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Journal articles on the topic 'Santonin'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Zhumagaliyeva, Zh Zh, R. I. Dzhalmakhanbetova, Sh K. Eleupaeva та V. I. Korchyn. "Antioxidant activity of aminоderivatives of santonin extracted from the plant Artemisia gracil. Krasch." Bulletin of the Karaganda University “Biology medicine geography Series” 90, № 2 (2018): 40–45. https://doi.org/10.31489/2018bmg2/40-45.

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In this paper, the results of a study of the biologicalactivity of amino derivatives of sesquiterpene lactone santonin are shown. The study of the antioxidant activity of santonin and their amino derivatives was carried out using the method of initiated biochemiluminescence. And also the above-ground part of the plant Artemi-sia gracil.Krasch. — wormwood finely-chained by the chloroform extraction method, the sum of extractive substances is obtained. As a result of column chromatography of the sum of extractive substances, sesquiterpenoid santonin was isolated. Synthesis of natural sesquiteroi

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2

Birladeanu, Ludmila. "The Stories of Santonin and Santonic Acid." Angewandte Chemie International Edition 42, no. 11 (2003): 1202–8. http://dx.doi.org/10.1002/anie.200390318.

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3

Nie, Lin, та Lijiu Zhang. "Gastric cancer cell proliferation is inhibited by α-santonin via targeting of PI3K and AKT activation". Tropical Journal of Pharmaceutical Research 19, № 4 (2020): 765–71. http://dx.doi.org/10.4314/tjpr.v19i4.13.

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Purpose: To investigate the effect of α-santonin on proliferation of gastric cancer cells.Methods: Cell proliferation was analysed by 3-4-5-Dimethylthiazol-2-yl-25-diphenyltetrazolium bromide (MTT) assay and migration by wound healing assay. Matrigel coated Transwell chamber was used for determination of cell invasion. Expression of proteins and mRNA was assessed using western blot and RT-PCR assay, respectively.Results: In NUGC4 and MKN45 cell cultures, treatment with α-santonin promoted miR 145 expression significantly when compared to control. Treatment of NUGC4 cells with α-santonin for 48

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4

Ata, Athar, та Jason A. Nachtigall. "Microbial Transformations of α-Santonin". Zeitschrift für Naturforschung C 59, № 3-4 (2004): 209–14. http://dx.doi.org/10.1515/znc-2004-3-415.

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Fungal biotransformations of α-santonin (1) were conducted with Mucor plumbeus (ATCC 4740), Cunninghamella bainieri (ATCC 9244), Cunninghamella echinulata (ATCC 9245), Curvularia lunata (ATCC 12017) and Rhizopus stolonifer (ATCC 10404). Rhizopus stolonifer (ATCC 10404) metabolized compound 1 to afford 3,4-epoxy-α-santonin (2) and 4,5-dihydro- α-santonin (3) while Cunninghamella bainieri (ATCC 9244), Cunninghamella echinulata (ATCC 9245) and Mucor plumbeus (ATCC 4740) were capable of metabolizing compound 1 to give a reported metabolite, 1,2-dihydro-α-santonin (4). The structures of these trans

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5

Badria, F. A., A. M. Zaghloul, G. T. Maatooq та S. H. El-Sharkawy. "BIOTRANSFORMATION OFα-SANTONIN". International Journal of Pharmacognosy 35, № 5 (1997): 375–78. http://dx.doi.org/10.1080/09251619708951286.

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6

Sakipova, Zuriyadda, Thais Biondino Sardella Giorno, Tolkyn Bekezhanova, et al. "Pharmacological Evaluation of Artemisia cina Crude CO2 Subcritical Extract after the Removal of Santonin by Means of High Speed Countercurrent Chromatography." Molecules 25, no. 12 (2020): 2728. http://dx.doi.org/10.3390/molecules25122728.

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Artemisia species are highly important due to their economic significance as medicines, fodder and food. Artemisia cina is an endemic species to Kazakhstan. In folk medicine, water extract of A. cina was used in the treatment of bronchial asthma while the alcohol extract has larvicidal and antituberculosis activity. The most common and most extensively studied compound from this species is the terpenoid santonin. The toxicity of this compound occurs at the doses of 60 mg for children and 200 mg for adults causing among other issues xanthopsia, leading to blindness. Having this in mind, the mai

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7

Farooq, Afgan, та Satoshi Tahara. "Biotransformation of Two Cytotoxic Terpenes, α-Santonin and Sclareol by Botrytis cinerea". Zeitschrift für Naturforschung C 55, № 9-10 (2000): 713–17. http://dx.doi.org/10.1515/znc-2000-9-1008.

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Abstract Two cytotoxic terpenes, α-santonin (1) and sclareol (3) were biotransformed by a plant pathogenic fungus Botrytis cinerea to produce oxidized metabolites in high yields. α-Santonin (1 ) on fermentation with the fungus for ten days afforded a hydroxylated metabolite identified as 11β-hydroxy-α-santonin (2) in a high yield (83%), while sclareol (3) was metabolized to epoxysclareol (4) (64%) and a new compound 8-deoxy-14,15-dihydro-15-chloro-14-hydroxy- 8,9-dehydrosclareol (5) (7%), representing a rare example of microbial halogenation.

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8

Iskanderov, Amantay, Pavel Vojtisek, Saltanat Zhokizhanova, Aktoty Jadenova та Nurlan Merkhatuly. "Stereocontrolled intramolecular transformations of (-)-α santonin". Chemical Bulletin of Kazakh National University, № 1 (21 січня 2022): 44–49. http://dx.doi.org/10.15328/cb1251.

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Chemical transformations of eudesmane sesquiterpene γ-lactones, leading to new biologically active compounds, have become an important direction in medicinal chemistry. This article discusses the stereoscopic intramolecular transformations of the sesquiterpene γ-lactone of the eudesmanic structure (-)-α santonin, a perspective natural compound characterized by a wide spectrum of biological activity.Stereoselective synthesis of new practically significant cis-condensed keto-eudesmane esters and ethylated santonin derivatives was carried out at room temperature in an argon atmosphere by the reac

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9

Kitabayashi, C., Y. Matsuura, N. Tanaka, Y. Katsube та T. Matsuura. "Structure of α-santonin". Acta Crystallographica Section C Crystal Structure Communications 41, № 12 (1985): 1779–81. http://dx.doi.org/10.1107/s0108270185009428.

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10

Merkhatuly, N., S. K. Zhokizhanova, L. T. Balmagambetova та S. M. Adekenov. "Oximation of α-santonin". Russian Journal of Organic Chemistry 43, № 1 (2007): 150–51. http://dx.doi.org/10.1134/s1070428007010204.

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11

Naik, Ulhas, та Suneela Mavuinkurve. "α-Santonin 1,2-reductase and its role in the formation of dihydrosantonin and lumisantonin by Pseudomonas cichorii S". Canadian Journal of Microbiology 33, № 8 (1987): 658–62. http://dx.doi.org/10.1139/m87-115.

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1,2-Dihydrosantonin is the first stable product in the degradative pathway of α-santonin by Pseudomonas cichorii S. Its formation is catalyzed by an oxidoreductase, which is NADH or NADPH dependent and has an apparent Km value of 66.66 μM for santonin and 44.33 μM for NADH. The enzyme activity is stable at pH 6.0, 7.0, and 8.0, and is not affected by EDTA and divalent metal ions. It is postulated that the enzymic reduction of santonin occurs via formation of a transient zwitterionic intermediate, which undergoes nonenzymatic 1,4-sigmatropic rearrangement to yield lumisantonin during the solven

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12

TAKAYANAGI, Hiroaki, Haruo OGURA, and T. Brain H. McMURRY. "Studies on the chlorinated .ALPHA.-santonins. IV. Chlorination of .ALPHA.-santonin and stereochemistry therein." CHEMICAL & PHARMACEUTICAL BULLETIN 38, no. 3 (1990): 581–84. http://dx.doi.org/10.1248/cpb.38.581.

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13

Tsuboi, Sadao, Koichi Shinhama, and Akira Takeda. "Synthesis of santonin related compounds." Journal of Heterocyclic Chemistry 25, no. 2 (1988): 523–25. http://dx.doi.org/10.1002/jhet.5570250231.

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14

Paknikar, S. K., B. L. Malik, R. B. Bates, S. Caldera та T. V. Wijayaratne. "Stereochemistry of 45-dihydroxy-α-santonin and structure of a new santonin oxidation product". Tetrahedron Letters 35, № 44 (1994): 8117–18. http://dx.doi.org/10.1016/0040-4039(94)88258-4.

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15

Pellegrinet, Silvina C., Mar�a I. Colombo, Sebasti�n A. Testero, Manuel Gonz�lez Sierra, and Edmundo A. R�veda. "A New Laboratory Experiment Based on a Chemical Transformation of Santonin: Synthesis of Santonic Acid." Chemical Educator 7, no. 3 (2002): 155–58. http://dx.doi.org/10.1007/s00897020561a.

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16

Adekenov, Sergazy Mynzhasarovich. "Synthesis of new biologically active compounds based on α - santonin". chemistry of plant raw material, № 1 (21 березня 2025): 286–302. https://doi.org/10.14258/jcprm.20250116408.

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3-Keto-6,11β,7α(H)-eudesm-1(2),4(5)-dien-6,12-olide is a sesquiterpene γ-lactone of the eudesmane structural type, known as α-santonin, isolated from more than 20 species of the genus Artemisia L. and is a renewable chemical material for the synthesis of new biologically active compounds. The goal of the work is the synthesis of new compounds based on α-santonin with potential biological activity for the development of medicinal substances. Methods. Hydrogenation, halogenation, oximation, aminolysis, Michael, and O-alkyl- and alkenyl-substituted oxime santonin derivatives were synthesised on t

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17

Wang, Zhichao, Yoshi Yamano, Susumu Kawakami та ін. "New ψ-Santonin Derivatives from Crossostephium chinense and Their Anti-Proliferative Activities against Leishmania major and Human Cancer Cells A549". Molecules 28, № 24 (2023): 8108. http://dx.doi.org/10.3390/molecules28248108.

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Previously, we reported two cytotoxic ψ-santonin–amino acid conjugates isolated from the EtOAc layer of Crossostephium chinense. However, a further phytochemical investigation seems to be required because of the few reports of similar derivatives. In this study, we targeted the 1-BuOH layer, which resulted in the isolation of seven new ψ-santonin derivatives (1–7) together with ten known compounds (8–17). The structures of 1–7 were elucidated based on spectroscopic methods, including 1D and 2D NMR experiments (1H, 13C, DEPT, COSY, HSQC, and HMBC), IR spectrum, and high-resolution electrospray

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18

Domingo, Luis, Mar Ríos-Gutiérrez та Nivedita Acharjee. "A Molecular Electron Density Theory Study of the Chemoselectivity, Regioselectivity, and Diastereofacial Selectivity in the Synthesis of an Anticancer Spiroisoxazoline derived from α-Santonin". Molecules 24, № 5 (2019): 832. http://dx.doi.org/10.3390/molecules24050832.

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The [3 + 2] cycloaddition (32CA) reaction of an α-santonin derivative, which has an exocyclic C–C double bond, with p-bromophenyl nitrile oxide yielding only one spiroisoxazoline, has been studied within the molecular electron density theory (MEDT) at the MPWB1K/6-311G(d,p) computational level. Analysis of the conceptual density functional theory (CDFT) reactivity indices and the global electron density transfer (GEDT) account for the non-polar character of this zwitterionic-type 32CA reaction, which presents an activation enthalpy of 13.3 kcal·mol−1. This 32CA reaction takes place with total

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19

Blay, Gonzalo, Luz Cardona, Begoña García, Luisa Lahoz, and José R. Pedro. "Synthesis of Plagiochiline N from Santonin." Journal of Organic Chemistry 66, no. 23 (2001): 7700–7705. http://dx.doi.org/10.1021/jo010567d.

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20

Birladeanu, Ludmila. "Die Geschichte von Santonin und Santonsäure." Angewandte Chemie 115, no. 11 (2003): 1236–42. http://dx.doi.org/10.1002/ange.200390289.

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21

TAKAYANAGI, Hiroaki, Rieko IRIMAJIRI, Haruo OGURA, and T. Brian H. MCMURRY. "Studies on chlorinated .ALPHA.-santonin. V. Conformation of the cyclohexenone ring in 6.BETA.-santonin derivatives." CHEMICAL & PHARMACEUTICAL BULLETIN 39, no. 3 (1991): 780–83. http://dx.doi.org/10.1248/cpb.39.780.

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22

Bates, R. B., B. L. Malik, S. K. Paknikar, K. J. McClure та M. D. Carducci. "An unexpected oxidation product of α-santonin". Acta Crystallographica Section C Crystal Structure Communications 55, № 11 (1999): 1881–82. http://dx.doi.org/10.1107/s010827019901046x.

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23

Nagano, Hajime, Hiroko Sugihara, Noriko Harada та ін. "Transformation of α-Santonin into 7-Hydroxyeudesmanes". Bulletin of the Chemical Society of Japan 63, № 12 (1990): 3560–65. http://dx.doi.org/10.1246/bcsj.63.3560.

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24

KARUBE, Akio, and Masao MARUYAMA. "Stereochemistry of the reduction products of santonin." NIPPON KAGAKU KAISHI, no. 1 (1990): 53–59. http://dx.doi.org/10.1246/nikkashi.1990.53.

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25

Blay, Gonzalo, Luz Cardona, Begoña García, José R. Pedro, and Angel Serrano. "Synthesis of (+)-Isoalantolactone and (+)-Isoalloalantolactone from (−)-Santonin." Tetrahedron 48, no. 25 (1992): 5265–72. http://dx.doi.org/10.1016/s0040-4020(01)89024-4.

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26

Lamm, Andrew S., Avril R. M. Chen, William F. Reynolds, and Paul B. Reese. "Fungal hydroxylation of (−)-santonin and its analogues." Journal of Molecular Catalysis B: Enzymatic 59, no. 4 (2009): 292–96. http://dx.doi.org/10.1016/j.molcatb.2008.11.004.

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27

Blay, G. "Synthesis of 3-Oxa-guaianolides from Santonin." Tetrahedron 56, no. 34 (2000): 6331–38. http://dx.doi.org/10.1016/s0040-4020(00)00571-8.

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28

Banerjee, Ajoy K., William J. Vera та Nieves Canudas Gonzalez. "Synthesis of terpenoid compounds from α-santonin". Tetrahedron 49, № 22 (1993): 4761–88. http://dx.doi.org/10.1016/s0040-4020(01)80397-5.

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29

Mabtín, M. L., A. Morán, R. Carrón, M. J. Montero та L. San Roman. "Antipyretic activity of α- and β-santonin". Journal of Ethnopharmacology 23, № 2-3 (1988): 285–90. http://dx.doi.org/10.1016/0378-8741(88)90007-4.

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30

Jeyavijayan, S., M. Ramuthai та Palani Murugan. "Investigating Potential Part of α-Santonin in the Treatment of SARS-CoV-2 and Cervical Cancer based on Molecular Docking Strategy". Asian Journal of Chemistry 33, № 10 (2021): 2313–20. http://dx.doi.org/10.14233/ajchem.2021.23308.

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The widespread of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has been posturing extraordinary dangers globally. Additionally, cervical cancer is also the most predominant threatening tumor among ladies around the world. The investigation has progressively centered on improving treatments, such as anti-angiogenic and anti-hepatoma drugs. The conceivable inhibitory action of α-santonin, which has a good interacting affinity with the active protein sites of human SARS-COV-2 and cervical cancer was screened in this work. The molecular properties such as NBO, MEP, HOMO-LUMO, Mulli

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31

Dangroo, Nisar A., Jasvinder Singh, Nidhi Gupta та ін. "T- and B-cell immunosuppressive activity of novel α-santonin analogs with humoral and cellular immune response in Balb/c mice". MedChemComm 8, № 1 (2017): 211–19. http://dx.doi.org/10.1039/c6md00527f.

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Herein we report the synthesis of α-santonin analogs, and identification of potent immunosuppressant molecules. In vivo investigation on BALB/c mice revealed that compound 4e suppresses both humoral and cellular immunity.

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32

Gandomkar, Somayyeh, та Zohreh Habibi. "Biotransformation of 6α-santonin and 1,2-dihydro-α-santonin by Acremonium chrysogenum PTCC 5271 and Rhizomucor pusillus PTCC 5134". Journal of Molecular Catalysis B: Enzymatic 110 (грудень 2014): 59–63. http://dx.doi.org/10.1016/j.molcatb.2014.09.003.

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33

Merkhatuly, N., A. N. Iskanderov, А. Т. Omarova, P. Vojtíšek та S. K. Zhokizhanova. "The reaction of C-alkylation of eudesmanolide (–)-α-santonin". Bulletin of the Karaganda University. "Chemistry" series 94, № 2 (2019): 14–18. http://dx.doi.org/10.31489/2019ch2/14-18.

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34

Dai, Xiaoli, Jian Tang, Lingqiong Zhang, Lianzhi Tao, Zhen Ouyang та Min Wang. "Photocatalysis Synthesis and Cytotoxicity ofα-Santonin Rearrangement Derivatives". Chinese Journal of Organic Chemistry 35, № 10 (2015): 2142. http://dx.doi.org/10.6023/cjoc201505020.

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35

Iida, Mitsugi, Akiko Mikami, Koji Yamakawa та Kiyoshi Nishitani. "Microbial Hydroxylation of (−)-α-Santonin by Aspergillus niger". Journal of Fermentation Technology 66, № 1 (1988): 51–55. http://dx.doi.org/10.1016/0385-6380(88)90129-x.

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36

Blay, Gonzalo, Luz Cardona, Begona Garcia, Luisa Lahoz, and Jose R. Pedro. "ChemInform Abstract: Synthesis of Plagiochiline N from Santonin." ChemInform 33, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.200218180.

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37

Arantes, Francisco F. P., Luiz C. A. Barbosa, Elson S. Alvarenga та ін. "Synthesis and cytotoxic activity of α-santonin derivatives". European Journal of Medicinal Chemistry 44, № 9 (2009): 3739–45. http://dx.doi.org/10.1016/j.ejmech.2009.03.036.

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38

Xia, Wu-Jiong, Liang-Dong Sun, Lei Shi, Shu-Yu Zhang та Yong-Qiang Tu. "First Synthesis of (+)-2,14-Deoxyalatol from α-Santonin". Chinese Journal of Chemistry 22, № 4 (2010): 377–83. http://dx.doi.org/10.1002/cjoc.20040220412.

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39

Zhang, Lingqiong, Xiaoli Dai, Lianzhi Tao, Chunsong Xie, Min Zhang та Min Wang. "Total Synthesis of (+)-Chinensiolide B from α -Santonin". Chinese Journal of Chemistry 35, № 8 (2017): 1284–88. http://dx.doi.org/10.1002/cjoc.201600670.

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40

Kimani, Njogu, Solveig Backhaus, Josphat Matasyoh, et al. "Preparation of Sesquiterpene Lactone-Loaded PLA Nanoparticles and Evaluation of Their Antitrypanosomal Activity." Molecules 24, no. 11 (2019): 2110. http://dx.doi.org/10.3390/molecules24112110.

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Human African trypanosomiasis (HAT), also commonly known as sleeping sickness, is a neglected tropical disease affecting millions of people in poorly developed regions in sub-Saharan Africa. There is no satisfactory treatment for this infection. The investment necessary to bring new drugs to the market is a big deterrent to drug development, considering that the affected communities form a non-lucrative sector. However, natural products and many sesquiterpene lactones (STLs) in particular are very strong trypanocides. Research and applications of nano-drug delivery systems such as nanoparticle

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41

Blay, Gonzalo, Victoria Bargues, Luz Cardona та ін. "Stereoselective Synthesis of 4α-Hydroxy-8,12-Guaianolides from Santonin". Journal of Organic Chemistry 65, № 7 (2000): 2138–44. http://dx.doi.org/10.1021/jo991756n.

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42

KARUBE, Akio, and Masao MARUYAMA. "Structure of the Alkaline Reduction Products of Santonin C." NIPPON KAGAKU KAISHI, no. 7 (1998): 465–69. http://dx.doi.org/10.1246/nikkashi.1998.465.

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43

Blay, Gonzalo, Luz Cardona, Begona Garcia, and José R. Pedro. "Synthesis of torrentin, dihydrosantamarine, and saussurea lactone from santonin." Canadian Journal of Chemistry 70, no. 3 (1992): 817–22. http://dx.doi.org/10.1139/v92-107.

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The synthesis of the eudesmanolide torrentin (1) by sensitized photooxygenation of synthetic dihydrosantamarine (3) is reported. Both dihydrosantamarine and dihydroreynosin (11) were obtained from the 1,2-epoxide 9, which, in turn, was prepared from the diselenide 7. An improved procedure for the synthesis of the elemanolide saussurea lactone (4) is also reported. Keywords: eudesmanolide, elemanolide, santonin, torrentin, saussurea lactone.

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44

Kulyyasov, A. T., T. S. Seitembetov та S. M. Adekenov. "Synthesis and antioxidant activity of phenolic derivatives ofα-santonin". Chemistry of Natural Compounds 33, № 2 (1997): 185–86. http://dx.doi.org/10.1007/bf02291538.

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45

Ivasenko, S. A., T. T. Edil’baeva, A. T. Kulyyasov та ін. "Structure and biological activity of α-santonin chloro-derivatives". Chemistry of Natural Compounds 42, № 1 (2006): 36–40. http://dx.doi.org/10.1007/s10600-006-0031-8.

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46

Klochkov, S. G., S. V. Afanas’eva, A. N. Pushin, G. K. Gerasimova, N. K. Vlasenkova та Yu N. Bulychev. "Synthesis and cytotoxic activity of α-santonin amino-derivatives". Chemistry of Natural Compounds 45, № 6 (2009): 817–23. http://dx.doi.org/10.1007/s10600-010-9499-3.

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47

Zhang, Zhipeng, Maxim Ratnikov, Glen Spraggon, and Phil B. Alper. "Photoinduced Rearrangement of Dienones and Santonin Rerouted by Amines." Angewandte Chemie 130, no. 4 (2017): 916–20. http://dx.doi.org/10.1002/ange.201710463.

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48

Bates, R. B., B. L. Malik, S. K. Paknikar, K. J. McClure та M. D. Carducci. "ChemInform Abstract: An Unexpected Oxidation Product of α-Santonin." ChemInform 31, № 7 (2010): no. http://dx.doi.org/10.1002/chin.200007163.

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49

BANERJEE, A. K., W. J. VERA та N. C. GONZALEZ. "ChemInform Abstract: Synthesis of Terpenoid Compounds from α-Santonin". ChemInform 24, № 39 (2010): no. http://dx.doi.org/10.1002/chin.199339343.

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50

Furtado, I., U. M. X. Sangodkar, and S. Mavinkurve. "Mechanism of uptake of ?-santonin byPseudomonas cichorii strain S." Biotechnology and Bioengineering 30, no. 8 (1987): 991–94. http://dx.doi.org/10.1002/bit.260300812.

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