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Papers by William F. Wood

Biochemical and biophysical research communications, Jun 26, 2017

Tyrosinase-catalyzed l-tyrosine oxidation is a key step in melanogenesis, and intense melanin for... more Tyrosinase-catalyzed l-tyrosine oxidation is a key step in melanogenesis, and intense melanin formation is often a problem in chemotherapies or food preservation. Here we report that methyl cinnamate one of the constituents characterized from mycelium and sporocarp of American matsutake mushroom Tricholoma magnivelare inhibits both enzymatic and cellular melanin formation. Methyl cinnamate inhibits mushroom tyrosinase-catalyzed l-tyrosine oxidation while the oxidation of L-3,4-dihydroxyphenylalanine (l-DOPA) was not inhibited. In subsequent cellular assays, methyl cinnamate significantly suppressed melanogenesis of murine B16-F10 melanoma cells without affecting cell growth. However, methyl 3-phenylpropionate, a dihydro-derivative of methyl cinnamate, did not possess melanogenesis, indicating that the double bond in the enone moiety is a key Michael reaction acceptor to elicit the activity. In addition, a rather rare chlorinated benzaldehyde derivative, 3,5-dichloro-4-methoxybenzald...

GC-MS analysis of the anal sac secretion from the hooded skunk, Mephitis macroura, showed the fol... more GC-MS analysis of the anal sac secretion from the hooded skunk, Mephitis macroura, showed the following seven major components comprised 99% of the volatiles in this secretion: (E)-2-butene-1-thiol, 3-methyl-1-butanethiol, S-(E)-2-butenyl thioacetate, S-3-methylbutenyl thioacetate, 2phenylethanethiol, 2-methylquinoline, and 2-quinolinemethanethiol. Minor volatile components identified in this secretion are phenylmethanethiol, S-phenylmethyl thioacetate, S-2-phenylethyl thioacetate, bis[(E)-2-butenyl] disulfide, (E)-2-butenyl 3-methylbutyl disulfide, bis(3-methylbutyl) disulfide, and S-2-quinolinemethyl thioacetate. This secretion is similar to that of the striped skunk, Mephitis mephitis, differing only in that it contains four compounds not reported from the striped skunk: phenylmethanethiol, Sphenylmethyl thioacetate, 2-phenylethanethiol, and S-2-phenylethyl thioacetate.

CHEMICAL & PHARMACEUTICAL BULLETIN, 1985

Biochemical Systematics and Ecology, 2000

GC-MS analysis of the defensive secretion from the millipede Buzonium crassipes showed three vola... more GC-MS analysis of the defensive secretion from the millipede Buzonium crassipes showed three volatile components,-pinene (35%), limonene (6%) and a new alkaloid, buzonamine (59%). Buzonamine had an HRMS molecular ion at m/z"221.1785 (calculated for C H NO, 221.1781), 14 carbons in the C-NMR and 23 hydrogens by SFORD, DEPT and APT experiments. All distinct H nuclei were assigned to C resonances with 2D H}C COSY data, and the "nal structure was determined by H}H COSY, H}C HMBC and nOe experiments. Buzonamine contains four rings including an epoxy group and a tertiary nitrogen.-Pinene, limonene or buzonamine, kept the mound nesting ant, Formica obscuripes, from eating mealworms (Tenebrio molitor) treated with 1 mg of the chemical. A 150 mg millipede expels 4 mg of secretion.

Journal of Apicultural Research, 1983

Anaesthesia of honeybees by smoke from burning African puffball Langermannia wahlbergi Lycoperdal... more Anaesthesia of honeybees by smoke from burning African puffball Langermannia wahlbergi Lycoperdales : Lycoperdaceae is due in part to hydrogen sulphide, one of the products of pyrolysis, though hydrogen cyanide and other unidentified substances may act along with the hydrogen sulphide. Hydrogen sulphide is also produced during the pyrolysis of human hair and was shown to be the principal agent responsible for the anaesthesia of honeybees. Preliminary studies using human hair or chicken feathers as a source of smoke indicate that its use to anaesthetize bees does not shorten their lives. Properly used, human hair or chicken feathers might enable tropical African beekeepers to anaesthetize their bees when harvesting honey.

Annals of the Entomological Society of America, 1974

The defensive secretions of many millipedes contain quinones, of which the most common are toluqu... more The defensive secretions of many millipedes contain quinones, of which the most common are toluquinone and 2-methoxy-3-methylbenzoquinone (Weatherston and Percy 1970). I report identification of these quinones from Archispirostreptus gigas Peteres (Spirostreptida: Spirostreptidae), Prionopetalum frundsbergi Attems (Spirostreptida: Odontopygidae) and Prionopetalum tricuspis Brolemann (Spirostreptida: Odontopygidae).

Annals of the Entomological Society of America, 1975

Soldiers of the termite Odontotermes badius Haviland expel an odorous, opaque, aqueous, brown def... more Soldiers of the termite Odontotermes badius Haviland expel an odorous, opaque, aqueous, brown defensive secretion which becomes sticky and rubbery on exposure to air. Chemical analysis of the secretion shows it to contain a mixture of benzoquinone and protein. The amino acid residues making up the protein were determined, and the mechanism of secretion hardening was examined. Although many termites have been reported to use chemical means to repel predators, there have been only a few detailed studies on the chemical nature of these defenses (Noirot 1969). Moore (1968) has studied the chemistry of several Australian termite defensive secretions. More recently the defensive

Mycologia, 1986

, and-. 1985. Widespread haploidy in monokaryotic cells of mature basidiocarps of Armillaria bulb... more , and-. 1985. Widespread haploidy in monokaryotic cells of mature basidiocarps of Armillaria bulbosa. a member of the Armillaria mellea complex.

Phytochemistry, 1996

Methyl cinnamate was identified as the major volatile component from two populations of Conocepha... more Methyl cinnamate was identified as the major volatile component from two populations of Conocephalum conicum, but was not detected in other populations.

Mycologia, 2003

The odor emanating from sporocarps of Hygrophorus paupertinus is disagreeable and fecallike. Soli... more The odor emanating from sporocarps of Hygrophorus paupertinus is disagreeable and fecallike. Solid phase microextraction (SPME) and analysis by gas chromatography-mass spectrometry (GC-MS) showed 1-octen-3-ol, indole and 3-chloroindole were responsible for the odor. This is the first case in which 3-chloroindole has been identified from a terrestrial organism.

Mycologia, 2004

Clitolactone, 5-(chloromethyl)-3-methyl-2 (5H)-furanone, was isolated from sporocaps of the mushr... more Clitolactone, 5-(chloromethyl)-3-methyl-2 (5H)-furanone, was isolated from sporocaps of the mushroom Clitocybe flaccida. The structure was determined by HRMS, EIMS, 1 H & 13 C NMR, 2D 1 H-13 C COSY and 1 H-1 H COSY. This mushroom is not eaten by the banana slug Ariolimax columbianus (Gould), a mycophagist from the temperate rain forests of the Pacific Northwest. Clitolactone acts as an antifeedant because these slugs rejected 1.0 cm 2 pieces of lettuce treated with 25 g of clitolactone.