New Camptothecin and Ellagic Acid Analogues from the Root Bark of Camptotheca acuminata

Abstract

As part of a study on chemical constituents of Camptotheca species, one new natural camptothecin analogue (2), two new alkaloids (3, 4), one new ellagic acid analogue (5), and 19 known compounds (1, 6 - 23) have been isolated from the root bark, stem bark, fruits, and leaves of Camptotheca acuminata Decaisne. The structures of 2 - 5 were determined from spectral data to be 10-methoxy-20-O-acetylcamptothecin (2), 20-O-β-glucopyranosyl 18-hydroxycamptothecin (3), 20-formylbenz[6] [7]indolizino [1,2-b]quino-line-11(13H)-one (4), and 3,4-methylenedioxy-3′-O-methyl-5′-hydroxyellagic acid (5).

Key words

Camptotheca acuminata - Nyssaceae - camptothecin analogues - ellagic acid analogue

References

• 1 Wall M E, Wani M C, Cook C E, Palmer K H, McPhail A T, Sim G A. Plant antitumor agents. I. Isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata .  J Am Chem Soc. 1966;  88 3888-90
• 2 Li S Y, Adair K T. Camptotheca acuminata Decaisne, Xi Shu, a promising anti-cancer and anti-viral tree for the 21st century. A Henry M. Rockwell monograph. Nacogdoches; Stephen F. Austin State University 1994: pp 31-7
• 3 Editorial Committee of the Zhong Hua Ben Cao. Zhong Hua Ben Cao. Shanghai; Shanghai Science and Technology Press 1999 5(13): pp 730-3
• 4 Adamovics J A, Cina J A, Hutchinson C R. Minor alkaloids of Camptotheca acuminata .  Phytochemistry. 1979;  18 1085-6
• 5 Li S Y. A system for increasing the production of indole and quinoline alkaloids, particularly camptothecins and related compounds, from plants. R. O.  China Invention Patent. 1627;  20 2002, pp 1 - 56 (37 figures)
• 6 Li S Y. Camptotheca lowreyana tree named ‘Katie’. U.S. Patent PP11,959. 2001: p. 1 - 6 (6 figures)
• 7 Li S Y, Yi Y J, Wang Y J, Zhang Z Z, Beasley R S. Camptothecin accumulation and variation in Camptotheca .  Planta Medica. 2003;  68 1010-6
• 8 Lin L Z, Cordell G A. ¹³C-NMR assignments of camptothecine and 10-hydroxycamptothecine.  J Nat Prod. 1990;  53 186-9
• 9 Hsu J S, Chao T Y, Lin L T, Hsu C F. Chemical constituents of the anticancer plant Camptotheca acuminata Decne II. Chemical constituents of the fruits of Camptotheca acuminata Decne.  Acta Chim Sin. 1977;  35 193-200
• 10 Gunasekera S P, Badawi M M, Cordell G A, Farnsworth N R, Chitnis M. Plant anticancer agents X. Isolation of camptothecin and 9-methoxycamptothecin from Ervatamia heyneana .  J Nat Prod. 1979;  42 475-7
• 11 Zhang Z Z, ElSohly H N, Jacob M R, Pasco D S, Walker L A, Clark A M. Novel indole alkaloids from the bark of Nauclea orientalis .  J Nat Prod. 2001;  64 1001-5
• 12 Arbain D, Putra D P, Sargent M V. The alkaloids of Ophiorrhiza filistipula. Aust.  J Chem. 1993;  46 977-85
• 13 Subhadhirasakul S, Aimi N, Takayama H, Ponglux D, Sakai S. Hunterioside, first biose bound monoterpenoid indole alkaloid from Hunteria zeylanica .  Chem Pharm Bull. 1994;  42 991-3
• 14 Lin L Z, Song G Q, Xu R S. Chemical constituents of anticancer plant Camptotheca acuminata Decne. III. Ellagic acids from the fruits of Camptotheca acuminata Decne.  Acta Chim Sin. 1979;  37 207-14
• 15 Michael H N, Salib J Y, Ishak M S. Methylated ellagic acid glycosides from Eucalyptus rostrata .  Asian J Chem. 1998;  10 800-2
• 16 Atta-ur-Rahman  , Ngounou F N, Choudhary M I, Malik S, Makhmoor T, Nur-E-Alam M, Zareen S, Lontsi D, Ayafor J F, Sondengam B L. New Antioxidant and antimicrobial ellagic acid derivatives from Pteleopsis hylodendron .  Planta Medica. 2001;  67 335-9
• 17 Choi Y H, Pezzuto J, Kinghorn A D, Farnsworth N R. Ellagic acid derivatives of Agrostistachys hookeri .  Planta Medica. 1988;  54 511-3
• 18 Zhang Z Z, Guo D A, Li C L, Zheng J H, Koike K, Jia Z H, Nikaido T. Studies on the chemical constituents of Yunnan wintergreen roots (Gaultheria yunnanensis) (II).  Chin Trad Herb Drugs. 1999;  30 167-9
• 19 Markham K R, Geiger H. Advance in Research since 1986. In: Harborne JB, editor The flavonoids. London, Chapman & Hall 1993: pp 441-7
• 20 Matsuura S, Iinuma M. Studies on the constituents of useful plant. VI. Constituents of the calyx of Diospyros kaki and carbon-13 nuclear magnetic spectra of flavonol glycosides.  Chem Pharm Bull. 1978;  26 1936-41
• 21 Miyasaka T, Sawada S, Nokata K, Mutai M. Camptothecin derivatives formulations containing such derivatives and their use. European Patent Application 1993: pp 1-53
• 22 Lin L Z, Zhang J S, Shen J H, Zhou T, Zhang W Y. A new alkaloid - 18-hydroxycamptothecin.  Acta Pharmacol Sin. 1988;  23 186-8
• 23 Lin L Z, Cordell G A. Quinoline alkaloids from Camptotheca acuminata .  Phytochemistry. 1989;  28 1295-7
• 24 Lin L Z, Shen J H, He X, Zhang W Y. Indole alkaloids from Camptotheca acuminata .  Acta Chim Sin. 1988;  46 1207-11
• 25 Conrad J, Vogler B, Klaiber I, Reeb S, Guse J H, Roos G, Kraus W. Vanillic acid 4-O-β-d-(6′-O-galloyl)glucopyranoside and other constituents from the bark of Terminalia macroptera Guill. et Perr.  Nat Prod Lett. 2001;  15 35-42