Erratum: Author correction to "The FAPα-activated prodrug Z-GP-DAVLBH inhibits the growth and pulmonary metastasis of osteosarcoma cells by suppressing the AXL pathway" Acta Pharm Sin B 12 (2022) 1288-1304

[This corrects the article DOI: 10.1016/j.apsb.2021.08.015.].

The FAP α -activated prodrug Z-GP-DAVLBH inhibits the growth and pulmonary metastasis of osteosarcoma cells by suppressing the AXL pathway

Osteosarcoma is a kind of bone tumor with highly proliferative and invasive properties, a high incidence of pulmonary metastasis and a poor prognosis. Chemotherapy is the mainstay of treatment for osteosarcoma. Currently, there are no molecular targeted drugs approved for osteosarcoma treatment, particularly effective drugs for osteosarcoma with pulmonary metastases. It has been reported that fibroblast activation protein alpha (FAPα) is upregulated in osteosarcoma and critically associated with osteosarcoma progression and metastasis, demonstrating that FAPα-targeted agents might be a promising therapeutic strategy for osteosarcoma. In the present study, we reported that the FAPα-activated vinblastine prodrug Z-GP-DAVLBH exhibited potent antitumor activities against FAPα-positive osteosarcoma cells in vitro and in vivo. Z-GP-DAVLBH inhibited the growth and induced the apoptosis of osteosarcoma cells. Importantly, it also decreased the migration and invasion capacities and reversed epithelial-mesenchymal transition (EMT) of osteosarcoma cells in vitro and suppressed pulmonary metastasis of osteosarcoma xenografts in vivo. Mechanistically, Z-GP-DAVLBH suppressed the AXL/AKT/GSK-3β/β-catenin pathway, leading to inhibition of the growth and metastatic spread of osteosarcoma cells. These findings demonstrate that Z-GP-DAVLBH is a promising agent for the treatment of FAPα-positive osteosarcoma, particularly osteosarcoma with pulmonary metastases.

Chemical constituents of petroleum ether extract from the stems and leaves of Humulus scandens / 中国药科大学学报

@#To study the chemical constituents of petroleum ether extract from the stems and leaves of Humulus scandens (family of Moraceae), fifteen compounds were isolated from the stems and leaves of H.scandens by silica gel, Sephadex LH-20, ODS, and preparative HPLC chromatography.The structures were identified by physicochemical data and spectroscopic method as tectochrysin (1), chrysin (2), 5-hydroxy-3, 4'', 6, 7-tetramethoxyflavone (3), (2S)-5-hydroxy-7, 8-dimethoxyflavanone (4), imperatorin (5), phellopterin (6), ethyl 4-hydroxy-3-(3''-methyl-2''-butenyl)benzoate (7), p-hydroxy-phenylpropionic acid (8), ethyl p-hydroxycinnamate (9), p-hydroxybenzaldehyde (10), anofinic acid (11), 5,6-dehydrokavain (12), physcion (13), olean-12-ene-3,?11-dione (14) and ergosta-4, 6, 8 (14), 22-tetraen-3-one (15), respectively.All compounds were isolated from this plant for the first time.

Alkaloids of Ervatamia pandacaqui / 中国药科大学学报

@#Eleven alkaloids were isolated from the twigs and leaves of Ervatamia pandacaqui using chromatographic methods of silica gel, Sephadex LH-20, ODS, and HPLC.Their structures were elucidated by physical,chemical and spectroscopic methods and determined as voacristine 7-hydroxyindolenine (1),iboxygaine (2), 19S-hydroxyibogamine (3), 3-oxotabersonine (4), perivine (5), pericyclivine (6), rhazinalinol (7), geissoschizol (8), 3, 14-dihydroolivacine (9), vallesamine (10), and conolobine A (11), respectively.All compounds were isolated from this plant for the first time.

Qualitative and quantitative analyses of Chrysanthemum morifolium ‘Fubaiju’ by LC-MSn and HPLC-UV / 中国药科大学学报

@#A qualitative analytical method of liquid chromatography coupled with mass spectrometry(LC-MSn)was developed for the identification of main constituents in Chrysanthemum morifolium ‘Fubaiju’. High-performance liquid chromatography(HPLC)was developed for the quantification of five active components, including chlorogenic acid(1), luteolin-7-O-β-D-glucopyranoside(2), luteolin-7-O-β-D-glucopyranuronide(3), 3, 5-Di-caffeoylquinic acid(4), and apigenin-7-O-β-D-glucopyranoside(5). A total of 22 compounds, including 13 flavonoids and 9 phenolic acids, were identified based on their retention behaviors, UV profiles and MS fragment information. Furthermore, a validation method with good linearity(r> 0. 999 9), precision, stability, repeatability and recovery was successfully applied for simultaneous determination of five major components in 10 batches of C. morifolium ‘Fubaiju’ by HPLC-UV method. The established method was proved to be a validation strategy for the quality evaluation of C. morifolium ‘Fubaiju’.

Identification of major constituents from propolis by LC-IT-TOF-MS / 中国药科大学学报

A qualitative analytical method of liquid chromatography coupled with ion trap time-of-flight mass spectrometry (LC-IT-TOF/MS) was developed for identification of major constituents in propolis from China (Shandong).The LC-IT-TOF-MS was performed on a Shim-pack VP-ODS column (2.0 mm× 150 mm,5 μm) with the mobile phase consisting of acetonitrile and water containing 0.2％ formic acid in gradient mode,and the flow rate was set at 0.3 mL/min.Negative ion mode was used for IT-TOF-MS.According to the accurate molecular weight,MS fragment pathway,comparison with the retention time of reference compounds,total 31 compounds,including twenty-five phenolic acids and six flavonoids were identified.The LC-IT-TOF-MS qualitative analysis method can be used for analyzing major components of propolis quickly and accurately.

Phenols from Vitex negundo / 中成药

AIM To study the phenols from Vitex negundo Linn..METHODS The ethyl acetate fraction of 70％ ethanol extract from V.negundo was isolated and purified by silica,Sephadex LH-20 and ODS column,then the structures of obtained compounds were identified by spectral data.RESULTS Seven compounds were isolated and identified as luteolin-4'-O-β-D-glucopyranoside (1),isoorientin 6-O-caffeate (2),3,4,5-tricaffeoyl quinic acid (3),(+)-pinoresinol-4-O-β-D-glucoside (4),methyl isoferuloyl-7-(3,4-dihydroxyphenyl) lactate (5),benzyl 7-O-β-D-glucoside (6) and oresbiusin A (7).CONCLUSION All the compounds are isolated from this plant for the first time,and compounds 1,3,5-7 are first isolated from genus Vitex.

A new flavonoid glycoside from the stem barks of Premna fulva / 中国药科大学学报

@#A new flavonoid glycoside, named(2R)-naringenin-5-O-β-D- xylopyranosyl(1→6)-β-D-glucopyranoside(1), together with other eight known compounds(2-9), was isolated and characterized. Compounds 3-5, 7-9 were isolated from the stem barks of Premna fulva for the first time. The anti-inflammatory activities of all the isolates were evaluated for their inhibitory effects against LPS-induced nitric oxide(NO)production in RAW 264. 7 macrophages cells. Compounds 2, 6-9 exhibited moderate anti-inflammatory activities.

Phenolic constituents of Galla Chinensis and their antiviral activities / 中国药科大学学报

@#Seven compounds in the 95% ethanol extract of Galla Chinensis were isolated by silica gel, ODS, Toyopearl HW-40(s)and RP-HPLC. Their structures were identified on the basis of spectral data and physicochemical properties as benzoic acid, 3, 4-dihydroxy-5-［(3, 4, 5-trihydroxybenzoyl)oxy］-, 5-ethoxycarbonyl-2, 3-dihydroxyphenyl ester(1), trigallic acid(2), 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucose(3), shikimic acid(4), gallic acid(5), methyl gallate(6)and ethyl gallate(7). Among them, compound 1 was a novel compound, and compound 2 was firstly isolated from the Galla Chinensis. The inhibition tests of the constituents showed that compound 3 exhibited in vitro antiviral activity against HSV-1 and RSV A strain, RSV Long strain with IC50 values of 13. 3, 3. 3, 3. 3 mmol/L, respectively.

Non-C21 steroids from the Rhizome of Cynanchum stauntonii / 中国药科大学学报

@#Twelve compounds were isolated and purified from ethyl acetatefraction of Cynanchum stauntonii by silica gel, Sephadex LH-20 and ODS column chromatography. Their structures were identified by spectral techniques and physicochemical properties as syringaresinol(1), (-)-(7R, 7′R, 7″R, 8S, 8′S, 8″S)-4′, 4″-dihydroxy-3, 3′, 3″, 5-tetramethoxy-7, 9′ ∶7′, 9-diepoxy-4, 8″-oxy-8, 8′-sesquineolignan-7″, 9″-diol(2), prinsepiol(3), 4-hydroxyacetophenone(4), baishouwubenzophenone(5), 2, 4-dihydroxyacetophenone(6), benzoic acid(7), 1, 4-benzenediol(8), 6-O-［E］-sinapoyl-α-D-glucopyranoside(9a), 6-O-［E］-sinapoyl-β-D-glucopyranoside(9b), 1-O-methyl-α-D-cymadropyranoside(10), β-daucosterol(11), and β-sitosterol(12). Compounds 1-3, 5 and 7-11 were firstly isolated from this plant.

Chemical constituents of Fructus Gleditsiae Abnormalis / 中国药科大学学报

@#Twelve compounds were isolated from the ethanol extract of Fructus Gleditsiae Abnormalis by macroporous resin, silica gel, Sephadex LH-20, MCI and ODS column chromatographies. Their structures were identified on the basis of physicochemical properties and spectral data as gleditsioside A(1), gleditsioside B(2), gleditsioside H(3), gleditsioside I(4), gleditsioside J(5), gleditsioside K(6), gleditsia saponins C′(7), tamarixetin-7-O-β-D-glucopyranoside(8), neohesperidin(9), chrysoeirol-7-O-neohesperidoside(10); syringaresinol- O-β-D-glucopyranoside(11), liriodendrin(12). Compounds 8-12 were firstly isolated from this genus.

Chemical constituents from the twigs and leaves of Harrisonia perforate / 药学学报

This study was performed to investigate the chemical constituents in the twigs and leaves of Harrisonia perforate. Six compounds were isolated from the 95% EtOH extract of the twigs and leaves of Harrisonia perforate by silica gel, ODS, Sephadex LH-20 column chromatographies and preparative HPLC. On the basis of chemical properties and spectra data, these compounds were identified as harriperfin E (1), kihadanin A (2), kihadanin B (3), 6α-acetoxyobacunol acetate (4), gardaubryone C (5), and β-sitosterol methyl ether (6), respectively. Compound 1 is a new chromone, and compounds 2-6 are isolated from this plant for the first time.

Promoting effects of Guavenoic acid (GA)on proliferation,insulin synthesis and secretion in INS-1 cells and their mechanism / 中国药理学通报

Aim To investigate the effects of Guaveno-ic acid (GA)on proliferation,insulin synthesis and secretion in INS-1 cells and their possible mechanism. Methods INS-1 βcells were cultured in vitro.Control group,medium group,model group,drug groups and positive group were set.INS-1 cells were treated with GA (0.3,1 ,3,1 0,30 nmol·L -1 )for 48 h.The cell proliferation was tested by MTT assay.Acid-alco-hol was used to extract the insulin in the cells and the amount of insulin synthesis of INS-1 cells was tested by RIA.5.6,1 6.7 mmol·L -1 glucose was used to chal-lenge INS-1 cells for 1 h to the insulin secretion model (BIS and GSIS)was tested,and the insulin secretion of INS-1 cells was tested via RIA.The mRNA expres-sion of insulin gene,PDX-1 and MafA was tested by q-PCR.Results Compared with medium group,GA could promote the proliferation of INS-1 cells signifi-cantly (P <0.01 )and promote the synthesis of insulin in INS-1 cells significantly (P <0.01 ).GA(0.3 ~30 nmol· L -1 )could promote the BIS,GSIS of INS-1 cells significantly (P <0.05 or P <0.01 ).GA (3,30 nmol·L -1 )could up-regulate the mRNA expression of insulin gene,PDX-1 ,MafA in INS-1 cells signifi-cantly (P <0.01 ).Conclusions GA could signifi-cantly improve the proliferation of INS-1 cells and pro-mote the insulin synthesis and secretion of INS-1 cells, which may be associated with up-regulation of insulin gene,PDX-1 ,MafA mRNA expression.

Non-alkaloid chemical constituents from Coptis chinensis / 中国中药杂志

<p><b>OBJECTIVE</b>To separate and identify chemical constituents from Coptis chinensis.</p><p><b>METHOD</b>The compounds were separated and purified by various chromatographic techniques. Their structures were identified on the basis of their physicochemical properties using spectral techniques such as NMR and MS.</p><p><b>RESULT</b>Thirteen compounds were separated from ethanol extracts of C. chinensis, including seven lignans, three simple phenylpropanoids, two flavones and one phenolic acid, and identified as erythro-guaiacylglycerol-8-O-4'-(coniferyl alcohol) ether (1), threo-guaiacylglycerol-8-O-4'-(coniferyl alcohol) ether (2), (+)-pinoresinol (3), (+)-medioresinol (4), (+)-lariciresinol (5), (+)-5'-methoxylariciresinol (6), (+)-isolariciresinol (7), chlorogenic acid (8), ferulic acid (9), Z-octadecyl caffeate (10), rhamnetin (11), wogonin (12), and vanillic acid (13).</p><p><b>CONCLUSION</b>Compounds 1, 2, 4, 6, 10-13 were separated from the genus Coptis for the first time.</p>

Chemical constituents contained in roots of Pterospermum heterophyllum / 中国中药杂志

<p><b>OBJECTIVE</b>To study chemical constituents of contained in roots of Pterospermum heterophyllum.</p><p><b>METHOD</b>The chemical constituents of P. heterophyllum were separated and purified by silica gel, sephadex LH-20, ODS column chromatography and preparative HPLC. Their structures were identified by spectroscopic techniques.</p><p><b>RESULT</b>Ten compounds were separated and identified as asperglaucide (1), 2-methoxy4-hydroxyphenol-1-O-beta-D-apiofuranosyl (1-->6)-O-beta-D-glucopyranoside (2), 5, 5'-dimethoxy-9-beta-D-xylopyranosyl-(-) -isolariciresinol(3), (-)-epicatechin (4), eriodictyol (5), taxifolin (6), 3beta-hydroxy-12-en-28-ursolic acid (7), 2beta, 3beta-dihydroxy-12-en-28-oleanolic acid (8), quercetin (9), cholest-4-en-3-one (10).</p><p><b>CONCLUSION</b>Compounds 1-10 were separated from this plant for the first time.</p>

Studies on chemical constituents in roots of Helicteres angustifolia / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of the roots of Helicteres angustifolia.</p><p><b>METHOD</b>The compounds were isolated and purified by column chromatographic methods on silica gel, Sephadex LH-20, ODS and preparative HPLC. Their structures were elucidated on the basis of physicochemical properties and spectral data.</p><p><b>RESULTS</b>Fourteen compounds were isolated from this plant. Their structures were identified as methyl helicterate(1),3-acetoxybetulin(2),3beta-acetoxy-27-(p-hydroxyl)benzoyloxylup-20(29)-en-28-oic acid methyl ester(3),3beta-acetoxy-27-benzoyloxylup-20(29)-en-28-oic acid(4),3beta-acetoxybetulinic acid(5),pyracrenic acid(6),cucurbitacin D(7),cucurbitacin B(8),isocucurbitacin D(9),3beta-acetoxy-27-[(4-hydroxybenzoyl)oxy]olean-12-en-28-oic acid methyl ester (10),beta-sitosterol(11),2alpha,7beta,20alpha-trihydroxy-3beta,21-dimethoxy-5-pregnene(12), hexadecanoic acid(13), and daucosterol(14), respectively.</p><p><b>CONCLUSION</b>Compounds 5,8,9,13, 14 were isolated from this plant for the first time.</p>

Anti-angiogenetic effect of arenobufagin in vitro and in vivo / 药学学报

This study is to investigate the anti-angiogenetic effect of arenobufagin in vitro and in vivo. The anti-proliferation effect of arenobufagin on CNE-2, Hep2, SH-SY5Y, LOVO, PC-3 and DU145 cells as well as human umbilical vein endothelial cells (HUVECs) was determined by MTT assay. Cell morphological changes of LOVO and HUVECs after arenobufagin treatment were observed by microscopy. Arenobufagin inhibited the proliferation of CNE-2, Hep2, SH-SY5Y, LOVO, PC-3, DU145 and HUVECs in a dose-dependent manner. Furthermore, it was obviously observed that the subcytotoxic concentration of arenobufagin in human carcinoma cells induced a marked decrease in the viability of HUVECs. Chick embryo chorioallantoic membrane (CAM) model was used to detect the anti-angiogenetic effect of arenobufagin in vivo. Arenobufagin significantly suppressed the angiogenesis of CAM. Cell cycle analysis demonstrated that G2/M phase was arrested and the sub-G1 peak appeared with the increase of arenobufagin concentration. PI/Annexin V double staining assay further demonstrated that arenobufagin could induce apoptosis in a dose- and time-dependent manner. Mitochondrial potential collapse detected by flow cytometric analysis was increased after arenobufagin treatment. It also observed that PARP was cleaved to p85 active form by Western blotting. Taken together, arenobufagin has significant anti-angiogenetic effect in vitro and in vivo, and the action mechanisms behind its anti-angiogenesis may be associated with cell cycle arrest and apoptosis of vein endothelial cells.

Chemical constituents from root barks of Morus atropurpurea / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents from the root barks of Morus atropurpurea.</p><p><b>METHOD</b>The chemical constituents from the 70% ethanol extract of M. atropurpurea were isolated and purified by column chromatographic methods. Their structures were identified by physico-chemical properties as well as spectral data.</p><p><b>RESULT</b>Fifteen compounds were isolated and identified as sanggenol O(1), kuwanon S(2), moracin C(3), mulberrofuran A(4), mulberrofuran B(5), mulberrofuran C(6), mulberrofuran G(7), mulberroside A(8), mulberroside C(9), 1-deoxynojirimycin(10), 2-O-alpha-D-galactopyranosyl-1-deoxynojirimycin(11), fagomine(12), betulinic acid(13), ursolic acid(14) and beta-sitosterol(15).</p><p><b>CONCLUSION</b>Compounds 1-6 and 8-13 were isolated from M. atropurpurea for the first time.</p>

Alkaloids from the leaves of Nauclea officinalis / 药学学报

To study chemical constituents of the leaves of Nauclea officinalis, eight alkaloids were isolated from 95% ethanol extract by various chromatographic methods. The structures were elucidated on the basis of spectroscopic data (IR, UV, ESI-MS, 1D and 2D NMR) and identified as naucleactonin C (1), strictosamide (2), vincosamide (3), pumiloside (4), angustoline (5), angustine (6), 18, 19-dihydroangustine (7) and naucleofficine D (8). Compound 1 is a new indole alkaloid. Compounds 6 and 7 were isolated from this plant for the first time.

Advances in the study of structural modifications and biological activities of betulinic acids / 药学学报

Betulinic acids are lupine-type pentacyclic triterpenoid saponins commonly found in some plants of Betulaceae family, especially in the bark of betula alba (birch). The potent anti-HIV and anti-tumor activities of betulinic acids have been greatly concerned. The natural betulinic acids include betulinic acid, 23-hydroxy betulinic acid, betulin and so on. Some investigations on the structural modifications of betulinic acids were carried out, and many derivatives with excellent biological activity have been obtained nowadays. In this paper, the research advances of the structural modification of betulinic acids, as well as their anti-HIV and anti-tumor activities are reviewed.