A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea
Three new alkaloids were isolated from the bark extract of the Malayan Kopsia arborea, viz., arbophyllidine (1), an unusual pentacyclic, monoterpenoid indole characterized by an absence of oxygen atoms and incorporating a new carbon-nitrogen skeleton, and arbophyllinines A (2) and B (3), two pentacy...
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| Format: | Article |
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American Chemical Society
2019
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| _version_ | 1796961767685881856 |
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| author | Wong, Soon Kit Wong, Suet Pick Sim, Kae Shin Lim, Siew Huah Low, Yun Yee Kam, Toh Seok |
| author_facet | Wong, Soon Kit Wong, Suet Pick Sim, Kae Shin Lim, Siew Huah Low, Yun Yee Kam, Toh Seok |
| author_sort | Wong, Soon Kit |
| collection | UM |
| description | Three new alkaloids were isolated from the bark extract of the Malayan Kopsia arborea, viz., arbophyllidine (1), an unusual pentacyclic, monoterpenoid indole characterized by an absence of oxygen atoms and incorporating a new carbon-nitrogen skeleton, and arbophyllinines A (2) and B (3), two pentacyclic corynanthean alkaloids incorporating a hydroxyethyl-substituted tetrahydrofuranone ring. The structures of the alkaloids were deduced based on analysis of the MS and NMR data and confirmed by X-ray diffraction analyses. The absolute configuration of arbophyllidine (1) was established based on experimental and calculated ECD data, while that of arbophyllinine A was based on X-ray diffraction analysis (Cu Kα). A reasonable biosynthetic route to arbophyllidine (1) from a pericine precursor is presented. Arbophyllidine (1) showed pronounced in vitro growth inhibitory activity against the HT-29 human cancer cell line with IC50 6.2 μM. © 2019 American Chemical Society and American Society of Pharmacognosy. |
| first_indexed | 2024-03-06T05:59:02Z |
| format | Article |
| id | um.eprints-23156 |
| institution | Universiti Malaya |
| last_indexed | 2024-03-06T05:59:02Z |
| publishDate | 2019 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | um.eprints-231562019-11-29T05:09:29Z http://eprints.um.edu.my/23156/ A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea Wong, Soon Kit Wong, Suet Pick Sim, Kae Shin Lim, Siew Huah Low, Yun Yee Kam, Toh Seok Q Science (General) QD Chemistry QH Natural history QR Microbiology Three new alkaloids were isolated from the bark extract of the Malayan Kopsia arborea, viz., arbophyllidine (1), an unusual pentacyclic, monoterpenoid indole characterized by an absence of oxygen atoms and incorporating a new carbon-nitrogen skeleton, and arbophyllinines A (2) and B (3), two pentacyclic corynanthean alkaloids incorporating a hydroxyethyl-substituted tetrahydrofuranone ring. The structures of the alkaloids were deduced based on analysis of the MS and NMR data and confirmed by X-ray diffraction analyses. The absolute configuration of arbophyllidine (1) was established based on experimental and calculated ECD data, while that of arbophyllinine A was based on X-ray diffraction analysis (Cu Kα). A reasonable biosynthetic route to arbophyllidine (1) from a pericine precursor is presented. Arbophyllidine (1) showed pronounced in vitro growth inhibitory activity against the HT-29 human cancer cell line with IC50 6.2 μM. © 2019 American Chemical Society and American Society of Pharmacognosy. American Chemical Society 2019 Article PeerReviewed Wong, Soon Kit and Wong, Suet Pick and Sim, Kae Shin and Lim, Siew Huah and Low, Yun Yee and Kam, Toh Seok (2019) A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea. Journal of Natural Products, 82 (7). pp. 1902-1907. ISSN 0163-3864, DOI https://doi.org/10.1021/acs.jnatprod.9b00255 <https://doi.org/10.1021/acs.jnatprod.9b00255>. https://doi.org/10.1021/acs.jnatprod.9b00255 doi:10.1021/acs.jnatprod.9b00255 |
| spellingShingle | Q Science (General) QD Chemistry QH Natural history QR Microbiology Wong, Soon Kit Wong, Suet Pick Sim, Kae Shin Lim, Siew Huah Low, Yun Yee Kam, Toh Seok A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea |
| title | A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea |
| title_full | A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea |
| title_fullStr | A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea |
| title_full_unstemmed | A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea |
| title_short | A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea |
| title_sort | cytotoxic indole characterized by incorporation of a unique carbon nitrogen skeleton and two pentacyclic corynanthean alkaloids incorporating a substituted tetrahydrofuranone ring from kopsia arborea |
| topic | Q Science (General) QD Chemistry QH Natural history QR Microbiology |
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