Revision of structures of acridone alkaloids from natural sources

Hung Yi Chen; Sio Hong Lam; Mei Lin Yang; Hsin Yi Hung; Po Chuen Shieh; Fu An Chen; Ping Chung Kuo; Tian Shung Wu

doi:10.1002/jccs.202000345

Revision of structures of acridone alkaloids from natural sources

Hung Yi Chen, Sio Hong Lam, Mei Lin Yang, Hsin Yi Hung, Po Chuen Shieh, Fu An Chen, Ping Chung Kuo, Tian Shung Wu

Research output: Contribution to journal › Article › peer-review

Abstract

The reported chemical structures of tricyclic acridone alkaloids (1–6) from Severinia buxifolia and Pleiospermium alatum were reinvestigated through a comparison of the nuclear magnetic resonance (NMR) spectral data of similar compounds and a comprehensive study of their two-dimensional (2D) NMR spectra. The structures of 1–5 were further confirmed by a comparison of their spectral data with those of the authentic samples and standards. The different chemical shifts caused by substituted functional groups in the tricyclic acridones were summarized according to the results in the present study. Furthermore, the synthetic compound 10 (N-methyl-1,3-dihydroxy-4,5,6-trimethoxyacridine-9-one) has not been reported from any natural sources in the previous literature. In addition, the chemical structures of macranthanine (21) and 7-hydroxy-noracronycine (22) from Glycosmis macrantha were also revised.

Original language	English
Journal	Journal of the Chinese Chemical Society
DOIs	https://doi.org/10.1002/jccs.202000345
Publication status	Accepted/In press - 2020

All Science Journal Classification (ASJC) codes

Chemistry(all)

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@article{660b35c5e9174a7c8a347f8239bb7747,

title = "Revision of structures of acridone alkaloids from natural sources",

abstract = "The reported chemical structures of tricyclic acridone alkaloids (1–6) from Severinia buxifolia and Pleiospermium alatum were reinvestigated through a comparison of the nuclear magnetic resonance (NMR) spectral data of similar compounds and a comprehensive study of their two-dimensional (2D) NMR spectra. The structures of 1–5 were further confirmed by a comparison of their spectral data with those of the authentic samples and standards. The different chemical shifts caused by substituted functional groups in the tricyclic acridones were summarized according to the results in the present study. Furthermore, the synthetic compound 10 (N-methyl-1,3-dihydroxy-4,5,6-trimethoxyacridine-9-one) has not been reported from any natural sources in the previous literature. In addition, the chemical structures of macranthanine (21) and 7-hydroxy-noracronycine (22) from Glycosmis macrantha were also revised.",

author = "Chen, {Hung Yi} and Lam, {Sio Hong} and Yang, {Mei Lin} and Hung, {Hsin Yi} and Shieh, {Po Chuen} and Chen, {Fu An} and Kuo, {Ping Chung} and Wu, {Tian Shung}",

note = "Funding Information: Ministry of Science and Technology (MOST) Funding information Funding Information: This research is sponsored by the Ministry of Science and Technology (MOST), Taiwan, granted to T.‐S. W.",

year = "2020",

doi = "10.1002/jccs.202000345",

language = "English",

journal = "Journal of the Chinese Chemical Society",

issn = "0009-4536",

publisher = "Chinese Chemical Society",

}

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T1 - Revision of structures of acridone alkaloids from natural sources

AU - Chen, Hung Yi

AU - Lam, Sio Hong

AU - Yang, Mei Lin

AU - Hung, Hsin Yi

AU - Shieh, Po Chuen

AU - Chen, Fu An

AU - Kuo, Ping Chung

AU - Wu, Tian Shung

N1 - Funding Information: Ministry of Science and Technology (MOST) Funding information Funding Information: This research is sponsored by the Ministry of Science and Technology (MOST), Taiwan, granted to T.‐S. W.

PY - 2020

Y1 - 2020

N2 - The reported chemical structures of tricyclic acridone alkaloids (1–6) from Severinia buxifolia and Pleiospermium alatum were reinvestigated through a comparison of the nuclear magnetic resonance (NMR) spectral data of similar compounds and a comprehensive study of their two-dimensional (2D) NMR spectra. The structures of 1–5 were further confirmed by a comparison of their spectral data with those of the authentic samples and standards. The different chemical shifts caused by substituted functional groups in the tricyclic acridones were summarized according to the results in the present study. Furthermore, the synthetic compound 10 (N-methyl-1,3-dihydroxy-4,5,6-trimethoxyacridine-9-one) has not been reported from any natural sources in the previous literature. In addition, the chemical structures of macranthanine (21) and 7-hydroxy-noracronycine (22) from Glycosmis macrantha were also revised.

AB - The reported chemical structures of tricyclic acridone alkaloids (1–6) from Severinia buxifolia and Pleiospermium alatum were reinvestigated through a comparison of the nuclear magnetic resonance (NMR) spectral data of similar compounds and a comprehensive study of their two-dimensional (2D) NMR spectra. The structures of 1–5 were further confirmed by a comparison of their spectral data with those of the authentic samples and standards. The different chemical shifts caused by substituted functional groups in the tricyclic acridones were summarized according to the results in the present study. Furthermore, the synthetic compound 10 (N-methyl-1,3-dihydroxy-4,5,6-trimethoxyacridine-9-one) has not been reported from any natural sources in the previous literature. In addition, the chemical structures of macranthanine (21) and 7-hydroxy-noracronycine (22) from Glycosmis macrantha were also revised.

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