دورية أكاديمية
Efficient Synthesis of Glaziovianin A Isoflavone Series from Dill and Parsley Extracts and Their in Vitro/in Vivo Antimitotic Activity.
| العنوان: | Efficient Synthesis of Glaziovianin A Isoflavone Series from Dill and Parsley Extracts and Their in Vitro/in Vivo Antimitotic Activity. |
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| المؤلفون: | Semenov VV; N. D. Zelinsky Institute of Organic Chemistry, RAS , Leninsky Prospect, 47, 119991, Moscow, Russian Federation., Tsyganov DV; N. D. Zelinsky Institute of Organic Chemistry, RAS , Leninsky Prospect, 47, 119991, Moscow, Russian Federation., Semenova MN; Institute of Developmental Biology, RAS , Vavilov Street, 26, 119334, Moscow, Russian Federation.; Chemical Block Ltd. , 3 Kyriacou Matsi, 3723, Limassol, Cyprus., Chuprov-Netochin RN; Life Sciences Center, Moscow Institute of Physics and Technology , Institutsky Per., 9, Dolgoprudny, Moscow Region 141700, Russian Federation., Raihstat MM; N. D. Zelinsky Institute of Organic Chemistry, RAS , Leninsky Prospect, 47, 119991, Moscow, Russian Federation., Konyushkin LD; N. D. Zelinsky Institute of Organic Chemistry, RAS , Leninsky Prospect, 47, 119991, Moscow, Russian Federation., Volynchuk PB; Life Sciences Center, Moscow Institute of Physics and Technology , Institutsky Per., 9, Dolgoprudny, Moscow Region 141700, Russian Federation., Marusich EI; Life Sciences Center, Moscow Institute of Physics and Technology , Institutsky Per., 9, Dolgoprudny, Moscow Region 141700, Russian Federation., Nazarenko VV; Life Sciences Center, Moscow Institute of Physics and Technology , Institutsky Per., 9, Dolgoprudny, Moscow Region 141700, Russian Federation., Leonov SV; Life Sciences Center, Moscow Institute of Physics and Technology , Institutsky Per., 9, Dolgoprudny, Moscow Region 141700, Russian Federation.; Institute of Cell Biophysics, RAS , Institutskaya Street, 3, Pushchino, Moscow Region 142290, Russian Federation., Kiselyov AS; Life Sciences Center, Moscow Institute of Physics and Technology , Institutsky Per., 9, Dolgoprudny, Moscow Region 141700, Russian Federation. |
| المصدر: | Journal of natural products [J Nat Prod] 2016 May 27; Vol. 79 (5), pp. 1429-38. Date of Electronic Publication: 2016 Apr 21. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Society of Pharmacognosy Country of Publication: United States NLM ID: 7906882 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6025 (Electronic) Linking ISSN: 01633864 NLM ISO Abbreviation: J Nat Prod Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Cincinnati, American Society of Pharmacognosy. |
| مواضيع طبية MeSH: | Anethum graveolens/*chemistry , Antimitotic Agents/*chemical synthesis , Antineoplastic Agents/*chemical synthesis , Antineoplastic Agents/*pharmacology , Isoflavones/*chemical synthesis , Isoflavones/*pharmacology , Petroselinum/*chemistry, Animals ; Antimitotic Agents/chemistry ; Antimitotic Agents/pharmacology ; Antineoplastic Agents/chemistry ; Cell Proliferation/drug effects ; Combinatorial Chemistry Techniques ; Drug Screening Assays, Antitumor ; Humans ; Isoflavones/chemistry ; Leukocytes, Mononuclear/drug effects ; Molecular Structure ; Sea Urchins/drug effects ; Structure-Activity Relationship ; Tubulin Modulators/pharmacology |
| مستخلص: | A concise six-step protocol for the synthesis of isoflavone glaziovianin A (GVA) and its alkoxyphenyl derivatives 9 starting with readily available plant metabolites from dill and parsley seeds was developed. The reaction sequence involved an efficient conversion of the key intermediate epoxides 7 into the respective β-ketoaldehydes 8 followed by their Cu(I)-mediated cyclization into the target series 9. The biological activity of GVA and its derivatives was evaluated using a panel of seven human cancer cell lines and an in vivo sea urchin embryo assay. Both screening platforms confirmed the antimitotic effect of the parent GVA (9cg) and its alkoxy derivatives. Structure-activity relationship studies suggested that compounds 9cd and 9cf substituted with trimethoxy- and dillapiol-derived B-rings, respectively, were less active than the parent 9cg. Of the evaluated human cancer cell lines, the A375 melanoma cell line was the most sensitive to the tested molecules. Notably, the target compounds were not cytotoxic against human peripheral blood mononuclear cells up to 10 μM concentration. Phenotypic readouts from the sea urchin assay unequivocally suggest a direct microtubule-destabilizing effect of isoflavones 9cg, 9cd, and 9cf. |
| المشرفين على المادة: | 0 (Antimitotic Agents) 0 (Antineoplastic Agents) 0 (Isoflavones) 0 (Tubulin Modulators) 0 (glaziovianin A) |
| تواريخ الأحداث: | Date Created: 20160422 Date Completed: 20170605 Latest Revision: 20180112 |
| رمز التحديث: | 20240628 |
| DOI: | 10.1021/acs.jnatprod.6b00173 |
| PMID: | 27100701 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6025 |
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| DOI: | 10.1021/acs.jnatprod.6b00173 |