New Cytotoxic Biflavonoids from Selaginella delicatula

Abstract

Five new biflavonoids, robustaflavone 7,4′,4′′′-trimethyl ether, robustaflavone 4′,4′′′-dimethyl ether, 2,3-dihydroamentoflavone 7,4′,7′′-trimethyl ether, 2,3-dihydroamentoflavone 7,4′-dimethyl ether, and 2′′,3′′-dihydroisocryptomerin 7-methyl ether, together with six known compounds have been isolated from the aerial parts of Selaginella delicatula. The structures of these new compounds were determined through spectral analyses. Among the isolates, robustaflavone 4′,4′′′-dimethyl ether, 2,3-dihydroamentoflavone 7,4′-dimethyl ether, and α-tocopheryl quinone exhibited cytotoxicities (ED₅₀ values < 4 μg/mL) against P-388 and/or HT-29 cell lines in vitro.

Selaginella delicatula - Selaginellaceae - biflavonoids - robustaflavone 7,4′,4′′′-trimethyl ether - robustaflavone 4′,4′′′-dimethyl ether - 2,3-dihydroamentoflavone 7,4′,7′′-trimethyl ether - 2,3-dihydroamentoflavone 7,4′-dimethyl ether - 2′′,3′′-dihydroisocryptomerin 7-methyl ether - cytotoxicity

References

• 1 Tsai J L, Shieh W C. Selaginellaceae in Flora of Taiwan. 2nd edition. Editorial Committee of the Flora of Taiwan Taipei, Taiwan; 1994 Vol. 1: 45-57
• 2 Okigawa M, Hwa C W, Kawano N, Rahman W. Biflavones in Selaginella species.  Phytochemistry. 1971;  10 3286-7
• 3 Lee S W, Chen Z T, Chen M T, Chen C M. Biflavones of Selaginella doederlenii Hieron.  Chin Pharm J. 1992;  44 537-41
• 4 Lin R C, Skaltsounis A L, Seguin E, Tillequin F, Koch M. Phenolic constituents of Selaginella doederleinii .  Planta Med. 1994;  60 168-70
• 5 Silva G L, Chai H, Gupta M P, Farnsworth N R, Cordell G A, Pezzuto J M. et al . Cytotoxic biflavonoids from Selaginella willdenowii .  Phytochemistry. 1995;  40 129-34
• 6 Sun C M, Syu W J, Huang Y T, Chen C C, Ou J C. Selective cytotoxicity of ginkgetin from Selaginella moellendorffii .  J Nat Prod. 1997;  60 382-4
• 7 Lin L C, Kuo Y C, Chou C J. Cytotoxic biflavonoids from Selaginella delicatula .  J Nat Prod. 2000;  63 627-30
• 8 Voirin B. Distribution des composés polyphénoliques chez es lycopodinées.  Phytochemistry. 1972;  11 257-62
• 9 Teresa J de P, Urones J G, Marcos I S, Ferreras J F, Bertelloni A ML, Barcala P B. Diterpenoids from Nepeta tuberosa subsp. reticulata .  Phytochemistry. 1987;  26 1481-6
• 10 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
• 11 Chen J J, Duh C Y, Huang H Y, Chen I S. Furoquinoline alkaloids and cytotoxic constituents from the leaves of Melicope semecarpifolia .  Planta Med. 2003;  69 542-6
• 12 Markham K R, Sheppard C, Geiger H. ¹³C NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids.  Phytochemistry. 1987;  26 3335-7
• 13 Li S H, Zhang H J, Niu X M, Yao P, Sun H D, Fong H HS. Chemical constituents from Amentotaxus yunnanensis and Torreya yunnanensis .  J Nat Prod. 2003;  66 1002-5
• 14 Chen J J, Huang Y C, Chen Y C, Huang Y T, Wang S W, Peng C Y. et al . Cytotoxic amides from Piper sintenense .  Planta Med. 2002;  68 980-5
• 15 Kojima H, Sato N, Hatano A, Ogura H. Sterol glucosides from Prunella vulgaris .  Phytochemistry. 1990;  29 2351-5
• 16 Geran R I, Greenberg N H, Macdonald M M, Schumacher A M, Abbott B J. Protocols for screening chemical agents and natural products against animal tumors and other biological systems.  Cancer Chemother Rep, 3. 1972;  3 1-103