Immunosuppressive Sesquiterpenes from Buddleja daviddi

Abstract

Six new sesquiterpenes, 2,6(12),10-humulatrien-7β-ol-1-one (1), 2α-acetoxy-5α-methoxy-enantio-caryophylla-8(15)-en-3-one (2), 2α-acetoxy-5α-hydroxy-enantio-caryophylla-8(15)-en-3-one (3), 2α-acetoxy-4β,5α-hydroxy-enantio-caryophylla-8(15)-en-3-one (4), 2α-acetoxy-4β,5β-hydroxy-enantio-caryophylla-8(15)-en-3-one (5), 2β-acetoxy-4-caryophyllen-8β-ol-3-one (6), and nineteen known compounds were isolated from the ethanol extract of Buddleja daviddi. The structures were elucidated by spectroscopic methods. Compounds 8–11, 14, 16, 17, and 20 showed significant immunosuppressive activities, and 8–11 and 14 were cytotoxic on HeLa and L929 cell lines.

Key words

Buddleja daviddi - Loganiaceae - humulane sesquiterpene - caryophyllane sesquiterpene - immunosuppressive activity - cytotoxic activity

References

• 1 Wan D R, Chen W J, Qian C, Lei Y S. The antirheumatic Tujia herbal-medicine in the western of Hubei.  J Chin Med Mater. 1993;  18 581-584
• 2 Houghton P J. Lignans and neolignans from Buddleja davidii.  Phytochemistry. 1985;  24 819-826
• 3 Houghton P J. Phenylpropanoid glycosides in Buddleja davidii.  J Nat Prod. 1985;  48 1005-1006
• 4 Yoshida T, Uchida M, Okuda T. Buddledin A, B, C, piscicidal sesquiterpenes from Buddleja davidii Franch.  Tetrahedron Lett. 1976;  17 3717-3720
• 5 Yamamoto A, Nitta S, Miyase T, Ueno A, Wu L J. Phenylethanoid and lignan-iridoid complex glycosides from roots of Buddleja davidii.  Phytochemistry. 1993;  32 421-425
• 6 Lu J H, Tu G Z, Zhao Y Y, Lv Y, Liu L Y, Wu Y S. Structural determination of novel terpenes from Buddleia lindleyana.  Magn Reson Chem. 2004;  42 893-897
• 7 Liao Y H, Houghton P J, Hoult J R S. Novel and known constituents from Buddleja species and their activity against leukocyte eicosanoid generation.  J Nat Prod. 1999;  62 1241-1245
• 8 Sahyrbekov D T, Atazhanova G A, Kulyyasov A T, Raldugin V A, Gatilov Y V, Shakirov M M, Edil'baeva T T, Turdybekov K M, Adekenov S M. Buddledin C from prostrate and selective synthesis of its epoxy derivative.  Chem Nat Compounds. 2006;  42 41-45
• 9 Yoshida T, Nobuhara J, Uchida M, Okuda T. Studies on the constituents Buddleja species. I. Structures of Buddledin A and B. Two new toxic sesquiterpenes from Buddleja davidii Franch.  Chem Pharm Bull. 1978;  26 2535-2542
• 10 Yoshida T, Nobuhara J, Fujii N, Okuda T. Studies on the constituents of Budddleja species. II. Buddledin C, D and E. New sesquiterpenes from Buddleja davidii Franch.  Chem Pharm Bull. 1978;  26 2543-2549
• 11 Yarovaya O I, Korchagina D V, Rybalova T V, Gatilov Y V, Polovinka M P, Barkhash V A. Reactions of caryophyllene, isocaryophyllene, and their epoxy derivatives with acetonitrile under ritter reaction conditions.  Russian J Org Chem. 2004;  40 1593-1598
• 12 Wang G H, Ahmed A F, Sheu Y C, Wang L T, Shen J H. Suberosols A–D, four new sesquiterpenes with β-caryophyllene skeletons from a Taiwanses gorgonian coral Subergorgia suberosa.  J Nat Prod. 2002;  65 887-891
• 13 Banerji J, Das B, Chatterjee A, Shoolery J N. Gadain, a lignan from Jatropha gossypifolia.  Phytochemistry. 1984;  23 2323-2327
• 14 Zhang G, Shimokawa S, Mochizuki M, Kumamoto T, Nakanishi W, Watanabe T, Ishikawa T, Matsumoto K, Tashima K, Horie S, Higuchi Y, Dominguez O P. Chemical constituents of Aristolochia constricta: antispasmodic effects of its constituents in guinea-pig ileum and isolation of a diterpeno-lignan hybrid.  J Nat Prod. 2008;  71 1167-1172
• 15 Inara C P, Isabele R N, Lucia M X L. Configurational analysis of cubebins and bicubebin from Aristolochia lagesiana and Aristolochia pubescens.  Phytochemistry. 2006;  67 735-742
• 16 Marco J A, Cervera J F S, Morante M D, Lliso V G, Xirau J V, Jakupovic J. Tricyclic sesquiterpenes from Artemisia chamaemelifolia.  Phytochemistry. 1996;  41 837-844
• 17 Amaro L J M, Fronczek F, Massanet G, Pando E, Rodríguez L F, Watkins S, Zubía E. Meridinol, a lignan from Zanthoxylum fagara.  Phytochemistry. 1988;  27 3933-3935
• 18 Pieters L, Bruyne T, Claeys M, Vlietinck A. Isolation of a dihydrobenzofuran lignan from South American Dragon's blood (Croton SPP.) as an inhibitor of cell proliferation.  J Nat Prod. 1993;  56 899-906
• 19 Waibel R, Benirschke G, Benirschke M, Achenbach H. Sesquineolignans and other constituents from the seeds of Joannesia princeps.  Phytochemistry. 2003;  62 805-811
• 20 Shen G X. Experimental techniques of modern immunology. Hubei; Hubei Scientific and Technical Press 1998: 309-310