title: A novel natural phenyl alkene with cytotoxic activity.
abstract: A novel phenyl alkene (1) was isolated from a mixture of three Florida sponges,Smenospongia aurea, Smenospongia cerebriformis, andVerongula rigida. Unlike terpenoids or amino acid derivatives, which are commonly known classes of secondary metabolites from these genera, the chemical structure of1showed an unprecedented linear phenyl alkene skeleton. Through comprehensive analyses of NMR and MS data, the gross structure of1was determined to be (E)-10-benzyl-5,7-dimethylundeca-1,5,10-trien-4-ol. The absolute configuration at C-4 was established asRby a modified Mosher's method. Based on the relative configuration between C-4 and C-7, the absolute configuration at C-7 was assigned asS. Compound1showed in vitro cytotoxic activity against HL-60 human leukemia cancer cells with an IC50value of 8.1 µM. Molecular docking study suggests that the structure of compound1matches the pharmacophore of eribulin required to display cytotoxic activity through the inhibition of microtubule activity.
authors: College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk 712-749, Republic of Korea.
authors: In Hyun
authors: IH
authors: Hwang
authors: Department of Pharmacognosy and Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
authors: Joonseok
authors: J
authors: Oh
authors: Department of Pharmaceutical Sciences, School of Pharmacy, Texas Tech University Health Sciences Center, 1300 Coulter St., Amarillo, TX 79106, USA.
authors: Anna
authors: A
authors: Kochanowska-Karamyan
authors: Department of Medicinal Chemistry and Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
authors: Robert J
authors: RJ
authors: Doerksen
authors: College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
authors: MinKyun
authors: M
authors: Na
authors: Department of Pharmacognosy and Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
authors: Mark T
authors: MT
authors: Hamann
keywords: (4R,7S,E)-10-Benzyl-5,7-dimethylundeca-; 1,5,10-trien-4-ol; Cytotoxic activity; Phenyl alkene