Two triterpene glycosides from the sea cucumber Bohadschia marmorata Jaeger

Further studies on the sea cucumber Bohadschia marmorata Jaeger led to the isolation of a new holostan-type triterpene glycoside,Marmoroside C（1）together with a known triterpene glycoside（2）.On the basis of spectroscopic analyses,including two- dimensional NMR techniques,and chemical reactions,the structure of the new triterpene glycoside was elucidated as 3-O-[3-O- methyl-β-D-glucopyranosyl-（1→3）-β-D-glucopyranosyl-（1→4）-β-D-quinovopyranosyl-（1→2）-4-O-sodium-sulfato-β-D-xylo- pyranosyl]-25-acetoxy-22-oxo-9（11）-holostene-3β,12α,17α-triol.     

Hopanoins from the entomogenous fungus aschersonia aleyrodis.

The new triterpene triol 3β, 15α, 22-trihydroxyhopane, the triterpene diol dustanin (15α;,22-dihydroxyhopane) and the sterol ergosterol were isolated from the entomogenous fungus Aschersonia aleyrodis.     

Crystalline constituents from euphorbiaceae—XIII : The structure of a new triterpene from Euphorbia nerifolia L.

From the leaves and stems of Euphorbia nerifolia Linn., a new triterpene was isolated besides friedelan-3α- andβ-ols, and taraxerol. From a study of its chemical reactions and spectral data, the new triterpene was shown to be glut-5(10)-en-1-one(3).     

Gymnestrogenin, a new pentahydroxytriterpene from the leaves of Gymnema sylvestre R.Br

The structure of gymnestrogenin, a new triterpene from the leaves of Gymnema sylvestre R. Br. (Asclepiadaceae), is proposed to be that of 3β, 16β, 21β, 23, 28-pentahydroxy-olean-12-ene.     

Three New Cycloartenol Triterpenoid Saponins from the Roots of Cimicifuga simplex Wormsk

Three new cycloartenol triterpene saponins, named shengmaxinsides A-C, have been isolated from the ethyl acetate soluble fraction of an ethanol extract of Cimicifuga simplex Wormsk roots. Their structures were established by chemical tests and detailed spectroscopic analysis as 25-O-acetyl-7,8-didehydrocimigenol-3-O-β-D-galactopyranoside (1), 7,8-didehydrocimigenol-3-O-β-D-galactopyranoside (2) and 7,8-didehydro-24S-O-acetylhydroshengmanol-3-O-β-D-galactopyranoside (3), respectively.     

Two new olean-type triterpene fatty esters from Scorzonera mongolica

Two new triterpene fatty esters, 33-tetradecanoyl moradiol 1 and 3β-dodecanoyl moradiol 2, were isolated from Scorzonera mongolica. Their structures were elucidated as 3β-tetradecanoyloxy-28-hydroxylolean-18-ene and 3β-dodecanoyl-28-hydroxyl-olean-18-ene on the basis of IR, MS, ID NMR and extensive 2D NMR spectroscopic analyses.     

Triterpene glycosides ofSilphium perfoliatum. III. Structure of silphioside E

A new triterpene glycoside — silphioside E — has been isolated from the epigeal part ofSilphium perfoliatum L. and its structure has been established on the basis of chemical transformations and spectral characteristics as oleanolic acid 28-0-β-D-glycopyranoside 3-0-[0-β-D-glycopyranosyl-(1 → 2)-β-D-glucopyranoside].     

Structure of marsileagenin a; A new hexahydroxy triterpene from marsilea minuta linn

The crude saponin obtainable from Marsilea minuta Linn on acid hydrolysis yielded a mixture of sapogenols. The major sapogenol named Marsileagenin A was found to be a hexahydroxy triterpene of oleanene series. From a study of various spectrometric data together with chemical reactions the structure of this sapogenol has been assigned as olean-12-ene-2α, 3β, 16β, 21β, 22α, 28-hexol (1a).     

Triterpene glycosides of alfalfa. IV. Medicoside J

A new triterpene glycoside has been isolated from the roots ofMedicago sativa L. (family Fabaceae) — medicoside J, and its structure has been established as a medicagenic acid 3-O-β-D-glucopyranoside 28-O-[O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranoside].     

The structure of thelenotosides A and B from the holothurianThelenota ananas

Two new triterpene tetraosides — thelenotosides A and B — have been obtained from the holothurianThelenota ananas. Their complete structures have been determined as 23(S)-acetoxy-3β-[0-(3-0-methyl-β-D-glucopyranosyl)-(1→3)-0-β-D-xylopyranosyl-(1→4)-0-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyloxy]holost-7-ene (and 23(S)-acetoxy-3β-[0-(3-0-methyl-β-D-glucopyranosyl)-(1→3)-0-β-D-xylopyranosyl-(1→4)-0-β-D-glucopyranosyl-(1→2)-β-D-xylopyranosyloxy]holost-7-ene, respectively.     

Triterpenoids from the leaves of far eastern species of the shrubby birchesBetula ovalifolia andB. middendorfii

From the unsaponifiable fraction of an ethereal extract of the leaves ofBetula ovalifolia have been isolated the new triterpene 20(S),24(R)-epoxydammarane-3α,17α,25-triol (V) and the corresponding monoketone at C³ (VI). The leaves ofB. middendorfii have yielded the triterpene (IX) and (X), identified as, respectively, dammar-23-ene-3α,12β,20(S),25-tetraol and damman-25-ene-3α,12β,20-(S),24-tetraol, which have been obtained previously from the leaves ofBetula platyphylla Sukatchev var.japonica.     

A new polyoxygenated triterpene and two new aeginetic acid quinovosides from the roots of Rehmannia glutinosa

A new minor polyoxygenated triterpene named glutinolic acid (1) and two new aeginetic acid quinovosides (2, 3) were isolated from the roots of Rehmannia glutinosa LIBOSCH. (Scrophulariaceae) cultivated in Gunwi-gun, Korea. The structures of these compounds were established as 3α,19α,20β,24,30-pentahydroxyurs-12-en-28-oic acid (1, glutinolic acid), aeginetic acid 5-O-β-D-quinovoside (2) and aeginetoyl ajugol 5″-O-β-D-quinovoside (3) on the basis of chemical and spectroscopic evidence.     

A New Pentacyclic Triterpene from Ecdysanthera Rosea

D-friedours-14-en-11α, 12α-epoxy-3β-yl palmitate (1), a new pentacyclic triterpene of the ursane series, was isolated from the aerial parts of Ecdysanthera rosea, and the structure was elucidated on the basis of the spectral data. The partial synthesis of this compound from α-amyrin acetate via a few steps was also achieved.     

Lanostanoids Isolated from Ganoderma lucidum Mycelium Cultured by Submerged Fermentation

Three new lanostane triterpene acids, 3‐O‐acetylganoderic acid B ( 1 ), 8β,9α‐dihydroganoderic acid C ( 3 ), and 3‐O‐acetylganoderic acid K ( 4 ), as well as two new lanostane triterpene acid ethyl esters, ethyl 3‐O‐acetylganoderate B ( 2 ) and ethyl ganoderate J ( 5 ), were isolated and characterized from Ganoderma lucidum mycelia which was cultured by submerged fermentation method. Their structures were elucidated on the basis of spectroscopic methods. In addition, the identification of two known lanostane triterpene acid methyl esters, methyl O‐acetyl ganoderate C and methyl 3,7,11,15,23‐pentaoxo‐lanost‐8‐en‐26‐oate were identified by comparison of the NMR data with those reported in the literature.     

Glycosides of marine invertebrates. XII. Structure of a new triterpene oligoglycoside from holothurians of familyStichopodidae

From an ethanolic extract of the holothuriansStichopus chloronotus by column chromatography on silica gel a new triterpene oligoside has been isolated the structure of which has been established as 23(S)-acetoxy-3β-{4′-O-[O-(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl]-2′-O-[O-(3-O-methyl-β-D-glucopyranosyl(-(1→3)-O-β-D-xylopyranosyl-(1→4)-β-D-glucopyranosyl]-β-D-xylopyranosyloxy}holost-7-ene. A hypothesis has been put forward concerning the biosynthesis of the carbohydrate chains in the glycosides of holothurians of the orderAspidochirota from bioside blocks.     

中药枸骨叶中三萜皂苷和黄酮苷类成分研究

A new triterpene glycoside, pomolic acid 3-O-6″-methyl-β-D-glucuronopyranosyl-（1→3）-α-L-arabino- pyranoside, and a new flavonol glycoside, quercetin 3-O-β-D-glucopyranosyl-（1→2）-α-L-arabinopyranoside together with three known triterpene saponins and two flavonol glycosides, were isolated from the leaves of Ilex cornuta. Their structures were established on the basis of spectroscopic analysis.     

Structure of synaptogenin B — An artefactual aglycone of glycosides from the holothurianSynapta maculata

The structure of the previously unknown synaptogenin B, the main product of the acid hydrolysis of the triterpene oligosides synaptosides S-2 and S-3 from the holothurianSynapta maculata has been established. To prove the structure, diketones were obtained from synaptogenin B and the known stichopogenin, and their identity was shown on the basis of¹H NMR and mass spectra. Synaptogenin B is a 3β-hydroxyholost-9(11)-en-23-one. It has been shown that holost-9(11)-en-3β-o1 is formed as minor component in the acid hydrolysis of the synaptosides.     

A new triterpene from Scorzonera latifolia (Fisch. and Mey.) DC

A novel triterpene 1 (3-β-hydroxy-fern-7-en-6-one-acetate) together with four known compounds, urs-12-en-11-one-3-acetyl (2), 3-β-hydroxy-fern-8-en-7-one-acetate (3), olean-12-en-11-one-3-acetyl (4) and leucodin (5) were obtained from the S. latifolia roots. All compounds were isolated from the n-hexane extract of S. latifolia roots using several chromatographic techniques. The structure of the isolated compounds was elucidated on the basis of (1)H-NMR, (13)C-NMR and 2D NMR data (HMBC, HMQC, COSY, TOCSY, NOESY, DEPT) as well as GC EITOF-HRMS.     

灰色链霉菌ATCC 13273 位点特异性转化商陆皂苷元羟基化反应研究

为增加商陆皂苷元的结构多样性,本研究采用两步培养法,利用灰色链霉菌ATCC 13273对其进行生物转化,得到一个极性增大的羟基化产物。通过二维核磁、高分辨质谱等方法鉴定该转化产物为2β, 3β, 23, 29-四羟基-齐墩果烷-12-烯-28, 30-二酸-30-甲酯。     

Triterpene saponins with XOD inhibitory activity from the roots of Ilex pubescens

A new triterpene saponin with 28-nor-urs-12(13),18(17)-dien-3β-ol as aglycone,named ilexsaponin C(1) was isolated from the roots of Ilex pubescens,together with three known saponins 2,3 and 4.The structure of 1 was elucidated on the basis of spectral analysis including 1D and 2D NMR and HR-ESI-MS.Saponins 1 and 4 exhibited significant XOD inhibitory activity in the test.