title: Jonquailine, a new pretazettine-type alkaloid isolated from Narcissus jonquilla quail, with activity against drug-resistant cancer.
abstract: A new alkaloid, belonging to the pretazettine group of Amaryllidaceae alkaloids, was isolated from dried bulbs of Narcissus jonquilla quail and named jonquailine. Its structure, including the absolute configuration, was elucidated using various NMR, ECD and ESI MS techniques. Initial biological evaluation revealed significant antiproliferative effects against glioblastoma, melanoma, uterine sarcoma and non-small-cell lung cancer cells displaying various forms of drug resistance, including resistance to apoptosis and multi-drug resistance. Jonquailine was also found to synergize with paclitaxel in its antiproliferative action against drug-resistant lung cancer cells. The results obtained compared with literature data also showed that the hydroxylation at C-8 is an important feature for the anticancer activity but this seems unaffected by the stereochemistry or the acetalization of the lactol.
authors.affiliation: Dipartimento di Scienze Chimiche, Universita' di Napoli Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Masi
authors.affiliation: Department of Chemistry, New Mexico Tech, 801 Leroy Place, Socorro, NM 87801, USA; Department of Biology, New Mexico Tech, 801 Leroy Place, Socorro, NM 87801, USA.
authors.forename: Liliya V
authors.initials: LV
authors.lastname: Frolova
authors.affiliation: Greehey Children's Cancer Research Institute, UT Health Science Center at San Antonio, 8403 Floyd Curl Drive, San Antonio, TX 78229, USA.
authors.forename: Xiaojie
authors.initials: X
authors.lastname: Yu
authors.affiliation: Laboratoire de Cancérologie et de Toxicologie Expérimentale, Faculté de Pharmacie, Université Libre de Bruxelles (ULB), Brussels, Belgium.
authors.forename: Véronique
authors.initials: V
authors.lastname: Mathieu
authors.affiliation: Dipartimento di Scienze Chimiche, Universita' di Napoli Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Alessio
authors.initials: A
authors.lastname: Cimmino
authors.affiliation: Laboratoire de Cancérologie et de Toxicologie Expérimentale, Faculté de Pharmacie, Université Libre de Bruxelles (ULB), Brussels, Belgium.
authors.forename: Annelise
authors.initials: A
authors.lastname: De Carvalho
authors.affiliation: Laboratoire de Cancérologie et de Toxicologie Expérimentale, Faculté de Pharmacie, Université Libre de Bruxelles (ULB), Brussels, Belgium.
authors.forename: Robert
authors.initials: R
authors.lastname: Kiss
authors.affiliation: Department of Chemistry, New Mexico Tech, 801 Leroy Place, Socorro, NM 87801, USA; Department of Biology, New Mexico Tech, 801 Leroy Place, Socorro, NM 87801, USA.
authors.forename: Snezna
authors.initials: S
authors.lastname: Rogelj
authors.affiliation: Greehey Children's Cancer Research Institute, UT Health Science Center at San Antonio, 8403 Floyd Curl Drive, San Antonio, TX 78229, USA.
authors.forename: Alexander
authors.initials: A
authors.lastname: Pertsemlidis
authors.affiliation: Department of Chemistry and Biochemistry, Texas State University, 601 University Drive, San Marcos, TX 78666, USA. Electronic address: a_k76@txstate.edu.
authors.forename: Alexander
authors.initials: A
authors.lastname: Kornienko
authors.affiliation: Dipartimento di Scienze Chimiche, Universita' di Napoli Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy. Electronic address: evidente@unina.it.
authors.forename: Antonio
authors.initials: A
authors.lastname: Evidente
mesh_terms: D000470:Alkaloids / Q000302:isolation & purification / Q000494:pharmacology*; D047151:Amaryllidaceae Alkaloids / Q000302:isolation & purification / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D019008:Drug Resistance, Neoplasm; D006801:Humans; D015394:Molecular Structure; D031427:Narcissus / Q000737:chemistry*; D018517:Plant Roots / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D000972:Antineoplastic Agents, Phytogenic; C000598364:jonquailine
keywords: Alkaloids; Amaryllidaceae; Antiproliferative effects; Cancer cells; Jonquailine; Narcissus jonquilla quail