Nicolas-Theodore Gobley
Encyclopedia
Theodore Gobley, who first isolated, and ultimately determined the chemical structure of lecithin
, the first identified and characterized member of the phospholipid
s class, and a pioneer researcher in the study and analysis of the chemical components of brain
tissues, was born in Paris
on May 11, 1811 and died in Bagneres-de-Luchon
(a small city in central Pyrenees famous in the second half of the 19th century for its thermal waters) on September 1, 1876.
. His father had settled at the end of the 18th century as a wine broker in Paris, marrying a young lady in a family long established (since at least the beginning of the 17th century) in that trade in the capital city of France (that family, Boutron, was registered in the 17th and 18th centuries as one of the 12 suppliers of wines to the King’s Court ).
Wine trading had strong links with alcoholic distillation, some close kin of the Boutron family were indeed spirits distillers, and it is likely this environment that led Theodore to studies in chemistry and pharmacy.
Indeed, an historical study conducted in 1957 by P. et C.Chatagnon on the early steps of brain tissues chemical structure studies mentions that Gobley effected a stay as apprentice by one of his parents named Guerin, indicated as pharmacist (actually, his brother-in-law, Denis Guerin 1798-1888, pharmacist in Paris for a few years in the early 1830s, but more well known as mayor of the city of Fontainebleau
during close to 30 years, from 1843 till 1871, and so far as known, not related to the Boutron family).
Whatever the initial lead, further on Gobley enters full grade studies in pharmacy and in the early 1830s attends courses delivered by one of the great figures of French pharmaceutical and chemistry arts of that time, Pierre Jean Robiquet
, of whom he became a close collaborator, and ultimately his son-in-law, through marrying Laure Robiquet, one of the daughters of his master and mentor .
Robiquet (1780–1840), a long standing professor at the Ecole de Pharmacie in Paris (since 1811) was a very prominent, respected and honoured player amongst the French chemists/pharmacists community of the first half of the 19th century: member of the “Société de Pharmacie” later on designated as the “Académie Nationale de Pharmacie” (1817), of which he was Secretary General then President, (1817 till his death) (go to (http://www.shp-asso.org/)), member of the "Académie de Médecine" (1820), member of the “Académie des Sciences”, distinguished with the order of “Légion d’Honneur”, author of numerous studies and pioneering work in the research of complex molecules in natural bodies, either plants or animals, who had isolated such fundamentals products, as caffeine
, cantharidin
, and most of all the alizarin
, a powerful and stable red dye that was to become one of the first dyes to be mass produced through a pure chemical synthesis path,
Theodore Gobley qualifies as a pharmacist in 1835, marries Laure Robiquet in 1837, and establishes himself as pharmacist in Paris (60 rue du Bac; the place has been run down when Boulevard Saint Germain was opened some 30 years later); in parallel to his trade, in his personal lab he conducts his researches, and follows a path very similar to that of his father-in–law (demised in 1840): he enters the Ecole de Pharmacie as professor in 1842 (he will quit in 1847), becomes a member of the Académie Nationale de Pharmacie in 1843, of which he becomes President in 1861, and is admitted a member of the “Académie de Médecine” that same year.
While conducting various works on a very diversified range of topics very much like most pharmacist/chemists of the 19th century, Gobley singled himself out by a somehow unique lifelong pursuit in the study of lipids in the living animals reign, whereby he demonstrated the universal presence of a fundamental substance, which he will name “lecithin”, and the exact composition of which he will pursue during thirty years.
Theodore Gobley was also a philanthopist, and he was involved in the management of a local administration office for the housing of poorer people in the "Département de la Seine" (today, the greater Paris area including districts 75, 78, 91, 92, 93, 94, 95).
He dies on September 1, 1874 in the Pyrenean thermal resort of "Bagnères-de-Luchon
, where he was on a family trip. His burial place lies at "cimetière Montparnasse" in the southern half of Paris.
).
Obviously, the brain tissues were not solely composed of that, and confusion was high as to their actual composition, with especially Edmond Fremy holding, based on his work on “acide cerebrique”, for a blend of neutral lipids such as olein and phosphoric acid.
Gobley will masterly solve this question in a series of careful incremental steps.
Building on a succession of biological tissues models : egg yolk (1846–1847), carp fish eggs (1850), carp fish roe (1850), brain matter of sundry higher class vertebrae such as chicken, and ultimately man, fat matters in human fluids: blood (1852), bile (1856), Theodore Gobley will in a series of works assiduously pursued over a span of more than 30 years classify the several fat matters from a variety of biological tissues, characterize their several properties, identify their respective structure, establish bridges between wide apart categories (seminal matter, brain) and branches of zoology (birds, fish, mammals), shed light on similarities of tissues build-up and specify their differences depending on their function (1874).
- margaric acid, for the which he confirms the chemical breakdown obtained by Mr Varentrapp, at the expense of the variant sustained by Michel Eugène Chevreul
- oleic acid, for the which he confirms the chemical breakdown obtained by Mr Michel Eugène Chevreul
- an acid containing phosphor, that a very careful and delicate series of analyses leads him to indisputably identify as glycerophosphoric acid
While evidencing the first two could somehow be looked at with some more or less natural expectation, given their prevailing presence previously demonstrated in a variety of organs or corporeal fluids (such as blood, bile, brain tissues…), the latter one was until then exclusively known as a byproduct of direct chemical preparation.
Gobley in addition brings full details as to the constitution of the oily part of egg yolk, which he determines to be made up of oleine, margarine and a cholesterin, previously evidenced by Louis-René Le Canu and which he demonstrates has entirely identical properties to the one (cholesterol
) isolated from bile by Michel Eugène Chevreul.
In the immediate wake, in a second step in 1847 ("Recherches chimiques sur le jaune d'oeuf de poule"; par M. Gobley. Deuxième Mémoire. Comptes Rendus hebdomadaires Académie des Sciences 1847, 21, 988") Gobley takes a global view of the chemical structure of egg yolk and proposes for its lipid part a model comprising two distinct fractions:
- the one, in very small quantities (0.3% of total mass) which he qualifies as a nitrogenous fraction totally devoid of phosphor, and which he hints to be quite probably identical with the higher up mentioned "matière blanche" Louis-Nicolas Vauquelin, "cérébrote" (J.P.Couërbe), and "acide cérébrique" (Edmond Frémy
), identified and described from early 19th century years; for this fraction Gobley uses the denomination of « matière cérébrique » (« Recherches chimiques sur le jaune d’œuf 2ème mémoire ») , then later on the name of « cérébrine » ( (« Recherches chimiques sur les œufs de carpe ») ; this name "cerebrin" had been created some years before by a German chemist Müller, while fully characterizing its chemical composition and properties;
- the other, in significant quantities (8.5% of total mass) which he qualifies and characterizes as definitely containing phosphor under some form, that he prosaically denominates “matière phosphorée” (“phosphoric matter”) (« Recherches chimiques sur le jaune d’œuf 2ème mémoire »); this fraction can be degraded into a mixture of margaric acid, oleic acid and glycerophosphoric acid, for the which it is the sole and exclusive origin, Gobley effectively demonstrating that none of these three acids exists on its own within egg yolk;
« If therefore neither one of oleic acid, margaric acid nor glycerophosphoric acid exists as such in the viscous matter (of egg yolk), what kind of a (molecule) can that be (that is their source), that indisputably presents one of the most unusual set of properties within all the (fractions) of biological tissues »
"Mais si les acides oléïque, margarique et phosphoglycérique ne préexistent pas dans la matière visqueuse, quelle est donc la nature de ce corps, qui est sans contredit l’un des plus curieux de l’organisation animale ?"
Having recognized the uniqueness of this component from this work in the pivotal year 1847, Gobley will henceforth bear most of his research efforts on it.
Already in this same 1847, Theodore Gobley realizes the deep similarities of chemical structure between brain tissues and egg yolk.
Taking up the previous work of Vauquelin, Couërbe and Frémy, he isolates as they had from the fat matters of animal brain as well as from the human brain a phosphoric fraction, but going one step further, he demonstrates that this brain matter yields through hydrolysis exactly the same set of by-products that he had obtained from egg yolk: ever the triad oleic acid, margaric acid, glycerophosphoric acid (Journal de Pharmacie et de Chimie 1847, 12, 5).
“I have rerun all those experiments using the phosphoric viscous matter from the brain of chicken, of sheep, and finally of man, and ever I am come to the same results. There then exists in the brain, just as in egg yolk, a phosphoric substance which, under the conditions I exercised unto it, has always yielded as decomposition products oleic acid, margaric acid and glycerophosphoric acid.”
""J'ai répété toutes ces expériences avec la matière visqueuse phosphorée de la cervelle du poulet, du mouton et de l'homme, et je suis arrivé aux mêmes résultats. Il existe donc dans le cerveau, comme dans le jaune d'oeuf, une substance phosphorée qui, dans les conditions où je l'ai placée, m'a toujours donné, pour produits de décomposition, de l'acide oléique, de l'acide margarique et de l'acide phosphoglycérique"
This set of solid results led him into proposing for cerebral tissues a chemical structure parallel to that of egg yolk, relying on a phosphoric part, lecithin, and a non-phosphoric, nitrogenous part, cerebrin ("Recherches chimiques sur les oeufs de carpe . Journal de Pharmacie et de Chimie 1850, t17, 401, et t18, 107). This approach set him immediately at odds with the views developed up to then by Edmond Frémy
, the prominent specialist of that period regarding the chemical study of the brain and a member of the Académie des Sciences; Frémy’s views were that the phosphoric fraction of brain was related to the phospho-oleic acid.
Another twenty years will be employed by Gobley to fully demonstrate the point.
In 1850 (« Recherches chimiques sur les œufs de carpe »), he evidences the presence of his “matière phosphorée”, with identical properties, in carp fish eggs; he proposes for it the name of lecithin
which history will uphold, from the Greek ”lekithos” (egg yolk) (Journal de Pharmacie et de Chimie, Paris, 1850, 17, 401), thus underlining the clear link with his early studies.
And in its wake he demonstrates that lecithin, however obtained (from egg yolk, carp fish eggs, fish roe, human brain), and even though not totally purified, ALWAYS yields a mix of oleic acid, margaric acid and glycerophosphoric acid when hydrolyzed, and under no circumstances whatsoever anything like phosphoric acid which would have been expected if ordinary fat matter acids, such as phospho-oleic acid, had been involved ("Recherches chimiques sur la laitance de carpe . Journal de Pharmacie et de Chimie 1851, t19, 406").
Conversely, he demonstrates that the non phosphoric fraction of egg yolk, that he had called “cérébrine” is absolutely identical in chemical breakdown and reactive properties to the “acide cérébrique” identified by Edmond Frémy
and M.R.D.Thompson in the brain.
In 1852, he evidences the presence of lecithin in veinous blood (« Recherches chimiques sur les matières grasses du sang veineux de l’homme »), and in 1856, in bile as well (« Recherches sur la nature chimique et les propriétés des matières grasses contenues dans la bile »).
However there still lacks one brick for a complete breakdown of lecithin’s structure.
That brick is brought during the 1860s by parallel work conducted mainly in Germany, that identifies yet a new component of biological fat matters, choline
, first in the liver-produced bile by the German chemist A.Strecker (Ann Chem Pharm 1868, 148, 77), then shortly afterward in the human brain through the researches of Oscar Liebreich in Berlin (who believing he had identified a different matter named it initially "nevrin") and in his wake complementary contributions by Dibkowsky, Baeyer and Wurtz.
Using these additions to his own work, Theodore Gobley in 1874 crowns this long, patient and unyielding series of steps through a final proposal of a complete structure for lecithin, whose hydrolysis yields exactly one oleic acid, one margaric acid, one glycerophosphoric acid and one choline (“Sur la lécithine et la cérébrine”, Gobley J Pharm Chim 1874, 19, 346).
Later studies expanded the egg yolk lecithin into a wide family of lecithins answering to this structure, combining with a choline
head and glycerophosphoric acid a variety of fatty acids.
In general, a lecithin
, or more precisely a phosphatidylcholine
is obtained using a saturated fatty acid, in the example here palmitic acid or hexadecanoic acid H3C-(CH2)14-COOH (margaric acid identified by Gobley in egg yolk, now named heptadecanoïc acid H3C-(CH2)15-COOH, belongs to that class) and an unsaturated fatty acid, here oleic acid or 9Z-octadecenoic acid as in Gobley's original egg yolk lecithin).
- lecithin (5,5%),
- cerebrin (approximately 3%), characterized as a nitrogenous matter, identical to that of egg yolk, but in much higher quantities in the brain
- cholesterin (approximately 1%),
- and an abundant new component of albuminous type, that he names cephalin (approximately 7%), in addition to regular albumin (1%)
Theodore Gobley thus is the discoverer of the entirely new class of phospholipid
s and a founding pioneer in the understanding of the chemical basis of brain structure and build-up.
In cooperation with a French doctor, member of the “Academie de Medecine”, Jean-Louis-Marie Poiseuille, he publishes some results on urea in blood and urine.
In liaison with his commitment in public health matters and institutions, he involves himself in various studies on toxics, human nutrition and health, and the safety of industrial processes : thus he successively investigates toxics in toadstools (« Recherches chimiques sur les champignons vénéneux », 1856), medicinal real or supposed properties of diverse plants, herbs and preparations, toxicity of lead in widespread tins used for cooking utensils, poisonous effects of rye…
In the tradition of the methods of Robiquet, from the natural vanilla fruit, he obtains in 1858 the very first samples of pure vanillin
, its active flavoring principle.
Gobley lived just long enough to see this breakthrough bringing about the advent of artificial industrial vanillin synthesis, in a process based on glycosides extracted from the sap of pine trees (1874), opening the path to the extraordinary expansion of the use of that very popular flavour.
Incidentally that also brought about the complete collapse of the growing of natural vanilla and the related industry, but that was probably not intended by Gobley…
Lecithin
Lecithin is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues, and in egg yolk, composed of phosphoric acid, choline, fatty acids, glycerol, glycolipids, triglycerides, and phospholipids .The word lecithin was originally coined in 1847 by...
, the first identified and characterized member of the phospholipid
Phospholipid
Phospholipids are a class of lipids that are a major component of all cell membranes as they can form lipid bilayers. Most phospholipids contain a diglyceride, a phosphate group, and a simple organic molecule such as choline; one exception to this rule is sphingomyelin, which is derived from...
s class, and a pioneer researcher in the study and analysis of the chemical components of brain
Brain
The brain is the center of the nervous system in all vertebrate and most invertebrate animals—only a few primitive invertebrates such as sponges, jellyfish, sea squirts and starfishes do not have one. It is located in the head, usually close to primary sensory apparatus such as vision, hearing,...
tissues, was born in Paris
Paris
Paris is the capital and largest city in France, situated on the river Seine, in northern France, at the heart of the Île-de-France region...
on May 11, 1811 and died in Bagneres-de-Luchon
Bagnères-de-Luchon
Bagnères-de-Luchon , also referred to as Luchon, is a spa town and a commune in the Haute-Garonne department in southwestern France.-Geography:...
(a small city in central Pyrenees famous in the second half of the 19th century for its thermal waters) on September 1, 1876.
Biography and academical cursus
His namesake family originates from the Yonne region, a very rural hilly area of Burgundy, and precisely from a small city called FulvyFulvy
Fulvy is a commune in the Yonne department in Burgundy in north-central France....
. His father had settled at the end of the 18th century as a wine broker in Paris, marrying a young lady in a family long established (since at least the beginning of the 17th century) in that trade in the capital city of France (that family, Boutron, was registered in the 17th and 18th centuries as one of the 12 suppliers of wines to the King’s Court ).
Wine trading had strong links with alcoholic distillation, some close kin of the Boutron family were indeed spirits distillers, and it is likely this environment that led Theodore to studies in chemistry and pharmacy.
Indeed, an historical study conducted in 1957 by P. et C.Chatagnon on the early steps of brain tissues chemical structure studies mentions that Gobley effected a stay as apprentice by one of his parents named Guerin, indicated as pharmacist (actually, his brother-in-law, Denis Guerin 1798-1888, pharmacist in Paris for a few years in the early 1830s, but more well known as mayor of the city of Fontainebleau
Fontainebleau
Fontainebleau is a commune in the metropolitan area of Paris, France. It is located south-southeast of the centre of Paris. Fontainebleau is a sub-prefecture of the Seine-et-Marne department, and it is the seat of the arrondissement of Fontainebleau...
during close to 30 years, from 1843 till 1871, and so far as known, not related to the Boutron family).
Whatever the initial lead, further on Gobley enters full grade studies in pharmacy and in the early 1830s attends courses delivered by one of the great figures of French pharmaceutical and chemistry arts of that time, Pierre Jean Robiquet
Pierre Jean Robiquet
Pierre Jean Robiquet was a French chemist, who laid founding work in identifying amino acids, the fundamental bricks of proteins, through recognizing the first of them, asparagin, in 1806, in the take up of the industry of industrial dyes, with the identification of alizarin in 1826, and in the...
, of whom he became a close collaborator, and ultimately his son-in-law, through marrying Laure Robiquet, one of the daughters of his master and mentor .
Robiquet (1780–1840), a long standing professor at the Ecole de Pharmacie in Paris (since 1811) was a very prominent, respected and honoured player amongst the French chemists/pharmacists community of the first half of the 19th century: member of the “Société de Pharmacie” later on designated as the “Académie Nationale de Pharmacie” (1817), of which he was Secretary General then President, (1817 till his death) (go to (http://www.shp-asso.org/)), member of the "Académie de Médecine" (1820), member of the “Académie des Sciences”, distinguished with the order of “Légion d’Honneur”, author of numerous studies and pioneering work in the research of complex molecules in natural bodies, either plants or animals, who had isolated such fundamentals products, as caffeine
Caffeine
Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a stimulant drug. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants...
, cantharidin
Cantharidin
Cantharidin, a type of terpenoid, is a poisonous chemical compound secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. The false blister beetles and cardinal beetles also have cantharidin.-History:...
, and most of all the alizarin
Alizarin
Alizarin or 1,2-dihydroxyanthraquinone is an organic compound with formula that has been used throughout history as a prominent dye, originally derived from the roots of plants of the madder genus.Alizarin was used as a red dye for the English parliamentary "new model" army...
, a powerful and stable red dye that was to become one of the first dyes to be mass produced through a pure chemical synthesis path,
Theodore Gobley qualifies as a pharmacist in 1835, marries Laure Robiquet in 1837, and establishes himself as pharmacist in Paris (60 rue du Bac; the place has been run down when Boulevard Saint Germain was opened some 30 years later); in parallel to his trade, in his personal lab he conducts his researches, and follows a path very similar to that of his father-in–law (demised in 1840): he enters the Ecole de Pharmacie as professor in 1842 (he will quit in 1847), becomes a member of the Académie Nationale de Pharmacie in 1843, of which he becomes President in 1861, and is admitted a member of the “Académie de Médecine” that same year.
While conducting various works on a very diversified range of topics very much like most pharmacist/chemists of the 19th century, Gobley singled himself out by a somehow unique lifelong pursuit in the study of lipids in the living animals reign, whereby he demonstrated the universal presence of a fundamental substance, which he will name “lecithin”, and the exact composition of which he will pursue during thirty years.
Theodore Gobley was also a philanthopist, and he was involved in the management of a local administration office for the housing of poorer people in the "Département de la Seine" (today, the greater Paris area including districts 75, 78, 91, 92, 93, 94, 95).
He dies on September 1, 1874 in the Pyrenean thermal resort of "Bagnères-de-Luchon
Bagnères-de-Luchon
Bagnères-de-Luchon , also referred to as Luchon, is a spa town and a commune in the Haute-Garonne department in southwestern France.-Geography:...
, where he was on a family trip. His burial place lies at "cimetière Montparnasse" in the southern half of Paris.
Discoverer of Lecithin and Phospholipids
In the course of the first half of the 19th century, several French chemists had initiated some tries at the chemical components of brain tissues, but tools and methods for analysis were poor and results fairly unsatisfactory; however they had consistently obtained through different methods, mostly through dissolution in warm alcohol of brain matter, a lipidic substance of more of less stable composition which they had diversely called “matière blanche” (Louis-Nicolas Vauquelin), “cérébrote” (J.P.Couërbe), acide cérébrique (Edmond FrémyEdmond Fremy
Edmond Frémy was a French chemist. He is perhaps best known today for Frémy's salt, a strong oxidizing agent which he discovered in 1845...
).
Obviously, the brain tissues were not solely composed of that, and confusion was high as to their actual composition, with especially Edmond Fremy holding, based on his work on “acide cerebrique”, for a blend of neutral lipids such as olein and phosphoric acid.
Gobley will masterly solve this question in a series of careful incremental steps.
Building on a succession of biological tissues models : egg yolk (1846–1847), carp fish eggs (1850), carp fish roe (1850), brain matter of sundry higher class vertebrae such as chicken, and ultimately man, fat matters in human fluids: blood (1852), bile (1856), Theodore Gobley will in a series of works assiduously pursued over a span of more than 30 years classify the several fat matters from a variety of biological tissues, characterize their several properties, identify their respective structure, establish bridges between wide apart categories (seminal matter, brain) and branches of zoology (birds, fish, mammals), shed light on similarities of tissues build-up and specify their differences depending on their function (1874).
Early studies on egg yolk chemical components 1843-1847
In a first step during 1845 (« Recherches chimiques sur le jaune d’œuf », Compte Rendu hebdomadaire Académie des Sciences 1845, 21, 766) Gobley achieves a ground breaking first work where he analyses in detail the lipids in the egg yolk, obtaining from egg yolk byproducts never before evidenced in that matter:- margaric acid, for the which he confirms the chemical breakdown obtained by Mr Varentrapp, at the expense of the variant sustained by Michel Eugène Chevreul
- oleic acid, for the which he confirms the chemical breakdown obtained by Mr Michel Eugène Chevreul
- an acid containing phosphor, that a very careful and delicate series of analyses leads him to indisputably identify as glycerophosphoric acid
While evidencing the first two could somehow be looked at with some more or less natural expectation, given their prevailing presence previously demonstrated in a variety of organs or corporeal fluids (such as blood, bile, brain tissues…), the latter one was until then exclusively known as a byproduct of direct chemical preparation.
Gobley in addition brings full details as to the constitution of the oily part of egg yolk, which he determines to be made up of oleine, margarine and a cholesterin, previously evidenced by Louis-René Le Canu and which he demonstrates has entirely identical properties to the one (cholesterol
Cholesterol
Cholesterol is a complex isoprenoid. Specifically, it is a waxy steroid of fat that is produced in the liver or intestines. It is used to produce hormones and cell membranes and is transported in the blood plasma of all mammals. It is an essential structural component of mammalian cell membranes...
) isolated from bile by Michel Eugène Chevreul.
In the immediate wake, in a second step in 1847 ("Recherches chimiques sur le jaune d'oeuf de poule"; par M. Gobley. Deuxième Mémoire. Comptes Rendus hebdomadaires Académie des Sciences 1847, 21, 988") Gobley takes a global view of the chemical structure of egg yolk and proposes for its lipid part a model comprising two distinct fractions:
- the one, in very small quantities (0.3% of total mass) which he qualifies as a nitrogenous fraction totally devoid of phosphor, and which he hints to be quite probably identical with the higher up mentioned "matière blanche" Louis-Nicolas Vauquelin, "cérébrote" (J.P.Couërbe), and "acide cérébrique" (Edmond Frémy
Edmond Fremy
Edmond Frémy was a French chemist. He is perhaps best known today for Frémy's salt, a strong oxidizing agent which he discovered in 1845...
), identified and described from early 19th century years; for this fraction Gobley uses the denomination of « matière cérébrique » (« Recherches chimiques sur le jaune d’œuf 2ème mémoire ») , then later on the name of « cérébrine » ( (« Recherches chimiques sur les œufs de carpe ») ; this name "cerebrin" had been created some years before by a German chemist Müller, while fully characterizing its chemical composition and properties;
- the other, in significant quantities (8.5% of total mass) which he qualifies and characterizes as definitely containing phosphor under some form, that he prosaically denominates “matière phosphorée” (“phosphoric matter”) (« Recherches chimiques sur le jaune d’œuf 2ème mémoire »); this fraction can be degraded into a mixture of margaric acid, oleic acid and glycerophosphoric acid, for the which it is the sole and exclusive origin, Gobley effectively demonstrating that none of these three acids exists on its own within egg yolk;
Putting in light the chemical bridges from egg yolk to human brain 1847
In this very same work, Gobley develops an awareness that this phosphoric part is a new, non-characterized and complex component of a precise nature and stable structure, not a mixture of sub-products in varying proportions:« If therefore neither one of oleic acid, margaric acid nor glycerophosphoric acid exists as such in the viscous matter (of egg yolk), what kind of a (molecule) can that be (that is their source), that indisputably presents one of the most unusual set of properties within all the (fractions) of biological tissues »
"Mais si les acides oléïque, margarique et phosphoglycérique ne préexistent pas dans la matière visqueuse, quelle est donc la nature de ce corps, qui est sans contredit l’un des plus curieux de l’organisation animale ?"
Having recognized the uniqueness of this component from this work in the pivotal year 1847, Gobley will henceforth bear most of his research efforts on it.
Already in this same 1847, Theodore Gobley realizes the deep similarities of chemical structure between brain tissues and egg yolk.
Taking up the previous work of Vauquelin, Couërbe and Frémy, he isolates as they had from the fat matters of animal brain as well as from the human brain a phosphoric fraction, but going one step further, he demonstrates that this brain matter yields through hydrolysis exactly the same set of by-products that he had obtained from egg yolk: ever the triad oleic acid, margaric acid, glycerophosphoric acid (Journal de Pharmacie et de Chimie 1847, 12, 5).
“I have rerun all those experiments using the phosphoric viscous matter from the brain of chicken, of sheep, and finally of man, and ever I am come to the same results. There then exists in the brain, just as in egg yolk, a phosphoric substance which, under the conditions I exercised unto it, has always yielded as decomposition products oleic acid, margaric acid and glycerophosphoric acid.”
""J'ai répété toutes ces expériences avec la matière visqueuse phosphorée de la cervelle du poulet, du mouton et de l'homme, et je suis arrivé aux mêmes résultats. Il existe donc dans le cerveau, comme dans le jaune d'oeuf, une substance phosphorée qui, dans les conditions où je l'ai placée, m'a toujours donné, pour produits de décomposition, de l'acide oléique, de l'acide margarique et de l'acide phosphoglycérique"
This set of solid results led him into proposing for cerebral tissues a chemical structure parallel to that of egg yolk, relying on a phosphoric part, lecithin, and a non-phosphoric, nitrogenous part, cerebrin ("Recherches chimiques sur les oeufs de carpe . Journal de Pharmacie et de Chimie 1850, t17, 401, et t18, 107). This approach set him immediately at odds with the views developed up to then by Edmond Frémy
Edmond Fremy
Edmond Frémy was a French chemist. He is perhaps best known today for Frémy's salt, a strong oxidizing agent which he discovered in 1845...
, the prominent specialist of that period regarding the chemical study of the brain and a member of the Académie des Sciences; Frémy’s views were that the phosphoric fraction of brain was related to the phospho-oleic acid.
Another twenty years will be employed by Gobley to fully demonstrate the point.
The identification and chemical breakdown of lecithin, the first of phospholipids (1848-1874)
In the course of the next three years 1848-1849-1850, Theodore Gobley extends the scope of his research in parallel over egg yolk, carp fish eggs, fish roe, and brain.In 1850 (« Recherches chimiques sur les œufs de carpe »), he evidences the presence of his “matière phosphorée”, with identical properties, in carp fish eggs; he proposes for it the name of lecithin
Lecithin
Lecithin is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues, and in egg yolk, composed of phosphoric acid, choline, fatty acids, glycerol, glycolipids, triglycerides, and phospholipids .The word lecithin was originally coined in 1847 by...
which history will uphold, from the Greek ”lekithos” (egg yolk) (Journal de Pharmacie et de Chimie, Paris, 1850, 17, 401), thus underlining the clear link with his early studies.
And in its wake he demonstrates that lecithin, however obtained (from egg yolk, carp fish eggs, fish roe, human brain), and even though not totally purified, ALWAYS yields a mix of oleic acid, margaric acid and glycerophosphoric acid when hydrolyzed, and under no circumstances whatsoever anything like phosphoric acid which would have been expected if ordinary fat matter acids, such as phospho-oleic acid, had been involved ("Recherches chimiques sur la laitance de carpe . Journal de Pharmacie et de Chimie 1851, t19, 406").
Conversely, he demonstrates that the non phosphoric fraction of egg yolk, that he had called “cérébrine” is absolutely identical in chemical breakdown and reactive properties to the “acide cérébrique” identified by Edmond Frémy
Edmond Fremy
Edmond Frémy was a French chemist. He is perhaps best known today for Frémy's salt, a strong oxidizing agent which he discovered in 1845...
and M.R.D.Thompson in the brain.
In 1852, he evidences the presence of lecithin in veinous blood (« Recherches chimiques sur les matières grasses du sang veineux de l’homme »), and in 1856, in bile as well (« Recherches sur la nature chimique et les propriétés des matières grasses contenues dans la bile »).
However there still lacks one brick for a complete breakdown of lecithin’s structure.
That brick is brought during the 1860s by parallel work conducted mainly in Germany, that identifies yet a new component of biological fat matters, choline
Choline
Choline is a water-soluble essential nutrient. It is usually grouped within the B-complex vitamins. Choline generally refers to the various quaternary ammonium salts containing the N,N,N-trimethylethanolammonium cation....
, first in the liver-produced bile by the German chemist A.Strecker (Ann Chem Pharm 1868, 148, 77), then shortly afterward in the human brain through the researches of Oscar Liebreich in Berlin (who believing he had identified a different matter named it initially "nevrin") and in his wake complementary contributions by Dibkowsky, Baeyer and Wurtz.
Using these additions to his own work, Theodore Gobley in 1874 crowns this long, patient and unyielding series of steps through a final proposal of a complete structure for lecithin, whose hydrolysis yields exactly one oleic acid, one margaric acid, one glycerophosphoric acid and one choline (“Sur la lécithine et la cérébrine”, Gobley J Pharm Chim 1874, 19, 346).
Later studies expanded the egg yolk lecithin into a wide family of lecithins answering to this structure, combining with a choline
Choline
Choline is a water-soluble essential nutrient. It is usually grouped within the B-complex vitamins. Choline generally refers to the various quaternary ammonium salts containing the N,N,N-trimethylethanolammonium cation....
head and glycerophosphoric acid a variety of fatty acids.
In general, a lecithin
Lecithin
Lecithin is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues, and in egg yolk, composed of phosphoric acid, choline, fatty acids, glycerol, glycolipids, triglycerides, and phospholipids .The word lecithin was originally coined in 1847 by...
, or more precisely a phosphatidylcholine
Phosphatidylcholine
Phosphatidylcholines are a class of phospholipids that incorporate choline as a headgroup.They are a major component of biological membranes and can be easily obtained from a variety of readily available sources such as egg yolk or soy beans from which they are mechanically extracted or chemically...
is obtained using a saturated fatty acid, in the example here palmitic acid or hexadecanoic acid H3C-(CH2)14-COOH (margaric acid identified by Gobley in egg yolk, now named heptadecanoïc acid H3C-(CH2)15-COOH, belongs to that class) and an unsaturated fatty acid, here oleic acid or 9Z-octadecenoic acid as in Gobley's original egg yolk lecithin).
The first global overview of brain tissues chemical structure
The complete series of results leads Theodore Gobley into proposing for brain viscous matter a structure under four main components (« Recherches chimiques sur le cerveau de l’homme », Journal de Pharmacie et de Chimie 1874) (water set aside, an overwhelming 80%):- lecithin (5,5%),
- cerebrin (approximately 3%), characterized as a nitrogenous matter, identical to that of egg yolk, but in much higher quantities in the brain
- cholesterin (approximately 1%),
- and an abundant new component of albuminous type, that he names cephalin (approximately 7%), in addition to regular albumin (1%)
Theodore Gobley thus is the discoverer of the entirely new class of phospholipid
Phospholipid
Phospholipids are a class of lipids that are a major component of all cell membranes as they can form lipid bilayers. Most phospholipids contain a diglyceride, a phosphate group, and a simple organic molecule such as choline; one exception to this rule is sphingomyelin, which is derived from...
s and a founding pioneer in the understanding of the chemical basis of brain structure and build-up.
Other Researches, Investigations and discoveries
In parallel, Theodore Gobley develops a number of additional threads of research of a more mainstream type.In cooperation with a French doctor, member of the “Academie de Medecine”, Jean-Louis-Marie Poiseuille, he publishes some results on urea in blood and urine.
In liaison with his commitment in public health matters and institutions, he involves himself in various studies on toxics, human nutrition and health, and the safety of industrial processes : thus he successively investigates toxics in toadstools (« Recherches chimiques sur les champignons vénéneux », 1856), medicinal real or supposed properties of diverse plants, herbs and preparations, toxicity of lead in widespread tins used for cooking utensils, poisonous effects of rye…
In the tradition of the methods of Robiquet, from the natural vanilla fruit, he obtains in 1858 the very first samples of pure vanillin
Vanillin
Vanillin is a phenolic aldehyde, an organic compound with the molecular formula C8H8O3. Its functional groups include aldehyde, ether, and phenol. It is the primary component of the extract of the vanilla bean. It is also found in Leptotes bicolor, roasted coffee and the Chinese red pine...
, its active flavoring principle.
Gobley lived just long enough to see this breakthrough bringing about the advent of artificial industrial vanillin synthesis, in a process based on glycosides extracted from the sap of pine trees (1874), opening the path to the extraordinary expansion of the use of that very popular flavour.
Incidentally that also brought about the complete collapse of the growing of natural vanilla and the related industry, but that was probably not intended by Gobley…
Publications
- "Sur l'existence des acides oléique, margarique et phosphoglycérique dans le jaune d'oeuf. Premier Mémoire: Sur la composition chimique du jaune d'oeuf; par M. Gobley. (Extrait). C R hebd Acad Sci 1845, 21, 766
- "Recherches chimiques sur le jaune d'oeuf de poule"; par M. Gobley. Deuxième Mémoire. C R hebd Acad Sci 1845, 21, 988"
- "Recherches chimiques sur le jaune d'oeuf - Examen comparatif du jaune d'oeuf et de la matière cérébrale. Journal de Pharmacie et de Chimie 1847, t11, 409 et 412"
- "Recherches chimiques sur les oeufs de carpe . Journal de Pharmacie et de Chimie 1850, t17, 401, et t18, 107"
- "Recherches chimiques sur la laitance de carpe . Journal de Pharmacie et de Chimie 1851, t19, 406"
- "Recherches chimiques sur la matière grasse du sang veineux de l'homme . Journal de Pharmacie et de Chimie 1852, t21, 241"
- "Recherches sur la nature chimique et les propriétés des matières grasses contenues dans la bile. Journal de Pharmacie et de Chimie 1856, t30, 241"
- "Recherches chimiques sur le cerveau; par M. Gobley. Journal de Pharmacie et de Chimie 1874,4ème série, t19, p346-354
- "Sur la lécithine et la cérébrine"; par M. Gobley. Journal de Pharmacie et de Chimie 1874,t20, 98-103, 161-166"
- "Note sur l'Elaïomètre, nouvel instrument d'essai pour les huiles d'olive. M. Gobley. J Pharm Chim 1843, 4, 285"
- "Recherches sur la nature chimique et les propriétés des matières grasses contenues dans la bile", par M. Gobley. Journal de Pharmacie et de Chimie, 1856
- "Recherches physiologiques sur l'urée (avec Mr le docteur Poiseuille)", par M. Gobley. Comptes rendus de l'Académie des Sciences et Gazette hebdomadaire de médecine et de chirurgie, 1859
- "Recherche sur le principe odorant de la vanille", par M.Gobley. Journal de Pharmacie et de Chimie 1858
See also
- Pierre Jean RobiquetPierre Jean RobiquetPierre Jean Robiquet was a French chemist, who laid founding work in identifying amino acids, the fundamental bricks of proteins, through recognizing the first of them, asparagin, in 1806, in the take up of the industry of industrial dyes, with the identification of alizarin in 1826, and in the...
- Eugène Chevreul
- Louis-Nicolas Vauquelin
- Théophile-Jules PelouzeThéophile-Jules PelouzeThéophile-Jules Pelouze was a French chemist. He was born at Valognes, and died in Paris....
- Edmond FrémyEdmond FremyEdmond Frémy was a French chemist. He is perhaps best known today for Frémy's salt, a strong oxidizing agent which he discovered in 1845...
- PhospholipidPhospholipidPhospholipids are a class of lipids that are a major component of all cell membranes as they can form lipid bilayers. Most phospholipids contain a diglyceride, a phosphate group, and a simple organic molecule such as choline; one exception to this rule is sphingomyelin, which is derived from...
- Phosphoric acidPhosphoric acidPhosphoric acid, also known as orthophosphoric acid or phosphoric acid, is a mineral acid having the chemical formula H3PO4. Orthophosphoric acid molecules can combine with themselves to form a variety of compounds which are also referred to as phosphoric acids, but in a more general way...
- PhosphatidylcholinePhosphatidylcholinePhosphatidylcholines are a class of phospholipids that incorporate choline as a headgroup.They are a major component of biological membranes and can be easily obtained from a variety of readily available sources such as egg yolk or soy beans from which they are mechanically extracted or chemically...
- Glycerophosphoric acid
- CholineCholineCholine is a water-soluble essential nutrient. It is usually grouped within the B-complex vitamins. Choline generally refers to the various quaternary ammonium salts containing the N,N,N-trimethylethanolammonium cation....
- Saturated fatty acid
- Unsaturated fatty acid
- VanillinVanillinVanillin is a phenolic aldehyde, an organic compound with the molecular formula C8H8O3. Its functional groups include aldehyde, ether, and phenol. It is the primary component of the extract of the vanilla bean. It is also found in Leptotes bicolor, roasted coffee and the Chinese red pine...
- VanillaVanillaVanilla is a flavoring derived from orchids of the genus Vanilla, primarily from the Mexican species, Flat-leaved Vanilla . The word vanilla derives from the Spanish word "", little pod...
- Oscar Liebreich
- Strecker amino acid synthesisStrecker amino acid synthesisThe Strecker amino acid synthesis, devised by Adolph Strecker, is a series of chemical reactions that synthesize an amino acid from an aldehyde . The aldehyde is condensed with ammonium chloride in the presence of potassium cyanide to form an α-aminonitrile, which is subsequently hydrolyzed to give...
- Jean Louis Marie PoiseuilleJean Louis Marie PoiseuilleJean Louis Marie Poiseuille was a French physician and physiologist.Poiseuille was born in Paris, France.From 1815 to 1816 he studied at the École Polytechnique in Paris. He was trained in physics and mathematics. In 1828 he earned his D.Sc...
External links
- http://cat.inist.fr/?aModele=afficheN&cpsidt=15271599 La Création de l'Ecole de Pharmacie (in French)
- http://acadpharm.net/ Académie Nationale de Pharmacie (in French)
- http://www.shp-asso.org/index.php?PAGE=salledesactes Portrait of Robiquet at The Ecole de Pharmacie, Salle des actes (in French)
- http://www.fontainebleau-tourisme.com/pays-fontainebleau/ville-fontainebleau/rue-fete-fontainebleau-2.asp Fontainebleau streets denomination, origin (in French)