Phytohormones regulate the protective responses of plants against both biotic and abiotic stresses by means of synergistic or antagonistic actions referred to as signaling crosstalk. A bottleneck in crosstalk research is the quantification of numerous interacting phytohormones and regulators. The chemical analysis of salicylic acid, jasmonic acid, indole-3-acetic acid, and abscisic acid is typically achieved by using separate and complex methodologies. Moreover, pathogen-produced phytohormone mimics, such as the phytotoxin coronatine (COR), have not been directly quantified in plant tissues. We address these problems by using a simple preparation and a GC-MS-based metabolic profiling approach. Plant tissue is extracted in aqueous 1-propanol and mixed with dichloromethane. Carboxylic acids present in the organic layer are methylated by using trimethylsilyldiazomethane; analytes are volatilized under heat, collected on a polymeric absorbent, and eluted with solvent into a sample vial. Analytes are separated by using gas chromatography and quantified by using chemical-ionization mass spectrometry that produces predominantly [M+H]+ parent ions. We use this technique to examine levels of COR, phytohormones, and volatile organic compounds in model systems, including Arabidopsis thaliana during infection with Pseudomonas syringae pv. tomato DC3000, corn (Zea mays) under herbivory by corn earworm (Helicoverpa zea), tobacco (Nicotiana tabacum) after mechanical damage, and tomato (Lycopersicon esculentum) during drought stress. Numerous complex changes induced by pathogen infection, including the accumulation of COR, salicylic acid, jasmonic acid, indole-3-acetic acid, and abscisic acid illustrate the potential and simplicity of this approach in quantifying signaling crosstalk interactions that occur at the level of synthesis and accumulation.

https://www.pnas.org/content/pnas/100/18/10552.full.pdf

Simultaneous analysis of phytohormones, phytotoxins, and volatile organic compounds in plants

An element of surprise: A series of functionalized 2-alkynyl arylazides has beed converted into 3-substituted indoles or 2,2-disubstituted indolin-3-ones in the presence of a gold(I) complex. Various oxygen or aryl nucleophiles can be used in this process to trap the intermediate a-imino gold carbene. The structural motifs of the products are found in a large variety of biologically active compounds and natural products. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Gold‐Catalyzed Transformation of 2‐Alkynyl Arylazides: Efficient Access to the Valuable Pseudoindoxyl and Indolyl Frameworks

Induction of volatile biosynthesis in the lima bean (Phaseolus lunatus) by leucine- and isoleucine conjugates of 1-oxo- and 1-hydroxyindan-4-carboxylic acid: evidence for amino acid conjugates of jasmonic acid as intermediates in the octadecanoid signalling pathway.

The Willgerodt–Kindler reaction has, in recent years, received limited attention and application in synthetic organic chemistry. With the advent of new technology such as microwave-assisted heating, several new, high-yielding, practical, and more environmentally friendly reaction protocols have been developed. This review aims to once again draw attention to this relatively underutilised process by highlighting the recent developments in the Willgerodt–Kindler reaction in the synthesis of (thio)amides, carboxylic acids, and heterocycles.

Recent advances in the Willgerodt–Kindler reaction

The present invention relates to novel aryl isoxazoline derivatives having excellent insecticidal activity as insecticides and represented by the formula ( I ): and their use as insecticides and acarizides.

Insecticidal aryl isoxazoline derivatives

Syntheses of 19-Nor-3-ketosteroids

6-Chloro-5-cyclohexylindan-l-carboxylic Acid (TAI-284), a New Antiinflammatory Agent

Spiro [cyclopropane-1, 2'-[2H] indol]-3'(1'H)-ones with various substituents on the benzene ring and at the 1'-position were synthesized. Investigation of their biological activities revealed that significant anti-inflammatory and analgesic activities were exhibited by some compounds of this series. Their structure-activity relationships are discussed.

https://www.jstage.jst.go.jp/article/cpb1958/29/7/29_7_1912/_pdf

Spirocyclopropane Compounds. II. Synthesis and Biological Activities of Spiro [cyclopropane-1, 2'-[2H] indol]-3'(1'H)-ones

The relative reactivity in each position of 1-indancarboxylic acid (IV) toward electro-hilic substitution reaction such as chlorination, bromination, acylation, sulfonation and nitration was examined and it was found that the 6-position is the most reactive. By these reactions, pharmacologically interesting meta-substituted phenylacetic acid derivatives were readily obtained. Electrophilic chlorination of IV followed by cycloalkylation provided an improved alternative synthetic method of antiinflammatory 6-chloro-5-cyclohexyl-1-indancarboxylic acid (TAI-284, I) and its analogs.

1-Indancarboxylic Acids. I. Electrophilic Substitution Reactions of 1-Indancarboxylic Acid and Synthesis of 6-Substituted 1-Indancarboxylic Acids as Potential Antiinflammatory Agents

5'-Methyl-5α-androstano[16, 17-c]isoxazolin-3β-ol (Va) and 5'-methylandrost-5-eno[16, 17-c]isoxazolin-3β-ol (Vb), were obtained by treatment of 3β, 20α-dihydroxy-5α-pregnan-16-one 3-acetate 16-oxime (IIIa) or 3β, 20α-dihydroxypregn-5-en-16-one 3-acetate 16-oxime (IIIb) with tosyl chloride in pyridine followed by alkaline hydrolysis Oxidation of Va and Vb gave the corresponding 3-oxo-compounds, VIa and VIb VIb was further isomerized to 5'-methylandrost-4-eno[16, 17-c]isoxazolin-3-one (VIIb)

Shunsaku Noguchi

Papers

Syntheses of 19-Nor-3-ketosteroids

6-Chloro-5-cyclohexylindan-l-carboxylic Acid (TAI-284), a New Antiinflammatory Agent

Spirocyclopropane Compounds. II. Synthesis and Biological Activities of Spiro [cyclopropane-1, 2'-[2H] indol]-3'(1'H)-ones

1-Indancarboxylic Acids. I. Electrophilic Substitution Reactions of 1-Indancarboxylic Acid and Synthesis of 6-Substituted 1-Indancarboxylic Acids as Potential Antiinflammatory Agents

Steroid(16,17-c)isoxazoline.