Structural studies of naturally occurring toxicogenic compounds
The paralytic shellfish poison (PSP), saxitoxin, is a neurotoxin isolated from Alaska butter clams (Saxidomus giganteus), mussels (Mytilus californianus) and axenic cultures of the dinoflagellate Gonyaulax catenella. The structure of saxitoxin has been determined through the use of single crystal X-ray diffraction. It possesses a unique tricyclic arrangement of atoms containing two guanidinium moieties and also a hydrated ketone. The relative stereochemistry is presented as well as the absolute configuration. The chemical constitution of a tremorgenic metabolite, paxilline, isolated from extracts of the fungus Penicillium paxilli Bainier has been determined. Paxilline represents a previously unreported class of natural compounds formed by the combination of tryptophan and mevalonate subunits. The complete stereostructure of two other fungal metabolites, paspaline and paspalicine, closely related to paxilline but isolated from Claviceps paspali Stammes have also been determined and are presented. The stereochemistries of paxilline, paspaline and paspalicine are identical at corresponding chiral centers.
- Research Organization:
- Ames Lab., Ames, IA (United States)
- DOE Contract Number:
- W-7405-ENG-82
- OSTI ID:
- 5307954
- Report Number(s):
- IS-T-757
- Resource Relation:
- Other Information: Thesis
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
MOLLUSCS
TOXINS
PENICILLIUM
PROTOZOA
MOLECULAR STRUCTURE
STEREOCHEMISTRY
METABOLITES
X-RAY DIFFRACTION
ANIMALS
ANTIGENS
AQUATIC ORGANISMS
BIOMASS
COHERENT SCATTERING
DIFFRACTION
ENERGY SOURCES
FUNGI
INVERTEBRATES
MICROORGANISMS
PLANTS
RENEWABLE ENERGY SOURCES
SCATTERING
TOXIC MATERIALS
550200* - Biochemistry