دورية أكاديمية
Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae).
| العنوان: | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae). |
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| المؤلفون: | Noulala CGT; Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, Yaoundé P.O. Box 812, Cameroon.; Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany., Ouete JLN; Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, Yaoundé P.O. Box 812, Cameroon., Atangana AF; Department of Chemistry, Faculty of Science, University of Maroua, Maroua P.O. Box 55, Cameroon., Mbahbou GTB; Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany.; Department of Chemistry, Faculty of Science, University of Dschang, Dschang P.O. Box 67, Cameroon., Fotso GW; Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, Yaoundé P.O. Box 812, Cameroon., Stammler HG; Department of Chemistry, Inorganic and Structural Chemistry, Bielefeld University, 33501 Bielefeld, Germany., Lenta BN; Department of Chemistry, Higher Teacher Training College, University of Yaoundé 1 1, Yaoundé P.O. Box 47, Cameroon., Happi EN; Department of Chemistry, Faculty of Science, University of Douala, Douala P.O. Box 24157, Cameroon., Sewald N; Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany., Ngadjui BT; Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, Yaoundé P.O. Box 812, Cameroon. |
| المصدر: | Molecules (Basel, Switzerland) [Molecules] 2022 Feb 07; Vol. 27 (3). Date of Electronic Publication: 2022 Feb 07. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Basel, Switzerland : MDPI, c1995- |
| مواضيع طبية MeSH: | Alkaloids/*pharmacology , Antineoplastic Agents, Phytogenic/*pharmacology , Plant Bark/*chemistry , Plant Extracts/*pharmacology , Rutaceae/*chemistry , Uterine Cervical Neoplasms/*drug therapy, Female ; Humans ; Indoles/chemistry ; Pyridines/chemistry ; Quinazolines/chemistry ; Tumor Cells, Cultured |
| مستخلص: | The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1 ) along with nine previously known alkaloids 2 - 10 . In addition, six semi-synthetic derivatives 3a - c , 4b , 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate ( 5 ), edulinine ( 3 ), ribalinine ( 4 ) and arborinine ( 6 ). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new N -allylindolopyridoquinazoline 5a is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds 2 - 4 were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate ( 5 ). The TAE, fractions, compounds 1 - 7 and 9 , and semi-synthetic derivatives 3a - c , 4b , 5a and 6a were evaluated for their cytotoxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for 9 , which showed moderate activity against the tested cancer cell lines. |
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| معلومات مُعتمدة: | 57316173 German Academic Exchange Service; Open Access Publication Fund Bielefeld University |
| فهرسة مساهمة: | Keywords: Araliopsis soyauxii; Rutaceae; alkaloids; cytotoxic activity; soyauxinine |
| المشرفين على المادة: | 0 (Alkaloids) 0 (Antineoplastic Agents, Phytogenic) 0 (Indoles) 0 (Plant Extracts) 0 (Pyridines) 0 (Quinazolines) |
| تواريخ الأحداث: | Date Created: 20220215 Date Completed: 20220228 Latest Revision: 20220228 |
| رمز التحديث: | 20231215 |
| مُعرف محوري في PubMed: | PMC8838469 |
| DOI: | 10.3390/molecules27031104 |
| PMID: | 35164367 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1420-3049 |
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| DOI: | 10.3390/molecules27031104 |