Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia

D Handayani, Ruangelie Edrada-Ebel, P Proksch, V Wray, L Witte, R W Van Soest, A Kunzmann, [No Value] Soedarsono

Research output: Contribution to journalArticle

104 Citations (Scopus)

Abstract

The marine sponge Dysidea herbacea collected from Indonesia yielded four new polybrominated diphenyl ether congeners 2-5 and the known derivatives 1, 6, and 7. The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, 1H-detected direct and long-range 13C-1H correlations) and mass spectrometric (EIMS) data. All of the compounds were active against the Gram-positive bacteria Bacillus subtilis and the phytopathogenic fungus Cladosporium cucumerinum. The isolated polybrominated compounds were also active in the brine shrimp lethality test. In the latter bioassay, compounds 1 and 6 were the most active with LC50's of 0.96 [SE +/- 0.19] and 0.94 [SE +/- 0.70] microg/mL, respectively.

LanguageEnglish
Pages1313-1316
Number of pages4
JournalJournal of Natural Products
Volume60
Issue number12
DOIs
Publication statusPublished - Dec 1997

Fingerprint

Dysidea
Halogenated Diphenyl Ethers
Cladosporium
Artemia
Indonesia
Bioassay
Gram-Positive Bacteria
Porifera
Bacilli
Bacillus subtilis
Fungi
Biological Assay
Bacteria
Nuclear magnetic resonance
Derivatives
Proton Magnetic Resonance Spectroscopy
brine

Keywords

  • animals
  • artemia
  • bacillus subtilis
  • cladosporium
  • drug screening assays, antitumor
  • lethal dose 50
  • magnetic resonance spectroscopy
  • polybrominated biphenyls
  • porifera

Cite this

Handayani, D ; Edrada-Ebel, Ruangelie ; Proksch, P ; Wray, V ; Witte, L ; Van Soest, R W ; Kunzmann, A ; Soedarsono, [No Value]. / Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia. In: Journal of Natural Products. 1997 ; Vol. 60, No. 12. pp. 1313-1316.
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title = "Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia",
abstract = "The marine sponge Dysidea herbacea collected from Indonesia yielded four new polybrominated diphenyl ether congeners 2-5 and the known derivatives 1, 6, and 7. The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, 1H-detected direct and long-range 13C-1H correlations) and mass spectrometric (EIMS) data. All of the compounds were active against the Gram-positive bacteria Bacillus subtilis and the phytopathogenic fungus Cladosporium cucumerinum. The isolated polybrominated compounds were also active in the brine shrimp lethality test. In the latter bioassay, compounds 1 and 6 were the most active with LC50's of 0.96 [SE +/- 0.19] and 0.94 [SE +/- 0.70] microg/mL, respectively.",
keywords = "animals, artemia, bacillus subtilis, cladosporium, drug screening assays, antitumor, lethal dose 50, magnetic resonance spectroscopy, polybrominated biphenyls, porifera",
author = "D Handayani and Ruangelie Edrada-Ebel and P Proksch and V Wray and L Witte and {Van Soest}, {R W} and A Kunzmann and Soedarsono, {[No Value]}",
note = "(1) Faulkner, D. J.; Unson, M. D.; Bewley, C. A. Pure Appl. Chem. 1994, 66, 1983−1990.[CrossRef], [CAS] (2) Hofheinz, W.; Oberh{\"a}nsli, W. E. Helv. Chim. Acta 1977, 60, 660−669.[CrossRef], [CAS] (3) Kazlauska, R.; Lidgard, R. O.; Wells, R. J.; Vetter, W. Tetrahedron Lett. 1977, 3183−3186.[CrossRef] (4) Kazlauska, R.; Murphy, P.T.; Wells, R. J. Tetrahedron Lett. 1978, 4945−4950.[CrossRef] (5) Charles, C.; Braekman, J. C.; Daloze, D.; Tursch, B.; Declercq, J. P.; Germain, G.; Van Meerssche, M. Bull. Soc. Chim. Belg. 1978, 87, 481−486.[CAS] (6) Sharma, G. M.; Vig, B. Tetrahedron Lett. 1972, 1715−1718.[CrossRef] (7) Sharma, G. M.; Vig, B.; Burknolder, P. R. Food, Drugs from the Sea, Proc. Marine Technol. Soc. 1969, 307. (8) Norton, R. S.; Croft, K. D.; Wells, R. J. Tetrahedron 1981, 37, 2341−2349.[CrossRef], [CAS] (9) Unson, M. D.; Faulkner, D. J. Experientia 1993, 49, 349−353.[CrossRef], [CAS] Unson, M. D.; Holland, N. D.; Faulkner, D. J. Mar. Biol. 1994, 119, 1−11.[CrossRef], [CAS] (11) Fu, X.; Schmitz, F. J.; Govindan, M.; Abbas, S. A.; Hanson, K. M. Horton, P. A.; Crews, P.; Laney, M.; Schatzman, R. C. J. Nat. Prod. 1995, 58, 1384−1391.[ACS Full Text ACS Full Text], [PubMed], [CAS] (12) Cart{\'e}, B.; Faulkner, D. J. Tetrahedron 1981, 37, 2335−2339.[CrossRef] (13) Utkina, N. K.; Kazantseva, M. V.; Denisenko, V. A. Khim. Prir. Soedin. 1987, 603−605.[CAS] (14) Salva, J.; Faulkner, D. J. J. Nat. Prod. 1990, 53, 757−760[ACS Full Text ACS Full Text], [CAS] (15) Gottstein, D.; Gross, D.; Lehmann, H. Arch. Phytopathol. Pflanzenschutz 1984, 20(2), 111−116.[CrossRef] (16) Homans, A. L.; Fuchs, A. J. Chromatogr. 1970, 51, 327−329.[CrossRef], [PubMed], [CAS] (17) Villar, A.; Rios, J. L.; Recio, M. C.; Cortes, D.; Cav{\'a}, A. Planta Med. 1986, 52, 556−557.[CrossRef], [PubMed], [CAS] (18) Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nichols, D. E.; McLauglin, J. L. Planta Med. 1982, 31−34.[CrossRef], [PubMed]",
year = "1997",
month = "12",
doi = "10.1021/np970271w",
language = "English",
volume = "60",
pages = "1313--1316",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
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}

Handayani, D, Edrada-Ebel, R, Proksch, P, Wray, V, Witte, L, Van Soest, RW, Kunzmann, A & Soedarsono, NV 1997, 'Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia' Journal of Natural Products, vol. 60, no. 12, pp. 1313-1316. https://doi.org/10.1021/np970271w

Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia. / Handayani, D; Edrada-Ebel, Ruangelie; Proksch, P; Wray, V; Witte, L; Van Soest, R W; Kunzmann, A; Soedarsono, [No Value].

In: Journal of Natural Products, Vol. 60, No. 12, 12.1997, p. 1313-1316.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia

AU - Handayani, D

AU - Edrada-Ebel, Ruangelie

AU - Proksch, P

AU - Wray, V

AU - Witte, L

AU - Van Soest, R W

AU - Kunzmann, A

AU - Soedarsono, [No Value]

N1 - (1) Faulkner, D. J.; Unson, M. D.; Bewley, C. A. Pure Appl. Chem. 1994, 66, 1983−1990.[CrossRef], [CAS] (2) Hofheinz, W.; Oberhänsli, W. E. Helv. Chim. Acta 1977, 60, 660−669.[CrossRef], [CAS] (3) Kazlauska, R.; Lidgard, R. O.; Wells, R. J.; Vetter, W. Tetrahedron Lett. 1977, 3183−3186.[CrossRef] (4) Kazlauska, R.; Murphy, P.T.; Wells, R. J. Tetrahedron Lett. 1978, 4945−4950.[CrossRef] (5) Charles, C.; Braekman, J. C.; Daloze, D.; Tursch, B.; Declercq, J. P.; Germain, G.; Van Meerssche, M. Bull. Soc. Chim. Belg. 1978, 87, 481−486.[CAS] (6) Sharma, G. M.; Vig, B. Tetrahedron Lett. 1972, 1715−1718.[CrossRef] (7) Sharma, G. M.; Vig, B.; Burknolder, P. R. Food, Drugs from the Sea, Proc. Marine Technol. Soc. 1969, 307. (8) Norton, R. S.; Croft, K. D.; Wells, R. J. Tetrahedron 1981, 37, 2341−2349.[CrossRef], [CAS] (9) Unson, M. D.; Faulkner, D. J. Experientia 1993, 49, 349−353.[CrossRef], [CAS] Unson, M. D.; Holland, N. D.; Faulkner, D. J. Mar. Biol. 1994, 119, 1−11.[CrossRef], [CAS] (11) Fu, X.; Schmitz, F. J.; Govindan, M.; Abbas, S. A.; Hanson, K. M. Horton, P. A.; Crews, P.; Laney, M.; Schatzman, R. C. J. Nat. Prod. 1995, 58, 1384−1391.[ACS Full Text ACS Full Text], [PubMed], [CAS] (12) Carté, B.; Faulkner, D. J. Tetrahedron 1981, 37, 2335−2339.[CrossRef] (13) Utkina, N. K.; Kazantseva, M. V.; Denisenko, V. A. Khim. Prir. Soedin. 1987, 603−605.[CAS] (14) Salva, J.; Faulkner, D. J. J. Nat. Prod. 1990, 53, 757−760[ACS Full Text ACS Full Text], [CAS] (15) Gottstein, D.; Gross, D.; Lehmann, H. Arch. Phytopathol. Pflanzenschutz 1984, 20(2), 111−116.[CrossRef] (16) Homans, A. L.; Fuchs, A. J. Chromatogr. 1970, 51, 327−329.[CrossRef], [PubMed], [CAS] (17) Villar, A.; Rios, J. L.; Recio, M. C.; Cortes, D.; Cavá, A. Planta Med. 1986, 52, 556−557.[CrossRef], [PubMed], [CAS] (18) Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nichols, D. E.; McLauglin, J. L. Planta Med. 1982, 31−34.[CrossRef], [PubMed]

PY - 1997/12

Y1 - 1997/12

N2 - The marine sponge Dysidea herbacea collected from Indonesia yielded four new polybrominated diphenyl ether congeners 2-5 and the known derivatives 1, 6, and 7. The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, 1H-detected direct and long-range 13C-1H correlations) and mass spectrometric (EIMS) data. All of the compounds were active against the Gram-positive bacteria Bacillus subtilis and the phytopathogenic fungus Cladosporium cucumerinum. The isolated polybrominated compounds were also active in the brine shrimp lethality test. In the latter bioassay, compounds 1 and 6 were the most active with LC50's of 0.96 [SE +/- 0.19] and 0.94 [SE +/- 0.70] microg/mL, respectively.

AB - The marine sponge Dysidea herbacea collected from Indonesia yielded four new polybrominated diphenyl ether congeners 2-5 and the known derivatives 1, 6, and 7. The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, 1H-detected direct and long-range 13C-1H correlations) and mass spectrometric (EIMS) data. All of the compounds were active against the Gram-positive bacteria Bacillus subtilis and the phytopathogenic fungus Cladosporium cucumerinum. The isolated polybrominated compounds were also active in the brine shrimp lethality test. In the latter bioassay, compounds 1 and 6 were the most active with LC50's of 0.96 [SE +/- 0.19] and 0.94 [SE +/- 0.70] microg/mL, respectively.

KW - animals

KW - artemia

KW - bacillus subtilis

KW - cladosporium

KW - drug screening assays, antitumor

KW - lethal dose 50

KW - magnetic resonance spectroscopy

KW - polybrominated biphenyls

KW - porifera

U2 - 10.1021/np970271w

DO - 10.1021/np970271w

M3 - Article

VL - 60

SP - 1313

EP - 1316

JO - Journal of Natural Products

T2 - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 12

ER -