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  • 小田切 孝人, 田代 眞人
    ウイルス
    2013年 63 巻 2 号 233-240
    発行日: 2013/12/25
    公開日: 2014/10/31
    ジャーナル フリー
  • Cbesseredes HORTS
    Journal of Human Ergology
    1982年 11 巻 Supplement 号 429-440
    発行日: 1982/12/15
    公開日: 2011/02/23
    ジャーナル フリー
  • Katsuaki SHIRAI, Takeo SAKAI, Momo FUKUDA, Tatsuya OIKE
    Journal of Veterinary Medical Science
    1998年 60 巻 3 号 291-293
    発行日: 1998年
    公開日: 2001/10/06
    ジャーナル フリー
    A monoclonal antibody,
    6
    E
    9
    established from mice injected with dolphin peripheral blood lymphocytes (PBLs) was characterized. In addition to its reactivity against
    89
    .
    4
    % of dolphin PBLs,
    6
    E
    9
    reacted with 33.
    1
    % of bovine PBLs of which
    22
    % were CD
    5
    +, 11.
    1
    % were
    CD5
    -.
    6
    E
    9
    recognized a 34 kD protein on the surface of dolphin and bovine PBLs. Analysis of the protein's N-terminal amino acid sequence indicated that
    6
    E
    9
    recognizes bovine major histocompatibility complex (MHC) class II antigens. These results suggested that
    6
    E
    9
    recognized MHC class II antigens on bovine PBLs. As we have already produced an anti-dolphin MHC class I monoclonal antibody, analysis of immune system using these monoclonal antibodies will advance our understanding of the evolution of the mammalian immune system.
  • George W. Lee
    燃料協会誌
    1973年 52 巻 3 号 171-177
    発行日: 1973/03/20
    公開日: 2010/06/28
    ジャーナル フリー
  • LIVIO SIROVICH
    地盤工学会論文報告集
    1996年 36 巻 4 号 23-34
    発行日: 1996/12/15
    公開日: 2008/02/29
    ジャーナル フリー
    Repetitive liquefactions in angular and subangular gravels from an alluvial fan, in the case of two earthquakes with accelerations lower than that of a former which had caused liquefaction some months before, are described. The liquefaction took place from the surface, down to a depth of approximately 10 m. Water laden with sediments spouted out for some tens of minutes after the strong motion ceased. Knowledge of the grain size distribution of the sediments inside the body of the alluvial fan roughly defines the areas of the fan prone to future liquefaction. Non-repetitive liquefaction in overconsolidated fine fluvio-lacustrine sand of glacial origin at the unusual depth of 14 m to 16 m is also described. From the observation of sand lifted up for 10 m inside a large diameter well, and of that which spouted out from several microvents, it was estimated that extra-pore pressure was close to lithostatic conditions. Nevertheless, modeling of intrinsic pore pressure buildup on the DESRA2 programme gives lower values than the experimental one. Geotechnical characteristics of the 12 m-thick sandy stratum indicate that the upper part is unusually soft, either due to water circulation or past repetitive liquefactions which prevented reconsolidation. It is suggested that excess pore pressure generated by the earthquake was also due to redistribution of pressure from adjacent sediments.
  • Mohd Suhail, Mohd Faizul Suhail, Hina Khan
    Journal of Clinical Biochemistry and Nutrition
    2008年 43 巻 3 号 210-220
    発行日: 2008年
    公開日: 2008/10/31
    ジャーナル フリー
    We compared three groups of pregnant women: placebo with normotensive women, group A which included preeclamptics, and group
    B
    which comprised preeclamptics who were supplemented their diets with vitamins
    C
    and
    E
    . MDA increased from
    6
    .
    22
     ± 2.
    8
    (placebo) to
    8
    .48 ± 
    1
    .2 (A) and
    8
    .02 ± 
    1
    .
    8
     nmol/gHb (
    B
    ). NO concentrations were enhanced from 19.3 ± 
    4
    .2 (P) to 23.
    8
     ± 
    6
    .
    4
    (A) and 24.
    1
     ± 
    5
    .
    4
     μmol/L (
    B
    ). GSH contents were decreased from 10.42 ± 2.81 (P) to
    8
    .02 ± 2.92 (A) and
    9
    .39 ± 
    1
    .02 μmol/g Hb (
    B
    ), whereas GSSG concentrations increased from 0.98 ± 0.28 (P) to
    1
    .24 ± 0.29 (A) and
    1
    .08 ± 0.12 μmol/g Hb (
    B
    ). SOD activity decreased 23% in A and 14% in
    B
    ; GRx decreased 27% in A and
    5
    .
    5
    % in
    B
    ; GPx decreased 12% in A and
    9
    .
    6
    % in
    B
    . Catalase activity, however, increased 27% in A and 29% in
    B
    as compared to control. Thus, we conclude that the use of vitamins
    C
    and
    E
    should be considered for the control of certain important biochemical indices during the development of preeclampsia; however, further studies are needed to develop methods for the prevention of preeclampsia in women at high risk.
  • 香山 滉一郎, 森下 政夫, 張 国鋒
    粉体および粉末冶金
    2006年 53 巻 5 号 419-429
    発行日: 2006年
    公開日: 2006/12/19
    ジャーナル オープンアクセス
    The phase diagrams of the Ni-Mo-
    B
    and Ni-W-
    B
    ternary systems in the region of less than 50mol%
    B
    were constructed by thermodynamic calculation, based on the data obtained by thermodynamic measurement of the related materials. We found three ternary eutectic points and three or two ternary peritecto-eutectic points as follows:
    E1
    :L (1365K, 71.
    5
    mol%Ni-
    6
    .0mol%Mo-
    22
    .
    5
    mol%
    B
    )=(Ni)+
    Ni3B
    +
    NiMo2B2

    E2
    :L (1355K, 62.
    5
    mol%Ni-2.
    5
    mol%Mo-30.
    5
    mol%
    B
    )=
    Ni3B
    +
    Ni2B
    +
    NiMo2B2

    E3
    :L (1445K, 42.0mol%Ni-30.
    6
    mol%Mo-10.3mol%
    B
    )=(Ni)+NiMo+
    NiMo2B2

    P1
    :L (1812K, 34.
    9
    mol%Ni-42.3mol%Mo-
    22
    .
    8
    mol%
    B
    )+MoB=
    Mo2B
    +
    NiMo2B2

    P2:L (1633K, 42.3mol%Ni-40.
    4
    mol%Mo-17.3mol%
    B
    )+Mo=
    Mo2B
    +
    NiMo2B2

    P3:L (1812K, 53.
    5
    mol%Ni-33.7mol%Mo-12.
    8
    mol%
    B
    )+Mo=NiMo+
    NiMo2B2

    E1
    :L (1622K, 51.0mol%Ni-31.
    6
    mol%W-17.
    4
    mol%
    B
    )=(Ni)+W+
    NiW2B2

    E2
    :L (1260K, 71.0mol%Ni-7.0mol%W-
    22
    .0mol%
    B
    )=(Ni)+
    Ni3B
    +
    NiW2B2

    E3
    :L (1291K, 65.
    4
    mol%Ni-
    4
    .
    8
    mol%W-29.
    8
    mol%
    B
    )=
    Ni2B
    +
    Ni3B
    +
    NiW2B2

    P1
    :L (2115K, 23.
    8
    mol%Ni-43.
    1
    mol%W-33.
    1
    mol%
    B
    )+WB=
    W2B
    +
    NiW2B2

    P2:L (1657K, 48.
    9
    mol%Ni-33.
    1
    mol%W-18.0mol%
    B
    )+
    W2B
    =W+
    NiW2B2

    The calculated phase diagrams are expected to be useful for the development of new Ni-based heat-, corrosion- or wear-resistance alloys.
  • 小林 優, V. Anjaneyulu, M. M. Krishna
    天然有機化合物討論会講演要旨集
    1993年 35 巻 78
    発行日: 1993/09/10
    公開日: 2017/08/18
    会議録・要旨集 フリー
    Five new marine
    C
    _<29> sterols (2-
    6
    ) were isolated from the soft coral Sinular ia mayi of the Ishigaki Island, Okinawa. The Spectrosocpic data showed that they are the polyhydroxy derivative of sarcosterol (
    1
    ), a marine sterol having a unique 23-methyl and a 17(20)
    E
    -double bond. Sterol 2 was the 25-monohydroxy derivative of
    1
    . The NOE experiment of its 25, 26-didehydro derivative indicated that the stereochemistry at
    C
    -23 and 24 was identical with that of peridinosterol, whose absolute configuration has previously been established. Sterol 3 was the 25,26-dihydroxy derivative of
    1
    . It was converted to 2 by reductive cleavage of the
    C
    -26 tosyloxy bond by LAH. Sterols
    5
    and
    6
    were shown, by spectroscopic analyses, to be
    22
    , 25-dihydroxy and
    22
    ,23,25-trihydroxy derivatives of
    1
    . The stereochemistry in the side chain was derived from interpretation of the coupling pattern and the results obtained by NOE experiments. On storage sterol
    5
    was found to be converted, by dehydration, to sterol
    4
    having a tetrahydrofuran ring on the side chain Two new cembranoids sinulariol
    E
    (7) and mayolide
    E
    (
    8
    ), simultaenously isolated from S. mayi, were correlated to the known compounds sinulariol A (
    9
    ) and mayolide
    B
    (10) by dehydration. The pyridine-induced deshielding effects, observed in the ^
    1
    H NMR spectra of
    8
    and 10-12, indicated that the absolute configuration at
    C
    -
    8
    of
    8
    to be (R) and that of 10-12 to be (S). A new polyhydroxygorgostane (15) was obtained from the Andaman Sea soft coral Lobophytum strictum. The structure was derived, by spectroscopic data. to be
    1
    β-hydroxy-
    9
    -deoxy derivative of the known compound andamansterol.
  • Suguru TAKATSUTO, Kiyomi KOBAYASHI, Tsuyoshi WATANABE, Hiroki KURIYAMA, Tokuo FURUSE
    Agricultural and Biological Chemistry
    1988年 52 巻 12 号 3217-3218
    発行日: 1988年
    公開日: 2006/04/05
    ジャーナル フリー
  • 廣谷 正男, 金子 麻美, 廣谷 聖子, 浅田 善久, 吉川 孝文
    天然有機化合物討論会講演要旨集
    2000年 42 巻 48/P-13
    発行日: 2000/10/01
    公開日: 2017/08/18
    会議録・要旨集 フリー
    Agaricus blazei is an important fungus for producing bioactive compounds. There are some reports of polysaccharides and steroid derivatives from the fruiting bodies of A. blazei. However, the chemical examination of the secondary metabolites of the cultured mycelia of this species has not been reported. Eight compounds, an unprecedented skeleton have been isolated from the cultured mycelia of A. blazei. The structures of the novel compounds each named blazeispirols A (
    1
    ),
    B
    (2),
    C
    (3), D (
    4
    ),
    E
    (
    5
    ) X(
    6
    ), Y (7) and Z (
    8
    ) were confirmed by extensive
    1
    D and 2D NMR spectral data and X-ray analysis. Blazeispirols A (
    1
    ),
    B
    (2),
    C
    (3), D (
    4
    ) and
    E
    (
    5
    ) were des-A-ergostane type compounds having spiroacetal structure as a side chain. Blazeispirols X (
    6
    ) and Y (7) were determined to be (20S,
    22
    S, 23R, 24S)-
    1
    (10→
    6
    ) abeo-14β,
    22
    :
    22
    , 25-diepoxyergosta-
    5
    ,7,
    9
    ,11-tetraene-3α,23-diol and (20S,
    22
    S, 23R, 24S)-14β,
    22
    :
    22
    ,25-diepoxy-
    9
    ,23-dihydroxyergosta-
    4
    ,7,11-triene-3,
    6
    -dione by comparison of extensive
    1
    D and 2D NMR spectral data with that of blazeispirol A. The biosynthesis of blazeispirol A was investigated by feeding ^<13>
    C
    -labeled acetates and methionine to the growing cultures of A. blazei. The labeling patterns of
    1
    derived from singly and doubly ^<13>
    C
    -labeled acetates were consistent with that of ergosterol reported previously except for the A-ring and then ^<14>
    C
    -labeled ergosterol was incorporated into blazeispirol A. Taking the structures of blazeispirols Z and D into consideration, it can be assumed that blazeispirol A is biosynthesized from ergosterol by the cleavage of
    C
    -
    4
    ,
    C
    -
    5
    and
    C
    -
    1
    ,
    C
    -10 bonds on retro aldol condensation and Michael reaction via such as intermediate A as shown in Fig.
    4
    . A large number of ergostane-type steroids have been isolated from many fungi. However, blazeispirol A is the first example of a naturally occurring des-A-ergostane-type steroid including a spiroacetal structure moiety as a side chain.
  • Özkan ASLANTAŞ, Ebru Şebnem YILMAZ
    Journal of Veterinary Medical Science
    2017年 79 巻 6 号 1024-1030
    発行日: 2017年
    公開日: 2017/06/16
    [早期公開] 公開日: 2017/04/27
    ジャーナル フリー

    This study aimed to determine the prevalence of fecal carriage of extended spectrum β-lactamase (ESBL) and/or plasmidic AmpC β-lactamase (pAmpC) producing Escherichia coli among dogs (n=428) in Turkey. Polymerase chain reaction (PCR) and sequencing were used to characterize genes encoding β-lactamase and plasmid mediated quinolone resistance (PMQR). Antimicrobial susceptibility testing and PCRs for virulence genes and phylogenetic groups were also performed. Cefotaxime resistant

    E
    . coli isolates were detected in 95 (
    22
    .2%) of the swab samples. Sequencing analysis results showed occurrence of various β-lactamase genes: blaCTX-M-15 (62), blaTEM-
    1b
    (42), blaCMY-2 (
    22
    ), blaCTX-M-3 (16), blaCTX-M-
    1
    (15), blaOXA-
    1
    (
    9
    ) and blaSHV-12 (3) alone or in combination. The most frequently encountered phylogenetic group was group
    A1
    (35.
    8
    %), followed by group D2 (
    22
    .
    1
    %),
    B
    1
    (15.
    8
    %),
    D1
    (
    9
    .
    5
    %), A0 (7.
    4
    %),
    B22
    (
    5
    .3%) and
    B23
    (
    4
    .2%), respectively. PMQR genes, aac(
    6
    ’)-Ib-cr,
    qnrS1
    and qnrB10 were detected in 25.3, 10.
    5
    and
    1
    .
    1
    % of the isolates, respectively. While all isolates were susceptible to imipenem and amikacin, resistance rates to non-β-lactam antibiotics ranged from 20.0% for tobramycin to 56.
    8
    % for tetracycline. The virulence genes were only detected in 34 (36.2%) of the isolates and this isolates carried single or various combination of virulence genes of iucD, papC, papE, f17a-A and eaeA. Four isolates were identified as human virulent pandemic CTX-M-15 producing
    E
    . coli
    clone O25
    b
    :ST131/
    B
    2. To the best of our knowledge, this is the first study to show fecal carriage of ESBL/pAmpC type β-lactamase producing
    E
    . coli
    isolates among dogs in Turkey.

  • FRANÇOIS LE GOFFIC, FRÉDÉRIC TANGY, BERNARD MOREAU
    The Journal of Antibiotics
    1979年 32 巻 12 号 1288-1292
    発行日: 1979年
    公開日: 2006/04/12
    ジャーナル フリー
    A sample of [3H] tobrarnycin (
    5
    , 000 Ci/Mole) has been synthetized and incubated with
    the bacterial ribosome and its subunits. The results obtained show that this antibiotic has
    two types of binding sites. The primary one is probably responsible for the inhibition of
    protein synthesis whereas the secondary one is probably related to the misreading and reading
    tiirough of the messenger RNA.
  • Grover Loening
    日本航空学会誌
    1963年 11 巻 119 号 373-380
    発行日: 1963年
    公開日: 2009/05/25
    ジャーナル フリー
  • 黒川 美貴雄, 吉田 耕治, 永井 保嵩, 宇野 準
    Chemical and Pharmaceutical Bulletin
    1983年 31 巻 12 号 4312-4318
    発行日: 1983/12/25
    公開日: 2008/03/31
    ジャーナル フリー
    Two new partially saturated tricyclic ring systems,
    6
    ,
    6
    a, 7,
    8
    ,
    9
    , 10, 10a, 11-octahydro-11-oxodibenz [
    b
    ,
    e
    ] oxepins (3a and 3
    b
    ), and -thiepins (
    4
    a and
    4
    b
    ) were synthesized. Compounds
    4
    a and
    4
    b
    were desulfurized to give a pair of isomeric 2-methylbenzoylcyclohexanes (10a and 10
    b
    ). Deuterated
    4
    a and
    4
    b
    (11a and 11
    b
    ) were prepared starting from butadiene-
    d6
    (12). The stereochemical features of 3a (trans), 3
    b
    (cis),
    4
    a (trans) and
    4
    b
    (cis) are compared with those of 10a, 10
    b
    , 11a and 11
    b
    on the basis of proton nuclear magnetic resonance data.
  • Ichiro KAWASAKI, Fujitoshi KON'NO
    Journal of Physics of the Earth
    1984年 32 巻 3 号 229-244
    発行日: 1984年
    公開日: 2009/04/30
    ジャーナル フリー
    The group velocities of surface waves in the period range
    22
    -
    89
    s were measured to retrieve the anisotropy pattern of the surface wave velocities in the Eastern Pacific Ocean. WWSSN long period records at KIP, Hawaii, from ridge events in the Gulf of California, the East Pacific rise, and the Easter Island Cordillera were used to cover propagation directions N60°
    E
    -N140°
    E
    . These station and epicenters are in very favorable positions to minimize the effects of the lateral heterogeneity owing to ocean floor ages. The fast direction of the Rayleigh wave group velocity is normal to ridge, showing 3-
    5
    % azimuthal anisotropy. The Love wave group velocity shows little azimuthal anisotropy. A model of a possible type of preferred orientation of constituent olivine beneath the Pacific Ocean is proposed, based on the elastic constants and the petrofabrics of dunite from Hidaka, Hokkaido, Japan, and that of olivine nodules in the ophiolite complex from the Bay of Islands and Oman. In this model, a-axis is concentrated along a particular direction and
    b
    - and
    c
    -axes form a girdle. Elastic constants of the model are
    C11
    =2.44,
    C22
    =
    C33
    =2.05,
    C12
    =
    C13
    =0.72,
    C23
    =0.67,
    C44
    =0.69, and
    C55
    =
    C86
    =0.75 (1012 dyn·cm), where
    X1
    -axis, or the direction of the a-axis concentration, is normal to ridge and X3-axis is vertical. If we assume that the type of the preferred orientation is an age-independent property of suboceanic lithosphere, this model can explain the overall features of the large-scale anisotropy in the Pacific Ocean: the azimuthal anisotropy of surface wave velocities as described above; the SH-SV anisotropy of surface waves of about 0.15 km/s; the Pn, anisotropy of 7.
    9
    km/s to
    8
    .
    6
    km/s; the high Sm, velocity of about
    4
    .
    8
    km/s; and the ScS polarization anisotropy
  • 宮本 富美子, 直木 秀夫, 納谷 洋子
    天然有機化合物討論会講演要旨集
    1979年 22 巻 11
    発行日: 1979/09/20
    公開日: 2017/08/18
    会議録・要旨集 フリー
    Examination of the secreted wax of a scale insect, Ceroplastes ceriferus has shown the presence of various compounds of considerable biogenetic interest. (a) The sesquiterpenes were enantiomeric with respect to those from
    C
    . rubens, which infests the same host tree. Each insect may possess a specific set of
    C
    -
    C
    cyclases for the formation of sesquiterpenes. (
    b
    ) Among the identified twelve diterpenes, two of labdane skeletons were the first naturally occurring compounds. (
    c
    ) The sesterterpenes (
    1
    -
    6
    )(7-10) having 14-membered monocyclic skeletons were the first naturally occurring compounds being independent of the host tree. Remarkable is the finding of sesterterpenes resulting from different biogenetic cyclization mode from the same species, collected in different districts, or from the different species of the same genus. (d) The "cyclic" wax were the esters consisting of fatty acids (
    C
    _<10>-
    C
    _<32>) and unusual cyclic alcohols (diterpenes and sesterterpenes). Structures and stereochemistry of nine new sesterterpenes will be discussed on the basis of spectroscopic and chemical methods: Cericerol-I (
    1
    ), cericerol-II (2), 13-methoxy cericerene (3), 13-ethoxy cericerene (
    4
    ), α-cericerol-I (
    5
    ), cericeroic acid (
    6
    ), 18-dihydro-19-ol cericeroic acid (7), cericera-2(
    E
    ),
    6
    (Z),10(
    E
    ),15(
    22
    ), 18-pentene-25-acid (
    8
    ), cericera-2(
    E
    ),
    6
    (Z),10(
    E
    ),15(
    22
    ), 18-pentene-24-acid (
    9
    ), and cericerene-15,24-diol (10). Possibility of the configurational isomers for the structures (
    8
    )and (
    9
    ) at the position
    C
    -24 and
    C
    -25 are still remained to be elucidated. Bridged hydrocarbon (16) which was obtained by acid treatment of tosylate of cericerol-I (
    1
    ) indicated the crown shape (A) for (
    1
    ).
  • ―特にアポ蛋白Eの変化について―
    本間 康彦, 三神 美和, 佐藤 美智子, 石原 仁一, 吉川 広, 木下 栄治, 田川 隆介, 星合 充基, 古屋 秀夫, 井出 満, 田辺 晃久, 玉地 寛光, 兼本 成斌, 友田 春夫, 中谷 矩章, 五島 雄一郎
    動脈硬化
    1984年 12 巻 3 号 599-603
    発行日: 1984/08/01
    公開日: 2011/09/21
    ジャーナル フリー
    Seven hundred fifty mg of cholesterol were fed daily to 32 patients of the ischemic heart disease (IHD) for 2 weeks. Cholesterol amounts in VLDL, LDL, HDL, HDL2 and HDL3 were estimated on the 0th, 7th and 14th days of cholesterol load. Plasma apoprotein A-I, A-II,
    B
    ,
    C
    -II,
    E
    levels were also measured in 16 from 32 IHD subjects. Apoprotein levels were estimated by a method of single radial immunodiffusion (SRID). Before cholesterol administration, cholesterol amounts in VLDL, LDL, HDL, HDL2 and HDL3 were 15.
    9
    ±7.
    5
    mg/dl (mean±SD), 150.
    9
    ±58.
    1
    mg/dl 43.
    8
    ±
    9
    .
    6
    mg/dl, 16.
    4
    ±
    5
    .
    8
    mg/dl and 24.
    9
    ±
    6
    .3mg/dl respectively. Plasma apoprotein A-I, A-II,
    B
    ,
    C
    -II and
    E
    levels were 81.7±
    22
    .0 mg/dl, 15.
    1
    ±
    5
    .
    4
    mg/dl, 93.7±36.0mg/dl, 3.83±
    1
    .00mg/dl and
    4
    .29±
    1
    .36mg/dl respectively. After 2 weeks' cholesterol feeding, all plasma lipoprotein cholesterol and apoprotein levels did not change significantly. Correlation coefficients between plasma apoprotein and lipoprotein cholesterol levels were calculated. Apoprotein A-I and A-II correlated with HDL-
    C
    (r=0.348), HDL2-
    C
    (r=0.612) and HDL3 (r=0.569). Apoprotein
    B
    correlated with total cholesterol (TC) (r=0.610), VLDL-
    C
    (r=0.341), LDL-
    C
    (r=0.726), HDL-
    C
    (r=0.432) and HDL2-
    C
    (r=0.465). Apoprotein
    C
    -II correlated with TC (r=0.765), TG (r=0.679), VLDL-
    C
    (r=0.651), LDL-
    C
    (r=0.461) and HDL2-
    C
    (r=0.326). Apoprotein
    E
    correlated with TC (r=0.580), TG (r=0.575) and VLDL-
    C
    (r=0.666). Interapoprotein's correlations were also calculated. Apoprotein A-I correlated with apoprotein A-II (r=0.468). Apoprotein
    B
    correlated with apoprotein
    C
    -II (r=0.393). Apoprotein
    C
    -II correlated with apoprotein
    B
    (r=0.393) and
    E
    (r=0.549). Apoprotein
    E
    only correlated with apoprotein
    C
    -II (r=0.549).
  • *森元 陽子, 川原 幸一, 菊池 清志, 松山 孝司, 中島 結実子, 小薗(藤崎) 清香, 町頭 三保, 丸山 征郎, 和泉 雄一
    会議録・要旨集 フリー
  • 小林 優, 家坂 貴子, 中野 江身子, 平山 耕一郎
    天然有機化合物討論会講演要旨集
    1989年 31 巻 71/P2-1
    発行日: 1989/09/17
    公開日: 2017/08/18
    会議録・要旨集 フリー
    Six new cembranoids sarcophytol P (3), R (
    4
    ), S (
    5
    ), K (
    8
    ), F (11), and T (13) were isolated from the soft coral Sarcophyton glaucum. Sarcophytol P (3) was shown to be the 20-hydroxy derivative of the major component sarcophytol A (
    1
    ), and afforded the cyclization product
    6
    in CHCl_3 at room temperature, in a same way as in
    1
    . Sarcophytols R (
    4
    ) and S (
    5
    ) were correlated to
    1
    , by conversion of its 7R,
    8
    R and 7S,
    8
    S epoxide derivatives. Sarcophytol K(
    8
    ) was a 13, 14-dihydroxycembranoid having a
    1
    E
    ,3Z-diene moiety. The absolute configuration of
    8
    and its
    1
    Z,3
    E
    - and
    1
    Z,3Z-isomers sarcophytol
    B
    (2) and J (10) were determined by circular dichroism study of their bis-p-dimethylaminobenzoate derivatives. Sarcophytols F (11) and T (13) were
    1
    E
    - and
    1
    E
    ,3Z-isomers of
    1
    . Compound 11 showed characteristic broadening of the ^
    1
    H-NMR chemical shifts, due to the restricted conformational interconversion. Using the three cembranoids sarcophytols F (11,
    1
    E
    ,3
    E
    ), N (15,
    1
    Z,3Z) and T (13,
    1
    E
    ,3Z), spontaneous autoxidation-cyclization, in CHCl_3,was examined, in order to compare the stereochemical course of the reaction with that of
    1
    (
    1
    Z,3
    E
    ), which affords trans-fused bicyclo[
    9
    .3.0]tetradecene systems. The
    1
    E
    ,3Z-isomer 13 gave the same cyclization product 18, as in the reaction of
    1
    , even though it is isomeric at
    C
    -
    1
    ,3. The
    1
    Z,3Z isomer 15 gave 19, in consequence of the reversed geometry at
    C
    -3 of 15. The
    1
    E
    ,3
    E
    -isomer (11) gave the bicyclic product
    22
    , having an antipodal fusion as compared with 19. This was confirmed by PCC oxidation of 19 and
    22
    , giving enantiomeric ketones 23 and 24 respectively. The
    1
    (14)-epoxide 26 was shown to be the immediate precursor of
    22
    , and acounted for the inversion of the geometry at
    C
    -
    1
    of the cyclization product. Compound 26 is isomeric with the epoxide 17 derived from
    1
    . The epoxide 17 is the postulated precursor in the conversion of 13 to 18. It is noteworthy that the mode of antipodal fusion of the cyclopentane rings, in 18 and
    22
    , was controlled by the chirality of the epoxy rings. The
    C
    -14 hydroxyl group participates in the transannular cyclization, but was found not to be the requisite functional group for the reaction. Similar treatment of cembrene
    C
    (30), the parent hydrocarbon of
    1
    , also reacted in CHCl_3 giving the bicyclic product 32.
  • Yasunori YAOITA, Keiko AMEMIYA, Hiroyuki OHNUMA, Katsuyuki FURUMURA, Akihiro MASAKI, Toshihiko MATSUKI, Masao KIKUCHI
    Chemical and Pharmaceutical Bulletin
    1998年 46 巻 6 号 944-950
    発行日: 1998/06/15
    公開日: 2008/03/31
    ジャーナル フリー
    Eight new sterols,
    ,
    -epidioxy-(
    22
    E
    , 24R)-23-methylergosta-
    6
    ,
    22
    -dien-3β-ol (
    1
    ), 3β,
    ,
    -trihydroxy-(
    22
    E
    , 24R)-23-methylergosta-7,
    22
    -dien-
    6
    -one (2), 3β,
    ,
    -trihydroxy-(24S)-ergost-7-en-
    6
    -one (3), 3β,
    ,
    , 14α-tetrahydroxy-(
    22
    E
    , 24R)-ergosta-7,
    22
    -dien-
    6
    -one (
    4
    ), (
    22
    E
    , 24R)-ergosta-7,
    22
    -diene-3β,
    ,
    ,
    -tetrol (
    5
    ),
    ,
    -epidioxy-3β-hydroxy-(
    22
    E
    , 24R)-ergosta-7,
    22
    -dien-
    6
    -one (
    6
    ),
    ,
    -epidioxy-3β-hydroxy-(24S)-ergost-7-en-
    6
    -one (7) and
    ,
    -epoxy-(
    22
    E
    , 24R)-ergosta-
    8
    ,
    22
    -diene-3β, 7β, 14α-triol (
    8
    ), have been isolated from five edible mushrooms, Lentinus edodes, Flammulina velutipes, Hypsizigus marmoreus, Pleurotus ostreatus and Pholiota nameko together with fifteen known ones (
    9
    -23), of which two (16 and 17) are reported for the first time from a fungal source. The structures of these new compounds were elucidated on the basis of their spectral data.
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