TY - JOUR
T1 - Di- and sesqui-terpenoids isolated from the pods of Sindora sumatrana and their potential to inhibit lipopolysaccharide-induced nitric oxide production
AU - Dae, Sik Jang
AU - Min, Hye Young
AU - Jeong, Yeon Hee
AU - Sang, Kook Lee
AU - Seo, Eun Kyoung
N1 - Funding Information:
This investigation was supported by a grant of the Korea Health 21 R&D project, Ministry of Health & Welfare, Republic of Korea (01-PJ2-PG6-01NA01-0002). We are grateful to Prof. Tri Windono and Dr. Gwang-Ho Jeohn at Surabaya University, Surabaya, Indonesia for plant collection.
PY - 2004/3/31
Y1 - 2004/3/31
N2 - Activity-guided fractionation of the n-hexane and CHCl3-soluble fractions of Sindora sumatrana using a bioassay based on the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production by inducible nitric oxide synthase (iNOS) in murine macrophage RAW 264.7 cells led to the isolation of the known compound, (+)-7β-acetoxy-15,16-epoxy-3,13(16),14- clerodatriene-18-oic acid (2) as an active constituent. In addition, a new trans-clerodane diterpenoid, (+)-2-oxokolavenic acid (1), together with six known compounds, (+)-3,13-clerodadiene-16,15-olide-18-oic acid (3), (+)-7β-acetoxy-3,13-clerodadiene-16,15-olide-18-oic acid (4), (+)-7β-acetoxy-16-hydroxy-3,13-clerodadiene-16,15-olide-18-oic acid (5), β-caryophyllene oxide (6), clovane-2β,9β-diol (7), and caryolane-1,9β-diol (8) were isolated and found to be inactive. The structure of compound 1 was determined using physical and spectroscopic methods such as 1D and 2D-NMR experiments. The known compounds 2-8 were identified by the spectroscopic data and by comparison with the published values. Of eight isolates (1-8), only compound 2 exhibited an iNOS inhibitory activity with IC50 value of 51.6 μM.
AB - Activity-guided fractionation of the n-hexane and CHCl3-soluble fractions of Sindora sumatrana using a bioassay based on the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production by inducible nitric oxide synthase (iNOS) in murine macrophage RAW 264.7 cells led to the isolation of the known compound, (+)-7β-acetoxy-15,16-epoxy-3,13(16),14- clerodatriene-18-oic acid (2) as an active constituent. In addition, a new trans-clerodane diterpenoid, (+)-2-oxokolavenic acid (1), together with six known compounds, (+)-3,13-clerodadiene-16,15-olide-18-oic acid (3), (+)-7β-acetoxy-3,13-clerodadiene-16,15-olide-18-oic acid (4), (+)-7β-acetoxy-16-hydroxy-3,13-clerodadiene-16,15-olide-18-oic acid (5), β-caryophyllene oxide (6), clovane-2β,9β-diol (7), and caryolane-1,9β-diol (8) were isolated and found to be inactive. The structure of compound 1 was determined using physical and spectroscopic methods such as 1D and 2D-NMR experiments. The known compounds 2-8 were identified by the spectroscopic data and by comparison with the published values. Of eight isolates (1-8), only compound 2 exhibited an iNOS inhibitory activity with IC50 value of 51.6 μM.
KW - Diterpenoids
KW - Leguminosae
KW - Nitric oxide synthase
KW - Sesquiterpenoids, (+)-2-Oxokolavenic acid
KW - Sindora sumatrana
UR - http://www.scopus.com/inward/record.url?scp=7044260755&partnerID=8YFLogxK
U2 - 10.1007/BF02980062
DO - 10.1007/BF02980062
M3 - Article
C2 - 15089033
AN - SCOPUS:7044260755
SN - 0253-6269
VL - 27
SP - 291
EP - 294
JO - Archives of Pharmacal Research
JF - Archives of Pharmacal Research
IS - 3
ER -