Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica

Ruangelie Edrada-Ebel, P Proksch, V Wray, L Witte, W E Müller, R W Van Soest

Research output: Contribution to journalArticle

104 Citations (Scopus)

Abstract

Analysis of the Philippine marine sponge Xestospongia ashmorica afforded four new manzamine congeners 1-4 and four known compounds 5 and 7-9. Compound 1 is the 6-deoxy derivative of manzamine X, while 2-4 are the N-oxides of manzamine J (5), 3,4-dihydromanzamine A (6), and manzamine A (7), respectively. 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 (EI, FAB-MS, and electrospray ionization) data. Alkaloid N-oxide structures were confirmed by conversion to the corresponding tertiary bases by reduction with Zn/HCl. This is the first report of the occurrence of bioactive manzamine N-oxides in marine sponges. Compound 7 exhibited insecticidal activity toward neonate larvae of the polyphagous pest insect Spodoptera littoralis (with an ED50 of 35 ppm) when incorporated in artificial diet and offered to larvae in a chronic feeding bioassay. Compound 7 was also active against the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus. Cytotoxicity was studied in vitro using L1578y mouse lymphoma cells. From the alkaloids studied, the N-oxides 3 and 4 were the most active (ED50 = 1.6 micrograms/mL) followed by compound 7 (ED50 = 1.8 micrograms/mL).

LanguageEnglish
Pages1056-1060
Number of pages5
JournalJournal of Natural Products
Volume59
Issue number11
Early online date22 Nov 1996
DOIs
Publication statusPublished - Nov 1996

Fingerprint

Xestospongia
Philippines
Porifera
Alkaloids
Oxides
Larva
Spodoptera
Electrospray ionization
Bioassay
Gram-Positive Bacteria
Bacilli
Cytotoxicity
Nutrition
Bacillus subtilis
Biological Assay
Insects
Staphylococcus aureus
Lymphoma
Bacteria
Nuclear magnetic resonance

Keywords

  • alkaloids
  • animals
  • anti-bacterial agents
  • antineoplastic agents
  • drug screening assays, antitumor
  • insecticides
  • magnetic resonance spectroscopy
  • mice
  • microbial sensitivity tests
  • philippines
  • porifera
  • spectrometry, mass, fast atom bombardment
  • spectrophotometry, infrared
  • tumor cells, cultured

Cite this

Edrada-Ebel, Ruangelie ; Proksch, P ; Wray, V ; Witte, L ; Müller, W E ; Van Soest, R W. / Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica. In: Journal of Natural Products. 1996 ; Vol. 59, No. 11. pp. 1056-1060.
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abstract = "Analysis of the Philippine marine sponge Xestospongia ashmorica afforded four new manzamine congeners 1-4 and four known compounds 5 and 7-9. Compound 1 is the 6-deoxy derivative of manzamine X, while 2-4 are the N-oxides of manzamine J (5), 3,4-dihydromanzamine A (6), and manzamine A (7), respectively. 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 (EI, FAB-MS, and electrospray ionization) data. Alkaloid N-oxide structures were confirmed by conversion to the corresponding tertiary bases by reduction with Zn/HCl. This is the first report of the occurrence of bioactive manzamine N-oxides in marine sponges. Compound 7 exhibited insecticidal activity toward neonate larvae of the polyphagous pest insect Spodoptera littoralis (with an ED50 of 35 ppm) when incorporated in artificial diet and offered to larvae in a chronic feeding bioassay. Compound 7 was also active against the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus. Cytotoxicity was studied in vitro using L1578y mouse lymphoma cells. From the alkaloids studied, the N-oxides 3 and 4 were the most active (ED50 = 1.6 micrograms/mL) followed by compound 7 (ED50 = 1.8 micrograms/mL).",
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Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica. / Edrada-Ebel, Ruangelie; Proksch, P; Wray, V; Witte, L; Müller, W E; Van Soest, R W.

In: Journal of Natural Products, Vol. 59, No. 11, 11.1996, p. 1056-1060.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica

AU - Edrada-Ebel, Ruangelie

AU - Proksch, P

AU - Wray, V

AU - Witte, L

AU - Müller, W E

AU - Van Soest, R W

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N2 - Analysis of the Philippine marine sponge Xestospongia ashmorica afforded four new manzamine congeners 1-4 and four known compounds 5 and 7-9. Compound 1 is the 6-deoxy derivative of manzamine X, while 2-4 are the N-oxides of manzamine J (5), 3,4-dihydromanzamine A (6), and manzamine A (7), respectively. 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 (EI, FAB-MS, and electrospray ionization) data. Alkaloid N-oxide structures were confirmed by conversion to the corresponding tertiary bases by reduction with Zn/HCl. This is the first report of the occurrence of bioactive manzamine N-oxides in marine sponges. Compound 7 exhibited insecticidal activity toward neonate larvae of the polyphagous pest insect Spodoptera littoralis (with an ED50 of 35 ppm) when incorporated in artificial diet and offered to larvae in a chronic feeding bioassay. Compound 7 was also active against the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus. Cytotoxicity was studied in vitro using L1578y mouse lymphoma cells. From the alkaloids studied, the N-oxides 3 and 4 were the most active (ED50 = 1.6 micrograms/mL) followed by compound 7 (ED50 = 1.8 micrograms/mL).

AB - Analysis of the Philippine marine sponge Xestospongia ashmorica afforded four new manzamine congeners 1-4 and four known compounds 5 and 7-9. Compound 1 is the 6-deoxy derivative of manzamine X, while 2-4 are the N-oxides of manzamine J (5), 3,4-dihydromanzamine A (6), and manzamine A (7), respectively. 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 (EI, FAB-MS, and electrospray ionization) data. Alkaloid N-oxide structures were confirmed by conversion to the corresponding tertiary bases by reduction with Zn/HCl. This is the first report of the occurrence of bioactive manzamine N-oxides in marine sponges. Compound 7 exhibited insecticidal activity toward neonate larvae of the polyphagous pest insect Spodoptera littoralis (with an ED50 of 35 ppm) when incorporated in artificial diet and offered to larvae in a chronic feeding bioassay. Compound 7 was also active against the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus. Cytotoxicity was studied in vitro using L1578y mouse lymphoma cells. From the alkaloids studied, the N-oxides 3 and 4 were the most active (ED50 = 1.6 micrograms/mL) followed by compound 7 (ED50 = 1.8 micrograms/mL).

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KW - animals

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KW - antineoplastic agents

KW - drug screening assays, antitumor

KW - insecticides

KW - magnetic resonance spectroscopy

KW - mice

KW - microbial sensitivity tests

KW - philippines

KW - porifera

KW - spectrometry, mass, fast atom bombardment

KW - spectrophotometry, infrared

KW - tumor cells, cultured

U2 - 10.1021/np9604083

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M3 - Article

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SP - 1056

EP - 1060

JO - Journal of Natural Products

T2 - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

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