title: Pyrrolidine-type iminosugars from leaves of Suregada glomerulata.
abstract: Phytochemical investigation of the H2O extract of leaves of Suregada glomerulata led to the isolation of ten pyrrolidine-type iminosugars. The chemical structures of the six new compounds (4-6, 8-10) were elucidated as 2,5-imino-2,4,5-trideoxy-d-manno-heptitol (4-deoxy-homoDMDP) (4), 2,5-imino-2,4,5-trideoxy-d-gulo-heptitol (5), 2,5-imino-2,4,5,6-tetradeoxy-d-gulo-heptitol (6), 6-C-butyl-4-deoxy-DMDP (8), 6-C-(8-hydroxyoctyl)-DMDP (9), and 6-C-(8-hydroxyoctyl)-2,5-dideoxy-2,5-imino-d-galactitol (10), respectively, on the basis of spectroscopic data analysis (NMR and HRESIMS). Compounds 4-6 and 8 were characterized as rarely seen 4-deoxy pyrrolidine-type iminosugars. Pyrrolidine-type iminosugars with a long-side chain have been found in the restrictive plant families Moraceae, Campanulaceae, and Hyacinthaceae. The discovery of compounds 9 and 10 with a C8 side chain from S. glomerulata (Euphorbiaceae) expands the range of distribution for the iminosugars in plants. The 8-hydroxyoctyl side-chain represents a new addition for the molecular diversity of iminosugars. The compounds 1-10 were evaluated for inhibitory activity against rat intestinal α-glucosidase. However, all the test compounds showed no significant inhibitory activities to the glucosidase.
authors: Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, People's Republic of China; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
authors: Ren-Yi
authors: RY
authors: Yan
authors: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
authors: Hong-Qing
authors: HQ
authors: Wang
authors: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
authors: Jie
authors: J
authors: Kang
authors: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China. Electronic address: rych@imm.ac.cn.
authors: Ruo-Yun
authors: RY
authors: Chen
mesh_terms: D050111:Imino Sugars / Q000737:chemistry* / Q000302:isolation & purification*; D008968:Molecular Conformation; D018515:Plant Leaves / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D029843:Suregada / Q000737:chemistry*
chemical_list: D050111:Imino Sugars; D011759:Pyrrolidines; C032519:pyrrolidine
keywords: Euphorbiaceae; Iminosugar; Pyrrolidine; Suregada glomerulata