ent-Abietane diterpenoids with anti-neuroinflammatory activity from the rare Chloranthaceae plant Chloranthus oldhamii.
Twelve new ent-abietane diterpenoids, chlorabietins A-L (), were isolated from the roots of Chloranthus oldhamii. Their structures and absolute configurations were determined by extensive spectroscopic analyses, X-ray diffraction, and experimental/calculated electronic circular dichroism (ECD) spectroscopy. Among the new isolates, chlorabietins D () and E () are the first two naturally occurring 8-spiro-fused 9,10-seco-ent-abietanes containing an unexpected cis-fused A/B ring system. Chlorabietin F () is a rare chinane-type diterpenoid featuring a hitherto unknown C-ring cleavage between C-13 and C-14, which might be derived from a common precursor of the above spiro-diterpenoid epimers and , and their biosynthetic relationships are briefly discussed. Meanwhile, chlorabietin I () is the first representative of the abietane-type diterpenoids possessing a tetrahydrofurano function bridging C-6 and C-19. Chlorabietins B (), C (), F (), and G () showed anti-neuroinflammatory effects by inhibiting the nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine BV-2 microglial cells, with IC50 values ranging from 16.4 to 33.8 μM.
Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, PR China. jfhu@fudan.edu.cn.
Juan
J
Xiong
Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, PR China. jfhu@fudan.edu.cn.
Zhi-Lai
ZL
Hong
Department of Pharmacology, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, PR China.
Peng
P
Xu
Department of Chemistry, University of Pennsylvania, 231 S. 34 Street, Philadelphia, PA 19104-6323, USA.
Yike
Y
Zou
Department of Chemistry, Fudan University, No. 220 Handan Road, Shanghai 200433, PR China.
Shang-Bo
SB
Yu
Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, PR China. jfhu@fudan.edu.cn.
Guo-Xun
GX
Yang
Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, PR China. jfhu@fudan.edu.cn.
Jin-Feng
JF
Hu
D045784:Abietanes / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D019684:Magnoliopsida / Q000737:chemistry*; D051379:Mice; D017628:Microglia / Q000187:drug effects* / Q000378:metabolism; D008958:Models, Molecular; D008968:Molecular Conformation; D009569:Nitric Oxide / Q000096:biosynthesis; D018517:Plant Roots / Q000737:chemistry
D045784:Abietanes; D000893:Anti-Inflammatory Agents; D009569:Nitric Oxide