Anti-inflammatory activity of compounds from Boesenbergia longiflora rhizomes.
BACKGROUND
The rhizomes of Boesenbergia longiflora (Wall.) Kuntze have been traditionally used in treatment of inflammatory bowel disease, ulcerative colitis, aphthous ulcer and abscess. Our previous study indicated that CHCl3 fractions of Boesenbergia longiflora had potential on anti-inflammatory properties. In the present study, we investigated the active constituents of this plant for anti-inflammatory activity in order to support its traditional use.


METHODS
The CHCl3 fraction was isolated using chromatographic techniques. Isolated compounds were tested using relevant in vitro anti-inflammatory assays against LPS-induced NO and TNF-α releases as well as their mechanisms in transcription levels in murine macrophage RAW264.7 cells.


RESULTS
The isolation of the CHCl3 fraction from Boesenbergia longiflora rhizomes led to the isolation of three new daucane sesquiterpenes, which were identified as 8-hydroxy-dauca-9, 11-diene-7-one (longiferone A; 1), dauca-8, 11-diene-7-one (longiferone B; 2) and dauca-8, 11-diene-7, 10-dione (longiferone C; 3); together with four known flavonoids, six known diarylheptanoids as well as one sterol. The longiferone B (2) and longiferone C (3) showed anti-inflammatory activity against NO release with IC50 values of 21.0 and 31.3µM, respectively. Longiferone B (2) also suppressed the iNOS and COX-2 mRNA expression. Moreover, the flavonoids and diarylheptanoids inhibited NO and TNF-α production in a dose dependent manner.


CONCLUSIONS
This study demonstrated that sesquiterpenes, diarylheptanoids and some methoxyflavonoids found in Boesenbergia longiflora are responsible for anti-inflammatory activity.
Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand; Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand; Faculty of Oriental Medicine, Rangsit University, Patumthani 12000, Thailand.
Teeratad
T
Sudsai
Department of Chemistry and Center for Excellence in Protein Structure and Function, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
Samran
S
Prabpai
Department of Chemistry and Center for Excellence in Protein Structure and Function, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
Palangpon
P
Kongsaeree
Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand.
Chatchai
C
Wattanapiromsakul
Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand; Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand. Electronic address: supinyat@yahoo.com.
Supinya
S
Tewtrakul
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use / Q000633:toxicity; D018929:Cell Culture Techniques; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D051546:Cyclooxygenase 2 / Q000096:biosynthesis; D004487:Edema / Q000188:drug therapy; D020834:Ethnopharmacology; D008264:Macrophages / Q000187:drug effects / Q000201:enzymology / Q000276:immunology; D008297:Male; D051379:Mice; D015394:Molecular Structure; D052247:Nitric Oxide Synthase Type II / Q000096:biosynthesis; D010936:Plant Extracts / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use / Q000633:toxicity; D017208:Rats, Wistar; D027343:Rhizome / Q000737:chemistry*; D014409:Tumor Necrosis Factor-alpha / Q000096:biosynthesis; D030521:Zingiberaceae / Q000737:chemistry*
D000894:Anti-Inflammatory Agents, Non-Steroidal; D010936:Plant Extracts; D014409:Tumor Necrosis Factor-alpha; D052247:Nitric Oxide Synthase Type II; C496317:Nos2 protein, mouse; C077623:Ptgs2 protein, mouse; D051546:Cyclooxygenase 2
Anti-inflammatory activity; Boesenbergia longiflora; Daucane sesquiterpenes; Diarylheptanoids; Flavonoids