Ancistrobrevidines A-C and related naphthylisoquinoline alkaloids with cytotoxic activities against HeLa and pancreatic cancer cells, from the liana Ancistrocladus abbreviatus
[Display omitted] •Eight new axially chiral alkaloids were isolated from Ancistrocladus abbreviatus.•The series comprises alkaloids of three different subclasses of naphthylisoquinolines.•Two of them are the very first naphthylisoquinolines with a 3,4-naphthoquinone portion.•Ancistrobrevine C elimin...
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Published in | Bioorganic & medicinal chemistry Vol. 30; p. 115950 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
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Elsevier Ltd
15.01.2021
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Abstract | [Display omitted]
•Eight new axially chiral alkaloids were isolated from Ancistrocladus abbreviatus.•The series comprises alkaloids of three different subclasses of naphthylisoquinolines.•Two of them are the very first naphthylisoquinolines with a 3,4-naphthoquinone portion.•Ancistrobrevine C eliminates the tolerance of pancreatic cancer cells to nutrition starvation.•Ancistrobrevine C is a potent antiausterity agent with antimetastatic activity.
From the leaves of Ancistrocladus abbreviatus (Ancistrocladaceae), six 5,1′-coupled naphthyldihydroisoquinoline alkaloids were isolated, ancistrobrevidines A-C (5–7), 5-epi-dioncophyllidine C2 (10), 6-O-methylhamatinine (8), and 6-O-methylancistectorine A3 (9); the two latter compounds were already known from related plants. Most strikingly, this series comprises alkaloids belonging to three different subclasses of naphthylisoquinolines. Ancistrobrevidine C (7) and the alkaloids 8 and 9, displaying the S-configuration at C-3 and an oxygen function at C-6, are three further representatives of the large subgroup of 5,1′-coupled Ancistrocladaceae-type compounds found in nature. 5-epi-Dioncophyllidine C2 (10), lacking an oxygen function at C-6 and having the R-configuration at C-3, is only the third representative of a 5,1′-linked Dioncophyllaceae-type naphthylisoquinoline. Likewise rare are 5,1′-coupled hybrid-type alkaloids, which are 6-oxygenated and 3R-configured. The ancistrobrevidines A (5) and B (6) are the only second and third examples of such 5,1′-linked naphthylisoquinolines in Ancistrocladus species showing the landmarks of both, Ancistrocladaceae- and Dioncophyllaceae-type naphthylisoquinolines. In the roots of A. abbreviatus, two further unprecedented 5,1′-coupled alkaloids were discovered, ancistrobreviquinones A (11) and B (12), consisting of a 3,4-naphthoquinone portion coupled to a tetrahydroisoquinoline subunit. They are the very first quinoid naphthylisoquinolines possessing an ortho-diketone entity. Ancistrobrevidine C (7) exerted pronounced antiproliferative activities against HeLa cervical cancer cells and preferential cytotoxicity towards PANC-1 human pancreatic cancer cells under nutrient-deprived conditions following the antiausterity approach. Moreover, 7 suppressed the migration of PANC-1 cells and significantly inhibited colony formation under nutrient-rich conditions in a concentration-dependent manner, and induced dramatic alteration in cell morphology, leading to cell death. |
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AbstractList | From the leaves of Ancistrocladus abbreviatus (Ancistrocladaceae), six 5,1'-coupled naphthyldihydroisoquinoline alkaloids were isolated, ancistrobrevidines A-C (5-7), 5-epi-dioncophyllidine C
(10), 6-O-methylhamatinine (8), and 6-O-methylancistectorine A
(9); the two latter compounds were already known from related plants. Most strikingly, this series comprises alkaloids belonging to three different subclasses of naphthylisoquinolines. Ancistrobrevidine C (7) and the alkaloids 8 and 9, displaying the S-configuration at C-3 and an oxygen function at C-6, are three further representatives of the large subgroup of 5,1'-coupled Ancistrocladaceae-type compounds found in nature. 5-epi-Dioncophyllidine C
(10), lacking an oxygen function at C-6 and having the R-configuration at C-3, is only the third representative of a 5,1'-linked Dioncophyllaceae-type naphthylisoquinoline. Likewise rare are 5,1'-coupled hybrid-type alkaloids, which are 6-oxygenated and 3R-configured. The ancistrobrevidines A (5) and B (6) are the only second and third examples of such 5,1'-linked naphthylisoquinolines in Ancistrocladus species showing the landmarks of both, Ancistrocladaceae- and Dioncophyllaceae-type naphthylisoquinolines. In the roots of A. abbreviatus, two further unprecedented 5,1'-coupled alkaloids were discovered, ancistrobreviquinones A (11) and B (12), consisting of a 3,4-naphthoquinone portion coupled to a tetrahydroisoquinoline subunit. They are the very first quinoid naphthylisoquinolines possessing an ortho-diketone entity. Ancistrobrevidine C (7) exerted pronounced antiproliferative activities against HeLa cervical cancer cells and preferential cytotoxicity towards PANC-1 human pancreatic cancer cells under nutrient-deprived conditions following the antiausterity approach. Moreover, 7 suppressed the migration of PANC-1 cells and significantly inhibited colony formation under nutrient-rich conditions in a concentration-dependent manner, and induced dramatic alteration in cell morphology, leading to cell death. [Display omitted] •Eight new axially chiral alkaloids were isolated from Ancistrocladus abbreviatus.•The series comprises alkaloids of three different subclasses of naphthylisoquinolines.•Two of them are the very first naphthylisoquinolines with a 3,4-naphthoquinone portion.•Ancistrobrevine C eliminates the tolerance of pancreatic cancer cells to nutrition starvation.•Ancistrobrevine C is a potent antiausterity agent with antimetastatic activity. From the leaves of Ancistrocladus abbreviatus (Ancistrocladaceae), six 5,1′-coupled naphthyldihydroisoquinoline alkaloids were isolated, ancistrobrevidines A-C (5–7), 5-epi-dioncophyllidine C2 (10), 6-O-methylhamatinine (8), and 6-O-methylancistectorine A3 (9); the two latter compounds were already known from related plants. Most strikingly, this series comprises alkaloids belonging to three different subclasses of naphthylisoquinolines. Ancistrobrevidine C (7) and the alkaloids 8 and 9, displaying the S-configuration at C-3 and an oxygen function at C-6, are three further representatives of the large subgroup of 5,1′-coupled Ancistrocladaceae-type compounds found in nature. 5-epi-Dioncophyllidine C2 (10), lacking an oxygen function at C-6 and having the R-configuration at C-3, is only the third representative of a 5,1′-linked Dioncophyllaceae-type naphthylisoquinoline. Likewise rare are 5,1′-coupled hybrid-type alkaloids, which are 6-oxygenated and 3R-configured. The ancistrobrevidines A (5) and B (6) are the only second and third examples of such 5,1′-linked naphthylisoquinolines in Ancistrocladus species showing the landmarks of both, Ancistrocladaceae- and Dioncophyllaceae-type naphthylisoquinolines. In the roots of A. abbreviatus, two further unprecedented 5,1′-coupled alkaloids were discovered, ancistrobreviquinones A (11) and B (12), consisting of a 3,4-naphthoquinone portion coupled to a tetrahydroisoquinoline subunit. They are the very first quinoid naphthylisoquinolines possessing an ortho-diketone entity. Ancistrobrevidine C (7) exerted pronounced antiproliferative activities against HeLa cervical cancer cells and preferential cytotoxicity towards PANC-1 human pancreatic cancer cells under nutrient-deprived conditions following the antiausterity approach. Moreover, 7 suppressed the migration of PANC-1 cells and significantly inhibited colony formation under nutrient-rich conditions in a concentration-dependent manner, and induced dramatic alteration in cell morphology, leading to cell death. |
ArticleNumber | 115950 |
Author | Fayez, Shaimaa Kim, Minjo Feineis, Doris Sun, Sijia Bringmann, Gerhard Awale, Suresh Aké Assi, Laurent Cacciatore, Alessia |
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BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33383442$$D View this record in MEDLINE/PubMed |
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CitedBy_id | crossref_primary_10_1016_j_biopha_2023_115704 crossref_primary_10_1016_j_rechem_2024_101352 crossref_primary_10_1080_14786419_2023_2194648 crossref_primary_10_1016_j_bioorg_2023_106573 crossref_primary_10_1039_D1NP00020A crossref_primary_10_1039_D3CC01705B crossref_primary_10_1134_S1070363223050286 crossref_primary_10_1248_bpb_b23_00224 crossref_primary_10_1039_D2RA05758A crossref_primary_10_1016_j_bmcl_2023_129234 crossref_primary_10_1016_j_phymed_2023_155267 crossref_primary_10_1016_j_ejmech_2023_115226 |
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Keywords | Ancistrobrevidines Naphthylisoquinoline alkaloids Anticancer agents Ancistrobreviquinones Ancistrocladus abbreviatus Pancreatic cancer |
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•Eight new axially chiral alkaloids were isolated from Ancistrocladus abbreviatus.•The series comprises alkaloids of three different... From the leaves of Ancistrocladus abbreviatus (Ancistrocladaceae), six 5,1'-coupled naphthyldihydroisoquinoline alkaloids were isolated, ancistrobrevidines A-C... |
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SubjectTerms | Ancistrobrevidines Ancistrobreviquinones Ancistrocladus abbreviatus Anticancer agents Naphthylisoquinoline alkaloids Pancreatic cancer |
Title | Ancistrobrevidines A-C and related naphthylisoquinoline alkaloids with cytotoxic activities against HeLa and pancreatic cancer cells, from the liana Ancistrocladus abbreviatus |
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