Pentacyclic Triterpenoid Saponins from Silene viscidula

Three new pentacyclic triterpenoid saponins, viscidulosides A and B ( 1 and 2 , resp.), and silenoviscoside D ( 3 ), were isolated from the roots of Silene viscidula, together with two known saponins, sinocrassulosides VIII and IX ( 4 and 5 , resp.). Their structures were elucidated by spectroscopic data and chemical methods. Compounds 1 / 2 and 4 / 5 were two inseparable mixtures, which are glycosides of quillaic acid whose fucose residue is acylated by (E)‐ or (Z)‐4‐methoxycinnamic acid.     

Isolation of 5 alpha- and 5 beta-dihydrorubrosterone from Silene otites L. (Wib)

5 alpha-Dihydrorubrosterone (2 beta, 3 beta, 14 alpha, 17 beta-tetrahydroxy-5 alpha-androst-7-ene-6-one), a new 19-carbon 5 alpha-ecdysteroid, was isolated together with its 5 beta counterpart from the aerial parts of Silene otites L. (Wib.) (Caryophyllaceae) by a combination of solvent partition, low-pressure column chromatography, thin-layer chromatography (normal-phase and reversed-phase) and finally HPLC. Mass spectrometry and nuclear magnetic resonance spectroscopic procedures were used for compound characterization.     

Two new sesquiterpenoids and two new prenylated phenylpropanoids from Illicium fargesii, and neuroprotective activity of macranthol

Two new seco-prezizaane-type sesquiterpenoids 1, 2 and two new prenylated phenylpropanoids 4, 5 were isolated along with 15 known compounds from Illicium fargesii. The structures of 1, 2 were elucidated as 10-O-(E)- and 10-O-(Z)-cinnamoyl-2-oxo-6-deoxyneoanisatin by analysis of spectroscopic data and by comparison of their NMR data with those of previously reported 2-oxo-6-deoxyneoanisatin (3), respectively, whereas the structures of 4, 5 were identified as 4-allyl-2-(3-methylbut-2-en-1-yl)phenol and 4-allyl-2-(2-methylbut-3-en-2-yl)phenol, respectively, on the basis of spectroscopic data. Among the isolated compounds, macranthol (7) was found to have neuroprotective activity at 5--10 microM in rat cortical neurons cultured in DMEM/N2 medium.     

Peduncularistin,Triabunnin und Aristolarin,drei neue Indolalkaloide aus Aristotelia peduncularis (LABILL.) HOOK. F., 191. Mitteilung über organische Naturstoffe

Peduncularistine, Triabunnine and Aristolarine, Three Ne Indole Alkaloids from Aristotelia peduncularis (L_LABILL.) H_OOK, F. Peduncularistine ( 1 ), triabunnine ( 2 ) and aristolarine ( 3 ), three new indole alkaloids, have been isolated from Aristotelia peduncularis (L_ABILL.) H_OOK. F.; the structure and absolute configuration of 1 were elucidated on the basis of spectroscopic data and confirmed byt transformation of 1 into aristeserratine ( 4 ), a known alkaloid isolated from the same plant. The proposed structure 2 for the second alkaloid and its absolute configuration were established but spectroscopic means and by partial synthesis from 4 . The relative configuration of 3 was postulated on the basis of spectroscopic and biogenetic arguments.     

5'-Hydroxyzearalenol, a new β-resorcylic macrolide from Fusarium sp. 05ABR26

A new β-resorcylic maerolide, 5'-hydroxyzearalenol (1), was isolated from the culture broth of a marine-derived fungus Fusarium sp. 05ABR26. Three known compounds, zearalenone (2), 8'-hydroxyzearalenone (3) and zearalenol (4) were also isolated. The structure and relative stereochemistry of 1 were elucidated on the basis of spectroscopic data and single-crystal X-ray diffraction data. Compound 2 displayed potent inhibitory activity against Pyricularia oryzae with a MIC value of 6.25 μg/mL, while compound 3 was much less active; however, 1 and 4 showed no obvious activity.     

Prenylated anthraquinones and other constituents from the seeds of Vismia laurentii

Two new prenylated anthraquinones, laurenquinone A (1) and B (2) were isolated from the seeds of Vismia laurentii together with four known compounds; xanthone V(1) (3), physcion (4), 3-geranyloxyemodin anthrone (5) and friedelin (6). The structures of the new metabolites were determined with the help of spectroscopic data including extensive 2D-NMR spectroscopy. The known compounds were identified by comparison of their physical and spectroscopic data with those reported in the literature. Compounds 1, 4 and 5 exhibited moderate algicidal activity against Chlorella fusca and 3 showed moderate activity against the gram-positive bacterium Bacillus megaterium.     

7-O-Methylvariecolortide A, a new spirocyclic diketopiperazine alkaloid from a marine mangrove derived endophytic fungus, Eurotium rubrum

A new spirocyclic diketopiperazine alkaloid, namely, 7-O-methylvariecolortide A (1), together with recently reported known compounds variecolortides A-C (2-4), were isolated and identified from the liquid fermentation cultures of Eurotium rubrum, an endophytic fungus that was isolated from the inner tissue of the stems of the mangrove plant Hibiscus tiliaceus. The structures of these compounds were determined by extensive analyses of their spectroscopic data.     

Cymosanine, a novel C19-quassinoid from Simaba subcymosa

Cymosanine (1) and three further known quassinoids, cedronin (2), chaparrinone (3), and simarolide (4), were isolated from the root bark of Simaba subcymosa. The structures were established by spectroscopic data, mainly 1D, 2D NMR and mass spectra.     

Alpha-glucosidase inhibitors from Millettia conraui

A new geranylated isoflavone, 7-O-geranyl-6-methoxypseudobaptigenin (1) was isolated from the stem barks of Millettia conraui, along with known compounds 5-methoxydurmillone (2), conrauinone A (3), beta-amyrine (4), sitosterol (5), 3-O-beta-D-glucopyranosyl sitosterol (6) and n-docosanol (7). Compounds 1 and 4 showed a significant alpha-glucosidase inhibitory activity. The structures of the compounds were determined by analysis of their spectroscopic data.     

New glycosides from the rhizomes of Tacca chantrieri

Five new glycosides, which are classified into two bisdesmosidic pseudofurostanol glycosides (1, 2), two new ergostanol glycosides (3, 4), and a new phenolic glycoside (5), were isolated from the rhizomes of Tacca chantrieri. The structures of 1-5 were determined on the basis of extensive spectroscopic analysis, including that of two-dimensional (2D) NMR data, as well as hydrolytic cleavage followed by spectroscopic and chromatographic analyses.     

A new isoflavone from the mangrove endophytic fungus Fusarium sp. (ZZF60)

A new isoflavone, 5-hydroxy-7-methoxy-4'-O-(3-methylbut-2-enyl) isoflavone (1), together with five known compounds, eriodictyol (2), vittarin-B (3), 3,6,7-trihydroxy-1-methoxyxanthone (4), 1,3,6-Trihydroxy-8-methylxanthone (5) and cyclo (Phe-Tyr) (6), was isolated from the mangrove endophytic fungus, Fusarium sp. ZZF60 obtained from the South China Sea. Their structures were determined by the analysis of spectroscopic data.     

A new triterpenoid acid from <Emphasis Type="Italic">Schisandra henryi</Emphasis>

A new lanostane triterpenoid acid, nigranoic acid 3-ethyl ester (1), together with two known lanostane triterpenoid acids, isoschizandronic acid (2) and anwuweizic acid (3), was isolated from the stems of Schisandra henryi Clarke. The new compound was identified based on extensive spectroscopic studies including HR-ESI-MS and 2D NMR spectra, and the known compounds were identified by their spectroscopic data analysis and comparison with reports in the literature. Compounds 2 and 3 were isolated from the plant for the first time.     

Pentacyclic triterpenoids from the mangrove plant Rhizophora stylosa

Seven pentacyclic triterpenoids including 3beta-O-(E)-coumaroyl-15alpha-hydroxy-beta-amyrin (1), 15alpha-hydroxy-beta-amyrin (2), 3beta-taraxerol (3), 3beta-taraxerol formate (4), 3beta-taraxerol acetate (5), 3beta-O-(E)-coumaroyl-taraxerol (6), and 3beta-O-(Z)-coumaroyl-taraxerol (7) were isolated and identified from the stems and twigs of the mangrove plant Rhizophora stylosa. The structures of the isolated compounds were determined by extensive analysis of their spectroscopic data. Among these metabolites, compound 1 is a new oleanane-type triterpenoid coumaroyl ester, while compound 4 is a new natural product obtained here as an isolated substance for the first time. The full spectroscopic detail of compound 4 is also reported here for the first time.     

Identification and quantitative analysis of the phytoecdysteroids in Silene species (Caryophyllaceae) by high-performance liquid chromatography. Novel ecdysteroids from S. pseudotites.

Many species in the genus Silene (Caryophyllaceae) have previously been shown to contain ecdysteroids and this genus is recognised as a good source of novel ecdysteroid analogues. We have used ecdysteroid-specific radioimmunoassays and the microplate-based Drosophila melanogaster B(II) cell bioassay for ecdysteroid agonist and antagonist activities to identify further phytoecdysteroid-containing species in this genus. The main ecdysteroid components from 10 Silene species (S. antirrhina, S. chlorifolia, S. cretica, S. disticha, S. echinata, S. italica, S. portensis, S. pseudotites, S. radicosa, S. regia) were isolated and identified, mainly by normal-phase and reversed-phase high-performance liquid chromatography. The amount of each ecdysteroid was determined by comparing chromatogram peak areas with those for reference 20-hydroxyecdysone (20E) on reversed-phase HPLC. 20E is the most abundant ecdysteroid in each of the Silene extracts. Polypodine B, 2-deoxy-20-hydroxyecdysone and ecdysone are also common ecdysteroids in these Silene species, but the proportions of these ecdysteroids vary between the Silene species. HPLC proved to be a quick and effective way to screen Silene species, determine ecdysteroid profiles and, hence, identify extracts containing novel analogues. An extract of the aerial parts of S. pseudotites was found to contain several new ecdysteroids. These have been isolated and identified spectroscopically (by NMR and mass spectrometry) as 2-deoxyecdysone 22beta-D-glucoside, 2-deoxy-20,26-dihydroxyecdysone and 2-deoxypolypodine B 3beta-D-glucoside. Additionally, (5alpha-H)-2-deoxyintegristerone A (5alpha-2H 91%, 5alpha-1H 9%) was isolated as an artefact. This study contributes to the understanding of ecdysteroid distribution in Silene species and provides further information on the chemotaxonomic significance of ecdysteroids in Silene species.     

Lupane-triterpene glycosides from the leaves of Acanthopanax gracilistylus

A novel lupane-triterpene glycoside, called wujiapioside B (1), was isolated from the leaves of Acanthopanax gracilistylus (Araliaceae) together with three known lupane-triterpene glycosides, acankoreoside C (2), acantrifoside A (3) and 3-epibetulinic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (4). Based on spectroscopic data, the chemical structure of 1 was determined as 3alpha,23-dihydroxy-lup-20(29)-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester. Compounds 2-3 were obtained for the first time from this plant and compound 4 has not been isolated from Acanthopanax genus yet.     

Isolation of toxic compounds from wild Phaeocystis globosa

Two new compounds, namely taenialactam C and globorin A (1 and 2), as well as six known compounds, cornoside (3), 2-phenylethyl-b-D-glucoside (4), 3-isopropyl-5-acetoxycyclohexene-2-one-1 (5), 4-methyl-phenol (6), 5-[(2S)-2-aminobutyl]-2-methyl-phenol (7), and 1-(4-methylphenyl)-1-propanone (8) were isolated from wild Phaeocystis globosa. The structures of the new compounds were established by detailed spectroscopic analysis and by comparison with spectral data of related known compounds. The structures of the known compounds were identified by comparing their spectroscopic data with those reported in the literature. This paper also reports toxicity properties of the eight compounds against the brine shrimp Artemia salina and juvenile Epinephelus akaara fish. Some of these compounds showed significant lethality on the brine shrimp A. salina and the juvenile E. akaara fish.     

Prenylisoflavone derivatives from the roots of Hedysarum scoparium

Four new prenylisoflavone derivatives, namely, 5-hydroxy-4'-methoxy-8-prenyl-2'-hydroxyisopropyldihydrofurano[4,5:6,7]-isoflavone (1), 5-hydroxy-4'-methoxy-6-prenyl-2'-hydroxyisopropyldihydrofurano[4,5:8,7]-isoflavone (2), 5-hydroxy-4'-methoxy-8-prenyl-1',2'-peroxyl-3',3'-dimethyldihydropyrano[5,6:6,7]-isoflavone (3), and 5-hydroxy-4'-methoxy-6-prenyl-1',2'-peroxyl-3',3'-dimethyldihydropyrano[5,6:8,7]-isoflavone (4), together with three known ones 5-7, were isolated from the roots of Hedysarum scoparium. Their structures were established by means of detailed spectroscopic analysis (IR, EI- or HR-ESI-MS as well as 1D- and 2D-NMR), and by comparison of their spectroscopic data with those reported for structurally related compounds.     

Nauplathizine, a new unusual O-heteroside from Nauplius aquaticus (L)

A novel O-heteroside, (3RS,4RS)-3,4-dihydroxy-4-(2-hydroxy-5-acetylphenyl)-2-[(beta-O-glucopyranosyl)methyl]-but-1-ene (1), named nauplathizine, and a previously known compound, acetophenone-4-O-glucoside (2), were isolated from the antibacterial acetone extract of the aerial parts of Nauplius aquaticus (L) (Asteraceae, Inulae). The structure of 1 was established via its acetylated derivative by means of spectroscopic and chemical data.     

Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC

A new 3-benzylphthalide, scorzoveratrin 4'-O-β-glucoside (1), together with the known 3-benzylphthalides, scorzoveratrin (2) and scorzoveratrozit (3), the caffeoyl derivatives, chlorogenic acid methyl ester (4), 4,5-dicaffeoylquinic acid (5), 4,5-dicaffeoylquinic acid methyl ester (6), 3,5-dicaffeoylquinic acid (7) and caffeic acid (8) were isolated from the subaerial parts of Scorzonera latifolia (Fisch. & Mey.) DC. All secondary metabolites were assigned using physicochemical and spectroscopic data. The known compounds 2-8 were isolated for the first time from this species.     

Isoflavones from the mangrove endophytic fungus Fusarium sp. (ZZF41)

A new isoflavone, 5-O-methyl-2'-methoxy-3'-methylalpinumisoflavone (1), together with four known compounds 6-methoxy-5,7,4'-trihydroxyisoflavone (2), 6-methoxy-7,4'-dihydroxyisoflavone (3), (+)-marmesin (4), and 4-methylbenzoic acid carboxymethyl ester (5), were isolated from the mangrove endophytic fungus, Fusarium sp. (ZZF41). Their structures were determined by analysis of spectroscopic data. Compound 1 inhibited HEp-2 and HepG2 cells with IC50 values of 4 and 11 micromol/mL, respectively.