title: Bioactive compounds from the aerial parts of Brachystemma calycinum and structural revision of an octacyclopeptide.
abstract: Four new cyclic peptides, brachystemins F-I (1-4), and 11 known compounds were isolated from the aerial parts of Brachystemma calycinum. The absolute configurations of compounds 1-4 were assigned using Marfey's method. The structure of compound 5 was revised from cyclo(Pro¹-Phe²-Leu³-Ala⁴-Thr⁵-Pro⁶-Ala⁷-Gly⁸) to cyclo(Pro¹-Pro²-Ala³-Gly⁴-Leu⁵-Ala⁶-Thr⁷-Phe⁸) with QTOF/MS and X-ray diffraction analysis. The N-containing compounds were assessed for their inhibitory effects on the secretion of monocyte chemokine ligand 2 (CCL-2), interleukin 6 (IL-6), and collagen IV against high-glucose-stimulated mesangial cells. Compound 5 was evaluated for its effects on collagen I, reactive oxygen species (ROS), superoxide anion (O₂(•⁻)) production, and cell viability in mesangial cells, and on nitric oxide (NO) production in macrophage cells.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China.
authors.forename: Jun
authors.initials: J
authors.lastname: Zhao
authors.forename: Li-Li
authors.initials: LL
authors.lastname: Zhou
authors.forename: Xi
authors.initials: X
authors.lastname: Li
authors.forename: Hong-Bin
authors.initials: HB
authors.lastname: Xiao
authors.forename: Fan-Fan
authors.initials: FF
authors.lastname: Hou
authors.forename: Yong-Xian
authors.initials: YX
authors.lastname: Cheng
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D029748:Caryophyllaceae / Q000737:chemistry*; D018932:Chemokine CCL2 / Q000037:antagonists & inhibitors; D024042:Collagen Type I / Q000187:drug effects; D024141:Collagen Type IV / Q000187:drug effects; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005947:Glucose / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D050527:Mesangial Cells / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D017382:Reactive Oxygen Species / Q000037:antagonists & inhibitors; D013481:Superoxides / Q000378:metabolism; D000093242:Interleukin-6 Inhibitors
chemical_list: D018932:Chemokine CCL2; D024042:Collagen Type I; D024141:Collagen Type IV; D004365:Drugs, Chinese Herbal; D005947:Glucose; D009569:Nitric Oxide; D010456:Peptides, Cyclic; D017382:Reactive Oxygen Species; D013481:Superoxides; D000093242:Interleukin-6 Inhibitors