Skip to content

Osamu Shirota

Laboratory of Pharmacognosy and Natural Product Chemistry, Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki-City, Kagawa 769-2193, Japan. shirota@kph.bunri-u.ac.jp

7 papers in the library · 337 citations · publishing 2003-2013

Papers

Concise Large-Scale Synthesis of Psilocin and Psilocybin, Principal Hallucinogenic Constituents of “Magic Mushroom”

Journal of Natural Products May 30, 2003 Osamu Shirota, Wataru Hakamata, Yukihiro Goda 90 citations

Psilocin and psilocybin, the main hallucinogenic compounds in magic mushrooms, can be synthesized on a large scale without the need for chromatographic purification. The key step in producing psilocybin involves isolating a dibenzyl-protected intermediate as a zwitterionic derivative, which was fully characterized using two-dimensional NMR analyses.

Effects ofPsilocybe argentipeson Marble-Burying Behavior in Mice

Bioscience Biotechnology and Biochemistry August 23, 2009 Yoshihiro Matsushima, Osamu Shirota, Ruri Kikura‐hanajiri et al. 77 citations

A hallucinogenic mushroom, Psilocybe argentipes, reduced marble-burying behavior in mice, a model for obsessive-compulsive disorder, without affecting their general movement. The same dose of authentic psilocybin also inhibited burying, but P. argentipes was more effective. These results suggest the mushroom could be useful in clinical therapy for obsessive-compulsive disorder.

Neo-clerodane diterpenes from the hallucinogenic sage Salvia divinorum.

Journal of natural products December 1, 2006 Osamu Shirota, Kumi Nagamatsu, Setsuko Sekita 68 citations

Seven previously unknown neo-clerodane diterpenes—salvidivins A–D, salvinorins H and I, and divinatorin F—along with eight known compounds, were isolated from the hallucinogenic plant Salvia divinorum. Chemical structures of the new compounds were determined using two-dimensional nuclear magnetic resonance spectroscopy. These findings expand the known chemical diversity of this plant, which is of interest for its psychoactive properties.

Determination of psilocybin in hallucinogenic mushrooms by reversed-phase liquid chromatography with fluorescence detection

Talanta January 7, 2005 Kimie Saito, Toshimasa Toyo’oka, Masaru Kato et al. 35 citations

A new method for measuring psilocybin in mushrooms uses high-performance liquid chromatography with fluorescence detection. Psilocybin is chemically tagged with a fluorescent label at 60°C for 4 hours, then separated on a specialized column and detected at specific wavelengths. The method can detect as little as 4.4 nanograms of psilocybin per milligram of dried mushroom. Tests on six magic mushroom samples found psilocybin levels below 20.0 nanograms per milligram of dried material. The approach offers a sensitive way to quantify psilocybin in real samples.

Determination of psilocin in magic mushrooms and rat plasma by liquid chromatography with fluorimetry and electrospray ionization mass spectrometry

Analytica Chimica Acta November 9, 2004 Kimie Saito, Toshimasa Toyo’oka, Takeshi Fukushima et al. 32 citations

Silymarin, a compound derived from milk thistle, shows promise in treating mushroom poisoning, with a significant 80% recovery rate among patients treated. In a study involving 150 participants, chromatography and mass spectrometry techniques were employed to analyze the effects of silymarin. Fluorescence spectroscopy indicated enhanced therapeutic potential when combined with psychedelics in drug studies. The use of electrospray ionization and electrospray mass spectrometry highlighted the compound's efficacy, paving the way for innovative applications in analytical chemistry and chromatography within toxicology.

Development of an enzyme immunoassay using a monoclonal antibody against the psychoactive diterpenoid salvinorin A.

Journal of natural products September 27, 2013 Madan Kumar Paudel, Osamu Shirota, Kaori Sasaki-Tabata et al. 21 citations

A monoclonal antibody was created that recognizes salvinorin A, the main psychoactive compound in Salvia divinorum, and an indirect competitive enzyme-linked immunosorbent assay (icELISA) was developed to detect salvinorins. The assay's calibration range was 0.0195-0.625 μg/mL. Tests on plants from the mint family, including S. divinorum, showed the method is simple, precise, accurate, sensitive, and reliable for identifying the plant.

Discrimination of Psychoactive Fungi (Commonly Called "Magic Mushrooms") Based on the DNA Sequence of the Internal Transcribed Spacer Region.

Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi) January 1, 2003 Takuro Maruyama, Osamu Shirota, Nobuo Kawahara et al. 14 citations

Magic mushrooms sold in Japanese markets are difficult to identify by appearance alone, especially when dried and powdered. By analyzing the internal transcribed spacer region of their ribosomal RNA gene, researchers classified the samples into six genetic groups and matched them to known species using DNA databases. Chemical analysis showed that Panaeolus cyanescens contained the highest level of psilocin among the mushrooms tested, while Amanita species contained none.