Lycopodium植物トリテルペノイドの化学分類学的研究
スポンサーリンク
概要
- 論文の詳細を見る
Fifty-one samples of Lycopodium plants (mostly Japanese species), including 17 species and 3 varieties, were collected and their triterpenoid constituents were examined firstly by comparing microchemically and then characterized by isolating them after alkaline hydrolysis. Discussions are made on thin-layer chromatography and chemotaxonomy of lycopodium triterpenoids, isolation and characterization of triterpenoids constituents, relationship between location of growth and the constituents, and relationship between species and the constituents. All the plants examined contained triterpenoids of serratane group or its assumed precursor, α-onocerin, the former including 13 new triterpenoids, 16-oxoserratenediol, 16-oxo-21-episerratenediol, 16-oxodiepiserratenediol, 16-oxoserratriol, 16-oxolycoclavanol, lycocryptol, 21-epilycocryptol, diepilycocryptol, lyclaninol, lyclanitin, 16-oxolyclanitin, lycernuic acid-A, and lycernuic acid-B, and two new glycosides of serratenediol and tohogenol. A new bisnortriterpenoid, clavatol, was isolated from L.clavatum. All these Lycopodium plants can be divided into three classes according to their major triterpenoids ; α-onocerin (L.clavatum, L.sitchense, L.obscurum, L.casuarinoides, L.inundatum), serratenediol (L.serratum, L.somae, L.cryptomerinum, L.chinense, L.sieboldii, L.fargesii, L.fordii, L.cernuum, L.phlegmaria), and 21-episerratriol (L.annotinum). Some of them (L.sitchense, L.annotinum, L.cernuum, and L.complanatum) showed variation in constituents depending on the locality of growth. Particularly, L.complanatum collected in Hokkaido contained α-onocerin as a major component, while the same plant from Taiwan did not contain α-onocerin but had 21-episerratriol as the major triterpenoid. Some plants of different species (cf. L.fargesii and L.fordii) were not distinguishable by their triterpenoid constituents suggesting their close relationship.
- 公益社団法人日本薬学会の論文
- 1974-08-25
著者
-
礒部 公明
昭和薬大
-
礒部 公明
Showa College of Pharmaceutical Sciences
-
小林 雅子
昭和薬科大学
-
藤本 琢憲
Showa College of Pharmaceutical Sciences
-
礒部 公明
昭和薬科大学
-
津田 喜典
昭和薬科大学
-
藤本 琢憲
昭和薬科大学
-
佐野 武弘
昭和薬科大学
関連論文
- クルクミン関連化合物の抗アレルギー作用 : マウスアトピー性皮膚炎モデルに対する抑制効果とその機序
- A Convenient Synthesis of Tertiary Amines by Alkylation of Secondary Amines with Alkyl Halides in the Presence of Potassium Hydride and Triethylamine
- Stereoselective Introduction of Oxygen Functionalities at the 11β-Position of Erythrinan Skeleton : Total Syntheses of (±)-Erythristemine and (+)-Erythrartine
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (5). Cyclization of Perhydro-2-epoxymethylene-6-oxo-6H-pyrido[2,1-i]indole-1-acetic Acid : Synthesis of 8-Oxoerythroidans
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids.(3). Synthesis of β-Erythroidine Skeleton (β-Erythroidan)
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (1). Synthesis and Isomerization of Unsaturated Bicyclic δ-Lactones
- 90(P04) β-エリスロイジンの合成研究(ポスター発表の部)
- ASYMMETRIC [2+2] PHOTOCYCLOADDITION REACTION OF A CHIRAL DIOXOPYRROLINE TO 2-(TRIMETHYLSILYLOXY)BUTADIENE : CHIRAL SYNTHESIS OF ERYTHRINA ALKALOIDS
- REARRANGEMENT OF 2,3-DIOXO-1,4-OXAZINES TO 4,5-DIOXOOXAZOLES IN THE REACTION WITH DIMETHYLSULFOXONIUM METHYLIDE
- Chiral Synthesis of Erythrina Alkaloids. I. Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure
- Synthesis of Highly Deydrogenated Oxoerythrinan Alkaloids, Erytharbine and Crystamidine
- Dioxypyrrolines. LV. Stereochemical Pathway of [2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Cycloalkadienes and Cycloalkenes
- Dioxopyrroline. LIV. Steretchemical Pathway of[2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Acyclic Olefins
- Dioxopyrrolines. LIII.Stereochemical Pathway of [2+2] Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Cyclic Enol Trimethylsilyl Ethers
- Synthesis and Reactions of 3,7-Cycloerythrinan : Skeletal Rearrangement of 2,7,8-Trioxoerythrinans to 4-Oxo-4H-pyrido[2,1,-a]isoquinolines
- Synthesis of Erythrina and Related Alkaloids.XXIV. Total Synthesis of Erysotrine from 1,7-Cycloerythrinan Derivatives by the Use of a New 1,2-Carbonyl Transposition Method
- Synthesis of Erythrina and Related Alkaloids. XXIII. : Intramolecular Cyclization Approach. (2). Synthesis and Reactions of 1,7-Cyclo-cis-erythrinans, Potential Intermediates to Natural Erythrina Alkaloids
- Synthesis of Erythrina and Related Alkaloids. XXII. : Intramolecular Cyclization Approach. (1) : New Synthetic Route to Erythrinan and Related Heterocycles and Synthesis of (±)-3-Demethoxy-erythratidinone
- Studies toward Total Synthesis of Non-aromatic Erythring Alkaloids. (6). Synthesis of 8-OXO-γ-erythroidine and 8-Oxo-cycloerythroidine, Isomers of the Natural Alkaloids.
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (4). Oxidation of Furan Ring of D-Furanoerythrinans with N-Bromoacetamide
- Photodecarboxylation of Arylacetic Acids
- Regioselective Introduction of a Methoxy Group at the Benzylic Position of Isochromane Derivatives by Cerium(IV) Oxidation in Methanol
- 43 リコリン及び関連アルカロイドの全合成
- Lycopodium Triterpenoids. (8). The Structures of Lycoclavanin, a Triterpenoid-tetraol Possessing Conjugated Ketone Chromophor, and a New Tetraol, Lyclaninol
- Triterpenoid Chemistry. VIII. : Stereospecific Reactions of Triterpenoid 1,3-Glycol Monotosylates and Ketotosylates
- 42 ヒカゲノカズラ中の16-Oxoserratene系トリテルペノイド
- 45 新しい数種のセラテン系トリテルペノイドの構造と相互関連
- 20 Lycoclavaninの構造 : 16-Oxoserratene系トリテルペノイドの相互関連とその部分合成
- Two New Morphinane Alkaloids from Stephania cepharantha HAYATA (Menispermanceae)
- Synthesis of Erythrina and Related Alkaloids. XXX. Photochemical Approach. (1). Synthesis of Key Intermediates to Erythrina Alkaloids by Intermolecular [2+2] Photocycloaddition Followed by 1,3-Shift
- Dioxopyrroline. L. Skeletal Rearrangements of 7-Vinyl-7-trimethylsilyloxy-5-ethoxycarbonyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-diones under Thermal, Basic, and Acidic Conditions
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (2). A General Method for Synthesis of Perhydro-6H-pyrido[2,1-i]indole Derivatives : Synthesis of Isoerythroidine Skeleton
- 誰にでもできる無水, 無酸素下の実験
- リコリンおよび関連アルカロイドの全合成
- Triterpenoid Chemistry. IX. Lycopodium Triterpenoid. (6). The Structures of Three New Tetra-ols, Lycocryptol, 21-Epilycocryptol, and Diepilycocryptol, and Two New Acids, Lycernuic Acid-A and -B
- Tritepenoid Chemistry. VII. Classification of Triterpenoid 1,3-Glycol Acetonides by NMR Spectra
- 25 ヒガンバナ科アルカロイドCrinamine,6-Hydroxycrinamine,Criwelline,およびMacronineの合成研究
- Lycopodium植物トリテルペノイドの化学分類学的研究
- 16 Haemanthamine,Haemanthidine,Tazettineの全合成 : 4,5-dioxo-Δ^2-pyrroline類のアルカロイド合成への利用
- [2+2] Photocycloaddition Reaction of 5-Arylfuran-2,3-diones to Trimethylsilyloxyethylenes
- Dioxopyrrolines. LXI. Cycloaddition Reaction of 4-Benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione with 1,3-Dienes : Competitive Occurrence of Normal and Hetero Diels-Alder Reaction and Claisen Rearrangement of the Hetero Diels-Alder Product
- Total Synthesis of Homoerythrinan Alkaloids, Schelhammericine and 3-Epischelhammericine
- Lycopodium Triterpenoids. (7). The Structures and Partial Syntheses of 16-Oxoserratenediol, 16-Oxo-21-episerratenediol, 16-Oxodiepiserratenediol, 16-Oxoserratriol, 16-Oxo-21-episerratriol, and 16-Oxolycoclavanol, α, β-Unsaturated Ketones of Serratane Grou
- クミスクチンよりイノシトールの単離
- Trichothecium roseum LINKの代謝産物の研究Rosein IIIの構造
- Alkaloidal Constituents of the Leaves of Stephania cepharantha Cultivated in Japan : Structure of Cephasugine, a New Morphinane Alkaloid
- Alkaloidal Constituents of the Tubers of Stephania cepharantha Cultivated in Japan : Structure of 3,4-Dehydrocycleanine, a New Bisbenzylisoquinoline Alkaloid
- A Synthesis of 3-Phenyl-1, 2, 3, 4-tetrahydroisoquinoline and 2-Phenyl-1, 2, 4, 5-tetrahydro-3H-3-benzazepine via Pummerer-Type Cyclization : Enhancing Effect of Boron Trifluoride Diethyl Etherate on the Cyclization
- A Synthesis of 2,3,4,5-Tetrahydro-1H-3-benzazepines via Pummerer-Type Cyclization of N-(2-Arylethyl)-N-(2-phenylsulfinylethyl)formamides
- A Synthesis of Chiral 1,1,3-Trisubstituted l,2,3,4-Tetrahydro-β-carbolines by the Pictet-Spengler Reaction of Tryptophan and Ketones: Conversion of (1R,3S)-Diastereomers into Their (1S,3S)-Counterparts by Scission of the C(1)-N(2) Bond
- A Convenient Synthesis of 1, 1-Disubstituted 1, 2, 3, 4-Tetrahydroisoquinolines via Pictet-Spengler Reaction Using Titanium(IV)Isopropoxide and Acetic-Formic Anhydride
- A Synthesis of Heteroaromatic Analogues of 1-Methyl-1,2,3,4-tetrahydroisoquinoline Using the Pummerer-Type Cyclization Reaction : Observation of Tandem Cyclization Reaction
- Super Acid-Induced Pummerer-Type Cyclization Reaction : Improvement in the Synthesis of Chiral 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinolines
- Intramolecular Capture of Pummerer Reaction Intermediates by an Aromatic Nucleophile : Selective Construction of 1, 4-Benzothiazine and Indole Ring Systems
- Synthesis of Methoxy-2-quinolones via Pummerer-type Cyclization of N-Aryl-N-methyl-3-(phenylsulfinyl)propionamides
- A Chiral Synthesis of Four Stereoisomers of 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline, an Inducer of Parkinson-like Syndrome
- [2+2] Photocycloaddition Reaction of 5-Phenyl-1H-furan-2,3-dione to Phenylethylene
- A Novel Synthesis of 1,2,3,4-Tetrahydroquinolines via Pummerer-Type Reaction of N-Aryl-N-[(phenylsulfinyl)propyl]formamide
- 脳内アミン,1-メチルテトラヒドロイソキノリンのパーキンソン病治療薬としての可能性
- A Synthesis of Mono- and Dimethoxy-1,2,3,4-tetrahydroisoquinolines via Pummerer Reaction : Effects of Methoxyl Groups on Intramolecular Cyclization
- General Method for Synthesis of Erythrinan and Homoerythrinan Alkaloids (1) : Synthesis of a Cycloerythrinan, as a Key Intermediate to Erythrina Alkaloids, by Pummerer-Type Reaction
- Determination of Ring Conformation in 1-Benzyl-1,2,3,4-tetrahydroisoquinolines and a New Synthesis of the Chiral Compounds
- An Improved Synthesis of 1,2,3,4-Tetrahydroisoquinolines via Intramolecular Cyclization of N-Acyl-N-(aryl)methyl-2-(phenylsulfinyl)ethylamine by Pummerer Reaction
- Synthesis of Homoerythrinan Alkaloids of 1(2)-Alkene and 1,6-Diene Types : Total Synthesis of Comosine, Dihydroschelhammeridine, Schelhammeridine, and 3-Epischelhammeridine
- Thermal Addition Reaction of Aroylketenes with Cyclic Enol Ethers
- Thermal Addition Reaction of Aroylketene with 1-Aryl-1-trimethylsilyloxyethylenes : Aromatic Substituent Effects of Aroylketene and Aryltrimethylsilyloxyethylene on Their Reactivity
- エリスリナおよび関連アルカロイドの合成
- Triterpenoid Chemistry. XIII. Lycopodium Triterpenoid. (9). The Structure of Lyclavatol, a Novel Triterpenoid of Bisnoronocerane Type
- 9 溶媒抽出 : 9.1 天然物の取り扱いにおける有機化合物の溶媒抽出
- Dioxopyrrolines. LX. Cycloaddition Reaction of 4-Benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione to Olefins : An Inverse-Electron-Demand Hetero Diels-Alder Reaction
- リコリンおよび関連アルカロイドの全合成
- Osmium Tetroxide Oxidation of Hopa-15,17(21)-diene, Dehydrozeorinin, and Hop-17(21)-ene
- Alkaloidal Constituents of Vines of Stephania cepharantha(Natural Medicine Note)
- ジオキソピロリンを利用した種々の含窒素複素環化合物の合成