Two new diterpenes from the seeds of Caesalpinia minax Hance.
Molecules with diterpene skeletons often possess valuable medicinal properties. Two new diterpenes 1α,6α,7β-triacetoxy-5α-hydroxy-14β-ethyl-O-vouacapane (1) and 2α-acetoxy-14,15-cyclopimara-7β,16-diol (2) were isolated from the seeds of Caesalpinia minax Hance. Their structures were established on the basis of extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, 1D, and 2D NMR (HSQC, HMBC, NOESY) methods. The stereochemical structure of 1 was confirmed via the circular dichroism spectrum and calculated ECD experiment. The inhibitory activity of nitric oxide production of RAW264.7 macrophages stimulated by lipopolysaccharide of compounds 1 and 2 was evaluated, and compound 1 was found to show significant inhibitory effect.
a School of Biopharmaceutical and Chemical Engineering, Liaoning Institute of Science and Technology , Benxi 117004 , China.
Lian
L
Lian
b School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University , Shenyang 110016 , China.
Xiao-Bin
XB
Li
b School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University , Shenyang 110016 , China.
Jiu-Zhi
JZ
Yuan
b School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University , Shenyang 110016 , China.
Li
L
Cheng
b School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University , Shenyang 110016 , China.
Zhao-Hua
ZH
Wu
c Department of Pharmacology , Mudanjiang Medical College , Mudanjiang 157001 , China.
Hui-Yuan
HY
Gao
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029911:Caesalpinia / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D012639:Seeds / Q000737:chemistry
C000603698:1alpha,6alpha,7beta-triacetoxy-5alpha-hydroxy-14beta-ethyl-O-vouacapane; C000603699:2alpha-acetoxy-14,15-cyclopimara-7beta,16-diol; D000893:Anti-Inflammatory Agents; D004224:Diterpenes; D004365:Drugs, Chinese Herbal; D008070:Lipopolysaccharides; D009569:Nitric Oxide
Caesalpinia minax; anti-inflammation; circular dichroism; diterpenes