Cytotoxic and antioxidant dihydrobenzofuran neolignans from the seeds of Crataegus pinnatifida.
Eight new dihydrobenzofuran neolignans, pinnatifidanin C I-VIII (1-8), together with two known analogs (9-10) were isolated from the seeds of Crataegus pinnatifida. Their structures were elucidated by spectroscopic analyses, especially 1D, 2D NMR and CD spectra. The cytotoxic activities of all isolates against human cancer cell lines were assayed, and most interestingly, compound 10 revealed preferred cytotoxicity on the HT-1080 cell line and displayed much stronger inhibitory activity (IC50=8.86 μM) compared with positive control 5-fluorouracil (IC50=35.62 μM). Meanwhile, antioxidant activities of all the isolates were evaluated using 2,2-diphenyl-1-pikrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) assays, and the results showed that most of the isolates exhibited potent antioxidant activity.
Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang 110016, PR 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, PR China; Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
Xiao-Xiao
XX
Huang
Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
Chen-Chen
CC
Zhou
Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang 110016, PR 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, PR China; Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
Ling-Zhi
LZ
Li
School of Pharmacy, Shenyang Pharmaceutical University, PR China.
Ying
Y
Peng
Harbin Pharmaceutical Group Co., LTD General Pharmaceutical Factory, Harbin 150046, PR China.
Li-Li
LL
Lou
Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
Sen
S
Liu
Harbin Pharmaceutical Group Co., LTD Second Chinese Medicine Factory, Harbin 150078, PR China.
Dian-Ming
DM
Li
China-Japan Research Institute of Medical Pharmaceutical Sciences, Shenyang Pharmaceutical University, PR China.
Takshi
T
Ikejima
Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang 110016, PR 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, PR China; Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China. Electronic address: songsj99@163.com.
Shao-Jiang
SJ
Song
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D052160:Benzothiazoles / Q000378:metabolism; D001713:Biphenyl Compounds / Q000378:metabolism; D045744:Cell Line, Tumor; D027825:Crataegus / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy*; D008517:Phytotherapy; D010851:Picrates / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D012639:Seeds / Q000737:chemistry; D013451:Sulfonic Acids / Q000378:metabolism
D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D001572:Benzofurans; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D017705:Lignans; D010851:Picrates; D010936:Plant Extracts; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C004931:1,1-diphenyl-2-picrylhydrazyl
Antioxidant activities; Crataegus pinnatifida; Cytotoxicities; Dihydrobenzofuran neolignans