requirement for aeration and agitation, efficient supply of oxygen, easy recovery of product, high regio- and stereoselectivity, and wide versatility. This paper reviews the principle, construction, characteristics, and application of these interfacial systems for producing lipophilic compounds such as useful aroma compounds, citronellol-related compounds, β-caryophyllene oxide, and 6-penty-α-pyrone.

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  • Hiromasa Shibuya, Takahiro Nakago, Seiichi Inoue, Yujiro Hoshino, Kiyo ...
    Volume 66 (2017) Issue 8 Pages 833-842
    Released: August 01, 2017
    [Advance publication] Released: April 04, 2017
    JOURNALS FREE ACCESS

    A tandem Brook rearrangement/silicon Polonovski reaction has been achieved by in situ generation of ammonium ylides via the oxidation of α-silyl-tertiary amines. Furthermore, we found that the oxidation of N-(1-cyano-1-silyl)methyl-tertiary amines with peracids induced the tandem Brook rearrangement/silicon Polonovski reaction/fragmentation to give formamide derivatives in moderate yields.

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  • Kento Kunihiro, Takao Myoda, Noriaki Tajima, Kotaro Gotoh, Tai Kaneshi ...
    Volume 66 (2017) Issue 8 Pages 843-849
    Released: August 01, 2017
    [Advance publication] Released: April 04, 2017
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    The sedative effects of volatile components in the essential oil of Artemisia montana (“Yomogi”) were investigated and measured using gas chromatography-mass spectrometry (GC-MS). Major components identified included 1,8-cineol, camphor, borneol, α-piperitone, and caryophyllene oxide. Among them, 1,8-cineol exhibited the highest flavor dilution (FD) value in an aroma extract dilution analysis (AEDA), followed by borneol, o-cymene, β-thujone, and bornyl acetate. The sedative effects of yomogi oil aroma were evaluated by sensory testing, analysis of salivary α-amylase activity, and measurement of relative fluctuation of oxygenated hemoglobin concentration in the brain using near-infrared spectroscopy (NIRS). All results indicated the stress-reducing effects of the essential oil following nasal exposure, and according to the NIRS analysis, 1,8-cineol is likely responsible for the sedative effects of yomogi oil.

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  • Shinsuke Marumoto, Yoshiharu Okuno, Mitsuo Miyazawa
    Volume 66 (2017) Issue 8 Pages 851-855
    Released: August 01, 2017
    [Advance publication] Released: April 04, 2017
    JOURNALS FREE ACCESS

    Inhibition of β-secretase (BACE1) is currently regarded as the leading treatment strategy for Alzheimer’s disease. In the present study, we aimed to screen the in vitro inhibitory activity of 80 types of aroma compounds (monoterpenes, sesquiterpenes, and C13 norisoprenoids), including plant-based types, at a 200-μM concentration against a recombinant human BACE1. The results showed that the most potent inhibitor of BACE1 was geranyl acetone followed by (+)-camphor, (-)-fenchone, (+)-fenchone, and (-)-camphor with the half-maximal inhibitory concentration (IC50) values of 51.9 ± 3.9, 95.9 ± 11.0, 106.3 ± 14.9, 117.0 ± 18.6, and 134.1 ± 16.4 μM, respectively. Furthermore, the mechanism of inhibition of BACE1 by geranyl acetone was analyzed using Dixon kinetics plus Cornish-Bowden plots, which revealed mixed-type mode. Therefore aroma compounds may be used as potential lead molecules for designing anti-BACE1 agents.

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  • Masanori Morimoto, Masamitsu Urakawa, Koichiro Komai
    Volume 66 (2017) Issue 8 Pages 857-862
    Released: August 01, 2017
    [Advance publication] Released: July 12, 2017
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    Electrochemically synthesized dihydrobenzofurans were evaluated for their insect antifeedant activities against phytophagous insects. They were prepared through the coupling reactions of various alkenes with a phenoxy cation generated by oxidation near the cathode in the electrolytic reaction. The insect antifeedant activities of these synthetic dihydrobenzofurans were evaluated in the common cutworm (Spodoptera litura) and diamond back moth (Plutella xylostella) with the dual choice leaf disk bioassay method. The insect antifeedant activities of most of the acetophenone-type dihydrobenzofurans were strong, while those of derivatives with a t-butyl group were weaker. The biological activities in insect species differed with the structural features of the compounds.

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  • Toshio Hasegawa, Kazuma Yoshitome, Takashi Fujihara, Mardi Santoso, Mu ...
    Volume 66 (2017) Issue 8 Pages 863-869
    Released: August 01, 2017
    [Advance publication] Released: July 12, 2017
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    Patchouli is used as an incense material and essential oil. The characteristic odor of patchouli leaves results from the drying process used in their production; however, there have to date been no reports on the changes in the odor of patchouli leaves during the drying process. We investigated the aroma profile of dried patchouli leaves using the hexane extracts of fresh and dried patchouli leaves. We focused on the presence or absence of the constituents of the fresh and dried extracts, and the differences in the content of the common constituents. Fourteen constituents were identified as characteristic of dried patchouli extract odor by gas chromatography-olfactometry analysis. The structures of seven of the 14 constituents were determined by gas chromatography-mass spectrometry (α-patchoulene, seychellene, humulene, α-bulnesene, isoaromadendrene epoxide, caryophyllene oxide, and patchouli alcohol). The aroma profile of the essential oil obtained from the dried patchouli leaves was clearly different from that of dried patchouli. The aroma profile of the essential oil was investigated by a similar method. We identified 12 compounds as important odor constituents. The structures of nine of the 12 constituents were determined by gas chromatography-mass spectrometry (cis-thujopsene, caryophyllene, α-guaiene, α-patchoulene, seychellene, α-bulnesene, isoaromadendrene epoxide, patchouli alcohol, and corymbolone). Comparing the odors and constituents demonstrated that the aroma profile of patchouli depends on the manufacturing process.

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  • Yoshinori Asakawa, Agnieszka Ludwiczuk, Kazutoshi Sakurai, Kenichi Tom ...
    Volume 66 (2017) Issue 8 Pages 871-876
    Released: August 01, 2017
    [Advance publication] Released: July 12, 2017
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    The volatile compounds obtained from the ether extracts, headspace gases and steam distillates of Alpinia japonica and Elettaria cardamomum were analyzed by GC/MS. Both species were rich sources of naturally rare fenchane-type monoterpenoids, fenchene, fenchone, fenchyl alcohol and its acetate, together with 1,8-cineole. The distributions of volatile sesquiterpenoids were very poor in both species. Chiralities of fenchone in A. japonica and E. cardamomum were 99% of (1S,4R)-(+)-form. Camphor in A. japonica is composed of a mixture of (1R,4R)-(+)-form (94.3%) and (1S,4S)-(-)-form (5.7%). On the other hand, E. cardamomum produced only (1R,4R)-(+)-camphor (99%).

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  • Toru Nakasugi, Takushi Murakawa, Koji Shibuya, Masanori Morimoto
    Volume 66 (2017) Issue 8 Pages 877-882
    Released: August 01, 2017
    [Advance publication] Released: July 12, 2017
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    A deodorizing substance in black cumin (Nigella sativa L.), a spice for curry and vegetable foods in Southwest Asia, was examined. The essential oil prepared from the seeds of this plant exhibited strong deodorizing activity against methyl mercaptan, which is a main factor in oral malodor. After purification with silica gel column chromatography, the active substance in black cumin seed oil was identified as thymoquinone. This monoterpenic quinone functions as the main deodorizing substance in this oil against methyl mercaptan. Metabolite analysis suggested that the deodorizing activity may be generated by the addition of a reactive quinone molecule to methyl mercaptan. In the present study, the menthane-type quinone and phenol derivatives exhibited deodorizing activities via this mechanism.

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  • Shinsuke Marumoto, Yoshiharu Okuno, Yuki Hagiwara, Mitsuo Miyazawa
    Volume 66 (2017) Issue 8 Pages 883-888
    Released: August 01, 2017
    [Advance publication] Released: July 12, 2017
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    Using biotransformation as a biocatalytic process has the advantage of being able to proceed under mild conditions and with high regio- and enantioselectivity. This study investigated the biotransformation of (–)-(1R,4S)-menthone (1) and (+)-(1S,4R)-menthone (2) by Spodoptera litura larvae. Compound 1 was converted to (–)-(1R,4S)-7-hydroxymenthone (1-1), (+)-(1R,3S,4S)-7-hydroxyneomenthol (1-2) and (–)-(1R,4S,8R)-p-menth-3-one-9-oic acid (1-3). The metabolism of substrate 2 generated three enantiomers of the above metabolites, designated as 2-1 to 2-3, respectively. The C-9 position of (–)-menthone and (+)-menthone was oxidized to carboxylic acid by S. litura, which is a metabolic pathway not observed in any other example of biocatalysis.

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  • Yoshinori Asakawa, Kenichi Tomiyama, Kazutoshi Sakurai, Yukihiro Kawak ...
    Volume 66 (2017) Issue 8 Pages 889-895
    Released: August 01, 2017
    [Advance publication] Released: July 12, 2017
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    The volatile compounds obtained from the different organs of Houttuynia cordata (Saururaceae) and Litsea cubeba (Lauraceae) were analyzed by Gas Chromatography/Mass Spectrometry (GC/MS), Headspace Solid Phase Micro Extraction-Gas Chromatography/Mass Spectrometry (HS-SPME-GC/MS), and GC/olfactometry (GC/O). The major component of all parts of H. cordata is assigned as 4-tridecanone. Each organ produces myrcene as the major monoterpenoid. The major monoterpene in the rhizomes and roots was β-pinene instead of myrcene. 1-Decanal which was responsible for the unpleasant odor of this plant, was the predominant polyketide in both leaves and stems. The presence of 1-decanal was very poor in flowers, stem collected in summer, rhizomes, and roots. GC/MS analyses were very simple in case of the crude extracts of flowers. The content of sesquiterpenoids was extremely poor. (8Z)-Heptadecene, geranial, and neral were detected as the major components in Litsea cubeba. Odor-contributing components by GC/O analysis of the ether extract of the fresh flowers of L. cubeba were neral and geranial which played an important role in sweet-lemon fragrance of the flowers. The role of a high content of (8Z)-heptadecene was still unknown but it might play a significant role in the dispersion of the volatile monoterpene hydrocarbons and aldehydes. The flower volatiles of the Japanese L. cubeba were chemically quite different from those of the Chinese same species.

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Oils and Fats
  • Samir Abd-elmonem A Ismail, Ayman Mohammed El-Anany, Rehab Farouk M Al ...
    Volume 66 (2017) Issue 8 Pages 897-905
    Released: August 01, 2017
    JOURNALS FREE ACCESS

    The present investigation aimed to evaluate the efficiency of coffee silverskin (CS), CS ash (CSA) and nanoparticles of CS (NCS) in regeneration the quality of used frying palm oil. The adsorbents were mixed individually with used frying palm oil at level 4% (w/v) for 60 min. The properties of CS, CSA and NCS adsorbents were studied using (SEM) scanning electron microscopy technique. Some of physico-chemical characteristics of used frying palm oil (UFPO) and UFPO treated with adsorbents were determined. The results showed that the CS ash particles composed of irregular spherical and semispherical grains with deep cavities. The size of particles of CS ash ranged in diameter from 1.1 to 1.7 µm. The morphology of NCS consisted of cluster-type spherical nanoparticles and flakes. The particle size of NCS varies from 0.9 to 1.7 µm. Purification treatments caused marked (p<0.05) increases in the quality parameters of treated oil compared to untreated oil. The treatment of UFPO with 4% of adsorbents caused significant reductions in the content of free fatty acids ranged from 51.2 to 65.0%. The lowest level of peroxide (2.1 meq/kg) was recorded for UFPO treated with 4% of NCS. The highest reductions (72.8; 70.0%) in p-anisidine value were observed in UFPO treated with 4% of CSA and NCS, respectively. Treatment of UFPO with 4% of CS, CSA and NCS significantly lowered the polar content from 13.9% to 6.3, 4.8 and 3.9%, respectively. The results also indicate that CSA and NCS have nearly the same adsorption efficiency in lowering polymer content of UFPO. Filtration treatment of UFPO with 4% of CS, CSA and NCS markedly lowered the viscosity and colour values of treated UFPO.

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  • Mouna Ben Rached, Gianni Galaverna, Martina Cirlini, Dalenda Boujneh, ...
    Volume 66 (2017) Issue 8 Pages 907-915
    Released: August 01, 2017
    [Advance publication] Released: July 12, 2017
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    The aim of this study examined the characterization of extra virgin olive oil samples from the main cultivar Chemlali, grown in five olive orchards with different soil type (Sandy, Clay, Stony, Brown, Limestone and Gypsum). Volatile compounds were studied using headspace-solid phase micro-extraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS) technics. Moreover, the sterol profile was established using gas chromatography-mass spectrometry. 35 different volatile compounds were identified: alcohols, esters, aldehydes, ketones and hydrocarbons. The chemical composition of the volatile fraction was characterized by the preeminence of 2-hexenal (32.75%) and 1-hexanol (31.88%). Three sterols were identified and characterized. For all olive oil samples, ß-sitosterol (302.25 mg/kg) was the most abundant sterol. Interestingly, our results showed significant qualitative and quantitative differences in the levels of the volatile compounds and sterols from oils obtained from olive trees grown in different soil type.

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Nutrition and Health Function
  • Shuhei Nishimura, Makoto Inai, Tetsuo Takagi, Yudai Nonaka, Shogo Uras ...
    Volume 66 (2017) Issue 8 Pages 917-924
    Released: August 01, 2017
    [Advance publication] Released: July 12, 2017
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    Previous studies have shown that medium-chain triacylglycerols (MCTs) exert favorable effects on protein metabolism. This study evaluated the effects of the dietary intake of MCTs on rat skeletal muscle mass and total protein content during casting-induced hindlimb immobilization, which causes substantial protein degradation and muscle atrophy. Rats were fed a standard diet containing long-chain triacylglycerols (LCTs) or MCTs for 3 days and then a unilateral hindlimb was immobilized while they received the same diet. After immobilization for 3, 7, and 14 days, muscle mass and total protein content in immobilized soleus muscle in the LCT-fed rats had markedly decreased compared to the contralateral muscle; however, these losses were partially suppressed in MCT-fed rats. Autophagosomal membrane proteins (LC-I and -II), which are biomarkers of autophagy-lysosome activity, did not differ significantly between the LCT- and MCT-fed rats. In contrast, the immobilization-induced increase in muscle-specific E3 ubiquitin ligase MuRF-1 protein expression in immobilized soleus muscle relative to contralateral muscle was completely blocked in the MCT-fed rats and was significantly lower than that observed in the LCT-fed rats. Collectively, these results indicate that the dietary intake of MCTs at least partly alleviates immobilization-induced muscle atrophy by inhibiting the ubiquitin-proteasome pathway.

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Chemistry and Organic Synthesis
  • Refat El-Sayed, Meshal H. K. Almalki
    Volume 66 (2017) Issue 8 Pages 925-938
    Released: August 01, 2017
    JOURNALS FREE ACCESS

    The aim of this study is a synthesis of new bioactive heterocyclic compounds incorporated fatty chain for use in different industrial applications. Cyanoacetamide derivative (2) was successfully transferred into five and six membered heterocyclic derivatives by the reaction with various chemical reagents. Addition number of moles of propylene oxide to these compounds gave nonionic surface-active agents having a good solubility, biodegradability and hence lowers the toxicity to human beings and becomes environmentally friendly. The antimicrobial and surface activities were investigated that showed the most of them have pronounced activity, which makes them suitable for diverse applications like the manufacturing of drugs, pesticides, emulsifiers, cosmetics, etc.

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