Actinoflavoside, a novel flavonoid-like glycoside produced by a marine bacterium of the genus Streptomyces

Tetrahedron Letters

Volumn 38, Issue 29, 1997, Pages 5065-5068

  Jiang, Zhi Dong ^a   Jensen, Paul R ^a   Fenical, William ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTINOFLAVOSIDE A; GLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STREPTOMYCES;

EID: 0030796013     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01127-1     Document Type: Article

References (19)

1. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682; Jensen, P. R.; Dwight, R.; Fenical, W. Appl. Envir. Micro. 1991, 57, 1102; Pathirana, C.; Tapiolas, D.; Jensen, P. R.; Dwight, R.; Fenical, W. Tetrahedron Lett. 1991, 32, 2323; Pathirana, C.; Jensen, P. R.; Dwight, R.; Fenical, W. J. Org. Chem. 1992, 57, 740; Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663; Fenical, W. Chem. Rev. 1993, 93, 1673; Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757; Jensen, P. R.; Fenical, W. Ann. Rev. Microbiol. 1994, 48, 559; Toske, S. G.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Nat. Prod. Lett. 1995, 6, 303; Lindel, T.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327.
2. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682; Jensen, P. R.; Dwight, R.; Fenical, W. Appl. Envir. Micro. 1991, 57, 1102; Pathirana, C.; Tapiolas, D.; Jensen, P. R.; Dwight, R.; Fenical, W. Tetrahedron Lett. 1991, 32, 2323; Pathirana, C.; Jensen, P. R.; Dwight, R.; Fenical, W. J. Org. Chem. 1992, 57, 740; Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663; Fenical, W. Chem. Rev. 1993, 93, 1673; Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757; Jensen, P. R.; Fenical, W. Ann. Rev. Microbiol. 1994, 48, 559; Toske, S. G.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Nat. Prod. Lett. 1995, 6, 303; Lindel, T.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327.
3. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682; Jensen, P. R.; Dwight, R.; Fenical, W. Appl. Envir. Micro. 1991, 57, 1102; Pathirana, C.; Tapiolas, D.; Jensen, P. R.; Dwight, R.; Fenical, W. Tetrahedron Lett. 1991, 32, 2323; Pathirana, C.; Jensen, P. R.; Dwight, R.; Fenical, W. J. Org. Chem. 1992, 57, 740; Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663; Fenical, W. Chem. Rev. 1993, 93, 1673; Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757; Jensen, P. R.; Fenical, W. Ann. Rev. Microbiol. 1994, 48, 559; Toske, S. G.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Nat. Prod. Lett. 1995, 6, 303; Lindel, T.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327.
4. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682; Jensen, P. R.; Dwight, R.; Fenical, W. Appl. Envir. Micro. 1991, 57, 1102; Pathirana, C.; Tapiolas, D.; Jensen, P. R.; Dwight, R.; Fenical, W. Tetrahedron Lett. 1991, 32, 2323; Pathirana, C.; Jensen, P. R.; Dwight, R.; Fenical, W. J. Org. Chem. 1992, 57, 740; Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663; Fenical, W. Chem. Rev. 1993, 93, 1673; Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757; Jensen, P. R.; Fenical, W. Ann. Rev. Microbiol. 1994, 48, 559; Toske, S. G.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Nat. Prod. Lett. 1995, 6, 303; Lindel, T.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327.
5. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682; Jensen, P. R.; Dwight, R.; Fenical, W. Appl. Envir. Micro. 1991, 57, 1102; Pathirana, C.; Tapiolas, D.; Jensen, P. R.; Dwight, R.; Fenical, W. Tetrahedron Lett. 1991, 32, 2323; Pathirana, C.; Jensen, P. R.; Dwight, R.; Fenical, W. J. Org. Chem. 1992, 57, 740; Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663; Fenical, W. Chem. Rev. 1993, 93, 1673; Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757; Jensen, P. R.; Fenical, W. Ann. Rev. Microbiol. 1994, 48, 559; Toske, S. G.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Nat. Prod. Lett. 1995, 6, 303; Lindel, T.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327.
6. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682; Jensen, P. R.; Dwight, R.; Fenical, W. Appl. Envir. Micro. 1991, 57, 1102; Pathirana, C.; Tapiolas, D.; Jensen, P. R.; Dwight, R.; Fenical, W. Tetrahedron Lett. 1991, 32, 2323; Pathirana, C.; Jensen, P. R.; Dwight, R.; Fenical, W. J. Org. Chem. 1992, 57, 740; Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663; Fenical, W. Chem. Rev. 1993, 93, 1673; Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757; Jensen, P. R.; Fenical, W. Ann. Rev. Microbiol. 1994, 48, 559; Toske, S. G.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Nat. Prod. Lett. 1995, 6, 303; Lindel, T.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327.
7. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682; Jensen, P. R.; Dwight, R.; Fenical, W. Appl. Envir. Micro. 1991, 57, 1102; Pathirana, C.; Tapiolas, D.; Jensen, P. R.; Dwight, R.; Fenical, W. Tetrahedron Lett. 1991, 32, 2323; Pathirana, C.; Jensen, P. R.; Dwight, R.; Fenical, W. J. Org. Chem. 1992, 57, 740; Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663; Fenical, W. Chem. Rev. 1993, 93, 1673; Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757; Jensen, P. R.; Fenical, W. Ann. Rev. Microbiol. 1994, 48, 559; Toske, S. G.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Nat. Prod. Lett. 1995, 6, 303; Lindel, T.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327.
8. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682; Jensen, P. R.; Dwight, R.; Fenical, W. Appl. Envir. Micro. 1991, 57, 1102; Pathirana, C.; Tapiolas, D.; Jensen, P. R.; Dwight, R.; Fenical, W. Tetrahedron Lett. 1991, 32, 2323; Pathirana, C.; Jensen, P. R.; Dwight, R.; Fenical, W. J. Org. Chem. 1992, 57, 740; Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663; Fenical, W. Chem. Rev. 1993, 93, 1673; Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757; Jensen, P. R.; Fenical, W. Ann. Rev. Microbiol. 1994, 48, 559; Toske, S. G.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Nat. Prod. Lett. 1995, 6, 303; Lindel, T.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327.
9. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682; Jensen, P. R.; Dwight, R.; Fenical, W. Appl. Envir. Micro. 1991, 57, 1102; Pathirana, C.; Tapiolas, D.; Jensen, P. R.; Dwight, R.; Fenical, W. Tetrahedron Lett. 1991, 32, 2323; Pathirana, C.; Jensen, P. R.; Dwight, R.; Fenical, W. J. Org. Chem. 1992, 57, 740; Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663; Fenical, W. Chem. Rev. 1993, 93, 1673; Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757; Jensen, P. R.; Fenical, W. Ann. Rev. Microbiol. 1994, 48, 559; Toske, S. G.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Nat. Prod. Lett. 1995, 6, 303; Lindel, T.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327.
10. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682; Jensen, P. R.; Dwight, R.; Fenical, W. Appl. Envir. Micro. 1991, 57, 1102; Pathirana, C.; Tapiolas, D.; Jensen, P. R.; Dwight, R.; Fenical, W. Tetrahedron Lett. 1991, 32, 2323; Pathirana, C.; Jensen, P. R.; Dwight, R.; Fenical, W. J. Org. Chem. 1992, 57, 740; Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663; Fenical, W. Chem. Rev. 1993, 93, 1673; Trischman, J. A.; Tapiolas, D. M.; Jensen, P. R.; Dwight, R.; McKee, T. C.; Ireland, C. M.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 757; Jensen, P. R.; Fenical, W. Ann. Rev. Microbiol. 1994, 48, 559; Toske, S. G.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Nat. Prod. Lett. 1995, 6, 303; Lindel, T.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327.
11. Actinomycete strain CNB-689 was isolated from a black, anaerobic intertidal sediment collected near Christchurch, New Zealand in 1994. The strain was initially isolated by serial dilution methods on solid agar (1.6% agar) using a medium composed of the following: soluble starch 1%, yeast extract 0.4%, peptone 0.2%, seawater 75%, deionized water 25%. FAME (Fatty Acid Methyl Ester) analysis (Microbial ID Inc., Newark, DE) resulted in a poor match (similarity index 0.436) with Streptomyces halstedii.
12. Strain CNB-689 was cultivated, in the medium described above, at the 50L scale using a New Brunswick, Fermatron FM-75 pilot scale fermenter, for 7 days at 23° C. The whole culture was filtered and the clear broth was extracted, using a new solid-phase method involving percolation over stearic acid impregnated charcoal. The filtered charcoal was washed with water and eluted with methanol to provide the crude culture extract (yield of 1 was ca. 3 mg/L).
13. 3).
14. Actinoflavoside perbenzoate was prepared by treatment of 1 (3 mg) with a solution of 0.5 ml dry pyridine and 0.5 ml benzoyl chloride. The solution was stirred for 20 min at RT, cooled in ice, and hydrolyzed with dist. water. The pH was adjusted to ca. 8.0 and the organic products were extracted with EtOAc. Purification of the ester was accomplished by silica HPLC using 50% EtOAc in isooctane.
15. 3 and the organic products were extracted by solid phase adsorption on RP C-18 resin. After elution of the reactions products with methanol, the aglycone was purified by silica HPLC (40% EtOAc/isooctane) to lead to pure 2 (2 mg).
16. Bognar, R.; Sztaricskai, P.; Munk, M.E.; Tamas, J. J. Org. Chem. 1974, 39, 2971.
17. Gauze, G. F.; Kudrina, E. S.; Ukholina, R. S.; Gavrilina, G. V. Antibiotiki 1963, 8, 387.
18. Maskens, K.; Polgar, N. J. Chem. Soc. Perkin 1 1973, 109.
19. Marchelli, R.; Vining, L. C. Can. J. Biochem. 1973, 51, 1624.