Lignans and Neolignans from Sinocalamus affinis and Their Absolute Configurations

• Published in: Journal of natural products (Washington, D.C.) Vol. 74; no. 5; pp. 1188 - 1200
• Main Authors: Xiong, Liang, Zhu, Chenggeng, Li, Yanru, Tian, Ye, Lin, Sheng, Yuan, Shaopeng, Hu, Jinfeng, Hou, Qi, Chen, Naihong, Yang, Yongchun, Shi, Jiangong
• Format: Journal Article
• Language: English
• Published: Northbrook, IL American Chemical Society and American Society of Pharmacognosy 27-05-2011; American Society of Pharmacognosy
• Subjects: Animals; Biological and medical sciences; Circular Dichroism; General pharmacology; Lignans - chemistry; Lignans - isolation & purification; Lignans - pharmacology; Macrophages, Peritoneal - drug effects; Medical sciences; Mice; Molecular Structure; PC12 Cells; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Stems - chemistry; Poaceae - chemistry; Rats; Asia; China; Monocotyledones; Rat; Adrenal glands; Leukocyte; Oxygen heterocycle; Stem; Medicinal plant; Folk medicine; Gramineae; Angiospermae; Lignan; Pharmacognosy; Rodentia; Tetracyclic compound; Aldehyde; In vitro; Biological activity; Vertebrata; Mammalia; Cell line; Neuron; Mouse; Animal; Nitric oxide; Absolute configuration; Plant origin; Phenols; Isolation; Spermatophyta; Structural analysis; Macrophage
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np200117y

Twenty-two new lignans and neolignans (1−22), together with 14 known analogues, have been isolated from an ethanolic extract of the stem (with skin removed) of Sinocalamus affinis. Their structures were elucidated by spectroscopic and chemical methods. On the basis of systematic NMR and circular dichroism (CD) data analysis, the validity of J 7,8 and ΔδC8−C7 values to distinguish threo and erythro aryl glycerol units in different neolignans and the CD data [particularly the Rh2(OCOCF3)4-induced CD data (the E band)] to determine the absolute configurations at C-8 (C-7) of the aryl glycerol units are discussed. At a concentration of 10 μM, compounds 20 and 22 inhibited NO production in mouse peritoneal macrophages 84.2 ± 5.9% and 71.7 ± 1.0%, respectively. Compounds 19, 20, and 22 showed activity against serum deprivation induced PC12 cell damage by increasing the cell viability from 80.7 ± 2.8% to 91.6 ± 6.4%, 107.2 ± 8.0%, and 97.6 ± 8.5%, respectively.