Cyanidin 3-(6-succinyl glucoside)-5-glucoside from flowers of seven Centaurea species

Extraction, purification and analysis of the anthocyanin pigments of ten taxa of the genus Centaurea yielded cyanidin 3-O-(6-O-succinyl-β-D-glucoside)-5-O-β-D-glucoside.     

Sesquiterpenoids and flavonoids from Pteris multifida Poir.

Phytochemical research of Pteris multifida Poir. led to the isolation of fifteen compounds, including six flavonoids (1–6) and nine sesquiterpenoids (7–15). Their structures were characterized by NMR, MS, ORD and CD data. Compounds kaempferol 3-O-α-L-rhamnoside-7-O-β-D-glucoside (1), myricetin 3-O-β-D-glucoside (2), kaempferol 3-O-β-D-glucoside (4), luteolin-7-O-β-D-rutinoside (5), quercetin-3-O-α-L-rhamnopyranoside (6), (2S,3S)-12-hydroxypterosin Q (7), (2S,3S)-pterosin Q (8), 2-hydroxypterosin C (9) and (2S)-12-hydroxypterosin A (10) were first isolated from P. multifida, and compounds 1–2 and 10 were first isolated from the family Pteridaceae. Furthermore, the chemotaxonomic significance of the isolates was discussed.     

Acylated flavonol glucosides of Pinus contorta needles

From fresh Pinus contorta Doug (Coastal) needles four flavonol acylated glucosides and 6-methyl-kaempferol 3-β-D-glucoside were isolated. The three monoacylated glucosides were kaempferol-3-β-D(6-O-p- coumaryl)glucoside, isorhamnetin-3-β-D-(6-O-acetyl)glucoside, quercetin-3-β-D-(p-coumaryl)glucoside and the diacyl compound was kaempferol-3-β-D-(di-p-coumaryl)glucoside.     

A lignan from Lonicera hypoleuca

A new lignan characterised as (-)-4-hydroxy-2,6-di-(4′-hydroxy-3′-methoxy)phenyl-3,7-dioxabicyclo-(3.3.0)octane along with n-10-nonacosanol, scopoletin, syringic acid, β-sitosterol and its glucoside, has been isolated from the aerial parts of Lonicera hypoleuca. The stereochemistry of the lignan has been established by its spectroscopic analysis and those of its derivatives, and by its conversion to (+)-pinoresinol. β-Sitosterol-β-D-glucoside displayed good spasmolytic activity.     

Purification and characterization of cellulolytic enzymes fromTrichoderma harzianum

Two forms of filter paper activity (filter paper activity; cellulose 1,4-β-cellobiosidase, EC 3.2.1.91) and single forms of CM-cellulase (carboxymethyl cellulase; endo-l,4-β-glucanase, EC 3.2.1.4) and β-glucosidase (β-D-glucoside glucohydrolase, EC 3.2.1.21) from the culture filtrate ofTrichoderma harzianum were separated and partially purified by (NH₄)₂SO₄ precipitation, ion-exchange chromatography and gel filtration. The final preparation was purified about 12-, 20- and 27-fold for FP-activity, CM-oellulase and β-glueosidase, respectively. The pH and temperature optima, stability, kinetic parameters, effeet of metal ions and molar mass of each was determined. A distinct type of synergistic action between cellulase components was observed for efficientin vitro saccharification of dewaxed cotton.     

Hypolaetin 8-glucoside from Sideritis leucantha

A new naturally occurring hypolaetin 8-β-D-glucoside has been isolated and identified from Sideritis leucantha. The natural compound suffered nuclear methylation during derivatization.     

Synthesis,oxygen radical absorbance capacity,and tyrosinase inhibitory activity of glycosides of resveratrol,pterostilbene, and pinostilbene

The stilbene compound resveratrol was glycosylated to give its 4′-O-β-D-glucoside as the major product in addition to its 3-O-β-D-glucoside by a plant glucosyltransferase from Phytolacca americana expressed in recombinant Escherichia coli. This enzyme transformed pterostilbene to its 4′-O-β-D-glucoside, and converted pinostilbene to its 4′-O-β-D-glucoside as a major product and its 3-O-β-D-glucoside as a minor product. An analysis of antioxidant capacity showed that the above stilbene glycosides had lower oxygen radical absorbance capacity (ORAC) values than those of the corresponding stilbene aglycones. The 3-O-β-D-glucoside of resveratrol showed the highest ORAC value among the stilbene glycosides tested, and pinostilbene had the highest value among the stilbene compounds. The tyrosinase inhibitory activities of the stilbene aglycones were improved by glycosylation; the stilbene glycosides had higher activities than the stilbene aglycones. Resveratrol 3-O-β-D-glucoside had the highest tyrosinase inhibitory activity among the stilbene compounds tested.     

水红木中两个新的酚苷成分

从水红木（Viburnum cylindricum）植物中分离出2个新化合物,1-phlomglucinyl-（6-methybutyryl）-β-D-glucopyranoside命名为cylindrin A（1）,1-[4-（3-hydroxyl-propyl）]-pyrocatechol-（6-methybutyryl）-β-D—glucopyranoside,命名为cylindrin B（2）。以及7个已知化合物tachioside（3）,syingic acid-4-β-D-glucopyran oside（4）,1-β-D—glucopyanosyloxy-3-methoxy-5-hydroxybenzene（5）,4-hydroxy-3-methoxyphenol-1-O-β-D-glucoside（6）,4-hydroxy-2,6-dimethoxyphen-1-O-β-D-glucoside（7）,phlorogluc inol-1-O-β-D-glucoside（8）,1-β-D-glucosyloxy-2-（3-nrethoxy-4-hydroxyphenyl）propane-1,3-diol（9）．它们的结构经波谱方法得到鉴定。3—9为首次从该种植物中分离得到。     

Glycosylation of capsaicinoids with Panax ginseng stimulated by salicylic acid

The efficient production of β-glycosides of capsaicin and 8-nordihydrocapsaicin by cultured cells of Panax ginseng is reported. Capsaicin 4-O-(6-O-β-D-xylopyranosyl)-β-D-glucopyranoside (β-primeveroside, 12%) together with capsaicin 4-O-β-D-glucoside (6%) was isolated from the cell suspension of P. ginseng after one week of incubation with capsaicin. On the other hand, 8-nordihydrocapsaicin was glycosylated to 8-nordihydrocapsaicin 4-O-β-D-glucoside (5%) and 8-nordihydrocapsaicin 4-O-β-primeveroside (9%) by P. ginseng. Pretreatment of the cultured cells with salicylic acid greatly enhanced the glucosylation activity toward capsaicinoids. When 500 μM of salicylic acid was added to the cultures prior to the addition of substrate, capsaicin was converted into capsaicin 4-O-β-D-glucoside (17%) and capsaicin β-primeveroside (21%) and 8-nordihydrocapsaicin was glycosylated to 8-nordihydrocapsaicin 4-O-β-D-glucoside (16%) and 8-nordihydrocapsaicin β-primeveroside (15%).     

Isoflavones and stilbenes from Juniperus macropoda

An ethanolic extract of Juniperus macropoda, after chromatography, yielded three isoflavones, viz.irigenin, iridin and a new compound. In addition two stilbenes, resveratrol and piceid (resveratrol-3-O-β-D-glucoside), were isolated and characterized.     

7-O-methyl-(2R:3R)-dihydroquercetin 5-O-β-D-glucoside and other flavonoids from Podocarpus nivalis

In the course of a chemotaxonomic survey of New Zealand Podocarpus species, a number of new flavonoid glycosides have been isolated from P. nivalis. These are: luteolin 3′-O-β-D-xyloside, luteolin 7-O-β-D-glucoside-3′-O-β-D-xyloside, dihydroquercetin 7-O-β-D-glucoside, 7-O-methyl-(2R:3R)-dihydrokaempferol 5-O-β-D-glucopyranoside, 7-O-methyl-(2R:3R)-dihydroquercetin 5-O-β-D-glucopyranoside, 7-O-methylkaempferol 5-O-β-D-glucopyranoside and 7-O-methylquercetin 5-O-β-D-glucopyranoside. Diagnostically useful physical techniques for distinguishing substitution patterns in dihydroflavonols are discussed and summarized. Glucosylation of the 5-hydroxyl group in (+)-dihydroflavonols is shown to reverse the sign of rotation at 589 nm.     

小金梅草化学成分研究(英文)

从小金梅草乙醇提取物中分离得到了12个化合物,分别为3-O-β-D-槲皮素葡萄糖苷(1)、3-O-β-D-山柰酚葡萄糖苷(2)、5-O-β-D-芹菜素葡萄糖苷(3)、α-菠甾醇(4)、2,6-二甲氧基苯甲酸(5)、3-吲哚甲酸(6)、(2S,3R,4E,8E)-1-(β-D-吡喃葡萄糖苷)-N-[(R)-2’-羟基-二十碳酰基]-9-甲基-4,8-二烯-1,3-二醇-2-氨基-十八烷(7)、正三十二烷醇(8)、14,15-二十碳烯酸(9)、木腊酸(10)、β-谷甾醇(11)、胡萝卜苷(12)。以上化合物均为首次从该植物中得到。     

广藿香大极性化学成分的研究

从广藿香(Pogostemon cablin (Blance)Benth.)地上部分乙醇提取物的正丁醇萃取部位分离得到13个化合物.通过光谱和波谱分析,分别鉴定为:芹菜素(1)、3,5,4'-三羟基-7-甲氧基黄酮(2)、3,5-二羟基_4',7-二甲氧基黄酮(3)、Apigenin 7-galacturonide(4)、Apigenin 7-(O-methylghacuronide)(5),Luteolin 7-O-(6-O-methyl-β-D-glucuronopyranoside)(6),4',5-二羟基-3',7-二甲氧基二氢黄酮(7)、Quercetha-7-β-D-ghcoside(8),3,23-Dihydroxy-12-oleanen-28-oic acid(9)、Syringaresinol-β-D-glucoside(10),毛蕊花糖苷(11)、列当苷(12)、紫葳新苷(13),化合物2～13均为首次从该植物中分离得到.     

Purification and Identification of Flavonoids from the Yellow Green Cocoon Shell (Sasamayu) of the Silkworm,Bombyx mori

Three quercetin glycosides, quercetin 5-O-β-D-glucoside, quercetin 7-O-β-D-glucoside, and quercetin 4′-O-β-D-glucoside, and two kaempferol glycosides, kaempferol 5-O-β-D-glucoside and kaempferol 7-O-β-D-glucoside, along with their aglycones, quercetin and kaempferol, were isolated from an ethanolic extract of Sasamayu cocoon shells. The chemical structures were characterized by chemical and spectroscopic methods including UV spectrometry and HPLC-ESI-MS. The five flavonol glycosides of the shell are different structurally from those of the leaves of mulberry (Morus alba). It was suggested that potent antioxidative activity in the cocoon is mainly due to flavonoid compounds since free radical scavenging activity was found in the cocoon flavonoids identified here.     

Studies on the Chemical Constituents of Elsholtzia eriostachya Benth.

Sixteen constituents were isolated from the hot alcohoic extract of the whole plant of a Chinese medicinal herb Elsholtzia eriostachya Benth.. Twelve of them were elucidated by spectroscopic and chemical evidences as follows: dotriacontanoic acid （l）, β-sitosterol（2）, succinic acid （3）, aretigenin (5), 3-hydroxyarctiin （7）, luteolin-5-O-β-D-glucoside （8）, luteolin-7-O-β-D-glucoside (9), gentisic acid -5-O-β-D-glucopranoside (10), hyperoside (11), morin-7-O-β-D-glucopranoside （12）, isoskuranetin-7-O-β-D-neohesperidoside （14）, acacetin-7-O-β-D-rutinoside （15） 7 is a new compound, and eight compounds (3, 5, 8, 10,11,12,14 and 15) were isolated from Elsholtzia for the first time.     

Cardenolides and a lignan from asclepias subulata

Four new glycosides (three cardenolides and a lignan), nine previously reported cardenolide glycosides and a known triterpenoid were isolated from the ethyl acetate extract of the aerial parts of Asclepias subulata. The elucidation of the structures and stereochemistry of the new glycosides has been accomplished using mainly ¹H and ¹³C NMR and mass (EI and FAB) spectral data of their acetyl derivatives and comparison of these data with those of known glycosides from the same plant as well as from other plants. The new compounds were identified as 16α-hydroxycalactin, 3β-(β-D-glucopyranosyloxy)-19-car coroglaucigenin 3β-D-glucoside and 4-(β-D-glucopyranosyloxy)-larciresinol.     

Phytochemical investigation of Eremostachys moluccelloides Bunge (Lamiaceae)

Phytochemical investigation of the aerial parts of Eremostachys moluccelloides Bunge led to the identification of a new diterpene, 2β,14-dihydroxy −11-formyl- 12-carboxy-13-des-isopropyl-13-hydroxymethyl-abieta-8,11,13- triene- 16(17)- lactone (1), along with the known compounds 12, 18-dicarboxy-14-hydroxy-13-des -isopropyl-13-hydroxymethyl- abieta-8,11,13-triene-16(17)-lactone (2), 5-hydroxy-3′,4′,7-trimethoxyflavone (3), 5-hydroxy-4’,7-dimethoxyflavone (4), luteolin-7-O-β-glucoside (5), verbascoside (6), luteolin 7-O-(6″-O-β-D-apiofuranosyl) -β-D-glucopyranoside (7), chlorogenic acid (8), echinacoside (9), apigenin-7-O-β-D-glucoside (10), p-coumaric acid (11), vanillic acid (12), apigenin-7-O-(6″-E-p-coumaroyl)-β-D-glucopyranoside (13), apigenin-7-O-(3″,6″-E-p-dicoumaroyl)-β-glucoside (14), lamalbide (15), 6β-hydroxy-7-epi-loganin (16), phloyoside II (17) The structures were elucidated on the basis of 1D and 2D NMR spectroscopy, UV, MS and by comparison with compounds previously reported in the literature. Compounds 1–4, 8, 9, 11, 12, 14 have not been reported previously from any species within the genus Eremostachys. Compounds 1–14, 17 were obtained from this species for the first time. The chemotaxonomic significance of the isolated compounds is discussed.     

Chemical constituents from Aristolochia tagala and their chemotaxonomic significance

Fifteen compounds were obtained from the extract of the whole herbs of Aristolochia tagala, which were divided into eight aristolactam-type alkaloids (1–6, 14 and 15) and seven aristolochic acid derivatives (7–13). Their structures were identified as aristolactam BII, aristolactam II, sauristolactam, aristolactam I, 7-methoxyaristolactam IV, aristolactam AII, 3-hydroxy-4-methoxy-10-nitrophenanthrene-1-carboxylic acid methyl ester, ariskanin A, ariskanin D, ariskanin E, aristolochic acid C, ariskanin C, ariskanin B, aristolactam-N-β-D-glucoside and cepharanone A N-β-D-glucoside by comparison of their spectral data with those reported previously in the literature. The chemotaxonomic relationships between A. tagala and other species of genus Aristolochia were also discussed. As a result, the isolated compounds closely matched the ones obtained in other species of the genus.     

Polyphenol Components in Cultured Cells of Amacha (Hydrangea macrophylla Seringe var. Thunbergii Makino)

In the course of our studies on the polyphenol components of the cultured cells of amacha, seven polyphenol compounds were isolated as pure crystals. The chemical structures of these compounds were determined by analytical methods (IR, UV, NMR and MS spectra) and colour reactions, and the compounds were identified as phyllodulcin, hydrangenol, daphnetin-8-monomethylether, umbelliferone, phyllodulcin-8-β-D-glucoside, hydrangenol-8-β-D-glucoside and skiminin (umbelliferone-7-β-D-glucoside). This is the first report of the isolation of phyllodulcin-8-β-D-glucoside and daphnetin-8-monomethylether from a natural source and of the other compounds from the cells of higher plants in suspension culture.     

中华青荚叶的一个新果糖酯

从山茱萸科中华青荚叶( Helwingia chinensis )的乙醇提取物中分离得到一个新果糖酯和十个已知化合物.通过现代波谱技术分别鉴定为:2- O -(E)-咖啡酰-3- O -(3, 5-二甲氧基香豆酰)-α-D-呋喃果糖甙(1),2- O -β-D-呋喃果糖基α-D-异吡喃糖酯(2),甘草甜素(3),4′-羟基-7- O -葡萄糖-2, 3-二羟黄酮甙(4),黄豆甙(5),5-葡萄糖芹菜甙(6),7- O -葡萄糖芹菜甙(7),4- O -葡萄糖香豆酸(8), 葡萄糖咖啡酸(9), 3β-赤杨醇(10), 薯蓣皂甙3- O -{α-L-鼠李糖吡喃糖基(1→2)-[α-L-阿拉伯呋喃糖基(1→3)]-β-D-葡萄糖吡喃糖} (11).