title: Monoterpenoid indole alkaloids from Alstonia rupestris with cytotoxic, antibacterial and antifungal activities.
abstract: A chemical investigation of the 80% EtOH extract of the aerial plant of Alstonia rupestris afforded four new monoterpenoid indole alkaloids, 6,7-epoxy-8-oxo-vincadifformine (1), 11-acetyl-6,7-epoxy-8-oxo-vincadifformine (2), 11-hydroxy-14-chloro-15-hydroxy-vincadifformine (3), and perakine N1,N4-dioxide (4), together with two known compounds, 11-hydroxy-6,7-epoxy-8-oxovincadifformine (5) and vinorine N1,N4-dioxide (6). Structural elucidation of all the compounds was performed by spectral methods such as 1D- and 2D-NMR, IR, UV, and HRESIMS. Alkaloids 1, 2 and 5 showed significant cytotoxicities against all the tested tumor cell lines of the head and neck squamous cell carcinoma with IC50 value less than 20 μM and antimicrobial activities against two fungi (Alternaria alternata and Phytophthora capsici). Alkaloids 4 and 6 exhibited the activity against bacterium Staphylococcus aureus.
authors.affiliation: Department of Oral and Maxillofacial Surgery, General Hospital of Shenyang Military Command, Shenyang, Liaoning 110016, China.
authors.forename: Li
authors.initials: L
authors.lastname: Zhang
authors.affiliation: Department of Oral and Maxillofacial Surgery, General Hospital of Shenyang Military Command, Shenyang, Liaoning 110016, China. Electronic address: zqhuasy@sohu.com.
authors.forename: Zequan
authors.initials: Z
authors.lastname: Hua
authors.affiliation: Department of Pharmacy, 455 Hospital of People's Liberation Army, West Huaihai Road 338, Shanghai 200052, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Song
authors.affiliation: Department of Organic Chemistry, College of Pharmacy, Second Military Medical University, Guohe Road 325, Shanghai 200433, China.
authors.forename: Chuanwei
authors.initials: C
authors.lastname: Feng
mesh_terms: D031051:Alstonia / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification*; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000972:Antineoplastic Agents, Phytogenic; D046948:Secologanin Tryptamine Alkaloids
keywords: Alkaloids; Alstonia rupestris; Antibacterial; Antifungal; Apocynaceae; Cytotoxic