The saw dust from the trunk of Lyonia ovalifolia var. elliptica was extracted with methanol. The extract was concentrated, treated with benzene, and the benzene layer was examined by alumina column chromatography. The presence of 2-nonacosanone, taraxerone, taraxerol, β-sitosterol, and ursolic acid acetate were detected.

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Lyoniol-A (I), the main component of the toxic principles of Lyonia ovalifolia var. elliptica, was identified as lyoniatoxin.⁵⁾ The structure of lyoniol-A (lyoniatoxin) was concluded as (I) through the reactions shown in Fig. 3 and from the physical data of the reaction products. Alkaline hydrolysis of I gave deacetyllyoniol-A, a pentahydric alcohol, which was proved to be identical with lyoniol-B (II), a minor constituent. II formed monoacetonide (IV) which did not react with chromic acid. Thus, the remaining three hydroxyl groups must be tertiary. II consumed one mole of sodium periodate but I did not. Chromic acid oxidation of I gave a monoketone (III), which was believed to be a six or more membered cyclic ketone from its IR spectrum. These results and nuclear magnetic resonance (NMR) data of I, II, and III suggested that I has a partial structure of 〓C-CH (OAc)-CH (OH)-C〓. Lithium aluminum hydride reduction of I or II gave dihydrolyoniol-B (V), which was derived to its triacetate (VI) with acetic anhydride and pyridine. These reactions suggested that I has an epoxide ring in its molecule and the epoxide group was reduced to an alcoholic group. When V was treated with p-toluenesulfonic acid in acetone, dihydrolyoniol-B acetonide (VII), dihydrolyoniol-B anhydroacetonide-I (VIII), and dihydrolyoniol-B anhydroacetonide-II (IX) were produced. VII afforded monoacetate on mild acetylation. Chromic acid oxidation of IX gave a cyclopentanone derivative X. Thus, the epoxide ring must be situated in the cyclopentane ring. Because of a close relationship between the plant source and similarity in biological activity, lyoniol-A seems to have the same carbon skeleton and a very similar stereostructure as grayanotoxin-I⁸⁾ and rhodojaponin-II.⁹⁾ Thus, the structure of lyoniol-A should be represented by formula I. From the coupling constant of C₆-H and C₇-H, and specu lation about stereo models, it was concluded that C₆-H and C₇-H are trans and, therefore, the C₇-hydroxyl group must be in α-configuration. The structures of IX and VIII were assumed to be △^{10, 20}-ene-6, 7-acetonide (20-terminal methylene protones) and △^{15, 16}-ene-6, 7-acetonide (allyl coupling of 17-methyl), respectively.

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Lyoniside, β-sitosteryl β-D-glucoside, and monotropein and its methyl ester were isolated from the benzene-insoluble portion of the methanol extract of the wood of Tripetaleia paniculata SIEB. et ZUCC. The steric structure of lyoniresinol, the aglycone of lyoniside, was determined as formula (II) from the optical rotatory dispersion (ORD) and circular dichroism curves of its various derivatives (I, III to VI). The sugar moiety of lyoniside was determined as D(+)-xylose from the ORD curve of the sugar and from the gas-liquid chromatography of its trimethylsilyl ether, and the bonding was determined as β-linkage from the nuclear magnetic resonance spectrum of completely methylated compound. The position of sugar linkage was concluded as the methylol in 3-position from the hydrolysis of the completely methylated compound, followed by oxidation of the aglycone.

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In fresh leaves of Acanthopanax sciadophylloides FR. et SAV. collected in June, the following substances were identified : (-)-β-caryophyllene, trans-β-farnesene, phytol, 1-dotriacontanol, taraxerol, a mixture of stigmasterol and β-sitosterol, trans-p-coumaric acid, trans-p-coumaric acid methylester, afzerin, kaemferitrin, kaempferol 7-O-α-L-rhamnopyranoside, 3-O-β-D-galactopyranosyl kaempferol 7-O-α-L-rhamnopyranoside and quercetin 3, 7-O-bis-α-L-rhamnopyranoside. On the other hand, from the fresh leaves collected in August, trans-p-coumaric acid and kaempferol were obtained as aromatic compounds, but flavonoid glycosides were not detected. It is interesting that the constituents of these leaves were quite different between June and August.

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Dried flowers of Lyonia ovalifolia var. elliptica were successively extracted with benzene, acetone, and methanol. From the benzene extract were isolated hydrocarbons, alcohols, oleanolic acid, maslinic acid, and a new compound, which is now under investigation. From the acetone extract were isolated glucose, fructose, quercetin, hyperoside (quercetin 3-galactoside), an unidentified flavonoid, β-sitosterol, ursolic acid, and maslinic aicd. Sucrose was detected from the methanol extract.

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Silica gel column chromatography of the benzene extract of the wood of Tripetaleia paniculata showed the presence of a mixture of normal saturated higher hydrocarbons (C₂₇-C₃₄, a mixture of esters composed of normal saturated higher alcohols (C₂₄-C₃₀) and higher carboxylic acids (C₂₂-C₂₈), friedelin, epifriedelinol, oleanolic acid, ursolic acid, betulinic acid, and ursolic acid 3-O-p-hydroxy-trans-cinnamate (a new compound).

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A new compound (I), mp 184°, [α]²³_D+7.1°(c=1.0, CHCl₃), was isolated from the terpenoid fraction of the benzene extract of the leaves of Acanthopanax sciadophylloides. I was hydrolyzed by alkali to yield taraxerol and a mixture of higher fatty acids. The acidic fraction was methylated without purification and examined by gas chromatography. The main components of the mixture were methyl stearate (15.6%), arachidate (38.2%), behenate (20.8%), and lignocerate (16.5%), accompanied by a small amount of methyl esters of higher normal saturated fatty acids of C₂₁, C₂₃, C₂₅, C₂₆, C₂₈ and C₃₀^-. Taraxeryl stearate, arachidate, behenate, and lignocerate were synthesized from taraxerol and GLC- pure acids. IR spectra of the natural mixture and the synthesized pure compounds were almost identical but differed in the range of 1180-1350cm^-1, as shown in Fig. 1 and 2.

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コシアブラ若芽の抗酸化活性をβ-カロテン退色法とDPPHラジカル消去活性で評価したところ，高い活性を示した．主たる抗酸化成分は，クロロゲン酸と同定された．グロースチャンバー試験で，その成分含量に影響する要因を検討したところ，光が強く，穂木が長いと含量が高まることが示された．その結果に基づいて，好適な促成栽培技術を確立するため，ガラス室内で栽培条件が収量と抗酸化成分含量に及ぼす影響を検討した．促成栽培では，10～15℃の水に30～40 cmの穂木を挿すことによって，クロロゲン酸含量の多い若芽を収穫できた．

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　奈良時代に編纂され，雄大な国引き神話が載ることでも知られる『出雲国風土記』に記載されている山の高さは，実際の標高と大きく相違するケースが多い．そこで，現在の登山時間と風土記記載の山の高さの関係に着目して検討し，歩測（単位高さ×歩数）をもとにしている可能性が高いという結果を得た．

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In a previous work, a new compound, innovanoside, was extracted from the leaves of Evodiopanax innovans and the structure was concluded as maltol glucoside 6-cis-p-coumarate, which was converted by alkali to isoinnovanoside, maltol glucoside 6-trans-p-coumarate. The methyl ether of isoinnovanoside was synthesized from maltol glucoside via 2, 3, 4-tris(trimethyl)silyl ether and its p-methoxy-trans-cinnamate. Both the synthesized and natural isoinnovanoside methyl ether consumed two moles of sodium periodate but innovanoside methyl ether consumed only one mole of periodate. Thus the position or the acid group in innovanoside must be 2 or 4 in sugar moiety. Since acylmigration from 4-to 6-position by alkali is well known, the structure of innovanoside should be revised as maltol glucoside 4-cis-p-coumarate. From the water-soluble part of the methanol extract of the leaves scyllitol, quinic acid, and syringin were also isolated.

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　『出雲国風土記』には，各郡の代表的な山の位置・高さ・周長が記述されている．このうち秋鹿郡の山について，実際の地理との照合を試みた．郡家及び登山口の位置，両地点間を結ぶルート，山の周長の測線等いずれも不明であったので，それらを推定した上で，風土記記述のほとんどの事項が現地と整合することを確認した．

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The benzene-soluble part of the methanol extract of the red shoots of Lyonia ovalifolia var. elliptica was treated by alumina column chromatography and following substances were isolated : Nonacosane, 2-nonacosanone, 1-tetracosanol, β-sitosterol, taraxerol, betulin 3-acetate, oleanolic acid, and ursolic acid. The crude nonacosane was examined through gas chromatography and it was found to be contaminated with a small amount of pentacosane, hexacosane, heptacosane, octacosane, triacontane, and hentriacontane. Betulin 3-acetate, mp 263°, was newly found as one of the natural products, and identified with the partially hydrolized product of betulin diacetate. The isomeric substance, betulin 28-acetate, mp 218.5°, a new compound, was synthesized by partial acetylation of betulin, which was obtained from the bark of Betula platyphylla var. japonica.

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In the previous paper, it was reported that kaempferitrin, antoside, myoinositol and scyllitol were isolated from the leaves of Acanthopanax sciadophylloides and the constituents were different according to the districts where the materials came from. By further investigation, kaempferol 7-rhamnoside and quercetin 7-rhamnoside were isolated and the differences of the constituents were found to be quantitative ; in some cases, some of these compounds were detected only by paper chromatography as shown in Table I. The benzene extract of the leaves was examined by column chromatography. Hydrocarbons, dotriacontanol, 2-nonacosanone, taraxerol and a new compound, mp 184°, were isolated. The gas chromatogram of the hydrocarbons (Fig. 2) showed that the main component was nonacosane (77%) accompanied by heptacosane (1%), octacosane (4%), triacontane (8%), and hentriacontane (10%). It was concluded that hirsutrin was identical with isoquercitrin (quercetin 3-β-D-glucoside).

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