Six new secoiridoids from the dried fruits of Ligustrum lucidum

Six new secoiridoid constituents, named isoligustrosidic acid (1), 6'-O-trans-cinnamoyl 8-epikingisidic acid (2), 6'-O-cis-cinnamoyl 8-epikingisidic acid (3), oleopolynuzhenide A (4), nuzhenals A (5) and B (6) were isolated from the dried fruits of Ligustrum lucidum AIT. Their structures were established on the basis of spectral and chemical data.     

A new iridoid glycoside from Paederia scandens

<正>A new glycoside named 6β-O-β-D-glucosylpaederosidic acid(1) was isolated from Paederia scandens and its structure was elucidated on the basis of spectroscopic and chemical evidence,together with four known iridoids,paederoside(2),paederosidic acid(3),paederosidic acid methyl ester(4),and deacetyl asperulosidic acid methyl ester(5).Compound 5 was isolated from this plant for the first time.     

A new benzofuranic acid from the leaves of Rhus alata

From leaves of Rhus alata, one new benzofuranic acid named [(2E)-3-(4-hydroxy-5,7-dimethyl- benzo[3,4-b] furan-6-yloxy)-prop-2-enoic acid has been isolated together with eight known compounds: dimethyl ester of terephthalic acid, beta-amyrin, friedelin, lupeol, beta-sitosterol, oleanolic acid, taraxerone and ethyl gallate. Structural elucidations were done on the basis of chemical and physical data (IR, UV, 1H-NMR, 13C-NMR and MS spectra).     

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.     

Three new compounds from the leaves of Acanthopanax senticosus Harms

<正>Three new compounds named(2E)-prenyl benzoate-4-O-α-L-arabinopyranosyl(1→6)β-D-glucopyranoside(1),7-methoxy-8- O-β-D-glucopyranosyl coumarin(2),and 3,4'-dihydroxy-3'-methoxy benzenepentanoic acid(3) were isolated from the leaves of Acanthopanax senticosus Harms.The structures of new compounds were determined by means of 2D NMR experiments and chemical methods.     

Seimatoric acid and colletonoic acid:Two new compounds from the endophytic fungi,Seimatosporium sp.and Colletotrichum sp.

A new metabolite,named seimatoric acid(1),representing a new oxobutanoic acid derivative has been isolated from Seimatosporium sp., in addition to four known compounds viz.,2-hydroxymethyl-4β,5α,6β-trihydroxycyclohex-2-enone(2),(-)-phyllostine(3),(+)-epiepoxydon(4) and(+)-epoxydon monoacetate(5).Similarly one new benzoic acid derivative,named colletonoic acid(6) was isolated from the ethyl acetate fraction of Colletotrichum sp.The structures of the new compounds were elucidated by detailed ~1 H NMR,~(13)C NMR,COSY,HMQC.HMBC spectroscopic analysis,and HR-E1-MS.Seimatoric acid(1)was also isolated from another taxonomical unidentified fungal strain 4295 in ourgroup.The structures of the known compounds were elucidated by their spectral data comparison to literature data.Preliminary studies showed that colletonoic acid(6) showed good antibacterial,antifungal,and antialgal activities.     

A new lupane glycoside from the leaves of Acanthopanax koreanum

A new lupane-type saponin, named acankoreoside E (1), was isolated from the methanol extract of the leaves of Acanthopanax koreanum, and its structure was established through chemical and spectroscopic analyses as (20S) 3alpha-hydroxy-30-oxolupan-23,28-dioic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester.     

Newbouldiaquinone and newbouldiamide: a new naphthoquinone-anthraquinone coupled pigment and a new ceramide from Newbouldia laevis

Newbouldiaquinone (1), a new naphthoquinone-anthraquinone coupled pigment and a new ceramide named newbouldiamide (2), have been isolated from Newbouldia laevis, besides the known compounds lapachol (3), canthic acid, oleanolic acid, 2-methyl-9,10-anthracenedione, 2-acetylfuro-1,4-naphthoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2-(4-hydroxyphenyl)ethyl triacontanoate, beta-sitosterol and beta-sitosterol glucopyranoside. The structure elucidations of the isolated new compounds were performed on the basis of spectroscopic and chemical evidence. Preliminary studies showed that 1 is moderately antibacterial against Gram-positive Bacillus megaterium and that 3 has moderate herbicidal and antibacterial activities.     

Schefflerins A-G, new triterpene glucosides from the leaves of Schefflera arboricola

From the 1-BuOH-soluble fraction of a MeOH extract of leaves of Schefflera arboricola, collected in Okinawa, six new lupane glucosides, named schefflerins A-F (1-6) and one new dammarane glucoside, named schefflerin G (7), were isolated together with three known compounds, citroside A (8), and oleanane saponins, oleanolic acid (9) and echinocystic acid (10) 3-O-α-L-rhamnopyranosyl(1→4')-O-β-D-glucuronopynosides. Their structures were elucidated through a combination of spectroscopic analyses and the structure of schefflerin F (6) was determined by X-ray crystallographic method using SPring-8 synchrotron radiation.     

Constituents of a fern, Davallia mariesii Moore. I. Isolation and structures of davallialactone and a new flavanone glucuronide

A new gamma-lactone derivative named davallialactone (4) and the 7-O-beta-D-glucuronide of (+/-)-eriodictyol (5a) have been isolated from Davallia mariessi Moore along with caffeic acid (1), 4-beta-D-glucopyranosylcaffeic acid (2) and 4-O-beta-D-glucopyranosyl-p-coumaric acid (3). The structures of the new compounds were determined by chemical and spectroscopic methods including two-dimensional nuclear magnetic resonance (2D NMR) techniques, especially 1H-detected heteronuclear multiple-bond multiple-quantum coherence and long-range C-H J-resolved 2D NMR techniques.     

Pterisolic acids A-F, new ent-kaurane diterpenoids from the fern Pteris semipinnata

Six new ent-15-oxokauran-19-oic acid derivatives, named pterisolic acids A-F (1-6), were isolated from the ethanol extract of the fern Pteris semipinnata (Pteridaceae), and the structures of these new ent-kauranoids were elucidated on the basis of extensive spectroscopic studies and single crystal X-ray diffraction analysis.     

A new triterpenoid saponin from Gleditisia sinensis and structure-activity relationships of inhibitory effects on lipopolysaccharide-induced nitric oxide production

A phytochemical investigation of the anomalous fruits of Gleditisia sinensis led to one new oleanane-type triterpenoid saponin acylated with one monoterpenic acid, 3-O-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-[(6S,2E)-6-hydroxy-2,6-dimethyl-2,7-octadienoyl-(1 --> 6)]-beta-D-glucopyranosyl ester, named gleditsioside Z (1), together with nine known ones (2-10). Their structural details were mainly established on the basis of 1D, 2D NMR and HR-MS analysis as well as some chemical methods. Structure-activity relationships of the isolated saponins that affected nitric oxide production from cultured mouse macrophages (RAW 264.7 cell lines) induced by lipopolysaccharide were discussed.     

Indonesia medicinal plants. III. On the constituents of the bark of Fagara rhetza (Rutaceae). (1): Alkaloids, phenylpropanoids, and acid amide.

Two new phenylpropanoids, named O-geranylsinapyl alcohol (1) and O-geranylconiferyl alcohol (2), and a new acid amide, named hazeleamide (3), were isolated from the bark of Fagara rhetza (Rutaceae), an Indonesian medicinal plant from Flores Island, Indonesia. The chemical structures of 1, 2, and 3 have been elucidated on the basis of their chemical and physicochemical properties. Among the three new compounds, hazeleamide (3) was found to show a pungent taste and to exert a moderate antimalarial activity in an in vitro test system.     

Galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, five new antioxidative glycosides, and suffruticoside E, A paeonol glycoside, from Chinese moutan cortex.

Five new antioxidative glycosides named galloyl-oxypaeoniflorin, suffruticosides A, B, C, and D, and a new paeonol glycoside named suffruticoside E have been isolated from Chinese Moutan Cortex, the root cortex of Paeonia suffruticosa ANDREWS, together with antioxidative galloyl-paeoniflorin. Their structures were elucidated on the basis of chemical and physicochemical evidences. Galloyl-oxypaeoniflorin, galloyl-paeoniflorin, suffruticosides A, B, C, and D showed more potent radical scavenging and antioxidative effects than alpha-tocopherol.     

Two new steroid glycosides and a new sesquiterpenoid glycoside from the underground parts of Trillium kamtschaticum

Two new steroid glycosides, named trikamsterosides A and B, and a new sesquiterpenoid glycoside named trikamsesuquiside A were isolated from the underground parts of Trillium kamtschaticum PALL. along with 18 known compounds comprising 12 steroids, one sesquiterpenoid glycoside, one phenylpropanoid, one flavonoid glycoside, and three phenylpropanoid sucrose esters. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. Among them, one phenylpropanoid sucrose ester showed almost the same radical-scavenging effect on 1,1-diphenyl-2-picrylhydrazyl as that of alpha-tocopherol.     

Two new triterpenoid saponins from Lonicera macranthoides

Two new triterpenoid saponins named lonimacranthoideⅣ(1) and lonimacranthoideⅤ(2) were isolated from the flower buds of Lonicera macranthoides Hand.-Mazz.(Caprifoliaceae).They have hederagenin as aglycone.LonimacranthoideⅣ(1) is a rare chlorogenic acid ester acylated on the C-23 of hederagenin.LonimacranthoideⅣis a new sulfated triterpenoid saponin.The structures of the saponins were established by chemical and spectral methods.     

A new dibenzofuran and other constituents from Ligularia caloxantha, a Chinese medicinal plant

A new dibenzofuran named 1,2,4-trimethyl-7,8-dimethoxy-dibenzofuran (1), together with seven known compounds, euparin (2), 2,5-diacetyl-6-hydroxy-benzofuran (3), 2-acetyl-5,6-dimethoxy-benzofuran (4), gummosogenin (5), lupeol (6), stigmasterol (7) and (E)-2,5-dihydroxy-cinnamic acid (8), were isolated from the roots of Ligularia caloxantha, a Chinese medicinal plant. The structures of the compounds were elucidated by spectroscopic methods.     

Izumiphenazine D, a new phenazoquinoline N-oxide from Streptomyces sp. IFM 11204

A new phenazine derivative named izumiphenazine D (1), together with three known metabolites, 1-hydroxyphenazine (2), phenazine-1-carboxylic acid (3) and 6-hydroxyphenazine-1-carboxylic acid (4) has been isolated from the ethyl acetate extract of culture of Streptomyces sp. IFM 11204. The structure of 1 was established via spectroscopic methods, including 1D- and 2D-NMR measurements.     

Studies on the constituents of Lonicera species. XVII. New iridoid glycosides of the stems and leaves of Lonicera japonica THUNB

Four new iridoid glycosides, named L-phenylalaninosecologanin (1), 7-O-(4-beta-D-glucopyranosyloxy-3-methoxybenzoyl)secologanolic acid (2), 6'-O-(7alpha-hydroxyswerosyloxy)loganin (3) and (Z)-aldosecologanin (5), were isolated, together with a known one, newly named (E)-aldosecologanin (4), from the stems and leaves of Lonicera japonica. Their structures were established on the basis of chemical and spectral data.     

Chemical constituents of Micromelum minutum. Isolation and structural elucidation of new coumarins

The chemical constituents of an acetone extract of the stems of Micromelum minutum Wight et Arn (Rutaceae), collected at Nakorn-Rachasima province in Thailand, were studied. Six new coumarins, named micromarin-A (1), -B (2), -C (3), -F (4), -G (5), and -H (6), were isolated along with six known coumarins, and their structures were elucidated by chemical and spectroscopic methods.