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1.
Acta Pharmaceutica Sinica ; (12): 3616-3620, 2022.
Artigo em Chinês | WPRIM | ID: wpr-964335

RESUMO

To investigate the chemical constituents of Anisodus tanguticus, silica gel column chromatography, Sephadex LH-20 column chromatography, preparative thin layer chromatography, and semi-preparative HPLC were used to separate and purify the chemical constituents from the extract of A. tanguticus. The planar structure of the isolated compound was identified by HRMS, IR, and 2D NMR experiments. The absolute configuration of the isolated compound was determined by a combination of NOESY, coupling constant, circular dichroism (CD), and transition metal chelate reagent dimolybdenum tetraacetate [Mo2(OAc)4]-induced circular dichroism (ICD) data analysis. A new compound of the anisotane-type sesquiterpene (1) was isolated, which was determined to be (1R,2S,3R,4R,6R,7R,9R)-anisotane-11(13)-ene-3,4,9-triol and named anisotanol F. This is the second report of anisotane-type sesquiterpene, which has previously been reported as a novel sesquiterpenoid skeleton by our research group. Furthermore, the cytotoxicity against HUVECs and inhibitory effect on NO release in LPS-induced RAW264.7 cells of compound 1 were investigated. However, the results showed that it was inactive. Compound 1 is a new compound isolated from A. tanguticus. It belongs to the unusual anisotane-type sesquiterpene. This result enriches the chemical composition of A. tanguticus.

2.
Acta Pharmaceutica Sinica ; (12): 3603-3607, 2022.
Artigo em Chinês | WPRIM | ID: wpr-964321

RESUMO

A new compound was isolated from the 95% ethanolic extract of the rhizomes of Curcuma longa L. using silica gel column chromatography, medium pressure liquid chromatography, and semi-preparative high performance liquid chromatography. The structure and absolute configuration of the compound was elucidated by HR-ESI-MS, NMR, and electronic circular dichroism (ECD) calculations. It is a novel sesquiterpenoid, which is named as isoturmeronol B (1). The carbon skeleton of compound 1 is similar to that of bisabolane-type sesquiterpenoid. The only difference is that the methyl group at C-4 in bisabolene-type sesquiterpenoid is migrated to C-5 in compound 1. Besides, the anti-inflammatory and antioxidant activities of the compound 1 were evaluated. The results showed that 1 has no anti-inflammatory and antioxidant activities.

3.
China Journal of Chinese Materia Medica ; (24): 579-583, 2020.
Artigo em Chinês | WPRIM | ID: wpr-1008541

RESUMO

This study is to investigate the chemical constituents from the whole plant Corydalis edulis. The chemical constituents were separated and purified by macroporous resin D101, silica gel, Sephadex LH-20, ODS, and semi-preparative HPLC. Their structures were determined by physicochemical properties and spectroscopic data. Four compounds were isolated from the dichloromethane and water extracts of the whole plant C. edulis, and identified as 6'-β-D-xylosylicariside B2(1),(3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one(2), loliolide(3), and 5,5'-dimethoxybiphenyl-2,2'-diol(4), respectively. Compound 1 is a new compound, of which the absolute configuration was established by electronic circular dichroism(ECD) calculations. Compound 4 is obtained from the plants of Papaveraceae family for the first time. Compounds 2 and 3 are firstly isolated from the Corydalis genus.


Assuntos
Cromatografia Líquida de Alta Pressão , Corydalis/química , Glicosídeos/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Sesquiterpenos/isolamento & purificação
4.
China Journal of Chinese Materia Medica ; (24): 1114-1119, 2020.
Artigo em Chinês | WPRIM | ID: wpr-1008480

RESUMO

Polygonflavanol B(1), a new flavonostilbene glycoside, was isolated from the roots of Polygonum multiforum(Polygonaceae) by various column chromatography methods including macroporous resin HP-20, silica gel, Sephadex LH-20, and preparative HPLC. The structure with absolute configuration of the new compound was identified by its physicochemical properties, spectroscopic data, ECD calculation, and chemical method.


Assuntos
Fallopia multiflora/química , Flavonóis/isolamento & purificação , Glicosídeos/isolamento & purificação , Raízes de Plantas/química , Estilbenos/isolamento & purificação
5.
Rev. bras. farmacogn ; 29(1): 30-35, Jan.-Feb. 2019. tab, graf
Artigo em Inglês | LILACS | ID: biblio-990757

RESUMO

Abstract In this study, sahandone (1) and a new diterpenoid named sahandol II (2) were isolated from the roots of Salvia chloroleuca Rech. f. & Aellen, Lamiaceae. The absolute configurations of compounds 1 and 2 were assigned by comparison of experimental electronic circular dichroism spectra and comparing with published data. Cytotoxic and apoptotic evaluation of the isolated compounds and the methanol crude extract and its subfractions including petroleum ether, dichloromethane, ethyl acetate, n-butanol and aqueous fraction on two human prostate cancer cell lines and a breast cancer cell lines, showed that non-polar and semi-polar subfractions had the potent cytotoxic effect on PC3 cells with the IC50 values of 24.19, 33.59, and 47.15 µg/ml, respectively. Sub-G1 peak in flow cytometry histogram of cells treated with petroleum ether, dichloromethane and ethyl acetate subfractions showed the induction of apoptosis. Change in the Bax/Bcl-2 ratio and cleavage of poly ADP-ribose polymerase were observed.

6.
Acta Pharmaceutica Sinica ; (12): 1075-1081, 2019.
Artigo em Chinês | WPRIM | ID: wpr-780184

RESUMO

Five alkaloids were isolated from a decoction of Uncaria rhynchophylla by a combination of various chromatographic techniques, including macroporous adsorbent resin, MCI resin, silica gel, Sephadex LH-20, and reversed phase HPLC. Their structures were characterized by comprehensive analyses of spectroscopic data as monoterpene indole alkaloids (+)-(7R)-3-oxo-7-hydroxy-3,7-seco-dihydrorhynchohylline (1), (+)-(7S)-3-oxo-7-hydroxy-3,7-seco-dihydrorhyncho-hylline (2), (+)-(7R)-3-oxo-7-hydroxy-3,7-seco-rhynchohylline (3) and (+)-(7S)-3-oxo-7-hydroxy-3,7-seco-rhynchohylline (4), and a β-carboline alkaloid 1,2,3,4-tetrahydro-1-oxo-β-carboline (5). Among them, 1 and 2 are new compounds, 3 and 4 are new natural products that were semi-synthesized from isorhynchohylline with incorrect specific rotations, and 5 is isolated for the first time from the genus Uncaria.

7.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 946-950, 2018.
Artigo em Inglês | WPRIM | ID: wpr-776913

RESUMO

Two new limonoids, 12-ethoxynimbolinins G and H (compounds 1 and 2), and one known compound, toosendanin (Chuanliansu) (compound 3), were isolated from the bark of Melia toosendan. Their structures were elucidated by spectroscopic analysis and X-ray techniques. The absolute configuration of toosendanin (3) was established by single-crystal X-ray diffraction. Compounds 1-3 were evaluated for their cytotoxicity against five tumor cell lines.


Assuntos
Humanos , Linhagem Celular Tumoral , Proliferação de Células , Limoninas , Melia , Química , Estrutura Molecular , Casca de Planta , Química , Extratos Vegetais , Química , Farmacologia , Difração de Raios X
8.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 63-69, 2018.
Artigo em Inglês | WPRIM | ID: wpr-773638

RESUMO

Two cyclopeptides, celogentin L (1) and its epimer lyciumin A (2) were firstly isolated from Celosia argentea L.. The planar structures of the two compounds were fully determined by spectroscopic data, including 1D-, 2D-NMR, and HR-ESI/MS. The absolute configurations of amino acid components were assigned via chiral-phase HPLC analyses after acid hydrolysis. Furthermore, the configuration of C-N linkage at the glycine Cα was elucidated by extensive analyses of 2D-NMR and comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. Cytotoxicity of the two compounds against human alveolar epithelial A549, hepatocellular carcinoma HepG2, and cervical cancer Hela cell lines was assayed. Although both of them were inactive in these cells, the present findings add new facets for the chemistry of Celosia argentea.


Assuntos
Humanos , Células A549 , Sobrevivência Celular , Celosia , Química , Técnicas de Química Analítica , Células HeLa , Células Hep G2 , Conformação Molecular , Estrutura Molecular , Peptídeos Cíclicos , Química , Toxicidade , Sementes , Química , Estereoisomerismo
9.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 63-69, 2018.
Artigo em Inglês | WPRIM | ID: wpr-812428

RESUMO

Two cyclopeptides, celogentin L (1) and its epimer lyciumin A (2) were firstly isolated from Celosia argentea L.. The planar structures of the two compounds were fully determined by spectroscopic data, including 1D-, 2D-NMR, and HR-ESI/MS. The absolute configurations of amino acid components were assigned via chiral-phase HPLC analyses after acid hydrolysis. Furthermore, the configuration of C-N linkage at the glycine Cα was elucidated by extensive analyses of 2D-NMR and comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. Cytotoxicity of the two compounds against human alveolar epithelial A549, hepatocellular carcinoma HepG2, and cervical cancer Hela cell lines was assayed. Although both of them were inactive in these cells, the present findings add new facets for the chemistry of Celosia argentea.


Assuntos
Humanos , Células A549 , Sobrevivência Celular , Celosia , Química , Técnicas de Química Analítica , Células HeLa , Células Hep G2 , Conformação Molecular , Estrutura Molecular , Peptídeos Cíclicos , Química , Toxicidade , Sementes , Química , Estereoisomerismo
10.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 946-950, 2018.
Artigo em Inglês | WPRIM | ID: wpr-812335

RESUMO

Two new limonoids, 12-ethoxynimbolinins G and H (compounds 1 and 2), and one known compound, toosendanin (Chuanliansu) (compound 3), were isolated from the bark of Melia toosendan. Their structures were elucidated by spectroscopic analysis and X-ray techniques. The absolute configuration of toosendanin (3) was established by single-crystal X-ray diffraction. Compounds 1-3 were evaluated for their cytotoxicity against five tumor cell lines.


Assuntos
Humanos , Linhagem Celular Tumoral , Proliferação de Células , Limoninas , Melia , Química , Estrutura Molecular , Casca de Planta , Química , Extratos Vegetais , Química , Farmacologia , Difração de Raios X
11.
Chinese Herbal Medicines ; (4): 14-22, 2018.
Artigo em Chinês | WPRIM | ID: wpr-842148

RESUMO

Monosaccharides are one of the most important structural components of biomolecules, such as polysaccharides, nucleic acids, glycolipids and glycoproteins. In structural analysis of polysaccharides and glycoconjugates, the absolute configurations (D or L) of the constituent monosaccharides are usually determined by measurement of the optical rotation, CD spectra or characteristic chromatographic retention behavior. However, each method has its unique advantages and limitations which should be considered while using them. In this review, an overview of the different methods for the determination of absolute configuration of monosaccharides and their underlying principles are summarized to serve as a reference for researchers.

12.
Chinese Traditional and Herbal Drugs ; (24): 225-231, 2017.
Artigo em Chinês | WPRIM | ID: wpr-853021

RESUMO

Determination of the absolute configuration is considered one of the most complicated works in the natural products study. Mosher's method provides a practical solution for the stereochemistry determination of natural products by means of NMR spectroscopy. This article, which reviews the classic application of Mosher's method, is one of the series of historical stories on natural product chemistry published in this journal.

13.
Acta Pharmaceutica Sinica B ; (6): 638-646, 2017.
Artigo em Inglês | WPRIM | ID: wpr-256713

RESUMO

Three pairs of glycosidic 8,4'-oxyneolignane diastereoisomers, named isatioxyneolignosides A-F (-), were isolated from an aqueous extract ofroots. Their structures and absolute configurations were elucidated by comprehensive spectroscopic data analysis and enzyme hydrolysis. The validity of Δvalues to distinguishandaryl glycerol units and Cotton effects at 235±5 nm to determine absolute configurations at C-8 in-and their aglycones (-) are discussed.

14.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 220-224, 2017.
Artigo em Inglês | WPRIM | ID: wpr-812121

RESUMO

Two new steroidal saponins, named timosaponin P (1) and timosaponin Q (2), were isolated from the rhizome parts of Anemarrhena asphodeloides Bunge using various chromatographic methods. Their structures and absolute configurations were elucidated by a combination of spectroscopic and spectrometric data, including 1D, 2D NMR, HR-ESI-MS and ECD calculations, and this is the first time the absolute configuration of C-23 of steroidal saponin was confirmed by ECD calculations.


Assuntos
Anemarrhena , Química , Medicamentos de Ervas Chinesas , Química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Saponinas , Química , Esteroides , Química
15.
Acta Pharmaceutica Sinica B ; (6): 62-66, 2015.
Artigo em Inglês | WPRIM | ID: wpr-329693

RESUMO

A bicyclic depsipeptide, chromopeptide A (1), was isolated from a deep-sea-derived bacterium Chromobacterium sp. HS-13-94. Its structure was determined by extensive spectroscopic analysis and by comparison with a related known compound. The absolute configuration of chromopeptide A was established by X-ray diffraction analysis employing graphite monochromated Mo K α radiation (λ=0.71073 Å) with small Flack parameter 0.03. Chromopeptide A suppressed the proliferation of HL-60, K-562, and Ramos cells with average IC50 values of 7.7, 7.0, and 16.5 nmol/L, respectively.

16.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 59-64, 2015.
Artigo em Inglês | WPRIM | ID: wpr-812173

RESUMO

Podophyllotoxone (1) was isolated from the roots of Dysosma versipellis. The structure was determined by spectroscopic analysis in combination with single-crystal X-ray analysis. The absolute configuration of compound 1 was assigned based on the Flack parameter. It showed significant inhibitory activities against human prostate cancer cells PC3 and DU145 with IC50 values being 14.7 and 20.6 μmol·L(-1), respectively. It also arrested the cells at G2/M phase. Tubulin polymerization assay showed that it inhibited the tubulin polymerization in a dose-dependent manner, and molecular docking analysis revealed a different binding mode with tubulin as compared with those known tubulin inhibitors.


Assuntos
Humanos , Masculino , Antineoplásicos , Química , Farmacologia , Berberidaceae , Química , Linhagem Celular Tumoral , Relação Dose-Resposta a Droga , Fase G2 , Ligação de Hidrogênio , Conformação Molecular , Simulação de Acoplamento Molecular , Fitoterapia , Extratos Vegetais , Química , Farmacologia , Raízes de Plantas , Química , Podofilotoxina , Química , Farmacologia , Polimerização , Neoplasias da Próstata , Tratamento Farmacológico , Tubulina (Proteína) , Moduladores de Tubulina , Farmacologia
17.
Journal of International Pharmaceutical Research ; (6): 811-828, 2015.
Artigo em Chinês | WPRIM | ID: wpr-845644

RESUMO

The difficulty in the structure elucidation of natural products is in the elucidation of stereochemistry, especially the determination of absolute configuration, which generally involves the key techniques of structure elucidation of natural products. This paper shows some examples of our work in elucidating the stereochemistry of new chiral natural products by the application of several physicochemical techniques, such as the dimolybdenum tetraacetate [Mo2(OAc)4] induced CD (ICD, Snatzke’s method), empirical rules of classical CD, modified Mosher’s method, theoretical ECD calculation and modified Marfey’s analysis. The fundamental rules of the techniques and our experiences in the application of these techniques are also described for related researcher’s reference in relevant studies.

18.
Journal of International Pharmaceutical Research ; (6): 802-810, 2015.
Artigo em Chinês | WPRIM | ID: wpr-845643

RESUMO

During the structural elucidation of natural products, one of the key steps is attributed to the solution of configuration including chiral carbons, axial and planar asymmetry. Stereogenic assignment is an essential work involved in natural product chemistry, while identification of stereogenic centers may be helpful to recognize the structure related to target function. Modern spectroscopic technology provided a reliable tool for the configurational assignment. In this paper, we intend to summarize part of our work regarding the application of extensive spectroscopic methods for the determination of the absolute configurations of marine-derived natural products.

19.
Journal of International Pharmaceutical Research ; (6): 794-801, 2015.
Artigo em Chinês | WPRIM | ID: wpr-845642

RESUMO

Flavonolignans, as a special class of flavonoid, have attracted people's attention for their remarkable hepatopro-tection and anti-cancer activity. However, separation of flavonolignans and identification of their absolute configuration have met with great challenges due to the complexity and similarity of structures. The circular dichroism (CD) rules and their application in analyzing the absolute configuration of flavonolignans are summarized in the review and hopefully it may be helpful for the structure elucidation of flavonolignans.

20.
Journal of International Pharmaceutical Research ; (6): 773-785, 2015.
Artigo em Chinês | WPRIM | ID: wpr-845640

RESUMO

The physical, chemical, biological and pharmacological properties of natural products (NP)are closely related to their absolute configurations, and the determination of the NP configurations is a great challenge for natural product chemists and has attracted widespread attention of researchers. People have summed up a variety of determination methods, such as single-crystal X-ray diffraction (XRD), Mosher" s method based on the chemical reaction with the chiral reagents and nuclear magnetic resonance NMR, circular dichroism CD and organic synthesis methods, etc. These methods have advantages and disadvantages for the determination of absolute configuration of NP with different structure characteristics. This paper reviewes the principles, advantages and limitations of these common methods.

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