The ethanol extract of the rhizomes of Kaempferia marginata showed a potent inhibitory effect against lipopolysaccharide (LPS)-induced nitric oxide (NO) and tumor necrosis factor-alpha (TNF-α) release in RAW264.7 cells. Moreover, the partition with various organic solvents also inhibited NO production. One new pimarane-type diterpene, 1α-acetoxysandaracopimaradien-2α-ol (5), along with four known diterpenes (1–4), were isolated from the n-hexane and chloroform layers, respectively. Among these metabolites, compounds 1 and 4 were isolated for the first time from K. marginata. Compounds 1–5 showed significant inhibitory effects on NO production, with IC50 values ranging from 38.6 to 51.9 μM. Furthermore, compound 2 also exhibited significant activity against TNF-α release (IC50 = 48.3 μM). These findings may support the use of K. marginata by traditional doctors for treatment of inflammatory-related diseases.
(a) HeoS-J, YoonW-J, KimK-N, AhnG-N, KangS-M, KangD-H, AffanA., OhC., JungW-K, JeonY-J. (2010) Evaluation of anti-inflammatory effect of fucoxanthin isolated from brown algae in lipopolysaccharide-stimulated RAW 264.7 macrophages. Food and Chemical Toxicology, 48, 2045–2051;(b) Walsh NC, Crotti TN, Goldring SR, Gravallese EM. (2005) Rheumatic diseases: the effects of inflammation on bone. Immunological Reviews, 208, 228–251; (c) Lee HJ, Hyun E-A, Yoon WJ, Kim BH, Rhee MH, Kang HK, Cho JY, Yoo ES. (2006) In vitro anti-inflammatory and anti-oxidative effects of Cinnamomum camphora extracts. Journal of Ethnopharmacology, 103, 208–216.
2.
KonkimallaV.B., BlunderM., BauerR., EfferthT. (2010) Inhibition of inducible nitric oxide synthase by bis(helenalinyl)glutarate in RAW264.7 macrophages. Biochemical Pharmacology, 79, 1573–1580.
3.
MakhijaR., KingsnorthA.N. (2002) Cytokine storm in acute pancreatitis. Journal of Hepato Biliary Pancreatic Surgery, 9, 401–410.
4.
(a) RiojaI., TerencioM.C., UbedaA., RigueraR., QuintelaJ.M., AlcarazM.J. (2002) A new ditriazine inhibitor of NF-κB modulates chronic inflammation and angiogenesis. Naunyn-Schmiedeberg's Archives of Pharmacology, 365, 357–364;(b) Nakao S, Ogtata y, Shimizu E, Yamazaki M, Furuyama S, Sugiya S. (2002) Tumor necrosis factor α (TNF-α)-induced prostaglandin E2 release is mediated by the activation of cyclooxygenase-2 (COX-2) transcription via NFκB in human gingival fibroblasts. Molecular and Cellular Biochemistry, 238, 11–18.
5.
ChoY-C, KimH.J., KimY-J, LeeK.Y., ChoiH.J., LeeI-S, KangB.Y. (2008) Differential anti-inflammatory pathway by xanthohumol in IFN-y and LPS-activated macrophages. International Immunopharmacology, 8, 567–573.
6.
TechaprasanT., KlinbungaS., NgamriabsakulC., JenjittikulT. (2010) Genetic variation of Kaempferia (Zingiberaceae) in Thailand based on chloroplast DNA (psbA-trnH and petA-psbJ) sequences. Genetics and Molecular Research, 9, 1957–1973.
7.
JenjittikulT., LarsenK. (2000) Kaempferia candida Wall. (Zingiberaceae), a new record for Thailand. Thai Forest Bulletin, 28, 45–49.
8.
PicheansoonthonC., KoontermS. (2009) A new species of Kaempferia L. (Zingiberaceae) from northeastern Thailand. Taiwania, 54, 52–56.
9.
(a) ThongnestS., MahidolC., SutthivaiyakitS., RuchirawatS. (2005) Oxygenated pimarane diterpenes from Kaempferia marginata. Journal of Natural Products, 68, 1632–1636;(b) Hooker JD (1894). Flora of British India. William Clowes and Sons, Limited, London and Beccles, UK. 6, 219.
10.
(a) TouchE.M.G., LopezE.G., ReyesP.A., SanchezH., HoneckerF., AchenbachH. (1997) Parryin, a diterpenes with a tricyclic 6–7–5-ring system from Salvia parryi. Phytochemistry, 45, 387–390;(b) Nagashima F, Murakami M, Takaoka S, Asakawa Y. (2003) ent-Isopimarane-type diterpenoids from the New Zealand liverwort Trichocolea mollissima. Phytochemistry, 64, 1319–1325.
11.
PintoA.C., SilvaA.J.R., MayerL.M.U., BrazF.R. (1979) Compactone, a new diterpenoid from Vellozia compacta. Phytochemistry, 18, 2036–2037.
12.
(a) ChangC.I., TsengM.H., KuoY.H. (2005) Five new diterpenoids from the bark of Taiwania cryptomerioides. Chemical and Pharmaceutical Bulletin, 53, 286–289;(b) Tuchinda P, Udchachon J, Reutrakul V, Santisuk T, Skelton BW, White AH, Taylor WC. (1994) Pimarane diterpenes from Kaempferia pulchra. Phytochemistry, 36, 731–734; (c) Pongprayoon U, Sematong T, Tuchinda P, Claeson P, Reutrakul V, Nahar N. (1996) Topical antiinflammatory activity of two pimarane diterpenes from Kaempferia pulchra. Phytotherapy Research, 10, 534–535.
13.
TewtrakulS., TansakulP., PanichayupakaranantP. (2009) Effects of rhinacanthins from Rhinacanthus nasutus on nitric oxide, prostaglandin E2 and tumor necrosis factor-alpha releases using RAW264.7 macrophage cells. Phytomedicine, 16, 581–585.
14.
BruceR.D. (1985) An up-and-down procedure for acute toxicity testing. Fundamental and Applied Toxicology, 5, 151–157.
