Sulfur (S) is an element of 15th largely existed in earth's crust, 10th in universe, and 7th in human body. S circulates the environmental sphere in various chemical forms, but SO₂ in atmosphere is largely responsible by human burning of S contained fuels and minerals. Underground resources of S and production type of S differ country by country. S content in crude oil varies ranging from less than 0.1% to more than 5% in every oilfield. Large S content unexpected from biological source theory of oil origin might be explained by that melted mineral origin elementary S in underground has met and dissolved into highly aromatic or naphthenic fractions of crude oil and secondarily converted to S compounds. Though supply of S as fertilizer to fields has been decreased, but SO₂ has played an important role of natural supply of S to the earth, especially in highly populated metropolitan areas.

View full abstract

Various organic compounds containing SH and/or SS are found in organisms, and are playing important roles to maintain life. In this review, the nature of the groups and their reactions of biological importance are described surrounding following topics : evolution of hydrogen sulfide from boiled egg, disulfide interchange, stereostructure of disulfide group, thioester linkage and its biological significance, role of acyl carrier protein, and metallothionein.

View full abstract

Abstract……Recent studies on the sulfur-containing amino acids, which are found in nature, are reviewed. The physiological significance, as well as their chemistry and metabolism, are also discussed. 194 references are cited.

View full abstract

Chemical and biochemical aspects of sulfur-containing vitamins, thiamine, lipoic acid and biotin, were outlined. About thiamine, especially the activity-structure relationship in the enzymatic degradation of pyruvate by pyruvate decarboxylase was described making refer to Schellenberger's work.

View full abstract

In this paper, the behavior of sulphur compounds in brewing of sake, beer and soy sauce was described.
The main sources of sulphur compounds in brewing are thought to be the chemical degradation of sulphur-containing amino acids, and the metabolism of microorganisms.
As sulphur compounds in sake-making process, dimethyl sulphide (DMS), methyl mercaptan (MeSH), hydrogen sulphide (H₂S) and dimethyl disulphide (DMDS) were detected.
DMDS was not found in fresh sake, but found in aged sake.
S-Adenosylmethionine (AMe) eluted from yeast cell was increased from the stage of 16% alcoholic formation in main mash, and gradually decomposed to 5'-methylthioadenosine (MTA) and homoserine for storage of sake.
AMe and MTA were the components characteristic of sake.
DMS was the main sulphur compounds through processing of beer, and the remaining DMS in finished beer was considered to contribute to beer flavor, especially to the flavor of Continental lager.
DMS in soy sauce was caused by hydrolysis of soybeans, therefore it was not found in soy sauce “kiage” which brewed with traditional method.
The sulphur compounds present in these fermented foodstuffs and beverages, although present in trace amounts, were thought to contribute to the flavor of them, but also they played unfavorite role causing the off-flavor of them.

View full abstract

The phenomenon of taste is best explained by selective adsorption of taste stimuli onto a taste receptor. The sulfur-containing compounds taste sweet, sour, salty, or flavorous, depending on their chmical structures. The structure-taste relationships of sulfur-containing compounds, such as sugars, amino acids, peptides, sulfamic acids, saccharin derivatives, oxathiazinone dioxides, thioureas, and 5'-nucleotides, are discussed. The recent concept of the taste receptor sites is also described.

View full abstract

The unpleasant odor of sulfur-containing organic substances has long been an annoyance to human beings as exemplified by the fact that the stench issued by the skunk is represented by 1-butanethiol and that many other mercaptans and hydrogen sulfide are currently under severe environmental regulations.
By the advent of recent chromatographic separation techniques together with micro-analytical tools, a variety of pleasant and unpleasant odorous substances have been isolated and characterized as being the aroma-bearing substances of many kinds of foods.
The present paper reviews these sulfur-containing substances in relation with their characteristic aroma of beef, “shiitake” an edible mushroom (Lentinus edodes Sing.), “sho-yu” a Japanese Soy-Sauce, tomato, potato and potato chips, coffee, cocoa, roasted nuts, bell peppers, and others.

View full abstract

Some of Cruciferous and Allinaceous vegetables are used as spices and their sulfur compounds are responsible, to a large extent, for their strong and distinctive flavors. The sulfur containing flavor compounds are formed enzymatically during chopping or crushing of those vegetables. Originally flavor enzymes and precursors exist independently, but they are brought in close contact to form the compounds.
The formation of sulfur containing flavor compounds in mustard, wasabi, horseradish, onion and garlic from their precursors is described in details in this chapter.

View full abstract

Typical ester sulfates found in nature are sulfated mucopolysaccharides from animal sources and sulfated glycans from seaweeds. This article deals with the distribution, variation of chemical structures and functions of sulfated mucopolysaccharides, such as chondroitin sulfates A, C, D, E, K, dermatan sulfate and dermatan polysulfates, heparin, heparan sulfate and keratan sulfates.

View full abstract

Malformins are cyclic pentapeptides which were isolated from the culture filtrate of the fungi of Aspergillus niger group as compounds causing curvatures on corn roots and malformations on the stems and petioles of bean plants. Malformin A (A₁>A₂), B (B₁+B₂), and C are known. Malformin A is cyclo-D-cysteinyl-D-cysteinyl-L-valyl-D-leucyl-L-isoleucyl. Malformin has a variety of biological activities : it inhibits adventitious root formation, stimulates abscission, inhibits ethylene- and phytochrome-mediated responses, potentiates and inhibits the effects of 2-chloroethylphosphonic acid, and also stimulates the stem elongation of bean seedlings or cuttings. A palindrome peptide, enantio- [5-valine] malformin, which was synthesized chemically, has one-tenth of activities of the natural malformin. Desthiomalformin has no activity showing the importance of the disulfide group of malformin.
Asparagusic acids, 1, 2-dithiolane-4-carboxylic acid and its derivatives, were isolated from Asparagus as compounds inhibiting lettuce seed germination and lettuce root and hypocotyl elongation. Asparagusic acid interacts with benzyladenine in radish cotyledon growth and lettuce seed germination and inhibits the activities of gibberellic acid and indoleacetic acid. Moreover asparagusic acid, which is structurally similar to lipoic acid, accelerates the biochemical oxidation of α-keto acids which is catalyzed by lipoic acid in vivo. The disulfide group and carboxylic acid are important in the activities of asparagusic acid.

View full abstract

The recent situations of sulphur-containing compounds which have been developed as agrochemicals for plant protection are reviewed from the standpoint of their use and biological properties in each field of fungicides, insecticides, acaricides and herbicides. In controlling plant diseases that are not easily controlled with the protectant fungicides such as the dithiocarbamates, many systemic fugicides including sulphur-containing compounds have been introduced commercially during the last 10 years. They are the oxathiins, thiabendazole, thiophanates and the other selective fungicides which are specifically effective against powdery mildew, soil fungal diseases and rice blast, respectively. In the field of insecticides, there are some new approaches to improve selectivity and toxicity in sulphur-containing compounds including organophosphates, oximcarbamates and natural toxin dervatives. The two new acaricides having the sulphur-containing group have been found from a series of diphenyl ether compounds. Although many commerical herbicides known so far genarally are used in pre-emergence treatment, recent advances in weed control have been made especially in post-emergence application with the selective type of sulphur-containing herbicides, such as the methylthio s-triazines, benzthiazoles, benzothiadiazine, sulphonamide derivatives and thiolcarbamates, etc.

View full abstract

Recently marketed and developing drugs are reviewed, whose mode of actions results from the functional groups containing sulfur atom, and whose molecular structures with sulfur atom possess characteristic biological activities.

View full abstract

This paper describes an extention of our previous work on the synthesis of fluorine containing alanine derivatives. Seven fluorine containing DL-phenylalanine derivatives have been prepared by the condensation reaction of fluorobenzyl chlorides, and trifluoromethyl- and chlorotrifluoromethylbenzyl chlorides with diethyl acetamidomalonate.
It was found that the new trifluoromethyl-substituted phenylalanines have higher solubilities in water compared with those of the parent phenylalanine.

View full abstract

Treatment of o-, m-, and p-acetotoluide and chloral with concsulfuric acid was found to give several products. Compounds isolated were 2-methyl-5- (1, 2, 2, 2-tetrachloroethyl) acetanilide (11), 3-acetamido-p-tolualdehyde (12) and 6, 6'-dimethy1-3, 3'-dichlorovinylidene-diacetanilide (13) from the reaction of o-acetotoluide with chloral. 3-Methyl-4- (1, 2, 2, 2-tetrachloroethyl) acetanilide (15), 4- (1-hydroxy-2, 2, 2-trichloroethyl) -3-methyl acetanilide (16) and an unidentified compound (17) were isolated from the eraction of m-acetotoluide. And then 4-methyl-3- (1, 2, 2, 2-tetrachloroethyl) acetanilide (3), an unidentified compound (18), 4-methyl-3- (2, 2, 2-trichloro-1-hydroxy ethyl) acetanilide (19), 5-acetamido-o-tolualdehyde (4) and α- (5-acetamido-o-tolyl) -α-chloroacetic acid (20) were isolated from the reaction products of p-acetotoluide. The structures of these compounds were established mainly by the spectroscopic studies and the process for the formation of these compounds was illustrated in Chart 1.

View full abstract