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DOI: 10.1055/s-0029-1240800
© Georg Thieme Verlag KG Stuttgart · New York
Blumeaenes A–J, Sesquiterpenoid Esters from Blumea balsamifera with NO Inhibitory Activity
Publication History
received Sept. 29, 2009
revised Dec. 14, 2009
accepted Dec. 18, 2009
Publication Date:
25 January 2010 (online)

Abstract
Chemical examination of the ethanol extract of the aerial parts of Blumea balsamifera led to the isolation of ten new sesquiterpenoid esters, blumeaenes A–J (1–10), with 13 known flavonoids. Their structures were determined mainly by use of 1D and 2D NMR spectroscopic techniques. All sesquiterpenoid esters were tested for their inhibitory activity against LPS-induced NO production in RAW264.7 macrophages. Compounds 1, 4 and 5 showed slight inhibitory effect on the production of NO with IC50 values of 40.06, 46.35 and 57.80 µg/mL, respectively.
Key words
Blumea balsamifera - Asteraceae - sesquiterpenoid esters - blumeaenes - NO production
References
- 1 Perry L M. Medicinal plants of East and Southeast Asia. Cambridge, MA; Harvard University 1980: 87
- 2 Burkill I H. A Dictionary of the economic products of the Malay peninsula, vol. 1. Kuala Lumpur; Ministry of Agriculture and Cooperatives 1966: 337
- 3 Osaki N, Koyano T, Kowithayakorn T, Hayashi M, Komiyama K, Ishibashi M. Sesquiterpenoids and plasmin-inhibitory flavonoids from Blumea balsamifera. J Nat Prod. 2005; 68 447-449
- 4 Ragasa C Y, Co A L, Rideout J A. Antifungal metabolites from Blumea balsamifera. Nat Prod Res. 2005; 19 231-237
- 5 Xu S B, Chen W F, Liang H Q, Lin Y C, Deng Y J, Long K H. Protective action of blumeatin against experimental liver injuries. Zhongguo Yao Li Xue Bao (Acta Pharmacol Sin). 1993; 14 376-378
- 6 Norikura T, Kojima-Yuasa A, Shimizu M, Huang X, Xu S, Kametani S, Rho S N, Kennedy A O, Matsui-Yuasa I. Mechanism of growth inhibitory effects of Blumea balsamifera extract in hepatocellular carcinoma. Biosci Biotechnol Biochem. 2008; 72 1183-1189
- 7 Norikura T, Kojima-Yuasa A, Shimizu M, Huang X, Xu S, Kametani S, Rho S N, Kennedy D O, Matsui-Yuasa I. Anticancer activities and mechanisms of Blumea balsamifera extract in hepatocellular carcinoma cells. Am J Chin Med. 2008; 36 411-424
- 8 Barua N C, Sharma R P. (2R,3R)-7,5′-Dimethoxy-3,5,2′-trihydroxyflavanone from Blumea balsamifera. Phytochemistry. 1992; 31 4040-4044
- 9 Ali D M, Wong K C, Lim P K. Flavonoids from Blumea balsamifera. Fitoterapia. 2005; 76 128-130
- 10 Chen M, Jin H Z, Zhang W D, Yan S K, Shen Y H. Chemical constituents of plants from genus Blumea. Chem Biodivers. 2009; 6 809-817
- 11 Radomski M W, Palmer R M J, Moncada S. The role of nitric oxide and cGMP in platelet adhesion to vascular endothelium. Biochem Biophys Res Commun. 1987; 148 1482-1489
- 12 Moncada S, Palmer R M J, Higgs E A. Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol Rev. 1991; 43 109-142
- 13 Chen Y C, Lin-Shiau S Y, Lin J K. Involvement of reactive oxygen species and caspase 3 activation in arsenite induce apoptosis. J Cell Physiol. 1998; 177 323-324
- 14 Schmidt H H H W, Kelm M. Methods in nitric oxide research, chapter 33. London; John Wiley & Sons, Ltd. 1996: 491-497
- 15 Cao J Q, Dang Q, Fu H W, Yao Y, Pei Y H. Isolation and identification of chemical constituents from Blumea riparia DC. J Shenyang Pharm Univ. 2007; 24 615-618
- 16 Dai H F, Mei W L, Wu J, Li X M, Wang B G. Studies on chemical constituents of Mangrove plant Scyphiphora hydrophyllacea. Chin Pharm J. 2006; 41 1452-1454
- 17 Vidavalur S, Chunduri V R, Somepalli V. A concise synthesis of polyhydroxydihydrochalcones and homoisoflavonoids. Tetrahedron. 2006; 62 841-846
- 18 Zhang J, Kong L Y. Flavonoids constituents in leaves of Artemisia selengensis. Zhongcaoyao. 2008; 39 23-26
- 19 Kumar N, Singh B, Kaul V K. Flavonoids from Rosa damascene Mill. Nat Prod Commun. 2006; 1 623-626
- 20 Shi G R, Li D M, Liu G M. Studies on the chemical constituents of Rodgersia sambucifolia. J Dali Univ. 2008; 7 1-2
- 21 Nessa F, Ismail Z, Mohamed N, Haris M R H M. Free radical-scavenging activity of organic extracts and of pure flavonoids of Blumea balsamifera DC leaves. Food Chem. 2004; 88 243-252
- 22 Zheng D, Zhang X Q, Wang Y, Ye W C. Chemical constituents of the aerial parts of Blumea riparia. Chin J Nat Med. 2007; 5 421-424
- 23 Marco J A, Sanz-Cervera J F, Yuste A. Ingenane and lathyrane diterpenes from the latex of Euphorbia canariensis. Phytochemistry. 1997; 45 563-570
- 24 Denizot F, Lang R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Methods. 1986; 89 271-277
Dr. Hui Zi
Jin
Dr. Wei Dong
Zhang
School of Pharmacy
Shanghai Jiao Tong University
Shanghai Dongchuan Rd 800
200240 Shanghai
People's Republic of China
Phone: + 86 21 34 20 59 89
Fax: + 86 21 34 20 59 89
Email: kimhz@sjtu.edu.cn
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