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Natural Product Research
Formerly Natural Product Letters
Volume 31, 2017 - Issue 5
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Research Article

Sesquiterpenes from Curcuma wenyujin with their inhibitory activities on nitric oxide production in RAW 264.7 cells

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Pages 548-554 | Received 21 Mar 2016, Accepted 02 Jun 2016, Published online: 19 Jul 2016

References

  • Claeson P, Pongprayoon U, Sematong T, Tuchinda P, Reutrakul V, Soontornsaratune P, Taylor W. 1996. Non-phenolic linear diarylheptanoids from Curcuma xanthorrhiza: a novel type of topical anti-inflammatory agents: structure–activity relationship. Planta Med. 62:236–240.10.1055/s-2006-957867
  • Committee of National Pharmacopoeia. 2015. Pharmacopoeia of P. R. China. Beijing: Chemical Industry Press.
  • Dirsch V., Stuppner H., Vollmar A. 1998. The Griess assay: suitable for a bio-guided fractionation of anti-inflammatory plant extracts?. Planta Med, 64:423–426.
  • Friedrich D., Bohlmann F. 1988. Total synthesis of various elemanolides. Tetrahedron. 44:1369–1392.
  • Firman K., Kinoshita T., Itai A., Sankawa U. 1988. Terpenoids from Curcuma heyneana. Phytochemistry. 27:3887–3891.
  • Frelek J, Szczepek WJ. 1999. [Rh2(OCOCF3)4] as an auxiliary chromophore in chiroptical studies on steroidal alcohols. Tetrahedron: Asymmetry. 10:1507–1520.10.1016/S0957-4166(99)00115-9
  • Gao J, Tamiko O, Kenzo H, Manabu H, Takeshi K, Wu X, Yoichi I, Seiichi I. 1986. The absolute configuration of curcumalactone. Chem Pharm Bull. 34:5122–5132.
  • Gerards M, Snatzke G, Circular dichroism. 1990. XCIII determination of the absolute configuration of alcohols, olefins, epoxides, and ethers rom the CD of their “in situ” complexes with [Rh2(O2CCF3)4]. Tetrahedron: Asymmetry. 1:221–236.10.1016/S0957-4166(00)86328-4
  • Hikino H, Meguro K, Sakurai Y, Takemoto T. 1966. Structure of curcumol. Chem Pharm Bull. 14:1241–1249.10.1248/cpb.14.1241
  • Inayama S, Gao J, Harimaya K, Hikichi M, Iitaka Y, Guo Y, Kawamata T. 1985. The absolute configuration of curdione and the stereostructure of curcumalactone from Curcuma wenyujin. Chem Pharm Bull. 33:2179–2182.10.1248/cpb.33.2179
  • Ishii T, Matsuura H, Kaya K, Vairappan C. 2011. A new bisabolane-type sesquiterpenoid from Curcuma domestica. Biochem Syst Ecol. 39:864–867.10.1016/j.bse.2011.05.011
  • Kuroyanagi M, Ueno A, ujiie K, Sato S. 1987. Structures of sesquiterpenes from Curcuma aromatica salisb. Chem Pharm Bull. 35:53–59.10.1248/cpb.35.53
  • Li J, Zhao F, Li M, Chen L, Qiu F. 2010. Diarylheptanoids from the Rhizomes of Curcuma kwangsiensis. J Nat Prod. 73:1667–1671.10.1021/np100392m
  • Li J, Liao C, Wei J, Chen L, Zhao F, Qiu F. 2011. Diarylheptanoids from Curcuma kwangsiensis and their inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages. Bioorg Med Chem Lett. 21:5363–5369.10.1016/j.bmcl.2011.07.012
  • Lim C, Ky N, Ng H, Hamza M, Zhao Y. 2010. Curcuma wenyujin extract induces apoptosis and inhibits proliferation of human cervical cancer cells in vitro and in vivo. Integr Cancer Ther. 9:36–49.10.1177/1534735409359773
  • Lin X, Ji S, Li R, Dong Y, Qiao X, Hu H, Yang W, Guo D, Tu P, Ye M. 2012. Terpecurcumins A–I from the rhizomes of Curcuma longa: absolute configuration and cytotoxic activity. J Nat Prod. 75:2121–2131.10.1021/np300551g
  • Liu Y, Ma J, Zhao Q, Liao C, Ding L, Chen L, Zhao F, Qiu F. 2013. Guaiane-type sesquiterpenes from Curcuma phaeocaulis and their inhibitory effects on nitric oxide production. J Nat Prod. 76:1150–1156.10.1021/np400202f
  • Liu Y, Ma J, Wang Y, Donkor P, Li Q, Gao S, Hou Y, Xu Y, Cui J, Ding L, et al. 2014. Eudesmane-type sesquiterpenes from Curcuma phaeocaulis and their inhibitory activities on nitric oxide production in RAW 264.7 Cells. Eur J Org Chem. 2014:5540–5548.10.1002/ejoc.v2014.25
  • Lou Y, Zhao F, He H, Peng K, Zhou X, Chen L, Qiu F. 2009. Guaiane-type sesquiterpenes from Curcuma wenyujin and their inhibitory effects on nitric oxide production. J Asian Nat Prod Res. 11:737–747.10.1080/10286020903042358
  • Lou Y, Zhao F, He H, Peng K, Chen L, Qiu F. 2010. Four new sesquiterpenes from Curcuma wenyujin and their inhibitory effects on nitric-oxide production. Chem Biodivers. 7:1245–1253.10.1002/cbdv.v7:5
  • Ma J, Zhao F, Wang Y, Liu Y, Gao S, Ding L, Chen L, Qiu F. 2015. Natural nitric oxide (NO) inhibitors from the rhizomes of Curcuma phaeocaulis. Org Biomol Chem. 13:8349–8358.10.1039/C5OB00964B
  • Matsuda H, Morikawa T, Toguchida I, Ninomiya K, Yoshikawa M. 2001. Medicinal foodstuffs. XXVIII. Inhibitors of nitric oxide production and new sesquiterpenes, zedoarofuran, 4-epicurcumenol, neocurcumenol, gajutsulactones A and B, and zedoarolides A and B, from Zedoariae rhizoma. Chem Pharm Bull. 49:1558–1566.10.1248/cpb.49.1558
  • Matsuda H, Morikawa T, Ninomiya K, Yoshikawa M. 2001. Absolute stereostructure of carabrane-type sesquiterpene and vasorelaxant-active sesquiterpenes from Zedoariae Rhizoma. Tetrahedron. 57:8443–8453.10.1016/S0040-4020(01)00828-6
  • Motterlini R, Foresti R, Bassi R, Green C. 2000. Curcumin, an antioxidant and anti-inflammatory agent, induces heme oxygenase-1 and protects endothelial cells against oxidative stress. Free Radical Bio Med. 28:1303–1312.10.1016/S0891-5849(00)00294-X
  • Ohshiro M, Kuroyanagi M, Ueno Akira. 1990. Structures of sesquiterpenes from Curcuma longa. Phytochemistry. 29:2201–2205.10.1016/0031-9422(90)83038-3
  • Parker W, Roberts JS. 1967. Sesquiterpene biogenesis. Q Rev Chem Soc. 21:331–363.10.1039/qr9672100331
  • Rameshkumar KB, Alan Sheeja DB, Nair MS, George V. 2015. Curcuma ecalcarata – new natural source of pinocembrin and piperitenone. Nat Prod Res. 29:1276–1279.
  • Satyavama D, Warjeet S. 2014. A new guaianolide sesquiterpene lactone from Curcuma leucorrhiza Roxb. Nat Pro Res. 28:477–482.10.1039/qr9672100331
  • Sasaki Y, Goto H, Tohda C, Hatanaka F, Shibahara N, Shimada Y, Terasawa K, Komatsu K. 2003. Effects of Curcuma drugs on vasomotion in isolated rat aorta. Biol Pharm Bull. 26:1135–1143.10.1248/bpb.26.1135
  • Sodsai A, Piyachaturawat P, Sophasan S, Suksamrarn A, Vongsakul M. 2007. Suppression by Curcuma comosa Roxb. of pro-inflammatory cytokine secretion in phorbol-12-myristate-13-acetate stimulated human mononuclear cells. Int Immunopharmacol. 7:524–531.10.1016/j.intimp.2006.12.013
  • Song E, Cho H, Kim J, Kim N, An N, Kim J, Lee S, Kim Y. 2001. Diarylheptanoids with free radical scavenging and hepatoprotective activity in vitro from Curcuma longa. Planta Med. 67:876–877.10.1055/s-2001-18860
  • Srinivasan KR. 1953. A chromatographic study of the curcuminoids in Curcuma longa, L. J Pharm Pharmacol. 5:448–457.10.1111/jphp.1953.5.issue-1
  • Sukari M, Saad S, Lajis N, Ranmani M, Muse R, Yusuf U, Riyanto S. 2007. Chemical constituents and bioactivity of Curcuma aeruginosa Roxb. Nat Prod Sci. 6:175–179.
  • Syu W, Shen C, Don M, Ou J, Lee G, Sun C. 1998. Cytotoxicity of curcuminoids and some novel compounds from Curcuma zedoaria. J Nat Prod. 61:1531–1534.10.1021/np980269k
  • Takano I, Yasuda I, Takeya K, Itokawa H. 1995. Guaiane sesquiterpene lactones from Curcuma aeruginosa. Phytochemistry. 40:1197–1200.10.1016/0031-9422(95)00425-7
  • Tang D, Hao Y, Liu Z, Miao S, Wei H, Wu J. 1984. The constituents of the essential oil from rhizome of Atractylodes macrocephala produced in Pingjiang and their antitumor effect. Chin Pharm Bull. 19:555–558.
  • Wu L. 1989. The application of ORD and CD spectroscopy in organic chemistry. Shenyang Yao Ke Da Xue Xue Bao. 2:148–153.
  • Wu H, Zheng H, Xu Y, Zhang P, Chen G, Zhu Y. 2014. Two New Sesquiterpenes from a Kind of TCM Pieces. Curcumae Radix Rec Nat Prod. 8:334–341.
  • Xia G, Zhou L, Ma J, Wang Y, Ding L, Zhao F, Chen L, Qiu F. 2015. Sesquiterpenes from the essential oil of Curcuma wenyujin and their inhibitory effects on nitric oxide production. Fitoterapia. 103:143–148.10.1016/j.fitote.2015.03.021
  • Zeng Y, Qiu F, Takahashi K, Liang J, Qu G, Yao X. 2007. New sesquiterpenes and calebin derivatives from Curcuma longa. Chem Pharm Bull. 55:940–943.10.1248/cpb.55.940

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