Chemical transformation and biological activities of ambrein, a major product of ambergris from Physeter macrocephalus (sperm whale).
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.
Shen
Ya-Ching
YC
School of Pharmacy, College of Medicine, National Taiwan University, Taipei, Taiwan 100, Republic of China. ycshen@ntu.edu.tw
Cheng
Shi-Yie
SY
Kuo
Yao-Haur
YH
Hwang
Tsong-Long
TL
Chiang
Michael Y
MY
Khalil
Ashraf Taha
AT
D018648:Ambergris / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects; D010196:Pancreatic Elastase / Q000378:metabolism; D050661:Sperm Whale; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
D018648:Ambergris; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000970:Antineoplastic Agents; D009284:Naphthols; D014315:Triterpenes; C074170:ambrein; D010196:Pancreatic Elastase