Three new cycloartane triterpene glycosides from Souliea vaginata

Three new cycloartane triterpene glycosides, soulieosides A (1), B (2), and C (3), were isolated from the rhizomes of Souliea vaginata, and their structures were elucidated on the basis of extensive NMR experiments and chemical methods. Soulieosides A-C were assigned as 25-O-acetylcimigenol-3-O-beta-D-(2-acetyl)xylopyranoside (1), 24-O-acetyl-isodahurinol-3-O-beta-D-(2-acetyl)xylopyranoside (2) and 20(S),22(R),23(S),24(R)-16beta:23;22:25-diepoxy-3beta,23,24-trihydroxy-9,19-cyclolanostane-3-O-beta-D-(4-acetyl)xylopyranoside (3), respectively.     

A new cycloartane triterpenoid from the leaves and stems of Fritillaria hupehensis

A new triterpenoid has been isolated from the leaves and stems of Fritillaria hupehensis Hsiao et K.C.Hsia.Its structure wasestablished as(23Z)-9,19-cycloart-23-ene-3α,25-diol 1 through chemical and spectroscopic studies including 2D NMR.Anotherknown triterpenoid 9,19-cycloart-25-ene-3β,24ξ-diol 2 was also isolated.     

Cyclolanostane triterpene glycosides from Souliea vaginata

Five new cyclolanostane triterpene glycosides, 12-deacetyloxy-15alpha-hydroxy-23-epi-26-deoxyactein, 12-deacetyloxy-23-epi-26-deoxyactein, 24-O-acetyldahurinol-3-O-beta-D-xylopyranoside, 12beta-hydroxycimigenol-3-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranoside, 25-anhydrocimicigenol-3-O-beta-D-(2'-O-acetyl)xylopyranoside, were isolated from the rhizome of Souliea vaginata collected in China. Their structures were elucidated by spectroscopic techniques, including 2D NMR spectra, and in the case of 5, by chemical correlation.     

New triterpenoids from the orchids Scaphyglottis livida and Nidema boothii

Two new triterpenoids, nidemin (1), a modified lanostane, and 9,19-cyclolanosta-24,24-dimethyl-25-en-3beta-yl trans-p-hydroxycinnamate (2) have been isolated from the orchids Nidema boothii and Scaphyglottis livida, respectively. The isolates were characterized by spectral methods. The structure of nidemin (1) was unambiguously confirmed by X-ray analysis.     

Structural revision of terpenoids with a (3Z)-2-methyl-3-penten-2-ol moiety by the synthesis of (23E)- and (23Z)-cycloart-23-ene-3beta,25-diols

Synthesis of (23E)-cycloart-23-ene-3beta,25-diol (1) and its 23Z-isomer 2 was achieved by using cycloartenol as a starting material, thus revising the proposed structure of natural 2 to 1 unequivocally. These synthetic studies revealed that the structural revision (Z-form --> E-form) should also be applied to terpenoids such as (23Z)-3beta-acetoxyeupha-7,23-diene-25-ol, (23Z)-tirucalla-7,23-diene-3beta,25-diol, quadrangularol A, quadrangularic acid K, and daurichromene C.     

Novel cycloartane saponins from Corchorus depressus L

Two novel bidesmosidic cycloartane-type glycosides, depressosides C and D were isolated from Corchorus depressus L. Their structures were elucidated as (22R)-16beta,22-epoxy-3beta,26-dihydroxy-9,19-cyclolanost-++ +24E-ene 3, 26-di-O-beta-D-glucopyranoside and (22R,24S)-22,25-epoxy-3beta,16beta,24-trihydroxy-9,19-cyclolano stane 3, 24-di-O-beta-glucopyranoside, respectively on the basis of chemical evidence and detailed spectroscopic studies.     

Cycloartane triterpenes from Euphorbia tuckeyana

Investigation of the acetone extract of the whole plant of Euphorbia tuckeyana afforded a new cycloartane-type triterpene named as cyclotucanol. Its structure was established as cycloartane-24-methylene-3beta,25-diol (1). The known cycloartane triterpenes cycloeucalenol (2), 3beta-hydroxycycloart-25-en-24-one (3), cycloart-25-ene-3beta,24-diol (4), 25,26,27-trisnor-3beta-hydroxycycloartan-24-al (5) and cycloart-23-ene-3beta,25-diol (6) were also isolated and identified.     

A New Cycloartane Glycoside from the Aerial Part of Astragalus grahamianus

Chemistry of Natural Compounds - A new 9,19-cyclolanostane type arabinoside, 16,23;22,25-diepoxy-3β,22,23,24-tetrahydroxy-9,19-cyclolanostane-3-O-α-L-arabinopyranoside (1), together with...     

Structures of two new steroidal glycosides, soladulcosides A and B from Solanum dulcamara

The structures of two new steroidal glycosides named soladulcosides A and B, isolated from the aerial parts of Solanum dulcamara including new sapogenols, were elucidated as (22R, 25R)-3 beta, 15 alpha, 23 alpha-trihydroxy-5 alpha-spirostan-26-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside and (22R, 25R)-3 beta,23 alpha-dihydroxy-5 alpha-spirostan-26-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-[alpha-L-rhamnopyranosyl-(1----4)]- beta-D-glucopyranoside, respectively.     

Triterpene saponins fromThalictrum minus. VII. Structure of thalicoside E

A new minor cycloartane glycoside — thalicoside E, 9,19-cyclo-20(S)-lanost-23-ene-3β,16β,22ζ,25,29-pentaol 3-O-β-D-galactoside 29-O-β-D-glucopyranoside — has been isolated from the epigeal part ofThalictrum minus L. (Ranunculaceae).     

Four new steroid constituents from the waste residue of fibre separation from Agave americana leaves

Three new steroidal saponins, named agamenosides H-J (1-3), and a new cholestane steroid agavegenin D (4) were isolated from the waste residue of fibre separation from Agave americana leaves, together with six known steroids. Structures of the new compounds 1-4 were deduced to be (22S,23S,24R,25S)-24-[(beta-D-glucopyranosyl)oxy]-5alpha-spirostane-3beta,6alpha,23-triol 6-O-beta-D-glucopyranoside (1), (22S,23S,24R,25S)-5alpha-spirostane-3beta,23,24-triol 24-O-beta-D-glucopyranoside (2), (22S,23S,25R,26S)-23,26-epoxy-5alpha-furostane-3beta,22,26-triol 26-O-beta-D-glucopyranoside (3), and (22S,25S)-5alpha-cholestane-3beta,16beta,22,26-tetrol (4), respectively, by means of spectroscopic analysis, including extensive 1D and 2D NMR data, and the results of hydrolytic cleavage.     

Two new triterpene glycosides with monomethyl malonate groups from the rhizome of Cimifuga foetida L

Two new 9,19-cycloartane triterpene glycosides 1-2, together with four known compounds--26-deoxyactein (3), actein (4), 7,8-didehydro-26-deoxyactein (5) and cimiaceroside B (6)--were isolated from the rhizome of Cimicifuga foetida. The new triterpene glycosides were identified as 23-O-methyl-24-deoxy-2'-O-(3'-methylmalonyl)-cimiaceroside B (1) and 2'-O-(3'-methylmalonyl)actein (2) based on analysis of their spectral data and chemical reactions.     

A new cerebroside from fruits of Ailanthus altissima Swingle

A new cerebroside and three known cycloartan triterpenes were isolated from fruits of Ailanthus altissima Swingle. Their structures were identified as 1-O-beta-D-glucopyranosyl-(2S, 3R, 4E, 9E)-2-(2'R-hydroxyhexadecenoy)-4, 9-octadecadiene-1, 3-diol (1), 9, 19-cyclolanost-23 (Z)-ene-3beta, 25-diol (2), cycloart-25-ene-3beta, 24R-diol (3), and cycloart-25-ene-3beta, 24S-diol (4) by means of chemical and spectroscopic analysis. Compounds 2, 3, and 4 were isolated from genus Ailanthus for the first time. The analgesic activity of 1 was also evaluated.     

New steroidal alkaloids from Fritillaria imperialis and their cholinesterase inhibiting activities

Two new cevanine steroidal alkaloids, impericine (1) and forticine (2) along with known bases delavine (3), persicanidine A (4), and imperialine (5) were isolated from the bulbs of Fritillaria imperialis. The structures of impericine (1) [(20R,22S,25S)-5alpha-cevanin-23-ene-3beta,6beta,16beta-triol] and forticine (2) [(20S,22S,25S)-5alpha-cevanine-3beta,6beta-diol] were determined with the help of spectroscopic studies. These steroidal bases showed anti-acetylcholinesterase and anti-butyrylcholinesterase inhibitory activity.     

Conversion of esculeoside A into esculeogenin B

Conversion of the spirosolane-type glycoside, esculeoside A, a major component contained in the ripe tomato Lycopersicon esculentum fruits, into a solanocapsine-type sapogenol, esculeogenin B-2, (5alpha,22S,23R,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, and esculeogenin B-1, (5alpha,22R,23S,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, which are rare naturally occurring compounds was attained by acid hydrolysis with 2 N HCl in dioxane and water (1 : 1).     

New diarylheptanoids from Alnus japonica and their antioxidative activity

In the course of research on the bioactive constituents of woody plants in the Cyugoku area of Japan, a methanol extract of the leaves of Alnus japonica were found to have strong antioxidative activity. Ethyl acetate soluble and n-buthanol soluble fractions of the methanol extract had a potent antioxidative effect. Both fractions were purified by silica gel column chromatography and HPLC using an ODS column to give four new diarylheptanoids along with known diarylheptanoids and flavonoids. These new compounds were elucidated to be 7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxyphenyl)-3-heptanone-5-O-beta-D-xylopyranoside (1), 1-(3,4-dihydroxyphenyl)-5-hydroxy-7-(4-hydroxyphenyl)-3-heptanone-5-O-beta-D-xylopyranoside (2), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxy-3-heptanone-5-O-[2-(2-methylbutenoyl)]-beta-D-xylopyranoside (3) and 1,7-bis-(3,4-dihydroxyphenyl)-5-methoxy-3-heptanone (4) using spectral methods and especially 1H-, 13C-NMR and 2D-NMR measurements. The isolated compounds including their main constituent, oregonin (5), were tested for antioxidative activity. Some of these compounds having two catechol structures showed potent antioxidative activity. Compounds having one catechol structure showed moderate antioxidative activity, but a peracetate of 5 having no catechol structure exhibited no antioxidative activity. Thus the catechol structure of the diarylheptanoids is indispensable for antioxidative activity.     

Two new polyporusterones isolated from the sclerotia of Polyporus umbellatus

In the course of searching for marker components, two new polyporusterones were isolated from the sclerotia of Polyporus umbellatus, together with another three known analogs. The structures of the new ones were elucidated as (20S,22R,24R)-16,22-epoxy-3beta,14alpha,23beta,25-tetrahydroxyergost-7-en-6-one (1) and (23R,24R,25R)-23,26-epoxy-3beta,14alpha,21alpha,22alpha-tetrahydroxyergost-7-en-6-one (2) by chemical and spectroscopic means, including HR-FAB-MS, 1D- and 2D-NMR.     

Tomato new sapogenols, isoesculeogenin A and esculeogenin B

Two novel sapogenols, isoesculeogenin A (1) and esculeogenin B (2) of steroidal alkaloid glycosides, lycoperoside F and esculeoside B, respectively, isolated from the ripe tomato have been characterized as (5alpha,22R,23R,25S)-3beta,23,27-trihydroxyspirosolane and (5alpha,22S,23R,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, respectively.     

Six new dammarane-type triterpene saponins from the leaves of Panax ginseng

Six new minor saponins, together with known ginsenosides, were isolated from the leaves of Panax ginseng. The new saponins were named as ginsenoside-Rh5, -Rh6, -Rh7 -Rh8, -Rh9 and -Rg7, and their structures were elucidated on the basis of chemical and physicochemical evidence to be as follows: ginsenoside-Rh5: 3beta,6alpha,12beta,24zeta-tetrahydroxy-dammar-20(22),25-diene 6-O-beta-D-glucopyranoside (1), -Rh6: 3beta,6alpha12beta,20(S)-tetrahydroxy-25-hydroperoxy-dammar-23-ene 20-O-beta-D-glucopyranoside (2), -Rh7: 3beta,7beta,12beta,20(S)-tetrahydroxy-dammar-5,24-diene 20-O-beta-D-glucopyranoside (3), -Rh8: 3beta,6alpha,20(S)-trihydroxy-dammar-24-ene-12-one 20-O-beta-D-glucopyranoside (4), -Rh9: 3beta,6alpha,20(S)-trihydroxy-12beta,23-epoxy-dammar-24-ene 20-O-beta-D-glucopyranoside (5) and -Rg7: 3-O-beta-D-glucopyranosyl 3beta,12beta,20(S),24(R)-tetrahydroxy-dammar-25-ene 20-O-beta-D-glucopyranoside (6).     

A Diterpenoid with a New Skeleton and Cytotoxic Terpenoids Isolated from Amentotaxus formosana

The new diterpenoid 6α‐hydroxy‐ent‐kaur‐16‐en‐15‐one ( 1 ) and a diterpenoid with a new skeleton, i.e., amentotaxin BB ( 5 ), as well as three new lanostanoids, i.e., (3β,23R)‐3‐methoxy‐24‐methylenelanost‐8‐en‐23‐ol ( 6 ), (23S)‐23‐methoxy‐24‐methylenelanost‐8‐en‐3‐one ( 7 ), and (3β,24ξ)‐3‐methoxy‐24‐methyl‐9,19‐cyclolanostan‐25‐ol ( 8 ), were isolated from the bark and leaves of Amentotaxus formosana. Their structures, including the relative configurations, were elucidated from spectroscopic data. Compound 1 and a known compound, ent‐kaur‐16‐en‐15‐one ( 2 ), showed potent cytotoxic effects against a number of cancer cells in vitro.