Monoterpenoid Indole Alkaloids Mediating DNA Strand Scission from Turpinia arguta

Abstract

Two new monoterpenoid indole alkaloid derivatives, turpiniside (1) and 11-methoxyjavaniside (2), along with the known alkaloids, vincosamide (3), (3R)-pumiloside (4), and paratunamide C (5), were isolated from the leaves of Turpinia arguta (Lindl.) Seem. Their structures were determined on the basis of spectroscopic data. Compounds 1 and 3–5 were found to effect relaxation of the supercoiled pBR322 plasmid DNA in the presence of Cu²⁺.

Key words

monoterpenoid indole alkaloid - Turpinia arguta - Staphyleaceae - DNA strand scission

References

• 1 Committee for the Chinese Materia Medica .Chinese Materia Medica, Vol. 5. Shanghai; Shanghai Science and Technology Press 1999: 218-219
• 2 Zhang L, Li J, Yu S C, Jin Y, Lv X W, Zou Y H. Therapeutic effects and mechanisms of total flavonoids of Turpinia Arguta Seem. on adjuvant arthritis in rats.  J Ethnopharmacol. 2008;  116 167-172
• 3 Zhang L, Li J, Yu S C. Anti-inflammatory activity of TFS in experimental models.  Acta Univ Med Anhui. 2003;  38 185-188
• 4 Li Y Q. Studies on the chemical constituents of Capparis himalayensis and Turpinia arguta [dissertation]. Beijing; Peking Union Medical College & Chinese Academy of Medical Sciences 2007
• 5 Sun J Y. The chemical constituents and their bioactivities of Nauclea officinalis Pierre ex Pitard and Turpinia arguta Seem. [dissertation]. Jinan; Shandong University 2008
• 6 Erdelmeier C A J, Wright A D, Orjala J, Baumgartner B, Rali T, Sticher O. New indole alkaloid glycosides from Nauclea orientalis.  Planta Med. 1991;  57 149-152
• 7 Kitajima M, Yoshida S, Yamagata K, Nakamura M, Takayama H, Saito K, Seki H, Aimi M. Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila.  Tetrahedron. 2002;  58 9169-9178
• 8 Kagata T, Saito S, Shigemori H, Ohsaki A, Ishiyama H, Kubota T, Kobayashi J. Paratunamides A-D, oxindole alkaloids from Cinnamodendron axillare.  J Nat Prod. 2006;  69 1517-1521
• 9 Henriques A T, Lopes S O, Paranhos J T, Gregianini T S, Poser G L V, Fett-Neto A G, Schripsema J. N,β-d-Glucopyranosyl vincosamide, a light regulated indole alkoild from the shoots of Psychotria leiocarpa.  Phytochemistry. 2004;  65 449-454
• 10 Itoh A, Tanahashi T, Nagakura N, Nishi T. Two chromone-secoiridoid glycosides and three indole alkaloid glycosides from Neonaucles sessilifolia.  Phytochemistry. 2003;  62 359-369
• 11 Feng T, Cai X H, Li Y, Wang Y Y, Liu Y P, Xie M J, Luo X D. Melohenines A and B, two unprecedented alkaloids from Melodinus henryi.  Org Lett. 2009;  11 4834-4837
• 12 Brown R T, Liu J, Santos C A M. Biogenetically patterned synthesis of camptothecin and 20-deoxycamptothecin.  Tetrahedron Lett. 2000;  41 859-862
• 13 Pham V C, Ma J, Thomas S J, Xu Z D, Hecht S M. Alkaloids from Alangium javanicum and Alangium grisolleoides that mediate Cu²⁺-dependent DNA strand scission.  J Nat Prod. 2005;  68 1147-1152
• 14 Ali E, Giri V S, Pakrashi S C. The oxindole alkaloids of Vinca elegantissima Hort.  Cell Mol Life Sci. 1975;  31 876-877
• 15 Aimi N, Shimizu T, Sada H, Takayama H, Sakai S, Wongseripipatana S, Ponglux D. Structures of Us-7 and Us-8: a new type of oxindole alkaloids isolated from Uncaria attenuata Korth.  J Chem Soc [Perkin I]. 1997;  187-188
• 16 Carte B K, DeBrosse C, Eggleston D, Hemling M, Mentzer M, Poehland B, Troupe N, Westley J W, Hecht S M. Isolation and characterization of a presumed biosynthetic precursor of camptothecin from extracts of Camptotheca acuminate.  Tetrahedron. 1990;  46 2747-2760
• 17 Deng J Z, Newman D J, Hetch S M. Use of COMPARE analysis to discover functional analogues of bleomycin.  J Nat Prod. 2000;  63 1269-1272