title: Novel sesquiterpenes from Schisandra grandiflora: isolation, cytotoxic activity and synthesis of their triazole derivatives using "click" reaction.
abstract: Phytochemical investigation of hexane extract from the fruits of Schisandra grandiflora afforded three novel sesquiterpenes (1-3) along with the three known compounds (4-6). The structures of these isolates were determined by extensive analysis of spectroscopic data (1D, 2D NMR). Further, a series of triazole analogues of 3 and 4 were prepared using "Click" reaction protocol. The reaction scheme involving one-carbon homologation of 3 and 4 using the Bestmann-Ohira reagent followed by regioselective Huisgen 1,3-dipolar cycloaddition reaction of various azides leading to the formation of triazole analogues (20a-20k &21a-21c) which is being reported for the first time. All the triazole products were characterized using spectral data analysis. The anti-proliferative activity of the isolates and the synthetic analogues were studied against Hela (Cervical cancer), A549 (Lung cancer), DU-145 (Prostate cancer), MCF-7 (Breast cancer) and B-16 (Mouse melanoma) cancer cell lines.
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India.
authors.forename: B
authors.initials: B
authors.lastname: Poornima
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India.
authors.forename: Bandi
authors.initials: B
authors.lastname: Siva
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India.
authors.forename: G
authors.initials: G
authors.lastname: Shankaraiah
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India.
authors.forename: A
authors.initials: A
authors.lastname: Venkanna
authors.affiliation: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: V Lakshma
authors.initials: VL
authors.lastname: Nayak
authors.affiliation: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: Sistla
authors.initials: S
authors.lastname: Ramakrishna
authors.affiliation: Department of Chemistry, Sri Venkateswara University, Tirupati 517502, India.
authors.forename: C
authors.initials: C
authors.lastname: Venkat Rao
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India. Electronic address: suresh@iict.res.in.
authors.forename: K Suresh
authors.initials: KS
authors.lastname: Babu
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D057930:Click Chemistry; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D056945:Hep G2 Cells; D006801:Humans; D061986:MCF-7 Cells; D051379:Mice; D015394:Molecular Structure; D032141:Schisandra / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D012717:Sesquiterpenes
keywords: Bestmann-Ohira homologation; Click reaction; Schisandra grandiflora; Sesquiterpenes; Triazole derivatives and anti-proliferative activity