Influenza A (H(1)N(1)) Antiviral and Cytotoxic Agents from Ferula assa-foetida.
Two new sesquiterpene coumarins, designated 5'-acetoxy-8'-hydroxyumbelliprenin (1) and 10'R-acetoxy-11'-hydroxyumbelliprenin (2), and a new diterpene, 15-hydroxy-6-en-dehydroabietic acid (3), along with 27 known compounds, were isolated from a CHCl(3)-soluble extract of Ferula assa-foetida through bioassay-guided fractionation. The structures of the new metabolites 1-3 were identified by spectroscopic data interpretation and by the Mosher ester method. Compounds 4 and 6-13 showed greater potency against influenza A virus (H(1)N(1)) (IC(50) 0.26-0.86 microg/mL) than amantadine (IC(50) 0.92 microg/mL), and 11 exhibited the best potency (IC(50) 0.51, 2.6, and 3.4 microg/mL) of these compounds against the HepG2, Hep3B, and MCF-7 cancer cell lines, respectively.
Lee
Chia-Lin
CL
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan, Republic of China.
Chiang
Lien-Chai
LC
Cheng
Li-Hung
LH
Liaw
Chih-Chuang
CC
Abd El-Razek
Mohamed H
MH
Chang
Fang-Rong
FR
Wu
Yang-Chang
YC
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002522:Chlorocebus aethiops; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005309:Ferula / Q000737:chemistry*; D006801:Humans; D053118:Influenza A Virus, H1N1 Subtype / Q000187:drug effects*; D007251:Influenza, Human / Q000188:drug therapy*; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
C544273:10'R-acetoxy-11'-hydroxyumbelliprenin; C544272:5'-acetoxy-8'-hydroxyumbelliprenin; D000972:Antineoplastic Agents, Phytogenic; D000998:Antiviral Agents; D003374:Coumarins; D012717:Sesquiterpenes