A new meroditerpenoid dimer from an undescribed Philippine marine sponge of the genus strongylophora

M Balbin-Oliveros, Ruangelie Edrada-Ebel, P Proksch, V Wray, L Witte, R W Van Soest

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

An undescribed Philippine marine sponge of the genus Strongylophora yielded a new meroditerpenoid-strongylophorine dimer (1) and the known meroditerpenoids, strongylophorine-2 (2), strongylophorine-3 (3), and strongylophorine-4 (4). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data. The position of the inter-unit linkage in the new compound was elucidated after methylation and 1D 1H NOE difference experiments. This is the first report wherein the1H and 13C NMR data of the strongylophorine congeners are fully and unambiguously assigned on the basis of 2D NMR spectroscopy. Compounds 2 and 3 exhibited slight activity against Micrococcus luteus and Salmonella typhii, respectively. Compound 3 was active against the phytopathogenic fungusCladosporium cucumerinum and also against the neonate larvae of the polyphagous pest insectSpodoptera littoralis (EC50 of 69 [+/-0.48 (S.E.)] ppm) when incorporated into artificial diet. Compound 1 was found to be the most active in the brine shrimp lethality test with a LC50 of 10.5 [+/-0.43 (S.E.)] microg/mL.

LanguageEnglish
Pages948-952
Number of pages5
JournalJournal of Natural Products
Volume61
Issue number7
DOIs
Publication statusPublished - Jul 1998

Fingerprint

Micrococcus luteus
Artemia
Philippines
Porifera
Salmonella
Dimers
Methylation
Larva
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
Diet
Nutrition
Nuclear magnetic resonance spectroscopy
Experiments
Carbon-13 Magnetic Resonance Spectroscopy
brine

Keywords

  • animals
  • antifungal agents
  • antineoplastic agents
  • artemia
  • bacteria
  • carbohydrate sequence
  • cladosporium
  • diterpenes
  • drug screening assays, antitumor
  • insecticides
  • magnetic resonance spectroscopy
  • mass spectrometry
  • microbial sensitivity tests
  • molecular conformation
  • molecular sequence data
  • philippines
  • porifera
  • spectrophotometry, infrared
  • spectrophotometry, ultraviolet
  • spores, fungal

Cite this

Balbin-Oliveros, M ; Edrada-Ebel, Ruangelie ; Proksch, P ; Wray, V ; Witte, L ; Van Soest, R W. / A new meroditerpenoid dimer from an undescribed Philippine marine sponge of the genus strongylophora. In: Journal of Natural Products. 1998 ; Vol. 61, No. 7. pp. 948-952.
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abstract = "An undescribed Philippine marine sponge of the genus Strongylophora yielded a new meroditerpenoid-strongylophorine dimer (1) and the known meroditerpenoids, strongylophorine-2 (2), strongylophorine-3 (3), and strongylophorine-4 (4). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data. The position of the inter-unit linkage in the new compound was elucidated after methylation and 1D 1H NOE difference experiments. This is the first report wherein the1H and 13C NMR data of the strongylophorine congeners are fully and unambiguously assigned on the basis of 2D NMR spectroscopy. Compounds 2 and 3 exhibited slight activity against Micrococcus luteus and Salmonella typhii, respectively. Compound 3 was active against the phytopathogenic fungusCladosporium cucumerinum and also against the neonate larvae of the polyphagous pest insectSpodoptera littoralis (EC50 of 69 [+/-0.48 (S.E.)] ppm) when incorporated into artificial diet. Compound 1 was found to be the most active in the brine shrimp lethality test with a LC50 of 10.5 [+/-0.43 (S.E.)] microg/mL.",
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A new meroditerpenoid dimer from an undescribed Philippine marine sponge of the genus strongylophora. / Balbin-Oliveros, M; Edrada-Ebel, Ruangelie; Proksch, P; Wray, V; Witte, L; Van Soest, R W.

In: Journal of Natural Products, Vol. 61, No. 7, 07.1998, p. 948-952.

Research output: Contribution to journalArticle

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T1 - A new meroditerpenoid dimer from an undescribed Philippine marine sponge of the genus strongylophora

AU - Balbin-Oliveros, M

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AU - Witte, L

AU - Van Soest, R W

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N2 - An undescribed Philippine marine sponge of the genus Strongylophora yielded a new meroditerpenoid-strongylophorine dimer (1) and the known meroditerpenoids, strongylophorine-2 (2), strongylophorine-3 (3), and strongylophorine-4 (4). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data. The position of the inter-unit linkage in the new compound was elucidated after methylation and 1D 1H NOE difference experiments. This is the first report wherein the1H and 13C NMR data of the strongylophorine congeners are fully and unambiguously assigned on the basis of 2D NMR spectroscopy. Compounds 2 and 3 exhibited slight activity against Micrococcus luteus and Salmonella typhii, respectively. Compound 3 was active against the phytopathogenic fungusCladosporium cucumerinum and also against the neonate larvae of the polyphagous pest insectSpodoptera littoralis (EC50 of 69 [+/-0.48 (S.E.)] ppm) when incorporated into artificial diet. Compound 1 was found to be the most active in the brine shrimp lethality test with a LC50 of 10.5 [+/-0.43 (S.E.)] microg/mL.

AB - An undescribed Philippine marine sponge of the genus Strongylophora yielded a new meroditerpenoid-strongylophorine dimer (1) and the known meroditerpenoids, strongylophorine-2 (2), strongylophorine-3 (3), and strongylophorine-4 (4). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data. The position of the inter-unit linkage in the new compound was elucidated after methylation and 1D 1H NOE difference experiments. This is the first report wherein the1H and 13C NMR data of the strongylophorine congeners are fully and unambiguously assigned on the basis of 2D NMR spectroscopy. Compounds 2 and 3 exhibited slight activity against Micrococcus luteus and Salmonella typhii, respectively. Compound 3 was active against the phytopathogenic fungusCladosporium cucumerinum and also against the neonate larvae of the polyphagous pest insectSpodoptera littoralis (EC50 of 69 [+/-0.48 (S.E.)] ppm) when incorporated into artificial diet. Compound 1 was found to be the most active in the brine shrimp lethality test with a LC50 of 10.5 [+/-0.43 (S.E.)] microg/mL.

KW - animals

KW - antifungal agents

KW - antineoplastic agents

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KW - bacteria

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KW - diterpenes

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KW - insecticides

KW - magnetic resonance spectroscopy

KW - mass spectrometry

KW - microbial sensitivity tests

KW - molecular conformation

KW - molecular sequence data

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KW - spectrophotometry, ultraviolet

KW - spores, fungal

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T2 - Journal of Natural Products

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SN - 0163-3864

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