Xylomexicanins E-H, new limonoids from Xylocarpus granatum

Yi Bing Wu; Xia Qing; Chang Hong Huo; Hui Min Yan; Qing Wen Shi; Françoise Sauriol; Yu Cheng Gu; Hiromasa Kiyota

doi:10.1016/j.tet.2014.04.062

Xylomexicanins E-H, new limonoids from Xylocarpus granatum

Yi Bing Wu, Xia Qing, Chang Hong Huo, Hui Min Yan, Qing Wen Shi, Françoise Sauriol, Yu Cheng Gu, Hiromasa Kiyota

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

23 Citations (Scopus)

Abstract

Four novel tetranortriterpenoids, xylomexicanins E-H (1-4), were isolated from the seeds of the Chinese mangrove, Xylocarpus granatum. Among them, xylomexicanin E (1) represents the first example of limonoid with azaspiro skeleton between B (pyrrolidine) and C rings, whose biosynthetic pathways were proposed. The structures were elucidated on the basis of one- and two-dimensional NMR (including ¹H, ¹³C NMR, DEPT, ¹H-¹H COSY, HSQC, HMBC, and NOESY) and confirmed by high-resolution mass spectrometry. Compound 2, the second example of a limonoid with a C-9-C-30 linkage, showed moderate activity against the A549 and RERF cell line with IC₅₀ value of 18.83 and 15.83 μM.

Original language	English
Pages (from-to)	4557-4562
Number of pages	6
Journal	Tetrahedron
Volume	70
Issue number	30
DOIs	https://doi.org/10.1016/j.tet.2014.04.062
Publication status	Published - Jul 29 2014

Keywords

Azaspiro compounds
Cytotoxicity
Limonoids
Structure elucidation
Xylocarpus granatum

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2014.04.062

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title = "Xylomexicanins E-H, new limonoids from Xylocarpus granatum",

abstract = "Four novel tetranortriterpenoids, xylomexicanins E-H (1-4), were isolated from the seeds of the Chinese mangrove, Xylocarpus granatum. Among them, xylomexicanin E (1) represents the first example of limonoid with azaspiro skeleton between B (pyrrolidine) and C rings, whose biosynthetic pathways were proposed. The structures were elucidated on the basis of one- and two-dimensional NMR (including 1H, 13C NMR, DEPT, 1H-1H COSY, HSQC, HMBC, and NOESY) and confirmed by high-resolution mass spectrometry. Compound 2, the second example of a limonoid with a C-9-C-30 linkage, showed moderate activity against the A549 and RERF cell line with IC50 value of 18.83 and 15.83 μM.",

keywords = "Azaspiro compounds, Cytotoxicity, Limonoids, Structure elucidation, Xylocarpus granatum",

author = "Wu, {Yi Bing} and Xia Qing and Huo, {Chang Hong} and Yan, {Hui Min} and Shi, {Qing Wen} and Fran{\c c}oise Sauriol and Gu, {Yu Cheng} and Hiromasa Kiyota",

note = "Funding Information: We are grateful for the financial supports from National Natural Science Foundation of China ( 81072551 , 81241101 ), Natural Science Foundation of Hebei Province ( H2014206230 ), Key Projects of Science & Technology of Hebei Province ( 13272508 ), and Scientific Research Foundation of Hebei Province ( C2010000489 ). We also wish to extend our sincere thanks for the financial support of Syngenta Ltd (2011-Hebei Medical University-Syngenta-03) and JSPS KAKENHI Grant Numbers ( 19580120 , 22560112 , and 25450144 ).",

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language = "English",

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T1 - Xylomexicanins E-H, new limonoids from Xylocarpus granatum

AU - Wu, Yi Bing

AU - Qing, Xia

AU - Huo, Chang Hong

AU - Yan, Hui Min

AU - Shi, Qing Wen

AU - Sauriol, Françoise

AU - Gu, Yu Cheng

AU - Kiyota, Hiromasa

N1 - Funding Information: We are grateful for the financial supports from National Natural Science Foundation of China ( 81072551 , 81241101 ), Natural Science Foundation of Hebei Province ( H2014206230 ), Key Projects of Science & Technology of Hebei Province ( 13272508 ), and Scientific Research Foundation of Hebei Province ( C2010000489 ). We also wish to extend our sincere thanks for the financial support of Syngenta Ltd (2011-Hebei Medical University-Syngenta-03) and JSPS KAKENHI Grant Numbers ( 19580120 , 22560112 , and 25450144 ).

PY - 2014/7/29

Y1 - 2014/7/29

N2 - Four novel tetranortriterpenoids, xylomexicanins E-H (1-4), were isolated from the seeds of the Chinese mangrove, Xylocarpus granatum. Among them, xylomexicanin E (1) represents the first example of limonoid with azaspiro skeleton between B (pyrrolidine) and C rings, whose biosynthetic pathways were proposed. The structures were elucidated on the basis of one- and two-dimensional NMR (including 1H, 13C NMR, DEPT, 1H-1H COSY, HSQC, HMBC, and NOESY) and confirmed by high-resolution mass spectrometry. Compound 2, the second example of a limonoid with a C-9-C-30 linkage, showed moderate activity against the A549 and RERF cell line with IC50 value of 18.83 and 15.83 μM.

AB - Four novel tetranortriterpenoids, xylomexicanins E-H (1-4), were isolated from the seeds of the Chinese mangrove, Xylocarpus granatum. Among them, xylomexicanin E (1) represents the first example of limonoid with azaspiro skeleton between B (pyrrolidine) and C rings, whose biosynthetic pathways were proposed. The structures were elucidated on the basis of one- and two-dimensional NMR (including 1H, 13C NMR, DEPT, 1H-1H COSY, HSQC, HMBC, and NOESY) and confirmed by high-resolution mass spectrometry. Compound 2, the second example of a limonoid with a C-9-C-30 linkage, showed moderate activity against the A549 and RERF cell line with IC50 value of 18.83 and 15.83 μM.

KW - Azaspiro compounds

KW - Cytotoxicity

KW - Limonoids

KW - Structure elucidation

KW - Xylocarpus granatum

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Xylomexicanins E-H, new limonoids from Xylocarpus granatum

Abstract

Keywords

ASJC Scopus subject areas

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