Planta Medica, Inhaltsverzeichnis Planta Med 2017; 83(03/04): 217-223DOI: 10.1055/s-0042-111440 Biological and Pharmacological Activity Original Papers Georg Thieme Verlag KG Stuttgart · New York Guaiane-Type Sesquiterpenoids from Fissistigma oldhamii Inhibit the Proliferation of Synoviocytes Xue-Ming Zhou 1 Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou, P. R. China , Cai-Juan Zheng 1 Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou, P. R. China , Yu-Qin Zhang 2 Fujian University of Traditional Chinese Medicine College Of Pharmacy, Fuzhou, Fujian, P. R. China , Xiao-Peng Zhang 1 Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou, P. R. China , Xiao-Ping Song 1 Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou, P. R. China , Wei Xu 2 Fujian University of Traditional Chinese Medicine College Of Pharmacy, Fuzhou, Fujian, P. R. China , Guang-Ying Chen 1 Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou, P. R. China › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Abstract Three guaiane-type sesquiterpenoids, dysodensiols G–I (1–3), together with five known sesquiterpenoids (4–8) were isolated from the stems of Fissistigma oldhamii (Hemsl.) Merr. Compound 1 represents the first example of an ene(6 → 5)-abeo-14-norguaiane sesquiterpenoid derived from natural products. Their structures were elucidated by a combination of 1D and 2D NMR and MS spectra. The absolute configuration of 2 was determined by an X-ray crystallographic analysis. The inhibitory effect of all compounds on the proliferation of primary synovial cells was evaluated. Compound 3 showed a potent inhibitory effect on the proliferation of synoviocytes with an IC50 value of 1.0 µM. Key words Key wordsAnnonaceae - Fissistigma oldhamii (Hemsl.) Merr - guaiane-type sesquiterpenoids - norisoprenoid - synoviocytes Volltext Referenzen References 1 Kuo RY, Chang FR, Wu YC. Chemical constituents and their pharmacological activities from Formosan Amnonaceous plants. Chin Pharm J 2002; 54: 155-173 2 SFDA. Chinese Herbal Medicine, Vol. 3. Shanghai: Shanghai Science and Technology Publishing Co.; 1997: 1594-1595 3 Zhang YN, Zhong XG, Zheng ZP, Hu XD, Zuo JP, Hu LH. Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr. Bioorg Med Chem 2007; 15: 988-996 4 Hu XD, Zhong XG, Zhang XH, Zhang YN, Zheng ZP, Zhou Y, Tang W, Yang Y, Yang YF, Hu LH, Zuo JP. 7′-(3′,4′-dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (Z23), an effective compound from the Chinese herb medicine Fissistigma oldhamii (Hemsl.) Merr, suppresses T cell-mediated immunity in vitro and in vivo . Life Sci 2007; 81: 1677-1684 5 Wicks I, McColl G, Harrison L. New perspectives on rheumatoid arthritis. Immunol Today 1994; 15: 533-556 6 Hasler P, Zouali M. B cell receptor signaling and autoimmunity. FASEB J 2001; 5: 2085-2098 7 Firestein GS, Zvaifler NJ. How important are T cells in chronic rheumatoid synovitis?: II. T cell-independent mechanisms from beginning to end. Arthritis Rheum 2002; 46: 298-308 8 Shevach EM. Regulatory/suppressor T cells in health and disease. Arthritis Rheum 2004; 50: 2721-2724 9 Wu JB, Cheng YD, Chiu NY, Huang SC, Kuo SC. A Novel Morphinandienone Alkaloid from Fissistigma oldhamii . Planta Med 1993; 59: 179-180 10 Chia YC, Chang FR, Teng CM, Wu YC. Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii . J Nat Prod 2000; 63: 1160-1163 11 Ge YW, Zhu S, Shang MY, Zang XY, Wang X, Bai YJ, Li L, Komatsu K, Cai SQ. Aristololactams and aporphines from the stems of Fissistigma oldhamii (Annonaceae). Phytochemistry 2013; 86: 201-207 12 Chia YC, Wu JB, Wu YC. Two novel cyclopentenones from Fissistigma oldhamii . Tetrahedron Lett 2000; 41: 2199-2201 13 Chia YC, Chang FR, Wu YC. Fissohamione, a novel furanone from Fissistigma oldhamii . Tetrahedron Lett 1999; 40: 7513-7514 14 Fu CY, Liu YH, Chen DW, Tang H, Feng F, Zhou ZL. Extraction and purification techniques and free radical scavenging activity of total flavonoids from Fissistigma oldhamii . Zhong Yao Cai 2011; 34: 446-449 15 Zhou YF, Peng XS. Studies on chemical constituents and antitumor activity of Fissistigma oldhamii (Hemsl.) Merr. Lishizhen Med Mater Med Res 2009; 20: 592-593 16 Hwang TL, Li GL, Lan YH, Chia YC, Hsieh PW, Wu YH, Wu YC. Potent inhibition of superoxide anion production in activated human neutrophils by isopedicin, a bioactive component of the Chinese medicinal herb Fissistigma oldhamii . Free Radic Biol Med 2009; 46: 520-528 17 Xie BJ, Yang SP, Yue JM. Terpenoids from Dysoxylum densiflorum . Phytochemistry 2008; 69: 2993-2997 18 Liu HB, Zhang CR, Dong SH, Yang SP, Sun Q, Ceng MY, Yue JM. Sesquiterpenes from Dysoxylum oliganthum and Dysoxylum excelsum . J Asian Nat Prod Res 2012; 14: 224-234 19 Nishizawa M, Inoue A, Hayashi Y, Sastrapradja S, Iwashita T. Structure of aphanamols I and II. J Org Chem 1984; 49: 3660-3662 20 Beechan CM, Djerassi C, Eggert H. Terpenoids. LXXIV. The sesquiterpenes from the soft coral Sinularia mayi . Tetrahedron 1978; 34: 2503-2508 21 Parker W, Roberts JS, Ramage R. Sesquiterpene biogenesis. Q Rev Chem Soc 1967; 21: 331-363 22 Ruecker G. Sesquiterpenes. Angew Chem 1973; 85: 895-907 23 Scudiero DA, Shoemaker RH, Paull KD, Monks A, Tierney S, Nofziger TH, Currens MJ, Seniff D, Boyd MR. Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res 1988; 48: 4827-4833 Zusatzmaterial Zusatzmaterial Supporting Information