title: Ervatamines A-I, Anti-inflammatory Monoterpenoid Indole Alkaloids with Diverse Skeletons from Ervatamia hainanensis.
abstract: Nine new monoterpenoid indole alkaloids, ervatamines A-I (1-9), and five known ones (10-14), were isolated from Ervatamia hainanensis. The new structures were elucidated by extensive spectroscopic analysis and comparison to known compounds. Their absolute configurations were determined by various methods including computational methods, X-ray diffraction analysis, and electronic circular dichroism spectroscopy, as well as chemical transformations. Ervatamine A (1) is a ring-C-contracted ibogan-type monoterpenoid indole alkaloid with an unusual 6/5/6/6/6 pentacyclic rearranged ring system. Ervatamines B-E (2-5) display a nitrogen-containing 9/6 ring system, which is rarely observed in nature. The epimeric ervatamines B (2) and C (3) possess a 22-nor-monoterpenoid indole alkaloid carbon skeleton, which was only found in deformylstemmadenine. Compounds 10 and 14 exhibited significant anti-inflammatory activities, with IC50 values of 25.5 and 41.5 μM, respectively, while the IC50 value of indomethacin as a positive control was found to be 42.6 μM. Additionally, compound 9 showed mild activity against 786-O and HL-60 cell lines.
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Dong-Bo
authors.initials: DB
authors.lastname: Zhang
authors.affiliation: ‡Tropical Crops Genetic Resources Institute, Chinese Academy of Tropical Agricultural Science, Danzhou 571737, People's Republic of China.
authors.forename: Dao-Geng
authors.initials: DG
authors.lastname: Yu
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Meng
authors.initials: M
authors.lastname: Sun
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Xu-Xin
authors.initials: XX
authors.lastname: Zhu
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Xiao-Jun
authors.initials: XJ
authors.lastname: Yao
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Shuang-Yan
authors.initials: SY
authors.lastname: Zhou
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Jian-Jun
authors.initials: JJ
authors.lastname: Chen
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Kun
authors.initials: K
authors.lastname: Gao
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D029062:Apocynaceae / Q000737:chemistry*; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018922:HL-60 Cells; D006801:Humans; D015394:Molecular Structure; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000893:Anti-Inflammatory Agents; D004365:Drugs, Chinese Herbal; D046948:Secologanin Tryptamine Alkaloids; C017291:ervatamine