Coumarin Derivatives from Gerbera saxatilis

Abstract

Phytochemical investigation of Gerbera saxatilis (Astraceae) afforded three new coumarin derivatives 1–3 and a known coumarin 4. Compounds 1 and 2 represent the first examples of the natural occurrence of the novel polycyclic pyrano[3-2c]coumarin carbon skeleton. The structures of compounds 1–4 were characterized based on extensive spectroscopic analyses as well as comparison to the spectroscopic data reported. The structures of compounds 1 and 3 were further confirmed by X‐ray data analyses. The cytotoxic activity of compounds 1–4 was evaluated against selected cancer cell lines, including human leukemia cell (HL-60), human hepatoma cell (SMMC-7721), and human cervical carcinoma cell (HeLa) lines.

Gerbera saxatilis - Astraceae - coumarin derivatives

References

• 1 Shanmugasundaram M, Manikandan S, Raghunathan R. High chemoselectivity in microwave accelerated intramolecular domino knoevenagel hetero diels–alder reactions–an efficient synthesis of pyrano[3-2c]coumarin frameworks.  Tetrahedron. 2002;  58 997-1003
• 2 Liu C M, Fei D Q, Wu Q H, Gao K. Bisabolane sesquiterpenes from the roots of Ligularia cymbulifera.  J Nat Prod. 2006;  69 695-699
• 3 Fei D Q, Li S G, Liu C M, Wu G, Gao K. Eremophilane-type sesquiterpene derivatives from the roots of Ligularia lapathifolia.  J Nat Prod. 2007;  70 241-245
• 4 Chen J J, Fei D Q, Chen S G, Gao K. Antimicrobial triterpenoids from Vladimiria muliensis.  J Nat Prod. 2008;  71 547-550
• 5 Chen J J, Li Z M, Gao K, Chang J, Yao X J. Vladimuliecins A and B: cytotoxic pentacyclic pregnanols from Vladimiria muliensis.  J Nat Prod. 2009;  72 1128-1132
• 6 Wang H X, Liu C M, Liu Q, Gao K. Three types of sesquiterpenoids from rhizomes of Atractylodes lancea.  Phytochemistry. 2008;  69 2088-2094
• 7 Li Z M, Chen J J, Li Y, Gao K, Chang J, Yao X J. Two novel iridoids with an unusual δ-lactone-containing skeleton from Triosteum himalayanum.  Tetrahedron Lett. 2009;  50 4132-4134
• 8 Li W X, Lei M, Fei D Q, Gao K. Eremophilane-type sesquiterpene derivatives from Ligularia hodgsonii.  Planta Med. 2009;  75 635-640
• 9 Fei D Q, Zhang Z X, Chen J J, Gao K. Eremophilane-type sesquiterpenes from Senecio nemorensis.  Planta Med. 2007;  73 1292-1297
• 10 Appendino G, Cravotto G, Giovenzana G B, Palmisano G. A straightforward entry into polyketide monoprenylated furanocoumarins and pyranocoumarins¹.  J Nat Prod. 1999;  62 1627-1631
• 11 Chen Y J, Li Y, Chen J J, Gao K. Benzofuran derivatives from Gerbera saxatilis.  Helv Chim Acta. 2007;  90 176-182
• 12 Hao G, Wang Z G, Fu W Y, Yang Y. Research progress on effect of coumarins compounds in anti-tumor.  Chin J Chin Mater Med. 2008;  33 2016-2019
• 13 Fong W F, Zhang J X, Wu J Y- C, Tse K W, Wang C, Cheung H Y, Yang M S. Pyranocoumarin (±)-4′-O-acetyl-3′-O-angeloyl-cis-khellact-one induces mitochondrial-dependent apoptosis in HL-60 cells.  Planta Med. 2004;  70 489-495