The structure of amoorastatone and the cytotoxic limonoid 12-hydroxyamoorastatin

Judith Polonsky; Zoïa Varon; Ch Marazano; Bernadette Arnoux; George Pettit; J. M. Schmid; M. Ochi; H. Kotsuki

doi:10.1007/BF01949897

The structure of amoorastatone and the cytotoxic limonoid 12-hydroxyamoorastatin

Judith Polonsky, Zoïa Varon, Ch Marazano, Bernadette Arnoux, George Pettit, J. M. Schmid, M. Ochi, H. Kotsuki

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Abstract

2 new limonoid-type terpenes have been isolated from an aqueous extract of seeds produced by the Eastern Himalayan (India) plant Aphanamixis grandifolia Bl. By interpreting principally mass spectral and nuclear magnetic resonance data, the structures of 12-hydroxyamoorastatin (2b) and amoorastatone (3) were elucidated. Unequivocal evidence for the 12-hydroxyamoorastatin structural assignment was obtained by chemical conversion to sendanin (4). Amoorastatin derivative 2b was found to significantly inhibit growth of the murine P388 lymphocytic leukemia cell lines but amoorastatone in the same system was inactive. In a comparative biological study, sendanin (4) and anthothecol (7) were also found significantly to inhibit growth of the P388 cell line, while rohitukin (8) and limonin (9) were found to be inactive.

Original language	English (US)
Pages (from-to)	987-989
Number of pages	3
Journal	Experientia
Volume	35
Issue number	8
DOIs	https://doi.org/10.1007/BF01949897
State	Published - Aug 1979

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Biochemistry, Genetics and Molecular Biology(all)

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title = "The structure of amoorastatone and the cytotoxic limonoid 12-hydroxyamoorastatin",

abstract = "2 new limonoid-type terpenes have been isolated from an aqueous extract of seeds produced by the Eastern Himalayan (India) plant Aphanamixis grandifolia Bl. By interpreting principally mass spectral and nuclear magnetic resonance data, the structures of 12-hydroxyamoorastatin (2b) and amoorastatone (3) were elucidated. Unequivocal evidence for the 12-hydroxyamoorastatin structural assignment was obtained by chemical conversion to sendanin (4). Amoorastatin derivative 2b was found to significantly inhibit growth of the murine P388 lymphocytic leukemia cell lines but amoorastatone in the same system was inactive. In a comparative biological study, sendanin (4) and anthothecol (7) were also found significantly to inhibit growth of the P388 cell line, while rohitukin (8) and limonin (9) were found to be inactive.",

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T1 - The structure of amoorastatone and the cytotoxic limonoid 12-hydroxyamoorastatin

AU - Polonsky, Judith

AU - Varon, Zoïa

AU - Marazano, Ch

AU - Arnoux, Bernadette

AU - Pettit, George

AU - Schmid, J. M.

AU - Ochi, M.

AU - Kotsuki, H.

PY - 1979/8

Y1 - 1979/8

N2 - 2 new limonoid-type terpenes have been isolated from an aqueous extract of seeds produced by the Eastern Himalayan (India) plant Aphanamixis grandifolia Bl. By interpreting principally mass spectral and nuclear magnetic resonance data, the structures of 12-hydroxyamoorastatin (2b) and amoorastatone (3) were elucidated. Unequivocal evidence for the 12-hydroxyamoorastatin structural assignment was obtained by chemical conversion to sendanin (4). Amoorastatin derivative 2b was found to significantly inhibit growth of the murine P388 lymphocytic leukemia cell lines but amoorastatone in the same system was inactive. In a comparative biological study, sendanin (4) and anthothecol (7) were also found significantly to inhibit growth of the P388 cell line, while rohitukin (8) and limonin (9) were found to be inactive.

AB - 2 new limonoid-type terpenes have been isolated from an aqueous extract of seeds produced by the Eastern Himalayan (India) plant Aphanamixis grandifolia Bl. By interpreting principally mass spectral and nuclear magnetic resonance data, the structures of 12-hydroxyamoorastatin (2b) and amoorastatone (3) were elucidated. Unequivocal evidence for the 12-hydroxyamoorastatin structural assignment was obtained by chemical conversion to sendanin (4). Amoorastatin derivative 2b was found to significantly inhibit growth of the murine P388 lymphocytic leukemia cell lines but amoorastatone in the same system was inactive. In a comparative biological study, sendanin (4) and anthothecol (7) were also found significantly to inhibit growth of the P388 cell line, while rohitukin (8) and limonin (9) were found to be inactive.

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The structure of amoorastatone and the cytotoxic limonoid 12-hydroxyamoorastatin

Abstract

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