Constituents of the twigs of Hernandia ovigera that inhibit the transformation of JB6 murine epidermal cells.
Activity-guided fractionation of an ethyl acetate extract of the twigs of Hernandia ovigera, using a soft agar assay with JB6 murine epidermal cells, led to the isolation of two new naturally occurring aryltetralin lignans, (7R,8S,7'R,8'R)-(+)-7'-acetyl-5'-methoxypicropodophyllin (1) and (7R,8S,7'R,8'R)-(+)-7'-acetylpicropodophyllin (2), of which 2 was previously identified as a synthetic product, along with eight known compounds, epiyangambin (3), caruilignan C, diasesartemin, (+)-epimagnolin A, N-methylcorydaldine, (-)-5'-methoxyyatein, (+)-syringaresinol dimethyl ether, and (-)-yatein. The structures and stereochemistry of 1 and 2 were determined using spectroscopic methods. Compounds 2 and 3 exhibited significant inhibition of the transformation of murine epidermal JB6 cells, with IC50 values of 0.15 and 0.4 microg/mL, respectively, while the other isolates were regarded as inactive (IC50 >4 microg/mL).
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, Illinois 60612, USA.
Jian-Qiao
JQ
Gu
Eun Jung
EJ
Park
Stephen
S
Totura
Soedarsono
S
Riswan
Harry H S
HH
Fong
John M
JM
Pezzuto
A Douglas
AD
Kinghorn
D000818:Animals; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002478:Cells, Cultured / Q000187:drug effects; D004817:Epidermis / Q000187:drug effects; D007214:Indonesia; D020128:Inhibitory Concentration 50; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C465910:7'-acetyl-5'-methoxypicropodophyllin; C465911:7'-acetylpicropodophyllin; D016588:Anticarcinogenic Agents; D017705:Lignans