title: Unusual ingenoids from Euphorbia erythradenia Bioss. with pro-apoptotic effects.
abstract: Dichloromethane-acetone extract of Euphorbia erythradenia Bioss., a spurge endemic to the Iran, afforded four novel tetrahydroingenol diterpenes, one new myrsinane type diterpene, and two known triterpenes. Tetrahydroingenoids are novel compounds not only for the double bond reduction but also for their unique hydroxylation pattern at C-11 and C-13. The structures of these compounds were elucidated by spectroscopic methods, and especially 2D NMR measurements. The biological effects of the compounds were done by the MTT and Annexin V-FITC & PI staining assays on different cancer cell lines. The results obtained on EJ-138, CAOV-4, and OVCAR-3 cell lines suggested that tetrahydroingenanes inhibit cell proliferation through apoptosis in cancer cell lines. In conclusion, the new pattern of hydrogenation and hydroxylation of these compounds compared to other ingenoids, along with their apoptosis inducing properties on cancer cells, makes them of great interest for more investigation.
authors.affiliation: Phytochemistry Research Center and School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Islamic Republic of Iran.
authors.forename: Seyed Mohammad
authors.initials: SM
authors.lastname: Zarei
authors.affiliation: Phytochemistry Research Center and School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Islamic Republic of Iran.
authors.forename: Abdul Majid
authors.initials: AM
authors.lastname: Ayatollahi
authors.affiliation: Department of Pharmacognosy, Isfahan Faculty of Pharmacy, Isfahan University of Medical Sciences, Isfahan, Islamic Republic of Iran. Electronic address: Ghannadian@gmail.com.
authors.forename: Mustafa
authors.initials: M
authors.lastname: Ghanadian
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshtee University of Medical Sciences, Tehran, Islamic Republic of Iran.
authors.forename: Farzad
authors.initials: F
authors.lastname: Kobarfard
authors.affiliation: Department of Clinical Biochemistry, School of Pharmacy, Isfahan University of Medical Sciences, Isfahan, Islamic Republic of Iran.
authors.forename: Mahmoud
authors.initials: M
authors.lastname: Aghaei
authors.affiliation: Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
authors.forename: M Iqbal
authors.initials: MI
authors.lastname: Choudhary
authors.affiliation: Cellular and Molecular Research Center, Qom University of Medical Sciences, Qom, Islamic Republic of Iran.
authors.forename: Faranak
authors.initials: F
authors.lastname: Fallahian
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D017209:Apoptosis / Q000187:drug effects; D002277:Carcinoma / Q000188:drug therapy*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D028481:Euphorbia / Q000737:chemistry*; D005260:Female; D006801:Humans; D015394:Molecular Structure; D010051:Ovarian Neoplasms / Q000188:drug therapy*; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D001749:Urinary Bladder Neoplasms / Q000188:drug therapy*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D010936:Plant Extracts
keywords: Cytotoxicity activity; Euphorbia erythradenia; Flora of Iran; Ingenane; Tetrahydroingenol