Cerasoidine, a Bis-aporphine Alkaloid Isolated from Polyalthia cerasoides during Screening for Wnt Signal Inhibitors

Takumi Shono; Naoki Ishikawa; Kazufumi Toume; Midori A. Arai; Hyuma Masu; Takashi Koyano; Thaworn Kowithayakorn; Masami Ishibashi

doi:10.1021/acs.jnatprod.6b00409

Cerasoidine, a Bis-aporphine Alkaloid Isolated from Polyalthia cerasoides during Screening for Wnt Signal Inhibitors

Takumi Shono, Naoki Ishikawa, Kazufumi Toume, Midori A. Arai, Hyuma Masu, Takashi Koyano, Thaworn Kowithayakorn, Masami Ishibashi

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

20 Citations (Scopus)

Abstract

A new bis-aporphine alkaloid, cerasoidine (1), was isolated from the root extract of Polyalthia cerasoides together with the known bis-aporphine bidebiline E (2) during screening for compounds with Wnt signal inhibitory activities. The structure of cerasoidine (1) was established by X-ray analysis and shown by chiral HPLC analyses and electronic circular dichroism to be a 57:43 mixture of R(-)- and S(+)-atropisomers. Bidebiline E (2) exhibited inhibition of transcriptional activity of TCF/β-catenin with an IC₅₀ value of 20.2 μM and was also found to inhibit Wnt signaling by decreasing nuclear β-catenin.

Original language	English
Pages (from-to)	2083-2088
Number of pages	6
Journal	Journal of Natural Products
Volume	79
Issue number	8
DOIs	https://doi.org/10.1021/acs.jnatprod.6b00409
Publication status	Published - 2016 Aug 26
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/acs.jnatprod.6b00409

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title = "Cerasoidine, a Bis-aporphine Alkaloid Isolated from Polyalthia cerasoides during Screening for Wnt Signal Inhibitors",

abstract = "A new bis-aporphine alkaloid, cerasoidine (1), was isolated from the root extract of Polyalthia cerasoides together with the known bis-aporphine bidebiline E (2) during screening for compounds with Wnt signal inhibitory activities. The structure of cerasoidine (1) was established by X-ray analysis and shown by chiral HPLC analyses and electronic circular dichroism to be a 57:43 mixture of R(-)- and S(+)-atropisomers. Bidebiline E (2) exhibited inhibition of transcriptional activity of TCF/β-catenin with an IC50 value of 20.2 μM and was also found to inhibit Wnt signaling by decreasing nuclear β-catenin.",

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AU - Shono, Takumi

AU - Ishikawa, Naoki

AU - Toume, Kazufumi

AU - Arai, Midori A.

AU - Masu, Hyuma

AU - Koyano, Takashi

AU - Kowithayakorn, Thaworn

AU - Ishibashi, Masami

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Y1 - 2016/8/26

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AB - A new bis-aporphine alkaloid, cerasoidine (1), was isolated from the root extract of Polyalthia cerasoides together with the known bis-aporphine bidebiline E (2) during screening for compounds with Wnt signal inhibitory activities. The structure of cerasoidine (1) was established by X-ray analysis and shown by chiral HPLC analyses and electronic circular dichroism to be a 57:43 mixture of R(-)- and S(+)-atropisomers. Bidebiline E (2) exhibited inhibition of transcriptional activity of TCF/β-catenin with an IC50 value of 20.2 μM and was also found to inhibit Wnt signaling by decreasing nuclear β-catenin.

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Cerasoidine, a Bis-aporphine Alkaloid Isolated from Polyalthia cerasoides during Screening for Wnt Signal Inhibitors

Abstract

ASJC Scopus subject areas

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