Chemical transformation and biological activities of ambrein, a major product of ambergris from Physeter macrocephalus (Sperm Whale)

Ya Ching Shen; Shi Yie Cheng; Yao Haur Kuo; Tsong Long Hwang; Michael Y. Chiang; Ashraf Taha Khalil

doi:10.1021/np068029p

Chemical transformation and biological activities of ambrein, a major product of ambergris from Physeter macrocephalus (Sperm Whale)

Ya Ching Shen^*, Shi Yie Cheng, Yao Haur Kuo, Tsong Long Hwang, Michael Y. Chiang, Ashraf Taha Khalil

^*Corresponding author for this work

School of Traditional Chinese Medicine

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

15 Scopus citations

Abstract

Ten new derivatives (2-11) of ambrein (1), isolated from ambergris, were prepared by chemical transformation. Oxidation and/or cyclization were effected by reactions with selenium oxide or p-toluenesulfonyl chloride or with the use of shortwave UV light. The structures of 2-12 were elucidated by spectroscopic analysis, with the structure and relative configuration of 9 confirmed by single-crystal X-ray crystallography. The cytotoxic activities of 1-12 were investigated against human liver carcinoma (Hepa59T/VGH), colon adenocarcinoma (WiDr), lung carcinoma (A-549), and human breast adenocarcinoma (MCF-7) cell lines. The anti-inflammatory activities of 1-11, in terms of the inhibition of human neutrophil function, were also evaluated.

Original language	English
Pages (from-to)	147-153
Number of pages	7
Journal	Journal of Natural Products
Volume	70
Issue number	2
DOIs	https://doi.org/10.1021/np068029p
State	Published - 02 2007

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abstract = "Ten new derivatives (2-11) of ambrein (1), isolated from ambergris, were prepared by chemical transformation. Oxidation and/or cyclization were effected by reactions with selenium oxide or p-toluenesulfonyl chloride or with the use of shortwave UV light. The structures of 2-12 were elucidated by spectroscopic analysis, with the structure and relative configuration of 9 confirmed by single-crystal X-ray crystallography. The cytotoxic activities of 1-12 were investigated against human liver carcinoma (Hepa59T/VGH), colon adenocarcinoma (WiDr), lung carcinoma (A-549), and human breast adenocarcinoma (MCF-7) cell lines. The anti-inflammatory activities of 1-11, in terms of the inhibition of human neutrophil function, were also evaluated.",

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AU - Shen, Ya Ching

AU - Cheng, Shi Yie

AU - Kuo, Yao Haur

AU - Hwang, Tsong Long

AU - Chiang, Michael Y.

AU - Khalil, Ashraf Taha

PY - 2007/2

Y1 - 2007/2

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Chemical transformation and biological activities of ambrein, a major product of ambergris from Physeter macrocephalus (Sperm Whale)

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