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Volume 33, 1900
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Art. XLIII.—Studies on the Chemistry of the New Zealand Flora.

By T. H. Easterfield, Professor of Chemistry in Victoria College, and B. C. Aston, Chemist to the Department of Agriculture.

[Read before the Wellington Philosophical Society, 24th July, 1900.]

Part I. The Tutu Plant.

The standard to which the study of any branch of science attains in a community may be accurately gauged by the quantity and quality of the research work produced by the members of that community. It is therefore to be regretted that, whereas the biological sciences have attracted in New Zealand a large and enthusiastic body of workers, chemical research has been almost entirely neglected, except in so far as its application to the mineral resources of the colony might be expected to yield a direct financial return. In consequence of this indifference to the value of chemical investigation very little is known about the chemistry of our native plants, a subject of the greater importance since the flora of these Islands is so largely endemic. The field for investigation is wide, and much work must be done before our knowledge of the subject can be placed upon a satisfactory basis. The authors of the present paper, however, hope by their own researches, and even more by inducing others to carry on similar inquiries, to lay the foundation for a fairly complete knowledge of the characteristic constituents of the more important New Zealand plants. The tutu has been chosen for the first of these investigations because it is the most widely spread and the best known of the native poisonous plants. A great interest therefore attaches to it.

The poisonous nature of the tutu is well known; of the animals brought by Captain Cook,* both of the sheep and one of the goats appear to have died from the effects of the plant.† Of the cows brought by the early Canterbury settlers, two

[Footnote] * Voyages.

[Footnote] † Lauder Lindsay, B. and F. Med. and Chir. Rev., No. 61, July, 1865.

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were poisoned within a few days of landing.* The same newspaper warns settlers of the danger of this plant to freshly landed cattle.

Lauder Lindsay,† who visited New Zealand in 1861–62, in an interesting article entitled “The Toot Plant and Poison of New Zealand,” says, “I was everywhere struck by the abundant evidences of the devastation produced amongst flocks and herds from their feeding on the toot plant…. In other words, he seemed a fortunate farmer or runholder who had not lost more than 25 per cent. of his stock from toot-poisoning, whilst in some instances the losses were so high as 75 per cent.”

Other animals are also affected by the plant. An interesting account of the poisoning, with death in seven hours, of an elephant belonging to a travelling menagerie is given by Haast, the skeleton being now in the Colonial Museum, Wellington.‡

Birds are said to be unaffected by the seeds, but cases have come under the notice of the authors in which, domestic fowls have been poisoned by eating the berries, the symptoms being typical of tutu-poisoning.

The number of recorded cases in which human beings have died from tutu-poisoning does not appear to be large. The authors have endeavoured to collect details of these fatal cases, and have in this connection issued a circular asking for the experience of every medical man in the colony. The following cases are taken in part from the replies already to hand:—

1. At Wakapu, Bay of Islands, 1835–36, twelve French sailors were poisoned; four are said to have died.§

2. Thomson, “Story of New Zealand,” 1859, states that up till that date several children had died from eating the berries.

3. Otago Colonist, 25th October, 1861, records the case of two children being poisoned by the shoots; one died.

4. Otago Daily Times, 16th November, 1862; death of a young man from eating the shoots.

5. H. C. Field∥ records the death of a girl in 1854–55 from eating tutu-berries.

6. E. Cross∥ lost a son from eating the berries in January, 1860; symptoms very distressing.

7. Mr. Giles, ex-Coroner at Westport and Auckland,∥

[Footnote] * Lyttelton Times, vol. i., No. 1, 11th Jan., 1851.

[Footnote] † Loc. et.

[Footnote] ‡ “The Student,” Feb., 1869; and Trans. N.Z. Inst., 1869, p. 399.

[Footnote] § W. G. Mair, private communication; also Lauder Lindsay, loc cit.

[Footnote] ∥ Private communication.

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records two cases of poisoning from the berries. One case was fatal; in the other the memory was much impaired.

The authors have received accounts of the treatment of patients who have recovered. These include bleeding from the arteries and veins, emetics, stimulants, lime-water, ammonia, compulsory exercise, inhalation of chloroform followed by sedatives. The experience of stock-owners points to bleeding as the most certain and rapid method of affording relief.

Botanical Affinities of Tutu.

The name “tutu” is applied to three distinct species of the monotypic natural order Coriariæ: Coriaria ruscifolia L. (C. sarmentosa, Forst., C. arborea and C. tutu, Lindsay, tutu, pohou, and tupakihi of the Maori), is commonly known as the tree-toot; it is a handsome shrub, with glossy acuminate leaves, and grows to a height of from 20 ft.–25 ft. C. thymifolia, Humb. and Bonp. (tutu-papa or tutu-heu-heu of the Maori), seldom exceeds 3 ft. in height, and is known as the ground-toot. C. angustissima, Hook, f., is of comparatively rare occurrence. It is a small herbaceous upland annual, with a characteristic fern-like appearance.

C. thymifolia also occurs in South America, where it is known as the “ink-plant.” The juice of the fruit is used in New Granada as an ink, under the name of “chanchi.”* C. ruscifolia occurs, too, in China,† where a black stain prepared from it is used by shoemakers. C. nepalensis, the Himalayan species, is not known to be poisonous, and the fruit is eaten. C. myrtifolia, the European species, is highly toxic. It is known as “gerberstrauch” (dyers-bush) in Germany and “redoul” in France.

Chemistry of C. myrtifolia.

In 1863 M. Riban showed that C. myrtifolia contained a very poisonous constituent, which he called “coriamyrtin.”‡ A. G. Perkin§ has recently shown that the same plant contains quercetin.

Chemistry of Tutu.

It is somewhat remarkable that the poisonous constituent of tutu has remained hitherto unisolated. Skey∥ has shown that ether removes from the seeds a highly poisonous green oil, which, he remarks, is or contains the poison. Hughes

[Footnote] * Jamieson, Proc. Linn. Soc., vol. 7, p. 120.

[Footnote] † Lauder Lindsay, loc. cit.

[Footnote] ‡ “Comptes Rendus,” 1863, p. 798, and 1866, p. 680.

[Footnote] § “Journal of the Chemical Society,” 77 (1900), p. 429.

[Footnote] ∥ Trans, N.Z. Inst., 1869, 153, 399, 400.

[Footnote] ¶ Trans. N.Z. Inst., 1870, 237.

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showed that C. ruscifolia contained crystalline constituents soluble in alcohol or water, but did not identify them. He found that boiling with slaked lime destroyed the poisonous action of the drug. Christie* has examined the physiological effect of decoctions of the plant, and denies that lime destroys the poison.

The results of the examination of tutu recorded in the present paper may be summarised as follows:—

(1.) No alkaloids can be detected in the plant. This result confirms the previous work of Skey.†

(2.) All the New Zealand species of Coriaria contain a highly poisonous crystalline glucoside of the formula C17H20O7, to which the authors give the name “tutin.” It differs in many respects from any known chemical compound. In physiological action tutin closely resembles Riban's coriamyrtin, described above. A comparison of the two compounds is given below.

Tutin is present in both the seeds and leaves of the plants.‡ No other poisonous constituent has been detected.

(3.) The following well-known acids occur in the leaves of C. ruscifolia and C. thymifolia: Acetic, ellagic, gallic, and succinic. C. angustissima contains, in addition, a volatile crystalline acid, C8H6O4.

(4.) The oil extracted by carbon-bisulphide from the seeds is a drying oil, and upon saponification yields salts of linoleic acid. The oil is not poisonous.

Experimental.

Coriaria thymifolia.

Eleven kilograms of the air-dried plant (root excluded) gathered at Dunedin at the time of flowering (January) were put through a chaff-cutter and boiled with successive quantities of water. The concentrated infusion was treated with a large volume of alcohol, which precipitated inorganic salts, ellagic acid, and a large quantity of black, tarry matter. The residue remaining after distilling off the alcohol from the supernatant liquid was extracted with ether. When the ether was distilled off the residue containing the characteristic glucoside tutin set to a semi-solid crystalline mass with a pungent odour.

Acetic acid was recognised by distilling the mass with steam. From the distillate a silver salt was prepared, which,

[Footnote] * N.Z. Med. Journ., July and October, 1890.

[Footnote] † Jurors’ Reports and Awards, New Zealand Exhibition, 1865.

[Footnote] ‡ The presence of the poison in the seeds and leaves is opposed to the view put forward by Manning (Lindsay, loc. cit.) that the seat of the poison is not the seed, but the “fur” on the fruitstalk.

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after a single recrystallisation, gave Ag = 64.3 per cent. Calculated for C2H3O2Ag, Ag = 64.7 per cent.

Gallic acid remained in quantity when the solution which had been distilled with steam was evaporated to the crystallising-point and the residue extracted with chloroform. It gave the usual colour reactions. After recrystallisation from water it was dried at 150° and gave—

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C = 49.4; H = 3.5 per cent.

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C7H6O5 requires C = 49.0; H = 3.5 per cent.

Quercetin, or some isomeric compound, was present in the crude gallic acid. After purification by repeated recrystal-lisation from water it showed the usual colour reactions and dyeing properties, lost 2 mols. of water at 160°, and, on analysis, gave—

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C = 59.2; H = 3.6 per cent.

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C15H10O7 requires C = 59.6; H = 3.2 per cent.

Quercetin has been definitely shown by Perkin to exist in C. myrtifolia.*

The chloroform solution separated from the gallic acid was evaporated and the product dissolved in ether; the remaining acids were then removed by sodium-carbonate.

Succinic acid was identified in the alkaline solution. It was recognised by qualitative reactions, melting-point, and analysis of the silver salt.

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C = 14.3; H = 1.25; Ag = 64.8 per cent.

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C4H4O4Ag2 requires C = 14.4; H = 1.2; Ag = 65.0 per cent.

Tutin.

The ethereal solution, from which all the acids had been removed, was evaporated, and yielded almost colourless crystals, which were repeatedly recrystallised from water and from alcohol. From water the substance separates in characteristic acicular forms, from alcohol in oblique-ended prisms. The compound is perceptibly volatile, may be slowly sublimed at 120°-130°, melts at 208°-209° (uncorr.), and has an intensely bitter taste. It contains no nitrogen, and after hydrolysis by dilute acids reduces Fehling's solution, and with phenylhydrazine gives an amorphous precipitate which is not phenylglucosazone. Strong sulphuric acid added to a few drops of a saturated aqueous solution of tutin gives a blood-red colouration.

Examination by Zeisel's method for methoxyl groups gave negative results. When evaporated to dryness with slaked lime solutions of tutin yield amorphous compounds amongst

[Footnote] * Trans. and Journal Chem. Soc., 1900, 77, 429.

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which tutin can no longer be detected, even when the residue has been acidified.

Some preliminary experiments upon the toxic effect of tutin were carried out by Mr. J. A. Gilruth, Chief Government Veterinary Surgeon. The compound is very poisonous. A dose of 0.129 gram killed a pig weighing 17 kilograms in five hours; 0.01 gram killed a kitten weighing 1 kilogram in forty minutes; 0.001 gram given to a cat weighing 2 kilograms caused a fit in three hours and illness for the next twenty-four hours. The same cat subsequently succumbed to a dose of 0.003 gram.

A dose of about a milligram produced nausea, vomiting, and incapacity for work extending over twenty-four hours in a healthy, full-grown man.

Three preparations were analysed, (i.) and (ii.) from C. thymifolia and (iii.) from C. ruscifolia:—

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(i.) 0.1299, dried at 120°-130°, gave 0.2899 CO2 and 0.0691 H2O. C = 60.78; H = 5.91.

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(ii.) 0.1255, dried in desiccator, gave 0.2793 CO2 and 0.0710 H2O. C = 60.70; H = 6.20.

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(iii) 0.1264, dried at 120°-130°, gave 0.2825 CO2 and 0.0658 H2O. C = 60.95; H = 5.78.

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C17H20O7 requires C = 60.71; H = 5.95 per cent.

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Molecular Weight Determinations.—Calculated for C17H20O7. M = 336.

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0.403 gram depressed the m.p. of 10 grams of acetic acid 0.47°. M = 332.

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0.319 gram depressed the m.p. of 10 grams of acetic acid 0.38°. M = 325.

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0.2448 gram depressed the m.p. of 8 grams of phenol 0.66° M = 333.

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1.1173 grams raised the b.p. of 11.65 grams of alcohol 0.35°. M = 320.

Solubilities.—One Hundred grams of water at 10°, of ether at 10°, and of alcohol at 16° dissolve 1.9, 1.5, and 8.2 grams of tutin respectively. It is very soluble in acetone, but dissolves only sparingly in chloroform, and is insoluble in benzine or carbon-disulphide.

The optical activity has been determined by Professor C. R. Marshall, of University College, Dundee, who reports as follows:—

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αD = +0.37°; l = 2 dcm.; d = 0.8; c = 2.5 per cent. in alcohol; whence, [α]19.5°D = +9.25.

Note on the Pharmacology of Tutin.—Professor Marshall has undertaken the pharmacology of tutin, and furnishes the following preliminary note:—

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“Tutin, pharmacologically, is closely allied to coriamyrtin, and belongs to what is known as the picrotoxin group of substances. After preliminary depression it induces salivation, a fall in the frequency of the pulse, and increased respiratory activity, followed by convulsions, for the most part clonic and limited in the earlier stages to the fore part of the body. The effect is apparently due to an action on the medulla oblongata and basal ganglia of the brain. It differs from coriamyrtin in being less toxic and slower in its action. On this account the preliminary depression is more marked. Its connection with this substance, however is close. Experiments suggest that it is broken up in the body into some substance, possibly coriamyrtin, which is the active convulsant factor. It ought to be stated that the coriamyrtin employed by me was obtained from Merck. After boiling for a short time with dilute hydrochloric acid (2 per cent.) it did not reduce copper-sulphate solution. It melted at 224° (uncorr.), and its solubility in physiological saline solution (0.6 percent. NaCl) was less than 0.1 per cent. Riban's coriamyrtin melted at 220°, and was soluble in water to the extent of 1.44 per cent, at 22°.”

Seeds of C. Thymifolia.—A kilogram and a half of the seeds of C. thymifolia were pulverised and exhausted by carbon-disulphide, which removed 22.6 per cent, of a green drying oil. The seeds, freed from oil, yielded to water a small quantity of tutin, which was extracted with ether, and after recrystallisation melted at 208°—209°. The oil, upon saponification, yielded a liquid acid, which was probably linoleic acid, since its calcium and barium salts, were readily soluble in ether.

Coriaria ruscifolia.

In the examination of this plant the juice expressed from the succulent asparagus-like shoots (gathered at Wellington early in October) was employed. It contained the same acids as the extracts of C. thymifolia. The yield of tutin was 0.03 per cent. Samples of the plant gathered later in the year from the same hillside contained a smaller percentage of the poison. The dried seeds of C. ruscifolia, on extraction with carbon-disulphide, yielded 22.8 per cent. of oil, which was very faintly toxic; 0.18 gram administered to a small kitten produced only very mild symptoms of tutu poisoning. From the extracted seeds water removed a few crystals of a substance which gave the characteristic bitter taste and colour reaction of tutin.

Coriaria angustissima.

Only 1 kilogram of the dried plant was obtainable. It was collected at Dunedin early in January. Tutin was obtained

– 352 –

from it, and identified by its melting-point. This species contains an acid which was not detected in the other two; when the aqueous extract of the plant was repeatedly shaken up with ether the latter extractions contained the acid in a comparatively pure condition. It crystallised from chloroform in silky yellowish needles, which were finally sublimed at 125° under diminished pressure. It was thus obtained in colourless iridescent plates, very readily soluble in water, alcohol, or ether. The acid has a characteristic smell, gives a transient violet colour with ferric chloride, and melts at 130° (uncorr.). On analysis—

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0.1214 gave 0.2537 CO2 and 0.0545 H2O. C = 56.99; H = 4.99.

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C8H8O4 requires C = 57.10; H = 4.76 per cent.

Forty-two compounds of the empirical formula C8H8O4 are already known. The acid from C. angustissima does not appear to be identical with any of these.

Coriamyrtin.

The physiological action of the New Zealand species of Coriaria and of the European species (C. myrtifolia) is so similar that a direct comparison of tutin with coriamyrtin, the glucoside isolated by Riban,* seemed desirable. A gram of coriamyrtin was obtained from Merck, of Darmstadt; the specimen melted at 225° (uncorr.),† and the melting-point was not altered by recrystallisation from alcohol. Like tutin,‡ the compound is somewhat volatile, sublimation commencing at about 150°. Analysis of the compound before and after crystallisation gave numbers agreeing closely with those obtained by Riban:—

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0.1389 gave 0.3288 CO2 and 0.0822 H2O. C = 64.56; H = 6.57.

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0.1263 gave 0.2976 CO2and 0.0734 H2O. C = 64.25; H = 6.45.

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Riban found (mean of three analyses) C = 64.07; H = 6.57

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C30H36O10 (Riban) requires C = 64.75; H = 6.47 per cent.

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C21H26O7 requires C = 64.61; H = 6.66 per cent.

If the latter formula were correct, coriamyrtin would differ from tutin by C4H6 only, and its higher melting-point, lower volatility, and solubility suggest strongly that it is a higher member of the series to which tutin belongs. Molecular

[Footnote] * Bull. Soc. Chim., 1864 [ii.], 1, 87; 1867 [ii.], 7, 79.

[Footnote] † Riban gives 220°; Merck (Chem; Centr., 1899, i., 706) gives 229°.

[Footnote] ‡ M. Riban has recently shown his continued interest in the subject by supplying us with a small quantity of the original sample of coriamyrtin, and providing us with copies of his valuable memoirs.

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weight determinations, however indicate that the true formula is smaller than either of the above, being probably half that assigned to coriamyrtin by Riban.

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0.2478 gram raised the b.p. of 3.76 grams of acetone 0.46°. M = 255.

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0.3196 gram raised the b.p. of 6.4 grams of acetone 0.33°. M = 265.

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0.1732 gram depressed the m.p. of 8 grams of phenol 0.62°. M = 250.

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0.2226 gram depressed the m.p. of 8 grams of phenol 0.80°. M = 250.

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Calculated for C15H18O5, M = 278; and for C21H26O7, M = 390.

The conclusion that the real formula is C15H18O5 harmonizes with the fact that, by the action of bromine, Riban obtained a crystalline derivative in which one-eighteenth of the hydrogen was replaced by the halogen. If, however, the compound is a glucoside, as its reactions suggest, the sugar which it yields upon hydrolysis cannot contain more than five atoms of oxygen, and the formula is remarkable in that it contains fewer oxygen-atoms than that of any glucoside hitherto described.

The appended table shows the chief differences between tutin and coriamyrtin:—

Tutin, C17H20O7 Coriamyrtin, C15H18O5 (E. and A.).
Solubility in 100 parts of water 1.8 at 10° 1.44 at 22° (Riban).
Solubility in 100 parts of alcohol 8.2 at 16° 2.00 at 22° "
Reaction with hydriodic acid followed by potash Nil Magenta*"
With concentrated sulphuric acid Blood-red Dirty-yellow.
Initial temperature of sublimation About 120° About 150°.
Melting-point 208°–209° 225°.
Optical activity [α]19.5°D = 9.4 [α]20°J = 24.5.

The labours of the authors in the above investigation have been materially lightened owing to the assistance received from a number of gentlemen. In addition to those already mentioned, the authors desire to thank Sir James Hector for drawing attention to points in the literature of tutu which otherwise would have escaped notice; to Dr. Hocken, of Dunedin, for placing his fine library at the authors’ disposal; to

[Footnote] * Reaction verified by the authors.

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Mr. J. D. Ritchie, Secretary of the Department of Agriculture, and to Mr. H. J. Mathews, Chief Government Forester, for obtaining much of the raw material used in the investigation; to Mr. A. R. Young, M.R.C.V.S., for experimental assistance; and to numerous correspondents.

Bibliography.

[Note.—The authors have not had an opportunity of perusing those works whose titles are marked with an asterisk.]

Elswell's “Boy Colonists.” 1834.

“Taylor on Poisons,” pp. 166, 745. 1849.

Lyttelton Times, vol. i., No. i., p. 6. 11th January, 1851.

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“On the Toot-poison of New Zealand,” by W. Lauder Lindsay, M.D. Report of the British Association's thirty-second meeting. Cambridge, 1862.

“Sur le Principe toxique du Coriaria myrtifolia” (Redoul). M. J. Riban, “Comptes Rendus,” Paris, 1863, p. 798.

*“Recherches expérimentales sur le Principe toxique du Redoul (Coriaria myrtifolia),” par Joseph Riban. Paris, 1863. In 8vo.

“Voyage de Novara,” by Karl Scherzer, p. 111. 1863.

*“On Coriaria myrtifolia as an Adulterant of Senna in France,” by M. Riban. B. and F. Medico-Chirurgical Review, 1864, p. 253.

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*B. and F. Medico-Chirurgical Review, October, 1868, p. 465.

“On the Botany of the North Island”: Essay by W. Colenso. Trans. N.Z. Inst., 1868.

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“On the Extraction of the Poisonous Principle of the Tutu Plant (Coriaria ruscifolia),” by Wm. Skey. Trans. N.Z. Inst., 1869, pp. 153, 400.

“On Certain Properties of the Tutu Plant (C. ruscifolia),” by H. G. Hughes. Trans. N.Z. Inst., 1870, p. 237.

“Dispensatory of United States of America,” by Wood and Bache, 13th ed. (1872), p. 1580.

“A General System of Botany,” by Le Maout and Decaisne. London, 1873.

“A Handy Book of Forensic Medicine and Toxicology,” by Woodman and Tidy, p. 292. London, 1877.

“The Organic Constituents of Plants and Vegetable Substances,” by Dr. G. C. Wittstein. Von Mueller's translation. Melbourne, 1878.

“On the Fertilisation, &c., of New Zealand Flowering-plants,” by George M. Thomson, F.L.S. Trans. N.Z. Inst., 1880, p. 258.

“Cyclopædia of India”: Art. “Coriaria.” Quaritch. 1885.

“On Medicinal Plants,” by C. E. Baber. Trans, N.Z. Inst., vol. xix., 1886.

“Forest Flora of New Zealand,” by T. Kirk, F.L.S. Wellington, 1889.

“On the Physiological Action of Coriaria ruscifolia, the Tutu-poison of New Zealand,” by W. Ledingham Christie, M.D. New Zealand Medical Journal, July and October, 1890.

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“Chemical Centralblat,” 1899, vol. i., p. 706: “Coriamyrtin.”

Annual Report, New Zealand Department of Agriculture. 1900.

“Journal of the Chemical Society,” vol. lxxvii., 1900, p. 429.

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“Seemann's Journal of Botany,” vol. i., p. 247.

*“On the Ink-plant of New Granada,” by Dr. Jamieson. Proc. Linn. Soc., vol. vii., p. 120.

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