Calycosin-7-O-β-D-glucopyranoside stimulates osteoblast differentiation through regulating the BMP/WNT signaling pathways

The iso fl avone calycosin-7-O-β-D-glucopyranoside(CG) is a principal constituent of Astragalus membranaceus(AR) and has been reported to inhibit osteoclast development in vitro and bone loss in vivo. The aim of this study was to investigate the osteogenic effects of CG and its underlying mechanism in ST2 cells. The results show that exposure of cells to CG in osteogenic differentiation medium increases ALP activity, osteocalcin(Ocal) m RNA expression and the osteoblastic mineralization process. Mechanistically, CG treatment increased the expression of bone morphogenetic protein 2(BMP-2), p-Smad 1/5/8, β-catenin and Runx2, all of which are regulators of the BMP- or wingless-type MMTV integration site family(WNT)/β-catenin-signaling pathways. Moreover, the osteogenic effects of CG were inhibited by Noggin and DKK-1 which are classical inhibitors of the BMP and WNT/β-catenin-signaling pathways, respectively. Taken together, the results indicate that CG promotes the osteoblastic differentiation of ST2 cells through regulating the BMP/WNT signaling pathways. On this basis, CG may be a useful lead compound for improving the treatment of bone-decreasing diseases and enhancing bone regeneration.

Lignans from Patrinia scabiosaefolia improve insulin resistance by activating PI-3K/AKT pathway and promoting GLUT4 expression

Patrinia scabiosaefolia,is used as wild vegetable in China for more than 2000 years,with a variety of pharmacological activities,including anti-inflammatory,anti-tumor and hypoglycemic.Based on our ongoing research on chemical constituents and hypoglycemic activity of P.scabiosaefolia,4 lignan compounds,(+)-isolariciresinol(1),7R,7’R,8S,8’S-(+)-neo-olivil-4-O-β-D-glucopyranoside(2),4-O-methylcedrusin(3)and patrinian A(4),were isolated and identifi ed.The hypoglycemic activity showed that compounds 2 and 3 could extremely signifi cantly improve insulin resistance at 100(P<0.001),50(P<0.001)and 25μmol/L(P<0.01)in IR 3T3-L1 cells.While compound 4 only promoted glucose uptake by IR 3T3-L1 cells at 100μmol/L(P<0.01).Western blotting experiments showed that compounds 2 and 4 up-regulated the protein expressions of p-IRS,PI-3K,p-AKT and glucose transporter 4(GLUT4),and promoted the transcription of GLUT4 mRNA.Therefore,the mechanisms of compounds 2 and 4 were presumed to improve IR by activating PI-3K/AKT signaling pathway.

Constituents from Ranunculus sieboldii Miq.

Aim To investigate the chemical composition of Ranunculus sieboldii Miq..Methods Repeated column chromatography over silica gel, polyamide and RP-18 followed by gelfiltration on sephadex LH-20 were used to isolate chemical constituents, and their structures wereelucidated by extensive spectroscopic methods (UV, IR, MS, ~1H NMR, ^(13)C NMR) including 2D NMR(COSY, HMQC, HMBC, NOESY) techniques and by direct comparing spectral data with those reported inliterature. Results Five flavonoid glycosides named apigenin-4'-O-α-L-rhamnopyranoside (1),apigenin-7-O-β-D-glucopyranosyl-4'-O-α-L-rhamnopyranoside (2), apigenin-8-C-α-L-arabinopyranoside(3), apigenin-8-C-β-D-ga-lactopyranoside (4) , tricin-7-O-β-D-glucopyranoside (5), together withtricin (6), luteolin (7), scopoletin (8), esculetin (9), scoparone (10), ferulic acid (11),protocatechuic acid (12) , and tematolide (13) were isolated from the 95% etha-nolic extract of itswhole plant, and their cytotoxic activities were preliminarily tested. Conclusion Compounds 1-12were obtained from this genus and compound 13 from this species for the first time. Furthermore,compound 1 was for the first time isolated from nature while the ^(13)C NMR data of compounds 2 and3 are reported for the first time. The bioassay revealed that compound 1 was active against BEL-7407and A549 cell lines (IC_(45) 43, 77 μg·mL^(-1)), 8 and 10 showed inhibitory activities on KB celllines (IC_(50) 78, 44 μg·mL^(-1)) and HL-60 cell lines (Ic_(50) 85, 85 μg·mL^(-1)), while 7exerted moderate cytotoxic activities on KB, BFL-7407, A549 and HL-60 cell lines with their IC_(50)being 51, 55, 44 and 10 μg·mL^(-1) , respectively.

青蕨植物化学成分的研究(英文)

从青蕨根部的乙酸乙酯提取物中分离得到4个化合物.通过化学及波谱分析鉴定其结构为:saucerneolD1,dehydrogoniothalamin2,1-acetoxyl-2-piperonyl-6-[6-methoxyl-piperonyl]-3,7-dioxabicyclo-[3,3,0]-octane3and5,5′-dihydroxy-3-methoxy-6,8,3″,3″-tetramethylpyran-3′,4′flavone-7-O-[β-D-apiofuranosyl-1→6]-β-D-glucopyranoside4.其中化合物4为新化合物,化合物1为首次从该属植物中分离得到.

Two New Flavonoid Glycosides from Chrysanthemum morifolium

Two new flavonoid glycosides were isolated from the flowering heads of Chrysanthemum morifolium. Their structures were determined to be luteolin 4＇-methoxy-7- O-（6＂-O-acetyl）-β-D-glucopyranoside （1） and acacetin 7-O-（3＂-O-acetyl）-β-D-glucopyranoside （2） by means of 1H and 13C NMR spectroscopic analysis, including 2D NMR technique.

A new flavone glycoside from Selaginella moellendorffii Hieron.

From the ethanol extract of Selaginella moellendorffii Hieron., a new flavone O-glycoside and three known flavone C-glycosides have been isolated and identified as 5-carboxymethyl-4′-hydroxyflavone-7-O-β-D-glucopyranoside 1, 6,8-di-C-β-D-glueopyranosylapigenin 2, 6-C-[3-D-glucopyranosyl-8-C-β-D-xylopyranosyl apigenin 3, 6-C-B-D-xylopyranosyl-8-C-β-glucopyranosylapigenin 4, respectively. Their structures were elucidated by spectroscopic methods.

Two new coumarin glucosides biosynthesized by transgenic hairy roots of Polygonum multiflorum

The glycosylation of hydroxylcoumarin was investigated by using suspension cultures of hairy roots of Polygonum multiflorum. Two new coumarin glucosides （3 and 4） were biosysthesized by regioselectively glycosylation of corresponding substrates （1 and 2） in the system. The structures of two products were identified as 7-hydroxy-4-methylcoumarin 5-O-β-D-glucopyranoside and 7- hydroxy-3,4-dimethylcoumarin 5-O-β-D-glucopyranoside on the ground of chemical and spectroscopic methods, respectively. 2007 Rong Min Yu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

A new polyacetylene glycoside from the rhizomes of Atractylodes lancea

A new polyacetylene glycoside,（1,3Z,11E）-tridecatriene-7,9-diyne-5-hydroxyl-6-O-β-D-glucopyranoside,was isolated from the rhizomes of Atractylodes lancea（Thunb.） DC.Its structure was elucidated on the basis of spectral analysis.

A New Flavan-3-ol Glucoside from Daphniphyllum oldhami

A new flavan-3-ol glucoside, (-)-afzelechin-7-O-β-D-glucopyranoside (1), has been isolated from the stem of Daphniphyllum oldhami. The structure of the new compound was elucidated on the basis of detailed spectroscopie analysis and comparison with related compounds.

Two new isoflavonoids from the rhizomes of Belamcanda chinensis

Two new isoflavonoids, 6-methoxy-5,7,8,4′-tetrahydryoxyisoflavone (1) and 4′-methoxy -5,6-dihydroxyisoflavone-7-O-β-d-glucopyranoside (2), were isolated from the rhizomes of Belamcanda chinensis (L.) DC. Their structures were elucidated by extensive spectroscopic evidence including 1D NMR, 2D NMR, MS and IR spectra.

New flavan and unusual chalcone glycosides from Drypetes parvifolia

Two new compounds 7-hydroxy-5-O-（β-D-glucopyranoside） flavan （1） and （Z）-4＇,6＇-dihydroxy-2＇-O-（β-D-glucopyranoside） chalcone （2）, along with eight known compounds, were isolated from the stem bark of Drypetes parvifolia （Euphorbiaceae）. Their structures were established on the basis of spectroscopic analysis and chemical evidence.

A New Flavone Glycoside from Isodon enanderianus

A new flavone glycoside, 5,8-dihydroxy-4',6,7-trimethoxyflavone 8-O-(-D-glucopyranoside 1, together with three known flavonoids, pedalitin 2, cirsimartin 3 and genkwanin 4, were isolated from the aerial parts of Isodon enanderianus. Their structures were determined on the basis of spectral data.

A New Diterpene Glycoside from Isodon forrestii

A new diterpene glycoside named 9(10-->20)-abeo-7 beta ,10 beta ,11,15-tetrahydroxy-8,11,13-abietatrien-12-O-beta -D-glucopyranoside was isolated from aerial parts of Isodon forrestii. Its structure was determined by means of spectroscopic studies.

何首乌化学成分的研究

目的研究何首乌Polygonum multiflorum的化学成分。方法采用大孔吸附树脂(DM-8型)、Sephadex LH-20、反相硅胶柱色谱和液相制备等多种色谱技术进行分离纯化,采用核磁共振等波谱技术进行结构鉴定。结果从何首乌提取物55%乙醇洗脱部位中分离得到10个化合物,分别鉴定为thunberginol C 6-O-β-D-glucopyranoside(1)、对羟基苯甲醛(2)、反式-N-咖啡酰酪胺(3)、(Z)-2,3,5,4′-四羟基二苯乙烯-2-O-β-D-葡萄糖苷(4)、(E)-2,3,5,4′-四羟基二苯乙烯-2-O-β-D-葡萄糖苷(5)、白藜芦醇-3-O-β-D-(2″-O-没食子酰)-葡萄糖苷(6)、(E)-2,3,5,4′-四羟基二苯乙烯-2-O-β-D-(3″-没食子酰)-葡萄糖苷(7)、苜蓿素-7-O-β-D-葡萄糖苷(8)、torachrysone-8-O-β-D-glucoside(9)、大黄素-8-O-β-D-葡萄糖苷(10)。结论化合物1为新化合物,命名为何首乌丁素。化合物3和8为首次从何首乌中分离得到。

续断的化学成分研究

目的研究续断的化学成分。方法运用大孔树脂、反相硅胶及制备高效液相等色谱技术进行分离纯化,并根据理化性质和波谱数据鉴定化合物的结构。结果分离得到13个化合物,其中7个环烯醚萜苷和6个木脂素类化合物,分别鉴定为马钱苷(1)、獐牙菜苷(2)、6'-O-β-D-apiofuranosyl-sweroside(3)、续断苷H(4)、续断苷F(5)、续断苷E(6)、triplostoside A(7)、(7R,8S,7'R,8'S)-5-methoxyprinsepiol-4-O-β-D-glucopyranoside(8)、(7R,8S,7'R,8'S)-prinsepiol-4-O-β-D-glucopyranoside(9)、acanthoside D(10)、(7R,8S,7'R,8'S)-fraxiresinol-4'-O-β-D-glucopyranoside(11)、(7R,8S,7'R,8'S)-8-hydroxypinoresinol-4'-O-β-D-glucopyranoside(12)、(7R,8S,7'R,8'S)-8-hydroxypinoresinol-4-O-β-D-glucopyranoside(13)。结论其中化合物8、9、11、12、13为首次从川续断属植物中分离得到。

忍冬叶中的一个新双黄酮苷

通过硅胶柱色谱和Sephadex LH-20柱色谱等分离手段,从忍冬(Lonicera japonica Thunb.)叶中分离得到一个新化合物,利用理化性质和波谱分析,鉴定其结构为ochnaflavone7″-O-β-D-glucopyranoside。

Chemical Constituents from Dried Aerial Parts of Eclipta prostrata

Abstract: Objective To study the constituents in the dried aerial parts of Eclipta prostrata. Methods The constituents wereisolated and purified by column chromatography and their structures were elucidated by spectroscopic methods (1D,2D NMR, UV, IR, and HRESI-TOF-MS) and chemical analyses. Results Eight compounds were isolated andidentified as 7-O-methylorobol-4′-O-β-D-glucopyranoside (1), 3′-hydroxybiochanin A (2), echinocystic acid28-O-β-D-glucopyranoside (3), ecliptasaponin A (4), eclalbasaponin I (5), eclalbasaponin IV (6), echinocystic acid(7), and 3-oxo-16α-hydroxy-olean-12-en-28-oic acid (8). Conclusion Compound 1 is a new compound andcompound 3 is obtained from this genus for the first time.

Lignan glucoside from Sinopodophyllum emodi and its cytotoxic activity

A new lignan glycoside was isolated from the n-butanol extract of the roots and rhizomes of Sinopodophyllum emodi.On the basis of spectral evidences,its structure was established and named as 4,5-didemethylpodophyllotoxin 7＇-O-β-D-glucopyranoside. This compound showed cytotoxicity against four human cancer cell lines（Hela,K562,SH-SY5Y and CNE） in vitro.