Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia

Yu Zhao; Xiaojiang Hao; Wei Lu; Junchao Cai; Hong Yu; Thierry Sevénet; Françoise Guéritte

doi:10.1021/np0200257

Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia

Yu Zhao, Xiaojiang Hao, Wei Lu, Junchao Cai, Hong Yu, Thierry Sevénet, Françoise Guéritte

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

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Abstract

Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB cancer cell lines.

Original language	English
Pages (from-to)	902-908
Number of pages	7
Journal	Journal of Natural Products
Volume	65
Issue number	6
DOIs	https://doi.org/10.1021/np0200257
State	Published - 2002
Externally published	Yes

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title = "Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia",

abstract = "Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB cancer cell lines.",

author = "Yu Zhao and Xiaojiang Hao and Wei Lu and Junchao Cai and Hong Yu and Thierry Sev{\'e}net and Fran{\c c}oise Gu{\'e}ritte",

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doi = "10.1021/np0200257",

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T1 - Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia

AU - Zhao, Yu

AU - Hao, Xiaojiang

AU - Lu, Wei

AU - Cai, Junchao

AU - Yu, Hong

AU - Sevénet, Thierry

AU - Guéritte, Françoise

PY - 2002

Y1 - 2002

N2 - Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB cancer cell lines.

AB - Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB cancer cell lines.

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DO - 10.1021/np0200257

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AN - SCOPUS:0036307679

SN - 0163-3864

VL - 65

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EP - 908

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 6

ER -

Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia

Abstract

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