title: Absolute configuration of podophyllotoxin related lignans from Bursera fagaroides using vibrational circular dichroism.
abstract: The ethanol extract from the dried exudate of Bursera fagaroides (Burseraceae) showed significant cytotoxic activity in the HT-29 (human colon adenocarcinoma) test system. The extract provided four podophyllotoxin related lignans, identified as (7'R,8R,8'R)-(-)-deoxypodophyllotoxin (3), (7'R,8R,8'R)-(-)-morelensin (4), (8R,8'R)-(-)-yatein (5), and (8R,8'R)-(-)-5'-desmethoxyyatein (6), whose spectroscopic and chiroptical properties were compared with those of (7R,7'R,8R,8'R)-(-)-podophyllotoxin (1) and its acetyl derivative (2). Their absolute configurations were assigned by comparison of the vibrational circular dichroism spectra of 1 and 3 with those obtained by density functional theory calculations.
authors.affiliation: Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Km 4.5 Carretera Pachuca-Tulancingo, Mineral de la Reforma, Hidalgo 42184, Mexico.
authors.forename: René
authors.initials: R
authors.lastname: Velázquez-Jiménez
authors.forename: J Martín
authors.initials: JM
authors.lastname: Torres-Valencia
authors.forename: Carlos M
authors.initials: CM
authors.lastname: Cerda-García-Rojas
authors.forename: Juan D
authors.initials: JD
authors.lastname: Hernández-Hernández
authors.forename: Luisa U
authors.initials: LU
authors.lastname: Román-Marín
authors.forename: J Jesús
authors.initials: JJ
authors.lastname: Manríquez-Torres
authors.forename: Mario A
authors.initials: MA
authors.lastname: Gómez-Hurtado
authors.forename: Alejandro
authors.initials: A
authors.lastname: Valdez-Calderón
authors.forename: Virginia
authors.initials: V
authors.lastname: Motilva
authors.forename: Sofía
authors.initials: S
authors.lastname: García-Mauriño
authors.forename: Elena
authors.initials: E
authors.lastname: Talero
authors.forename: Javier
authors.initials: J
authors.lastname: Avila
authors.forename: Pedro
authors.initials: P
authors.lastname: Joseph-Nathan
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D000230:Adenocarcinoma / Q000188:drug therapy*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D001572:Benzofurans / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D031233:Bursera / Q000737:chemistry*; D045744:Cell Line, Tumor; D002942:Circular Dichroism; D003110:Colonic Neoplasms / Q000188:drug therapy*; D004149:Dioxoles / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D004365:Drugs, Chinese Herbal; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D053147:Plant Exudates / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D011034:Podophyllotoxin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D001572:Benzofurans; D004149:Dioxoles; D004365:Drugs, Chinese Herbal; D010936:Plant Extracts; D053147:Plant Exudates; C499777:morelensin; C452802:yatein; C014451:deoxypodophyllotoxin; D011034:Podophyllotoxin; D015107:4-Butyrolactone