title: Chemical constituents from the linseed meal.
abstract: One megastigmane derivative 1, one methyl jasmonate glycoside derivative 2, and two C-28 steroids with 3β,5β-cis-dihydroxyl conformation 3 and 4, together with eight known compounds 5-12 were isolated from the 70% ethanol extract of linseed meal (Linum usitatissimum L). Structures of 1-4 were elucidated by spectroscopic methods including NMR, HRESIMS, and Mo2(OAc)4-induced CD. The absolute configuration of 1 and 3 was determined by observing their induced circular dichroism after addition of Mo2(OAc)4 in DMSO. The absolute configuration of 2 was determined by NOESY experiment together with conformational analysis. The structure of 4a was corrected as 4 by an extensive analysis of its 1D and 2D NMR, in combination with the Mo2(OAc)4-induced CD in DMSO. The effect of all the isolates on nitric oxide (NO) generation by stimulated macrophages was evaluated, and none of them showed active.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, and Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China.
authors.forename: Li
authors.initials: L
authors.lastname: Song
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, and Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China.
authors.forename: Xian-Fen
authors.initials: XF
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, and Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Wu
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, and Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China.
authors.forename: Wen-Yi
authors.initials: WY
authors.lastname: He
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, and Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China. Electronic address: yaocs@imm.ac.cn.
authors.forename: Chun-Suo
authors.initials: CS
authors.lastname: Yao
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, and Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China. Electronic address: shijg@imm.ac.cn.
authors.forename: Jian-Gong
authors.initials: JG
authors.lastname: Shi
mesh_terms: D000085:Acetates / Q000737:chemistry; D003512:Cyclohexanones / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D019597:Flax / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D015394:Molecular Structure; D045792:Norisoprenoids / Q000737:chemistry; D054883:Oxylipins / Q000737:chemistry; D010840:Phytosterols / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D000085:Acetates; D003512:Cyclohexanones; D003517:Cyclopentanes; D005960:Glucosides; D006027:Glycosides; D045792:Norisoprenoids; D054883:Oxylipins; D010840:Phytosterols; C413264:megastigmane; C072239:methyl jasmonate
keywords: Linaceae; Linseed meal; Linum usitatissimum L; Linustam