Scoliidines: Neuroprotective Peptides in Solitary Scoliid Wasp Venoms.

A comprehensive LC-MS study examined the venom components of the solitary scoliid wasp . Online mass fingerprinting showed that crude venom contains 25 small molecules (amino acids, biogenic amines, and nucleosides/nucleotides) and 45 peptides with MW 400-2700. The small molecules were identified by elemental composition analysis, and peptide sequences were determined by ESI-MS/MS and MALDI-TOF/TOF MS analyses.

Temporal dynamics of N-hydroxypipecolic acid and salicylic acid pathways in the disease response to powdery mildew in wheat.

Wheat (Triticum aestivum) is a major staple crop worldwide, and its yields are significantly threatened by wheat powdery mildew (Blumeria graminis f. sp. tritici).

"Fruiting Liquid" of Mushroom-Forming Fungi, A Novel Source of Bioactive Compounds - Fruiting-Body Inducer and HIF and Axl Inhibitors.

In general, mushroom-forming fungi secrete liquid on the surface of mycelia just before fruiting-body formation. However, no researchers in mushroom science have paid attention to the liquid until now. We formulated a hypothesis that the liquid plays an important role(s) in the formation of the fruiting body and produces various bioactive compounds and named it the "fruiting liquid (FL)".

Comprehensive Analysis and Biological Characterization of Venom Components from Solitary Scoliid Wasp .

Venoms of solitary wasps are utilized for prey capture (insects and spiders), paralyzing them with a stinger injection to be offered as food for their larvae. Thus, the identification and characterization of the components of solitary wasp venoms can have biotechnological application. In the present study, the venom components profile of a solitary scoliid wasp, , was investigated through a comprehensive analysis using LC-MS and -MS/MS.

Novel neuroprotective peptides in the venom of the solitary scoliid wasp .

Background: Solitary wasp venoms may be a rich source of neuroactive substances, since their venoms are used for paralyzing preys. We have been exploring bioactive constituents of solitary wasp venoms and, in this study, the component profile of the venom from a solitary scoliid wasp, , was investigated through a comprehensive analysis using LC-MS. Two peptides were synthesized, and their neuroprotective properties were evaluated.

Isolation and characterization of FMRFamide-like peptides in the venoms of solitary sphecid wasps.

Purification of small peptide components in the venoms of the solitary sphecid wasps, Sphex argentatus argentatus and Isodontia harmandi, led to the isolation of several major peptides. Analysis of MS/MS spectra by MALDI-TOF/TOF revealed the sequence of a new peptide Sa112 (EDVDHVFLRF-NH), which is structurally very similar to leucomyosupressin (pQDVDHVFLRF-NH) and SchistoFLRFamide (PDVDHVFLRF-NH), the FMRFamide-like peptides from cockroach and locust, respectively. Indeed, this new peptide, like SchistoFLRFamide, inhibited the frequency and amplitude of spontaneous contractions of the locust oviduct in a dose-dependent manner.

Synthesis, structural revision, and tyrosinase inhibitory activity of proposed phloretin-4-O-β-D-glucopyranoside from .

Phloretin-4--β-D-glucopyranoside (), isolated from , was synthesized for the first time through aldol condensation and Schmidt glycosylation reactions aiming to develop a novel hydrophilic tyrosinase inhibitor. However, the specific rotation of synthetic was found to be negative and different from that reported for natural product . Thus, L-glucoside was chemically synthesized using the established synthetic route of , suggesting that the configuration of the natural product was the same as that of , as their specific rotation and spectroscopic data were also the same.

Comprehensive analysis of peptides and low molecular weight components of the giant ant Dinoponera quadriceps venom.

Ants (Hymenoptera, Apocrita, Aculeata, Formicoidea) comprise a well-succeeded group of animals. Like bees and wasps, ants are mostly venomous, having a sting system to deliver a mixture of bioactive organic compounds and peptides. The predatory giant ant Dinoponera quadriceps belongs to the subfamily Ponerinae that includes one of the largest known ant species in the world.

Tyrosinase Inhibition by 4-Substituted Benzaldehydes with Electron-Withdrawing Groups.

The oxidation of 4-t-butylcatechol catalyzed by mushroom tyrosinase was inhibited by 4-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-fluorobenzaldehyde, 4-cyanobenzaldehyde, and 4-nitrobenzaldehyde with 50% inhibitory concentrations of 114 μM, 175 μM, 387 μM, 822 μM, and 1846 μM, respectively. The inhibition kinetics were analyzed by Dixon plots, which indicated that a series of 4-hallogenated benzaldehydes acted as partial noncompetitive inhibitors in the same manner as benzaldehyde. Although β values were decreased with an increase of the tyrosinase inhibitory activity, full inhibition could not be observed.

Comprehensive analysis of peptides and low molecular weight components of the giant ant Dinoponera quadriceps venom.

Ants (Hymenoptera, Apocrita, Aculeata, Formicoidea) comprise a well-succeeded group of animals. Like bees and wasps, ants are mostly venomous, having a sting system to deliver a mixture of bioactive organic compounds and peptides. The predatory giant ant Dinoponera quadriceps belongs to the subfamily Ponerinae that include one of the largest known ant species in the world.

Benzonitriles as tyrosinase inhibitors with hyperbolic inhibition manner.

As a novel mushroom tyrosinase inhibitor, 4-methoxybenzonitrile (anisnitrile) was identified (IC = 111.1 μM) with hyperbolic inhibition manner. The calculated αK (166.

Molecular design of potent, hydrophilic tyrosinase inhibitors based on the natural dihydrooxyresveratrol skeleton.

In this study, dihydrooxyresveratrol glucosides 3-6 were synthesized for the first time to the best of our knowledge by the Wittig reaction and Schmidt glycosylation as key steps for the purpose of developing novel hydrophilic tyrosinase inhibitors. Results obtained from inhibitory studies revealed 50% inhibitory concentration (IC) values of 12.80 μM and 2.

Resorcinol alkyl glucosides as potent tyrosinase inhibitors.

Resorcinol alkyl glucosides 7-12 were developed as novel tyrosinase inhibitors based on the structure of rhododendrin. These were synthesized from 2,4-dibenzyloxybenzaldehyde using either the Wittig or the Horner-Wadsworth-Emmons reaction with Koenigs-Knorr glycosylation as key steps. The tyrosinase inhibitory activity of 7-12 increased with the length of the alkyl spacer between resorcinol and glucose.

Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides.

Isotachioside (1) and its related natural product 2 are isolated from Isotachis japonica and Protea neriifolia, respectively, and are categorized as analogs of arbutin (3), a tyrosinase inhibitor for practical use. Both of the natural products and several derivatives such as glucoside 4, xyloside 5, cellobioside 6, and maltoside 7 were synthesized via Schmidt glycosylation as a key step, and their tyrosinase inhibitory activity was evaluated. The half maximal inhibitory concentration (IC) of 1-3 could not be determined even when the concentration was increased to 1000 μM.

Peptidomic analysis of the venom of the solitary bee .

Background: Among the hymenopteran insect venoms, those from social wasps and bees - such as honeybee, hornets and paper wasps - have been well documented. Their venoms are composed of a number of peptides and proteins and used for defending their nests and themselves from predators. In contrast, the venoms of solitary wasps and bees have not been the object of further research.

Chemical synthesis, redox transformation, and identification of sonnerphenolic C, an antioxidant in Acer nikoense.

Sonnerphenolic C (3), which was predicted in a redox product of epirhododendrin (1) isolated from Acer nikoense, was synthesized for the first time via the epimeric separation of benzylidene acetal intermediates as a key step. From a similar synthetic route, 1 was obtained concisely. As a result of their antioxidative evaluation, only 3 revealed potent activity.

Substituent effect of benzaldehydes on tyrosinase inhibition.

Benzaldehyde inhibited the oxidation of 4-t-butylcatechol catalyzed by mushroom tyrosinase with an IC of 31.0 μM. The inhibition kinetics analyzed by Dixon plot indicated that it acts as a partial noncompetitive inhibitor.

Anti-hyperuricemic effect of taxifolin in cultured hepatocytes and model mice.

Hyperuricemia is recognized as an important risk factor for gout. High dietary intake of purine-rich foods such as meats and sea foods increases uric acid (UA) levels in the blood. Taxifolin present in Siberian larch and strawberries has been reported to possess health promoting activities including anti-oxidant effect.

Dihydroresveratrol cellobioside and xylobioside as effective melanogenesis activators.

Dihydroresveratrol cellobioside and xylobioside, whose structures were designed based on that of the naturally occurring melanogenesis-controlling agent dihydroresveratrol glucoside, were synthesized via Schmidt glycosylation as the key step. Both analogues stimulated melanogenesis with efficacies comparable to that of 8-methoxypsoralen, a well-known melanogenesis activator. This suggests that diglycosyl modification of the 4'-OH on the dihydroresveratrol skeleton leads to the activation of melanogenesis, both with and without hydroxymethyl groups in the sugar moieties.

Cloning and Functional Analysis of Three Chalcone Synthases from the Flowers of Safflowers Carthamus tinctorius.

The flowers of safflowers (Carthamus tinctorius L.) are very important as they are the sole source of their distinct pigments, i.e.

Peptide Toxins in Solitary Wasp Venoms.

Solitary wasps paralyze insects or spiders with stinging venom and feed the paralyzed preys to their larva. Accordingly, the venoms should contain a variety of constituents acting on nervous systems. However, only a few solitary wasp venoms have been chemically studied despite thousands of species inhabiting the planet.

Rhododendrol glycosides as stereospecific tyrosinase inhibitors.

Rhododendrol derivatives 3-12 have been synthesized in six steps, including aldol condensation and/or trichloroacetimidate glycosylation as the key reactions. Each derivative showed effective inhibition of tyrosinase-catalyzed oxidation processes. In particular, a series of synthetic derivatives having an R-stereogenic center at C-2 proved to be more potent than their respective epimers.

Synthesis of dihydroresveratrol glycosides and evaluation of their activity against melanogenesis in B16F0 melanoma cells.

Dihydroresveratrol glucoside 1 isolated from Camellia oleifera and its xyloside derivative 2 were synthesized for the first time in 5 steps from TBS-protected aldehyde 4. Natural product 1 is a potent melanogenesis inhibitor in B16F0 melanoma cells (approximately 40 fold more potent than kojic acid). In contrast, the synthetic product 2 stimulates melanogenesis, suggesting that a single hydroxymethyl group in the glycoside substituent of dihydroresveratrols is responsible for inhibition or activation of melanogenesis.

Inhibitory effects of cardols and related compounds on superoxide anion generation by xanthine oxidase.

5-Pentadecatrienylresorcinol, isolated from cashew nuts and commonly known as cardol (C₁₅:₃), prevented the generation of superoxide radicals catalysed by xanthine oxidase without the inhibition of uric acid formation. The inhibition kinetics did not follow the Michelis-Menten equation, but instead followed the Hill equation. Cardol (C₁₀:₀) also inhibited superoxide anion generation, but resorcinol and cardol (C₅:₀) did not inhibit superoxide anion generation.

Chemical synthesis and tyrosinase inhibitory activity of rhododendrol glycosides.

The concise synthesis of rhododendrol glycosides 3-8, which are novel derivatives of (+)-epirhododendrin (1) and (-)-rhododendrin (2), has been achieved in six steps from benzaldehyde 9. The key reactions include aldol condensation and trichloroacetimidate glycosylation. From biological studies, it has been determined that synthetic derivatives of 1 and 2 possess potent tyrosinase inhibitory activity.