Welwitindolinones, Unusual Alkaloids from the Blue-Green Algae Hapalosiphon welwitschii and Westiella intricata. Relationship to Fischerindoles and Hapalinodoles

Klemens Stratmann, Richard E. Moore, Gregory M.L. Patterson, Rosanne Bonjouklian, Jack B. Deeter, Stacey Shaffer, Tim A. Smitka, Charles Smith

Research output: Contribution to journalArticle

239 Citations (Scopus)

Abstract

N-Methyl welwitindolinone C isothiocyanate (7), the major indole alkaloid in the blue-green algae (cyanobacteria) Hapalosiphon welwitschii W. & G. S. West UHIC-52-3 and Westiella intricata Borzi UH HT-29-1 (Stigonemataceae), is responsible for some of the multiple-drug-resistance (MDR) reversing activity in H. welwitschii and most of the insecticidal activity in W. intricata. The oxindole was isolated from the lipophilic extracts of the two cyanophytes and its structure and absolute stereochemistry determined by X-ray crystallography. Fourteen additional alkaloids were isolated from H. welwitschii as minor constituents, viz. a novel spiro oxindole, welwitindolinone A isonitrile (1), five tetracyclic oxindoles (1-6) related to 7, and eight biogenetically-related fischerindoles (8-11) and hapalindoles (12-15). In addition to 1, five other alkaloids were isonitriles and these six compounds collectively accounted for the fungicidal activity of H. welwitschii. The gross structures and relative stereochemistries of 1-6 and 8-15 were elucidated by spectral analysis. The biogenesis of these alkaloids is discussed.

Original languageEnglish (US)
Pages (from-to)9935-9942
Number of pages8
JournalJournal of the American Chemical Society
Volume116
Issue number22
DOIs
StatePublished - Nov 1 1994

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Alkaloids
Cyanobacteria
Stereochemistry
Indole Alkaloids
X ray crystallography
X Ray Crystallography
Multiple Drug Resistance
Spectrum analysis
Pharmaceutical Preparations
oxindole
fischerindole

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Stratmann, Klemens ; Moore, Richard E. ; Patterson, Gregory M.L. ; Bonjouklian, Rosanne ; Deeter, Jack B. ; Shaffer, Stacey ; Smitka, Tim A. ; Smith, Charles. / Welwitindolinones, Unusual Alkaloids from the Blue-Green Algae Hapalosiphon welwitschii and Westiella intricata. Relationship to Fischerindoles and Hapalinodoles. In: Journal of the American Chemical Society. 1994 ; Vol. 116, No. 22. pp. 9935-9942.
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abstract = "N-Methyl welwitindolinone C isothiocyanate (7), the major indole alkaloid in the blue-green algae (cyanobacteria) Hapalosiphon welwitschii W. & G. S. West UHIC-52-3 and Westiella intricata Borzi UH HT-29-1 (Stigonemataceae), is responsible for some of the multiple-drug-resistance (MDR) reversing activity in H. welwitschii and most of the insecticidal activity in W. intricata. The oxindole was isolated from the lipophilic extracts of the two cyanophytes and its structure and absolute stereochemistry determined by X-ray crystallography. Fourteen additional alkaloids were isolated from H. welwitschii as minor constituents, viz. a novel spiro oxindole, welwitindolinone A isonitrile (1), five tetracyclic oxindoles (1-6) related to 7, and eight biogenetically-related fischerindoles (8-11) and hapalindoles (12-15). In addition to 1, five other alkaloids were isonitriles and these six compounds collectively accounted for the fungicidal activity of H. welwitschii. The gross structures and relative stereochemistries of 1-6 and 8-15 were elucidated by spectral analysis. The biogenesis of these alkaloids is discussed.",
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Welwitindolinones, Unusual Alkaloids from the Blue-Green Algae Hapalosiphon welwitschii and Westiella intricata. Relationship to Fischerindoles and Hapalinodoles. / Stratmann, Klemens; Moore, Richard E.; Patterson, Gregory M.L.; Bonjouklian, Rosanne; Deeter, Jack B.; Shaffer, Stacey; Smitka, Tim A.; Smith, Charles.

In: Journal of the American Chemical Society, Vol. 116, No. 22, 01.11.1994, p. 9935-9942.

Research output: Contribution to journalArticle

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T1 - Welwitindolinones, Unusual Alkaloids from the Blue-Green Algae Hapalosiphon welwitschii and Westiella intricata. Relationship to Fischerindoles and Hapalinodoles

AU - Stratmann, Klemens

AU - Moore, Richard E.

AU - Patterson, Gregory M.L.

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AB - N-Methyl welwitindolinone C isothiocyanate (7), the major indole alkaloid in the blue-green algae (cyanobacteria) Hapalosiphon welwitschii W. & G. S. West UHIC-52-3 and Westiella intricata Borzi UH HT-29-1 (Stigonemataceae), is responsible for some of the multiple-drug-resistance (MDR) reversing activity in H. welwitschii and most of the insecticidal activity in W. intricata. The oxindole was isolated from the lipophilic extracts of the two cyanophytes and its structure and absolute stereochemistry determined by X-ray crystallography. Fourteen additional alkaloids were isolated from H. welwitschii as minor constituents, viz. a novel spiro oxindole, welwitindolinone A isonitrile (1), five tetracyclic oxindoles (1-6) related to 7, and eight biogenetically-related fischerindoles (8-11) and hapalindoles (12-15). In addition to 1, five other alkaloids were isonitriles and these six compounds collectively accounted for the fungicidal activity of H. welwitschii. The gross structures and relative stereochemistries of 1-6 and 8-15 were elucidated by spectral analysis. The biogenesis of these alkaloids is discussed.

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