Liquidambar styraciflua: a renewable source of shikimic acid

Tetrahedron Letters

Volumn 49, Issue 16, 2008, Pages 2503-2505

  Enrich, Liza B ^a   Scheuermann, Margaret L ^a   Mohadjer, Ashley ^a   Matthias, Kathryn R ^b   Eller, Chrystal F ^c   Newman, M Scott ^d   Fujinaka, Michael ^a   Poon, Thomas ^a  

^a SCRIPPS COLLEGE   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

^c WAKE FOREST SCHOOL OF MEDICINE   (United States)

^d RANDOLPH MACON COLLEGE   (United States)

Author keywords

Liquidambar styraciflua; Plant natural products; Shikimic acid

Indexed keywords

ANTIVIRUS AGENT; AROMATIC AMINO ACID; NATURAL PRODUCT; OSELTAMIVIR; SHIKIMIC ACID;

AMINO ACID SYNTHESIS; ARTICLE; DRUG ISOLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION PROCEDURE; LIQUIDAMBAR STYRACIFLUA; MEDICINAL PLANT; PLANT SEED; QUANTUM YIELD; UNITED STATES;

LIQUIDAMBAR; LIQUIDAMBAR STYRACIFLUA;

EID: 40849104789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.140     Document Type: Article

References (57)

1. Eijkman J.F. Recl. Trav. Chim. Pays-Bas 4 (1885) 32 The spelling 'Eijkman' has been taken verbatim from the original journal article. However, as indicated in Ref. 4b, the author's surname is commonly misspelled in the literature as 'Eykman'
2. Fischer H.O.L., and Dangschat G. Helv. Chim. Acta 17 (1934) 1200
3. Fischer H.O.L., and Dangschat G. Helv. Chim. Acta 18 (1935) 1204
4. Fischer H.O.L., and Dangschat G. Helv. Chim. Acta 18 (1935) 1206
5. Fischer H.O.L., and Dangschat G. Helv. Chim. Acta 20 (1937) 705
6. Davis B.D. J. Biol. Chem. 191 (1951) 315
7. For reviews (a and b) and more recent examples (c-g), see. Campbell M.M., Sainsbury M., and Searle P.A. Synthesis (1993) 1
8. Jiang S., and Singh G. Tetrahedron 54 (1998) 4697
9. Shinada T., Yoshida Y., and Ohfune Y. Tetrahedron Lett. 39 (1998) 6027
10. Mehta G., and Mohal N. Tetrahedron Lett. 39 (1998) 3285
11. Alves C., Barros M.T., Maycock C.D., and Ventura M.R. Tetrahedron 55 (1999) 8443
12. Takeuchi M., Taniguchi T., and Ogasawara K. Synthesis (2000) 1375
13. Yoshida N., and Ogasawara K. Org. Lett. 2 (2000) 1461
14. For reviews, see:. Hattori S., Yoshida S., and Hasegawa M. Physiol. Plantarum 7 (1954) 283
15. Bohm B.A. Chem. Rev. 65 (1965) 435
16. Haslam E. Shikimic Acid Metabolism and Metabolites (1993), John Wiley and Sons, New York and references cited therein
17. Knaggs A.R. Nat. Prod. Rep. 20 (2003) 119
18. Farrell N., Roberts J.D., and Hacker M.P. J. Inorg. Biochem. 42 (1991) 237
19. Reynolds K.A., Wallace K.K., Handa S., Brown M.S., McArthur H.A.I., and Floss H.G. J. Antibiot. 50 (1997) 701
20. Tan D.S., Foley M.A., Stockwell B.R., Shair M.D., and Schreiber S.L. J. Am. Chem. Soc. 121 (1999) 9073
21. Schuster M.C., Mann D.A., Buchholz T.J., Johnson K.M., Thomas W.D., and Kiessling L.L. Org. Lett. 5 (2003) 1407
22. Zhang Y.A., Liu A.L., Ye Z.G., Lin J., Xu L.Z., and Yang S.L. Chem. Pharm. Bull. 54 (2006) 1459
23. Stefan Abrecht S., Harrington P., Iding H., Karpf M., Trussardi R., Wirz B., and Zutter U. Chimia 58 (2004) 621
24. Ward P., Small I., Smith J., Suter P., and Dutkowski R. J. Antimicrob. Chemother. 55 (2005) 5
25. Thayer A. Chem. Eng. News 84 (2006) 5
26. Yeung Y.-Y., Hong S., and Corey E.J. J. Am. Chem. Soc. 128 (2006) 6310
27. Fukuta Y., Mita T., Fukuda N., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 128 (2006) 6313
28. Draths K.M., Knop D.R., and Frost J.W. J. Am. Chem. Soc. 121 (1999) 1603
29. Knop D.R., Draths K.M., Chandran S.S., Barker J.L., von Daeniken R., Weber W., and Frost J.W. J. Am. Chem. Soc. 123 (2001) 10173
30. Chandran S.S., Yi J., Draths K.M., von Daeniken R., Weber W., and Frost J.W. Biotechnol. Prog. 19 (2003) 808
31. Plouvier V. Compt. Rend. 252 (1961) 599
32. Johnson, R. L. Sweetgum, an American Wood. FS-266. Washington, DC: US Department of Agriculture, Forest Service, 1985.
33. Harrar E.S., and Harrar J.G. Guide to Southern Trees (1993), McGraw-Hill, New York
34. Gilman, E. F.; Watson, D. G. Liquidambar styraciflua Sweetgum. Fact Sheet ST-358. Gainesville, FL: University of Florida, Institute of Food and Agricultural Sciences, 1993.
35. For natural products studies on L. styraciflua, see:. Williams III G.J. Photosynthetica 5 (1971) 399
36. Hillis W.E. Wood Sci. Technol. 5 (1971) 272
37. Bonner F.T. Forest Sci. 8 (1972) 223
38. Tattje D.H.E., and Bos R. Phytochemistry 18 (1979) 876
39. Tattje D.H.E., Bos R., and Bruins A.P. Plant Med. 38 (1980) 79
40. Winstead J.E. Trans. Ky. Acad. Sci. 43 (1982) 175
41. Miura G.A., and Shih T.-M. Physiol. Plant 61 (1984) 417
42. Foster D.O., and Zinkel D.F. Wood Fiber Sci. 16 (1984) 298
43. Wyllie G.S., and Brophy J.J. Planta Med. 55 (1989) 316
44. Neera S., Arakawa H., and Ishimaru K. Phytochemistry 32 (1993) 921
45. Chalchat J.-C., Garry R.-P., and Mathieu J.-P. J. Essent. Oil. Res. 6 (1994) 73
46. Mills G.L., Wolfe C.P., and Dalton B.R. Commun. Soil. Sci. Plant Anal. 26 (1995) 3335
47. We have not encountered data regarding the impact of fruit removal on sweetgum health. For a discussion of the seeds of L. styraciflua see: Ickert-Bond,. Ickert-Bond S.M., Pigg K.B., and Wen J. Am. J. Bot. 92 (2005) 1234 and references cited therein
48. Washam C. Environ. Health Perspect. 114 (2006) A464
49. A voucher sample (No. RSA 723828) was deposited at the Rancho Santa Ana Botanic Garden in Claremont, CA.
50. 5 192.0866.
51. Mathews F.S. Field Book of American Trees and Shrubs (1915), G.P. Putnam's Sons, New York
52. 4 as eluent (flow rate: 0.5 mL/min). Detection of 1 at ret. time 5.5 min. was achieved at λ = 225 nm using a Varian Star 9080 UV-vis detector. This was a modified procedure from:. Palmer J.K., and List D.M. J. Agric. Food Chem. 21 (1973) 903
53. A quantitative analysis was also performed on the dry, emptied fruit of L. styraciflua, revealing as much as 8.0% 1 (w/w). However, in our hands, we were unable to isolate pure 1 from crude extracts of the dried fruit.
54. Colombo S.L., Pairoba C.F., and Andrea C.S. Plant Cell Physiol. 37 (1996) 870
55. Illick J.S. Tree Habits. How to Know the Hardwoods (1924), American Nature Association, Washington, DC
56. Merkle S.A., Neu K.A., Battle P.J., and Bailey R.L. Plant Sci. 132 (1998) 169
57. Merkle S.A., Battle P.J., and Ware G.O. Plant Cell Tiss. Org. Cult. 73 (2003) 95