A new steroidal saponin,yuccalan, from the leaves of<Emphasis Type="Italic">Yucca smalliana</Emphasis>

An extract of the leaves of Yucca smalliana Fern. (Agavaceae) showed potential antimicrobial activity. Employing a bioassay linked fractionation method, one of the active principles, namely yuccalan, was isolated as a new steroidal saponin. The structure of the new steroidal saponin was elucidated as 3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(3beta, 5alpha, 6alpha, 25S)-spirostan-3,6,27-triol (1) using various spectroscopic techniques, including IR, MS, 1D and 2D 1H-NMR, and 13C-NMR. The purified yuccalan showed antifungal activities against both Rhizoctonia solani and Fusarium oxysporum.     

A new anti-HIV lupane acid from Gleditsia sinensis Lam.

A new lupane acid, 2β-carboxyl,3β-hydroxyl-norlupA (1)-20 (29)-en-28-oic acid (1), together with five known lupane acid derivatives (2-6), were isolated from the stings of Gleditsia sinensis Lam.. Their structures were elucidated on the basis of 1D and 2D NMR techniques. All these known compounds were isolated from this genus for the first time. The new compound 1 showed strong anti-HIV activity.     

A new chromone glycoside from <Emphasis Type="Italic">Rhododendron spinuliferum</Emphasis>

A new chromone glycoside, 3,5,7-trihydroxylchromone-3-O-alpha-L-arabinopyranoside (1), together with quercetin (2), (+)-catechin (3), (-)-epi-catechin (4) were isolated from the aerial parts of Rhododendron spinuliferum. The structure of 1 was elucidated on the basis of spectroscopic and 2D-NMR spectral analysis. In addition, 1 exhibited mild inhibitory effect on NO production in LPS-stimulated RAW264.7 cells.     

可疑翼手参中的一个新三萜皂苷

目的：寻找结构新颖的三萜皂苷类化合物。方法：采用多种色谱方法．对属于枝手目瓜参科的可疑翼手参体内成分进行了分离纯化；并采用多种光谱(IR．UV，ESI-MS，2D-NMR)和化学方法对所分离化合物的结构进行了确定。结果与结论：得到一个新的三萜皂苷类化合物，我们把该化合物命名为coloehiroside A(1)。     

A new triterpene lactone from the roots ofPatrinia scabiosaefolia

A new triterpene lactone named patrinolide A (1) has been isolated from the roots of Patrinia scabiosaefolia (Valerianaceae). Its structure was determined to be 11beta,21beta-dihydroxy-3-oxooleanan-28,13beta-olide on the basis of spectral analysis, including 2D-NMR techniques. Key words: Patrinia scabiosaefolia, Valerianaceae, Lactone, Patrinolide, 11beta,21beta-dihydroxy-3-oxooleanan-28,13beta-olide.     

A new monoterpene glycoside from the roots of<Emphasis Type="Italic">Paeonia lacti- flora</Emphasis> increases the differentiation of osteoblastic MC3T3-E1 cells

A new monoterpene glycoside, 6'-O-beta-D-glucopyranosylalbiflorin (1), and four known compounds; albiflorin (2), 6'-O-benzoylalbiflorin (3), paeoniflorin (4) and benzoyl paeoniflorin (5), were isolated from the methanolic extract of the roots of Paeonia lactiflora Pall.. Their chemical structures were completely elucidated using a combination of 2D NMR techniques (COSY, HMQC and HMBC) and HRESI-MS analyses. To investigate the bioactivities of these compounds, their effects on the differentiation of osteoblastic MC3T3-E1 cells were tested. Compound 1 (0.01-10 microM) significantly increased the alkaline phosphatase activity and nodules mineralization of MC3T3-E1 cells compared to those of the control (P<0.05). These results suggest that newly isolated compound 1 has a direct stimulatory effect on bone formation in vitro and may contribute to the prevention for osteoporosis.     

In vivo growth-inhibition of Sarcoma 180 by an α-(1 → 4)-glucan–β-(1 → 6)-glucan-protein complex polysaccharide obtained from <Emphasis Type="Italic">Agaricus blazei</Emphasis> Murill

Agaricus blazei Murrill, a native mushroom of Brazil, has been widely consumed in different parts of the world due to its anticancer potential. This effect is generally attributed to its polysaccharides; however, the precise structure of these has not been fully characterized. To better understand the relationship between polysaccharide structures and antitumor activity, we investigated the effect of the intraperitoneally (i.p.) or orally (p.o.) administered α-(1 → 4)-glucan–β-(1 → 6)-glucan-protein complex polysaccharide from A. blazei alone or in association with 5-fluorouracil (5-FU) in tumor growth using Sarcoma 180 transplanted mice. Hematological, biochemical, and histopathological analyses were performed in order to evaluate the toxicological aspects of the polysaccharide treatment. The polysaccharide had no direct cytotoxic action on tumor cells in vitro. However, the polysaccharide showed strong in vivo antitumor effect. Thus, the tumor growth-inhibitory effect of the polysaccharide is apparently due to host-mediated mechanisms. The histopathological analysis suggests that the liver and the kidney were not affected by polysaccharide treatment. Neither enzymatic activity of transaminases (AST and ALT) nor urea levels were significantly altered. In hematological analysis, leucopeny was observed after 5-FU treatment, but this effect was prevented when the treatment was associated with the polysaccharide. In conclusion, this polysaccharide probably could explain the ethnopharmacological use of this mushroom in the treatment of cancer.     

Two new secoiridoid glycosides from the rhizomes of Gentiana scabra Bunge

Two new secoiridoid glycosides, 4‴-O-β-D-glucopyranosyltrifloroside 1 and 4‴-O-β-D-glucopyranosylscabraside 2, along with three known secoiridoids were isolated from the rhizomes of Gentiana scabra (Gentianaceae) in our recent phytochemical study. Their chemical structures were determined by spectroscopic data including 1D and 2D NMR spectra. The chemotaxonomic significance of the secoiridoid glycosides is briefly discussed.     

Sesquiterpene components from the flower buds ofMagnolia fargesii

From the Chinese crude drugshin-i, the flower buds ofMagnolia fargesii, four sesquiterpene, oplopanone (1), oplodiol (2), homalomenol A (3) and 1β,4β,7α-trihydroxyeudesmane (4) were isolated. These structures were elucidated and the¹³C-NMR chemical, shifts of these compounds were revised by means of various 2D-NMR techniques.     

A new stilbene glucoside gallate from the roots of Polygonum multiflorum

A new stilbenoid (1) was isolated from the root extract of Polygonum multiflorum together with eight known constituents (2∼9). The chemical structure of 1 was established as the 6″-O-monogalloyl ester of (E)-2,3,4′,5-β-tetrahydroxystilbene-2-β-D-glucopyranoside based on physicochemical and spectroscopic analyses, particularly by NMR spectroscopic data, i.e., COSY, HMQC and HMBC. Compound 1 weakly inhibited acetylcholinesterase in vitro.     

红蓼果实中的一个新三萜皂苷

为了研究红蓼果实的化学成分，利用硅胶和反相柱色谱方法进行分离纯化，根据理化性质和光谱数据鉴定其化合物结构，分离并鉴定了3个化合物：28-O-β-D-glucopyranosyl-3β,7β-dihydroxy-lup-20(29)-en-28-oate (1)，5,7-二羟基色原酮(2)和柚皮素(3)。化合物1为新化合物，化合物2，3为首次从该植物中分离得到。     

A triterpene glucosyl ester from the roots ofRubus crataegifolius

Along with five known triterpene glycosides, a new triterpene glucosyl ester, named crataegioside, was isolated from the roots of Rubus crataegifolius Bunge. The structure was established as ilexosapogenin A 28-O-beta-D-glucopyranosyl ester by chemical and spectroscopic methods.     

Potentially hepatoprotective glycolipid constituents ofLycium chinense fruits

Further investigation of Lycium chinense fruits gave a mixture of (6'-O-palmitoyl)- and (6'-O-stearoyl)-beta-sitosterol-3-O-beta-D-glucopyranoside (1) and two glycolipids, 1-O-(9Z,12Z, 15Z-octadecatrienoyl)-2-O-(9Z, 12Z, 15Z-octadecatrienoyl)-3-O-beta-D-galactopyranosyl glycerol (2) and 1-O-(9Z, 12Z-octadecadienoyl)-2-O-(9Z, 12Z, 15Z-octadecatrienoyl)-3-O-beta-D-galactopyranosyl glycerol (3). These compounds were newly isolated as constituents of L. chinense.     

A new lignan glycoside from the fruits of <Emphasis Type="Italic">Cornus kousa</Emphasis> Burg.

A new lignan glycoside, (7'S, 8'R)-dihydrodehydrodiconiferyl alcohol-4'-O-beta-D-xylopyranoside (1), named cornuskoside A, was isolated from the fruits of Cornus kousa. The structure of the compound was determined by spectroscopy, including FABMS, UV, IR, (1)H-and 13C-NMR, DEPT and 2D-NMR (COSY, HSQC, and HMBC). This new lignan glycoside, along with its aglycone, (7'S, 8'R)-dihydrodehydrodiconiferyl alcohol (3), and another lignan with a similar skeleton, (-)-balanophonin (2), which have been previously isolated from this plant, were evaluated for cytotoxicity in human cancer cell lines such as HeLa, MCF-7, SK-MEL-5, and SK-OV-3. Compounds 2 and 3 showed cytotoxicity against HeLa [IC50 = 29.1 microM (2), 45.5 microM (3)], MCF-7 [IC50 = 29.2 microM (2), 28.2 microM (3)], SK-MEL-5 [IC50 = 31.3 microM (2), 32.3 microM (3)], and SK-OV-3 [IC50 = 33.4 microM (2), 43.4 microM (3)] cell lines.     

苦马豆根和茎中一个新黄酮苷

目的研究苦马豆根和茎的化学成分。方法采用反复硅胶柱色谱、Sephadex LH-20色谱进行化合物的分离,根据波谱数据鉴定化合物结构。结果从95%乙醇提取物正丁醇萃取部分得到8个化合物,鉴定为：异鼠李素-3-O-［6″-(3-羟基-3-甲基戊二酸单酯)-β-D-吡喃葡糖苷］(I)、槲皮苷(II)、正丁基-β-D-吡喃果糖苷(III)、尼克酸(IV)、丁二酸(V)、赤藓醇(VI)、D-甘露醇(VII)和尿嘧啶核苷(VIII)。结论化合物I为新化合物,化合物I-VI均为首次从本属植物中得到。     

Isolation of 3-O-(4′-Hydroxybenzyl)-β-sitosterol and 4-[4′-(4″-Hydroxybenzyloxy)benzyloxy]benzyl methyl ether from fresh tubers ofGastrodia elata

Two new 4-hydroxybenzyl alcohol derivatives (1 and2) were isolated from the methanol extract obtained from fresh tubers ofGastrodia elata together with 4-hydroxybenzyl methyl ether, 4-hydroxybenzyl alcohol, bis(4-hydroxyphenyl)methane, 4-hydroxybenzaldehyde, β-sitosterol and palmitic acid.1 and2 were identified as 3-O-(4′-hydroxybenzyl)-β-sitosterol and 4-[4′-(4″-hydroxybenzyloxy) benzyloxy)benzyl methyl ether, respectively, according to the spectroscopic data.     

Identification of the main volatile compounds in the leaf and flower of <Emphasis Type="Italic">Tithonia diversifolia</Emphasis> (Hemsl) Gray

The composition of the essential oils of the leaves and flowers of Tithonia diversifolia (Hemsl) A. Gray, Mexican sunflower, are reported. The oils were obtained by hydrodistillation in an all-glass Clevenger-type apparatus and analyzed by GC–MS. The leaf oil was comprised of an abundance of α-pinene (32.9%), β-caryophyllene (20.8%), germacrene D (12.6%), β-pinene (10.9%) and 1, 8-cineole (9.1%). Germacrene D (20.3%), β-caryophyllene (20.1%) and bicyclogermacrene (8.0%) characterized the oil of the flower. A number of aliphatic fatty acids and a diterpenoid compound, sandaracopimaradiene, that were present in the flower, could not be detected in the leaf oil.     

A novel sulphur glycoside from the seeds of Descurainia sophia (L.)

A new sulphur glycoside, named descurainoside (1), and the known compound sinapic acid (2) have been isolated from the seeds of Descurainia sophia (L.) Webb ex Prantl. The structure of 1 has been identified as (1R,6S,8R,9S,10S)-9,10-dihydroxy-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylene]-8-(hydroxymethyl)-2,7-dioxa-5-thiabicyclo[4.4.0]decan-3-one by means of physico-chemical properties and spectroscopic methods (1D and 2D NMR, HRMS, ESI-MS).     

A new saponin from the leaves and stems of Panax quinquefolium L. collected in Canada

A new dammarane-type saponin named quinquenoside L3 (1) together with vina-ginsenoside R3 (2) were isolated from the leaves and stems of Panax quinquefolium L. collected in Canada. On the basis of physicochemical and spectral evidences, 1 was established as 3-O-β-D-glucopyranosyl-20-O-[β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranosyl] 20(S)-dammar-23-ene-3β, 12β,20,25-tetryol.     

Tissue factor inhibitory flavonoids from the fruits of Chaenomeles sinensis

Tissue factor (TF, tissue thromboplastin or coagulation factor III) accelerates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor. In order to isolate TF inhibitors from the fruits of Chaenomeles sinensis, an activity-guided purification utilizing a bio-assay method of prothrombin time prolongation, was carried out to yield five active flavoniods such as hovetrichoside C (1) (IC50 = 14.0 microg), luteolin-7-O-beta-D-glucuronide (3) (IC50 = 31.9 microg), hyperin (4) (IC50 = 20.8 microg), avicularin (6) (IC50 = 54.8 microg) and quercitrin (10) (IC50 = 135.7 microg), along with other inactive compounds such as (+/-)-(2E,4E-O-beta-D-glucopyranosyl-4'-hydroxy-beta-ionylideneacetic acid ester (2), genistein-7-O-beta-D-glucopyranoside (5), luteolin-3'-methoxy-4'-O-beta-D-glucopyranoside (7), luteolin-7-O-beta-D-glucuronide methyl ester (8), tricetin-3'-methoxy-4'-O-beta-D-glucopyranoside (selagin-4'-O-beta-D-glucopyranoside) (9), (-)-epicatechin (11), luteolin-4'-O-beta-D-glucopyranoside (12) and apigenin-7-O-beta-D-glucuronide methyl ester (13). The structures of the isolated compounds were elucidated through spectral analysis. Among them, compounds 1 to 9,12 and 13 were isolated for the first time from the fruits of this plant and the compound 9 is a new flavonoid.