Studies on the constituents of Broussonetia species VIII. Four new pyrrolidine alkaloids, broussonetines R, S, T, and V and a new pyrroline alkaloid, broussonetine U, from Broussonetia kazinoki Sieb

Four new pyrrolidine alkaloids, broussonetines R, S, T, and V and a new pyrroline alkaloid, broussonetine U were isolated from the branches of Broussonetia kazinoki SIEB. (Moraceae) in low yield. Broussonetines R, S and T were formulated as (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R)-1-hydroxy-3-[6-(4-hydroxybutyl)-cyclohexy-2-on-1(6)-enyllpropyl] pyrrolidine (1), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R,10S)-1,10,13-trihydroxytridecyl] pyrrolidine (2), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R,5S)-1,5, 13-trihydroxy-10-oxo-tridecyl] pyrrolidine (3). And broussonetines U and V were proposed to be (2S,3S,4S)-2-hydroxymethyl-3, 4-dihydroxy-5-(9-oxo-13-hydroxytridecyl)-5-pyrroline (4), (2R,3S,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)-9-oxo-13-hydroxy-3-tridecenyl] pyrrolidine (5), respectively, by spectroscopic and chemical methods.     

Studies on the constituents of Broussonetia species. VII. Four new pyrrolidine alkaloids, broussonetines M, O, P, and Q, as inhibitors of glycosidase, from Broussonetia kazinoki SIEB

Four new pyrrolidine alkaloids, broussonetines M, O, P, and Q, were isolated from the branches of Broussonetia kazinoki SIEB, (Moraceae). Broussonetines M, O, P, and Q were formulated as (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(10S)-10,13-dihydroxy-tri decyl]pyrrolidine (1), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)9-oxo-13-hydroxy-3- tridecenyl]pyrrolidine (2), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)10-oxo-13-hydroxy-3-++ +tridecenyl]pyrrolidine (3), and (2R,3S,4R,5R)-2-hydroxymethyl-3-hydroxy-4-(beta-D-glucopyranosyloxy++ +)-5-[10-oxo-13-(beta-D-glucopyranosyloxy)tridecyl]pyrrolidine (4) respectively, by spectroscopic and chemical methods. 1-4 inhibited beta-glucosidase, beta-galactosidase and beta-mannosidase.     

A New Isoprenylated flavonol from the Leaves of Broussonetia kazinoki

Broussonetia kazinoki Sieb (Moraceae) is distributed throughout China and Japan. Previous investigations of this plant revealed the presence of isoprenylated flavans, isoprenylated flavonoids, isoprenylated 1,3-diphenylpropanes1 and alkaloids2,3. Natural prenylated flavonoids have shown potent inhibition against human hepatoma PLC/PRF/5 and epidermoid carcinoma KB cells in vitro4. In order to search for its biologically active compounds, chemical study on this plant was carried out and le…     

托里贝母中新生物碱的结构研究

托里贝母产于中国西北的新疆,我们从其鳞茎中分得五个生物碱成分, 其中一个新生物碱名为托贝辛, 另外四个已知成分为西贝素, 茄次碱, Delavinone和Tortifoline.它们的结构由IR, MS, ^1H NMR 和 ^1^3C NMR确定.     

Studies on the constituents of Syringa species. X. Five new iridoid glycosides from the leaves of Syringa reticulata (Blume) Hara

Five new iridoid glycosides, (8Z)-ligstroside (1), (8Z)-nüzhenide (3), 6'-O-alpha-D-glucopyranosylsyringopicroside (4), 3'-O-beta-D-glucopyranosylsyringopicroside (5) and 4'-O-beta-D-glucopyranosylsyringopicroside (6) were isolated, together with a known one, (8E)-nüzhenide (2), from the leaves of Syringa reticulata. Their structures were established on the basis of chemical and spectral data. Compounds 1 and 3 are the first findings of a (8Z)-oleoside-type secoiridoid. Compound 4 is the first naturally occurring iridoid di-glycoside having an isomaltose.     

Microbial Transformation and Biological Activities of the Prenylated Aromatic Compounds from Broussonetia kazinoki

Broussonetia kazinoki has been used as a traditional medicine for the treatment of burns and acne, and its extracts have been found to show tyrosinase inhibitory and anticancer activities. In this study, the tyrosinase inhibitory and cytotoxic activities of B. kazinoki were explored, leading to the isolation of kazinol C (1), kazinol E (2), kazinol F (3), broussonol N (4), and kazinol X (5), of which the compounds 4 and 5 have not been previously reported. Microbial transformation has been recognized as an efficient tool to generate more active metabolites. Microbial transformation of the major compounds 1 and 3 was conducted with Mucor hiemalis, where four glucosylated metabolites (6–9) were produced from 1, while one hydroxylated (10) and one glucosylated (11) metabolites were obtained from 3. Structures of the isolated metabolites were determined by extensive spectroscopic analyses. All compounds were evaluated for their tyrosinase inhibitory and cytotoxic activities. Compound 3 and its metabolites, kazinol Y (10) and kazinol F-4″-O-β-d-glucopyranoside (11), exhibited the most potent tyrosinase inhibitory activities with the IC₅₀ values ranging from 0.71 to 3.36 µM. Meanwhile, none of the metabolites, except for kazinol C-2′,3″-di-O-β-d-glucopyranoside (7), showed moderate cytotoxic activities (IC₅₀ 17.80 to 24.22 µM) against A375P, B16F10 and B16F1 cell lines.     

Kazinol Q from Broussonetia kazinoki enhances cell death induced by Cu(II) through increased reactive oxygen species

The ability of the flavan kazinol Q (KQ) to induce DNA breakage in the presence of Cu(II) was examined by agarose gel electrophoresis using supercoiled plasmid DNA. In KQ-mediated DNA breakage reaction, the involvement of reactive oxygen species (ROS), H(2)O(2) and O(2)- was established by the inhibition of DNA breakage by catalase and revealed DNA breakage by superoxide dismutase (SOD). The cell viability of gastric carcinoma SCM-1 cells treated with various concentrations of KQ was significantly decreased by cotreatment with Cu(II). Treatment of SCM-1 cells with 300 μM Cu(II) enhanced the necrosis induced by 100 μM KQ. Treatment of SCM-1 cells with 100 mM KQ in the presence of 300 mM Cu(II) increased the generation of H(2)O(2). Taken together, the above finding suggested that KQ cotreatment with Cu(II) produced increased amounts of H(2)O(2), thus enhancing subsequent cell death due to necrosis.     

Six new indole alkaloids from Gelsemium sempervirens Ait. f.

One new yohimbane and five new sarpagine-type indole alkaloids were isolated from the radix of Gelsemium sempervirens Ait. f., and their structures were determined by spectroscopic analysis, chemical conversion or total synthesis. It was found that 2-acyl sarpagine-type alkaloids possessing an N_b-methyl group take a keto-amino structure or a transannular form in solution depending on the solvent.     

Studies of the constituents of Gardenia species. II. Terpenoids from Gardeniae Fructus

Four new terpenoids, gardenate A (1), 2-hydroxyethyl gardenamide A (2), (1R,7R,8S,10R)-7,8,11-trihydroxyguai-4-en-3-one 8-O-beta-D-glucopyranoside (3) and Jasminoside F (4), were isolated from Gardeniae Fructus. Their structures were established on the basis of spectral analysis.     

三尖彬属植物中生物碱的研究:VI.三尖杉中两种高刺桐类型的新生物碱的结构

本文报导从安徽产三尖杉弱碱部份分得五种高刺桐类型生物碱, 其中两种新生物碱经UV, IR光谱分析分鉴定为:2-O-乙基表福建三尖杉碱(2-O-ethglepicephalofortuneine)和2-O-乙基福建三尖杉碱(2-O-ethylcephalofortuneine)。     

Six new monoterpenoid indole alkaloids from the aerial part of Gelsemium elegans

Six new monoterpenoid indole alkaloids along with four known analogues were isolated from the aerial part of Gelsemium elegans. Their structures with absolute configurations were elucidated by NMR, HRESIMS, X-ray diffraction, CD spectra, and molecular modeling calculation. Among them, gelselenidine (1) is a new gelsedine-type alkaloid with a 2,3-epoxybutane unit. Gelseziridine (2) is the first example of monoterpenoid indole alkaloids with an oxaziridine residue. Compounds 6 and 7 are a pair of N₄ epimers of humantenine N₄-oxide. A plausible biogenetic pathway for compounds 1-4 was also proposed.     

Nakijinamines C-E, new heteroaromatic alkaloids from the sponge Suberites species

Three new heteroaromatic alkaloids, nakijinamines C-E (1-3), which are a hybrid of the aaptamine-type and bromoindole alkaloids possessing a taurine- or histidine-derived residue, have been isolated from an Okinawan marine sponge Suberites species. The structures of 1-3 were elucidated on the basis of spectroscopic data and chemical conversions. Nakijinamines C (1) and E (3) are the first natural products possessing a 1H-oxazolo[4',5':4,5]benzo[1,2,3-de][1,6]naphthyridine ring system.     

百部生物碱的化学研究 I. 细花百部新生物碱

从海南岛产野生百部, 细花百部(Stemona parviflora Wright C.H.)的根部又分得三个新生物碱, 分别命名为细化百部酰胺(parvistemoamide)(1), 细花百部次碱(parvistemolone)(2)和脱氢细花百部碱(didehydroparvistemonine)(3)。经IR, MS,^1H和^1^3C NMR、NOE差谱, 2D-同核及异核相关谱等技术推定了结构。同时归属了它们的^1H和^1^3C NMR信号。     

Studies on the constituents of Clematis species. VIII. Triterpenoid saponins from the aerial part of Clematis tibetana KUNTZ

From the aerial part of Clematis tibetana, two new hederagenin 3,28-O-bisdesmosides called clematibetosides A and C, and a new gypsogenin 3,28-O-bisdesmoside called clematibetoside B, have been isolated together with ten known saponins. The structures of the new saponins have been elucidated based on chemical and spectral evidence as follows: clematibetoside A, 3-O-(2-O-caffeoyl)-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)-beta-D-ribopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyraside; clematibetoside B, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl gypsogenin 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside; clematibetoside C, 3-O-beta-D-ribopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside.     

Studies on the constituents of Catalpa species. IX. Iridoids from the fallen leaves of Catalpa ovata G. Don

Two new iridoids, 6-O-trans-p-coumaroyl-7-deoxyrehmaglutin A (1) and 6-O-cis-p-coumaroyl-7-deoxyrehmaglutin A (2), were isolated from the fallen leaves of Catalpa ovata G. DON. together with six artifact iridoids (3-8). Their structures were established by spectral analysis. In addition, the scavenging effects of the principal compounds isolated from this plant on 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity were examined.