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BY

JOHN URI LLOYD,

CINCINNATI, O.

R E P R I N T E D F R O M

THE WESTERN DRUGGIST,

CHICAGO, SEPTEMBER, 1897.

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STROPHANTHUS HISPIDUS, D.C.*1

BY J OHN URI LLOYD.

BOTANICAL DESCRIPTION ANDHISTORICAL NOTES.

The genus s t rophanthus , which produces th i sdrug, is chiefly African, belonging to theapocynaceae and the tr ibe echitideae of thisorder, dist inguished from the other tr ibes of the

order chiefly from having the anthers unitedaf ter the manner of the asclepiadaceae. IndexKewensis mentions seventeen species , Bentham

and Hooker eighteen species, Pax29 twenty-fivespecies , and the genus is being rapidlyaugmented as the flora of Africa becomes betterknown. Plants of the genus have usual ly woodystems, emit t ing a milky juice when wounded,and are generally twining vines. The seed ofcommerce is probably collected from variousspecies indiscriminately, which have been

classified and differentiated by Pax29,

Planchon 31, Hartwich 28, Holmes 24, Blondel19

a n d oth ers . Spa ce will perm it u s t o m en tion on lythe two species which are acknowledged to beth e prin cipa l s ou rce of th e dru g.

S troph an thus his pid us , D. C., was one of fourspecies described by De Candolle as early as1802, and is the spec ies to which the drug was

f irs t ascr ibed. I ts habita t is Senegambia andGuinea and other parts of western Africa. The

* Th e th a n ks of th e writer a re exten ded to Mr. C. G. Lloyd

for botanical notes, and to Dr. Sigmond Waldbott,libr a rian of th e Lloyd Libr a ry, for in va lu a ble as s is ta n ce.

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stem is a twining, milky shrub, with oppositehirsute leaves. (Hence the name hispidus , Latinfor b ris tly, h a iry).

Th e flowers a re b orn e in term in a l, m a n y-flowereddense cymes. The calyx consists of five hairygreen sepals about the length of the corollatube. The corolla is white, with a short funnel-sh ap ed tu be yellowish with in an d fu rn ish ed withten small nectar iferous glands. The segments of the corolla are very long, tapering, slender, hairy

without, having a length sometimes of eightinches , and are the conspicuous par t of theflower, giving the plant its generic name (fromstrophos , Greek for a twisted chord). Thestamens are f ive , with sagi t ta te anthers andslender filaments. The pistil consists of twodistinct carpels, each of which, if fertilized,

r ipen s int o a lon g pod filled with n u m erou s s eed.The seed, which bears a s lender s tyleterminat ing in a p lumose pappus consis t ing of lon g fin e h a irs *2 , a re th e par t u sed in m edic in e .

S tropha nthus k om be, Oliver, is a similar plant,native, however, of eastern Africa. It was at first

referred to S . his pid us , and is st i l l considered bysome writers to be but the oriental form of thissp ecies . It h as th e sa m e h irsu te leaves , bu t th eyar e m ore cor iaceou s. Th e sepals a re sh orter th anthe corolla tube, and cymes are fewer floweredt h a n S . his pid us .*2Hartwich 21 calls special at tention to the fact that thehairs of s t rophanthus seed are very sensi t ive to mois ture ,sp read h orizont ally in dry air , an d b ecom in g erect in m oista tmosphere . He sugges ts tha t the pappus would thusmake an hygrometer sufficiently sensitive for practicalpurposes .


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As s ta ted before , the genus s t rophanthus wasestabl ished by De Candolle as far back as theyear 1802. I t was not until the early sixties,

however , that the drug came to the generalnotice of Europeans as being one of the arrowpoisons used among the African native tr ibes.There were two kinds of arrow poisons derivedfrom this source. A poison was prepared on thewest coast of Africa (Senegambia, Guinea andGaboon) called inee or onaye, which is derived

from Strophanthushispidus , D. C. This is on theauthority of Hendelot, who observed the plantyielding this poison in Senegambia at the r iver

Nunez6 . A specimen of this arrow poison wassent to Europe and investigated by Pelikan in

18654 .

On the east coast of Africa the kombe or gombepoison was in use in the Manganjah t r ibe ,located near Lake Nyassa on the banks of theriver Shire, a tributary of the Zambesi river.Consul Kirk in Zanzibar, in 1861, establishedtha t th is poison or ig ina ted f rom a s t rophanthusspecies, and forwarded specimens to Prof.

Sharpey in England for the purpose of investigation 6 . Subsequent ly , in 1865,Livin gst on e 's fa m ou s reports b rou gh t th e komb epoison to a more general not ice among the

Europeans3 .

This species of s trophanthus was a t f i rs tconsidered identical with S . his pid us , D. C., butthe plant was shown by Oliver in 1885 to bedistinct from the latter , and justif ied theestablishing of a new species, Strophanthus


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CHEMISTRY OF STROPHANTHUS.

The chemistry of this drug has not been so

closely elaborated as the importance of theremedy in medical practice would warrant. Thisis obviously due to the difficulty heretoforeexperienced, as already related, in obtainingstrophanthus f rom a re l iably uniform source,which fact natural ly makes any exact chemicalin ves tiga tion illu s ory from th e st a rt .

The active principle was first isolated fromst rophanthus kombe by Frase r in 1872 , whonamed i t strophanthin, but he took i t to be analkaloid, a s ta tement which he amply corrected

afterward6 .

In 1877 the name s t rophanth in was appl ied byHardy and Gallois to a crysta l l ine substanceobtained from the seed ofS . his pid us , D. C., byextracting the latter with alcohol acidulated

with h ydr och loric a cid8 . Th e resu lt in g su bs tan cewas found to contain no nitrogen, neither did i tprove to be a glucosid. The authors, besides,claim to have obtained from the hairy tufts(awns) of the seeds an alkaloid, which they

called ineine. Later researches by Elborne,12

Gerrard 13 and F ra se r10 , however, failed todiscover an a lkaloid in the awns, Fraser havingsubjected to examination one pound of tuf ts

with ou t su ccess .

Fraser , in the years 1885-90, found his or iginals trophanthin to be a glucosid, capable of spli t t ing under the action of acids into glucose


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a n d strophanthidin , a bi t ter nonnitrogenousbody, insoluble in water, soluble in alcohol. Thefailure of Hardy and Gallois to obtain theglucosid Fraser ascribed to their employing

acidulated alcohol for extraction, whereby theyprobably obtained s trophanthidin direct . Fraseralso succeeded in isolating, a peculiar acid,which he called kombic acid. Catillon, in 1880,affirmed the existence of two glucosids ins t r opha n thus s e e ds (S. kombe), one beingst rophanthin , the o ther n i t rogen-bear ing and

spli t t ing with acids into sugar and an a lkaloid.He s t a ted tha t when s t rophan thus seeds ,exhausted with a lcohol and ether (being thusdeprived of their strophanthin and fat) , aretreated with boiling acidulated water, they giveup to this solvent a considerable quantity of avery distinct glucosid associated with a perfectly

ch a ra cterized a lka loid 20.

Strophanthin is freely soluble in water and

alcohol, insoluble in pure ether or chloroform.13According to Merck, its melting point is about

18 5 d eg. C.17; s t rophanthin obta ined by Arnaud

from S . his pid us m elts a t 17 2.5 d eg. C.18

Arnaud ' s s t rophanth in has the formulaC31H48O12 which, as will be seen, bears a close

relation to ouabain, the active principle ofa n oth er African a rrow pois on.

The most str iking test of the seeds forstrophanthin is carr ied out as fol lows, by usinga low m a gn ifyin g m icros cope:

Mak e a cross sect ion of th e seed, an d tou ch with


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concentra ted sulfur ic acid. The end sperm is a ton ce colored blu e, th en a bea u tifu l green r esu lts .Th e cotyledon s likewis e tu rn green , bu t with lessintensity. Gradually the color changes to red,

a n d a fter a s h ort wh ile fad es ou t .

In Helbing's test the cross section of the seed ismoistened with a trace of solution of ferricch lorid th en with a dr op of con cen tra ted s u lfu ricacid. A red-brown precipitate occurs, which is

green a fter a la ps e of on e or two h ou rs 15.

Employing the first test, Hartwich 28 h a s dem on -stra ted that only a few species among thosefound in commercia l s t rophanthus conta ins t rophanth in , and he d iscovered the apparen trule tha t ca lc ium oxala te and s t rophanthinseem to exclude each other in the seeds.

However, a positive exception occurs in thestrophanthus seeds f rom the is land of Los,where both bodies are present , and a negativeexception is seen in S . Fis cheri, where both areabsen t .

The yield of strophanthin from S. kom bi is abou t

0.95 p er cent , from S . his pid us , 0 .65 per cent a n dfrom S . glaber5 p er cent72. Th e la tt er s pecies, inaddition to its high yield in alkaloid, is verypoisonous, and was for this reason expresslyexcluded from one of the European

pharmacopeias 27. I t contains ouabain as i ts

a ctive p rin cip le.

S trophanthus seed conta ins a la rge percentage(from 20 to 32 per cent) of fatty substance. Thebitter principle is claimed to reside in the fatty


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oil , and is said to be completely abstracted bypetroleum ether , without affect ing s trophan-

thin 32.

NOTE S ON ARROW POISONS.

In ou r p a per on cala ba r we referred b riefly to th eordeal poison of Africa. In the present paper wealso find a necessary diversion, and will givesom e a t ten t ion to a r row pois on s .

Arrow poisons are in common usage in warfare,as well as in hunting among var ious aboriginaltribes. While we find in Africa strophanthusyielding the inee and kombe poisons, andacokanthera yie lding ouabaio, poison, aconitumferox is used in Nepal (Himalaya mountains),an t iar is toxicar ia , or u pa s t r ee, in J ava, an d

cumane in South America . Neither are thesepoisons confined to vegetable origin. Livingstonecites a poisonous caterpil lar that is employed insouth Afr ica , and suggests tha t the animalprobably derives the poison from the plant i tfeeds on. Lewin mentions in this connectionDiamphidia simplex, Per inguey, an underground

chrysalis30.

As a rule, the African arrow poisons do notconsis t of s ingle substances , but compoundsmade up of var ious roots and leaves which ared ifficu lt to iden tify bota n ica lly a n d ch em ica lly.

The natives are very reluctant about disclosingthe origin or the manner of preparation of theirarrow poisons, only the init iated few amongthem being acquainted wi th the ar t . For the


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purpose of concocting the arrow poison one manbeta kes h im s elf in to th e fores t 's dept h s , fa r a wayfrom human habi ta t ions . He f rees the seeds of s t rophanthus f rom the ir ha i ry appendages

(which, by the way, are an article of commerce,serving in the making of vegetable silk29), andpounds them to a pu lp in a mor ta r ; he thenad ds wa ter an d th e expres sed ju ice of th e r in d of a t i l iaceae species yielding a gum that serves tomake the poison stick to the arrow. The poisonthu s p repa red is th en sm ea red u pon the sh a ft to

a len gth of ab ou t s ix in ch es. It is sa id t h at gam ewounded by an ar row poisoned by s t rophanthusdies at once, seldom being able to move ahundred yards. The f lesh of animals kil led inthis way is eaten without any evil effect, theprecaution a lone being taken ei ther to cut outan d exclu de th e flesh su rrou n din g th e wou n d, or

to squeeze into i t the sap from a branch of thebaobab tree (adansonia digi ta ta) . Elephants andhippopotami cannot be destroyed in thismanner , a s they do no t respond to the amount

of poison an a rrow can carry3,33.

Th e pigm ies u s e five in gredien ts in com pou n din g

their arrow poisons, and three to make theirant idote to this poison. Surgeon Parke was sofortunate as to secure detailed information withregard to the source of these ingredients. Anexceedingly interesting account thereof is givenin reference 22. The poison, however, is notconnected wi th s t rophanthus; i t has as i t s bas issome species of s trychnos and the bark of Ery throph lae um guineen s e , Don, the t ree thatyields the red-water ordeal of the Africann a tive tr ibes .


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Th e ouabaio poison of the Somali deservesspecial mention because i ts active principle,ou a ba in , is believed t o sta n d in close con n ection

with strophanthin. The ouabaio poison, l iberallyreferred to by Burton, according to our presentstate of knowledge, is derived from either of thefollowing species of apocynaceae: AcokantheraSchimperi (D. C.), Benth. and H., A. Deflersii,

Sch wein f., or A. ouaba io. Cath e lin eau 23,33 .

The making of this poison among the Somali isa t tended with the mystery tha t i s thrown abouttha t of the s t rophanthus ar row poison a l readyrelated. The wood is chipped and then boiledwith water in an ear thenware pot for hours oreven days until a pitch-like extract is obtained,which is smeared upon the i ron arrow point . To

prevent the poison from rubbing off , the barb issurrounded with parchment- l ike prepared goat-skins or plant f ibers, which are removedimmediately before use. To test this poison theSomali scratches his arm until the blood f lows;he then applies the poison to the lower end of the bloody pool and watches the blood

coagulating from below upward, estimatingth erefrom its viru len cy33.

In 1882 some roots , s tems and leaves of theplant yielding ouabaio poison were sent toFra n ce by Revoil, an d in vest iga ted by Arn a u d . In1888 Arnaud obtained from similar specimensan act ive pr inciple , an amorphous glucosid,which he ca l led ouabain . For th is substance hea rrived a t th e form u la C 30H46O12. Th is d iffers by

the group CH. f rom the formula for s trophan-S t rop h an t h us - Lloyd - Page 1 0

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th in , C 31H48O12, which he obtained from S .

hispidus , D. C. He therefore concluded thats t rophanthin represents the h igher homologueof ouabain . Besides , both substances have

identical physiological action which differs indegree only. Arnaud finally discovered thatouabain is identical with the active principleobtainable from Strophanthus glaber, to the

am ou n t of 4 .7 per cen t18.

PHARMACOPEIAL RECORD OF

STROPHANTHUS.

Consequent upon the recent in t roduct ion of s t rophanthus in to medic ine , only the la tes tissues of the different pharmacopeias carry thedrug. The t inc ture of s t rophanthus is the onlypreparation as yet officially recognized, but the

t inctures of the var ious pharmacopeias are notuniform in s trength nor in the mode of theirprepara t ion.

Th e Germ an ph ar m a copeia of 18 90 , for exam ple,directs a strength of 1:10, while the Brit ishpharmacopeia (additions of 1890), the Austr ianpharmacopeia , 1889, and the Uni ted Sta tespliarmacopeia, 1890, direct a strength of 1:20.According to the Brit ish and Austr ianpharmacopeias the fatty oil is to be previouslyremoved by ether . The German pharmacopeiadirects the fatty oil to be removed by cold

pressure , while the United States pharmacopeiagives no special direction for the removal of theoil. According to the latter authority, 50 gramsof the seeds in No. 30 powder are extracted witha mixture of 650 Cc of alcohol and 350 Cc of

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water.

In 1889 Mr. Beringer pointed out that thet inc ture of s t rophanthus should no t be

prescr ibed in aqueous solut ion, because, asLarmuth has observed, the bi t ter pr incipleundergoes some change in aqueous solut ion bystanding for a few days, thereby becoming far

m ore toxic th a n wh en r ecen tly prep a red25.

Of late some physiological experiments have

been carried on with favorable results by H. C.Wood and W. S. Carter in order to test theadvisability of introducing an alcoholic extractof definite strength, or the active principlestrophanthin, into the next edi t ion of the

Un ited Sta tes p h arm acopeia34.

LITERATURE ON STROPHANTHUS.

(1.) De Ca n dolle, An n . d. m u s e n a t. dh is t. n a tu relle,Paris, 180 2.

(2.) Burton, The Lake regions of Central Africa. Transl. byKa rl An dre , Leipzig, 1860 , Vol. I, p. 2 47 a n d 2 97 , Vol. I I, p.338 .

(3.) Livingstone, Narrative of an expedition to the Zambesian d its t r ibu tar ies , 1865.

(4.) Pelika n , Comp tes Ren du s, Vol. 60, p. 12 09 ,1865 .

(5.) Oliver, Hooker's Icones plantar. (3), Vol. 1, part 4, p.79,1871.

(6.) Fra ser Th. R., On th e Komb e poison . J ah resb , d.Pharm ., 1871, p . 543,1872 , p . 615, a lso see Ph arm . J ou r .(2), Vol. I I 1 , 187.1, p . 523.


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(7.) Polaillon and Carville, Arch. d. Physiologie, Vol. IV, p.523 an d 681, 1872.

(8.) Hardy & Gallois, Sur le principe actif du Stroph.h is pidu es. jou r. Ph a rm . Chim . Vol. XXV, P. 17 7, 1 87 7. See

also Comptes Rend. , Vol . 84, p , 261, 1877, and Pharm.J ou r. a n d Tr. (3), Vol VII, p. 7 56 ,18 77 .

(9.) Fra ser Th . R., Brit. Med J ou r., Nov. 14 th , 1885 .

(1 0 .) F ra s er , Th . R., S tr op h a n t h u s h is p id u s , it s n a t u r a lhistory, chemistry and pharmacology. Trans. Roy. Soc.Edin b. , Vol. 35, pp. 955 102 7,189 0. See also Pha rm .J our . ,

Vol. XVIII, 18 88-89 , p. 6 61 , an d Vol. XIX, 18 89-9 0, p . 32 8.

(11 .) Thom as C hr is t y, New com m ercia l p lan t s and d ru gs ,No. 10 , Lond on, 18 87 , an d 5t h ed., Ma y, 1888 .

(12 .) Wm . E lborne , A con t r ibu t ion t o t hePharmacognosy of Strophantus , Phar . Jour . , Vol .XVII,.1886 -87 , p. 7 42 .

(13. ) A. W. Gerrard, Strophanthus and Strophanthin.Pha rm . J ou r., XVII, 1886-87 , p. 92 3.

(14.) R. M. Holmes, Note on false Strophanthus seeds,Pha rm . J ou r., Vol. XVII, 18 86 -87, p . 90 3.

(15 .) Helbin g, Rea ction of Str oph a n th in , Ph a rm . J ou r. , Vol.XVII, 18 86 -87 , p. 924 .

(16.) Reber B. , Le genre Strophanthus et ses quali tsthrapeutiques, Le Progrs, Geneva, Vol. III, 1887, p, 277,293, 313.

(17 .) Merck , Pharm . J ou r., Vol. XVIII, 1887-88 , p. 72.

(1 8 .) Ar n a u d , Com p t es Ren d u s , Vol. 10 7 , p p . 1 7 9 a n d11 62 ,188 8. See a lso Ph ar m . J ou r. , Vol. XVIII, 18 88 -89, p p.162 and 606 .

(19 .) Blonde l, Les S tropha n th u s du com m erce, Pa r is ,18 88 . See also Pha rm . J ou r., Vol. XVIII, 18 88 89 , p. 74 4.


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(20 .) Cat illon , J ou r. de Ph a rm ., Vol. XV1, 1 88 8, p . 56 8, a n dXV11, 18 88, p. 221 . See also J ah resb. Pha rm ., 18 88 , p. 19.

(2 1 .) C. Ha r twich , Ueb er d en S tr op h a n t h u s Sa m e n .

Arch iv. d. Ph a rm .. Vol. 226, p . 500,18 88 .

(22 .) E. M. Holm es an d Su rgeon Park e. Th e a rrow poison ofth e pigm ies, Ph a rm . J ou r. , Vol. XX, 189 0-91 , pp. 917 an d927 .

(23 . ) E , M. Holmes , Ou aba io Ar row poison . Ph arm .J ou r., Vol. XXIII, 18 92 -93 , p. 96 5.

(2 4 .) E . M. Holm e s , On t h e S tr op h a n t h u s s eed s of com m erce, Pha rm . J ou r. , Vol. XXII, 189 2-93 9 p p. 86 8 a n d927 . See also J ah resb. Ph arm ., 189 3, p. 42.

(25 . ) Berin ger., George M., Tinc tu re of S t roph an thu s .Am . J ou r. Ph arm ., 188 9, p. 454.

(26 .) Fl ckiger, Ph a rm a cogn osie des Pfla n zen reich s, 3d ed.,Berlin , 1891 , p. 10 21 .

(27 . ) L. Reu ter , J ahresber , Pharm. , 1891, p . 35 .

(28 .) C. Ha r twich , Beit r ag. zu r Kenn tn is s d .St rophanthus und e in iger mi t dense lben verwandtensa m en. Arch . d. Ph ar m ., Vol. 230 , p. 401, 18 92 .

(29 .) F . Pax, Ueber d ie S t am m pflan ze der St rophan thu sSam en, Engler 's J ah rb cher , 1892 , pp . 362-386. See a lsoJ ah resb. Pha rm. , 1893, p . 40.

(30. ) L. Lewin . , Die afr ika n isch en Pfeilgifte , Berlin , 189 4.See also J ah resb. Ph arm ., 180 5,1). 4.

(31 . ) Ber in ger , George M. , Th e Apocyn aceae In Mater iaMedica, being an abstract of L. Planchon's monograph onsa m e su bject , Montp ellier , 18 94 , , Am er. J ou r. Ph a r. , 18 94 ,pp. 449 an d 540, and 189 5, pp. 35, 100 an d 157.

(32 . ) Caesa r & Loretz, J ahresb. d . Pharm ., 1895 , p . 31 .


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(33. ) En gler A. , Deu tsch Ost . -Afr ica , Vol. V, Par t B., pp.515-520.

(34 .) H. C. Wood an d W. S. Ca r t er . Am er . J ou r . Pha rm . ,

1896, p. 353.

(35 .) P. S ied ler , Adu lt er a t ion of S t ropha n th u s s eeds ,Zeitschr. allg. oest, Apoth. Ver., Vol. 35, p. 398. See alsoPha rm . Review, Au gu st 18 97 , p. 16 1.


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