INDOLE ALKYLAMINES FROM TACHIGALIA P A S I C U L A T A KAREXS . SVOBODA, STANISLAUS J . SMOLENSKI and A. DOUGLAS KISGHORS Departmetit of Pharmacognosy and Pharmacology, College of P h a r m a c y , L-nin'ersity of I l l i n o i s at the Jfediciil Center, Chicago, I l l i n o i s 60618
I n the course of an alkaloidal screen legume extracts, quailtities Of two indole alkylamines were detected in inflorescences of ~ ~ ~ hpa,2ii ~ c d a t a -Aubl. ( L e g u h o s a e , subfamily Caesalpinioideae). Although this arboreal species, indigenous to parts of peru alld ~ ~ ~does~ not i lappear , to have been subjected to Prior PhYtochemical studies, the leaves of another member of the genus, T . myymeOf
Sational Cancer Institute, formerly t,he Cancer Chemotherapy Sational Service Center, Bethesda, llaryland. -4specimen representing this collection IS deposited in ~ thel Herbarium i ~ of the Kational Arboretum, hgricultural Research Service, U.S. Department of A\griculture, Washington, D.C.
FRACTIOSATIOS ASD IDESTIFICATIOS OF ISDOLE ALECTL.AJIISES.--.~ portion of the plant
extract ( 2 g) was extracted according t o the method of Farnsworth and Euler (6). The resultant crude basic fraction (3 mgj n-as chromatographed by tlc in three solvent systems (methanol-ammonium hydroxide solution, 131:2:benzene-chloroform-diet hylacophila, contain skatole (3-methyl inmine 5:4:1; chloroform-methanol-ammonium hydroxide solution, 80:20:1). -\--Methyldole) (1j and tannins ( 2 ) . tryptamine and tryptamine had identical R f I n the present w - k an 80% extract values q-ith authentic compounds2 and exof Taclrigalia paiziculata inflorescences hibited a brilliant yellon- color in long-wave extracted for alkaloids, and the uv light when visualized with 1% ceric ammonium sulfate in 8 5 5 phosphoric acid presence of S-methyltryptanine and (1100, io minj. tryptamine was indicated by tlc and -1 chloroform solution (l%,w , v ) of the crude basic fraction was analyzed b?- gc-ms, by combined gc-ms. ~h~ using 57c SE-30 on Chromosorb I T as gc concentration of each base in the exstationary phase, temperature programmed t,raCt ~ y a sdetermined by hplc. -IT-a t 1' min-' from 150c, n-ith the flow rate of He 22 ml min-1. The mass spectrum of trj-p31ethyltrypta&e has not prel'iously tamine (R, 5.1 niin) was closely comparable been isolated from any plant in the t o that obtained previously using this techCaesalphioideae. T~ date, trl-ptanique (7). Although the molecular ion of ~ ~ - m e t h j - l t r y p t a m i n(R, e l . T mini was not mine has been shown t o occur in three observed, its mass spectr-im othern-ise species in this subfamily, namely, Petssimilar t o data from a previous study ( T j .
lostylis labicheodes var. casseoides (3), ~ i guia,tensis ~ (4) and ~ Buykea~
QV.ASTIFIC.kTIOS
OF I S D O L E .ALKYL.AMISES.-
A further ~ 2 g portion ~ of the~plant extract i was accurately weighed and subjected t o hplc on a Waters a4ssoc. 3 0 x 5 mm i . d . yBondapak CIS column n-ith 1,1-dioxane-0.1 31 ammonium carbonate (4:s)as solvent, as previouslv described by group ( 8 ) . The levels of tryptamine and -\--methyltryptamine in the extract n--ere 0.009% n - h and 0.005% w/n- respectively.
africana (5).
EXPERINESTAL' PL-~ST ~ ~ - ~ T E R I---in A L 80% ethanolic
of' t h e of Tacliigalin panicula:a, collected in Peru, was supplied by the Developmental Therapeutics Program (Katural Products Branch) of the ___-
ACKKOWLEDGPIIEKT The authors are indebted t o Dr Jonathan L , Hartn.ell, formerly Chief, Sa;ural Products section, Drug, Research and DevelopIllent 'hemotherap!-, Kational Cancer Institute, Maryland, for supplying the plant extract used in this study. Receiped 18 October 1978.
'All tlc n-as carried out onpre-coated silica gel GF-254 plates (E. Darmstadt, Germany). Combined gc-nis was performed on a 1 arlan->\IAIT1128 mass spectronieter, equipped with a 1-arian-MAT 1GG D a t a System, linked t o a 1400 model gas chromatograph, using a G' glass column. Hplc separations were obtained on a Waters -4ssoc. model 6000 liquid chromatograph, equipped with a Beckman 25 variable n-avelength uv spectrophotometer and recorder.
-~
2Reference samples of ,\--methyltrypt amine and tryptamine were obtained from Sigma Chemical Company, S t . Louis, ,110.
307
~
308
JOURSAL OF NATURAL PRODCCTS LITERATURE CITED
1.
R . F. A. ALTMAN,Insf. A\-ac. Pesqzr?.
Amaeoma, Publ. 2, 3 (1958); Clieni. Abstr., 52, li402d (1958). 2. W.B. MORSand C. T . RIZZISI,“Gseful Plants of Brazil”, Holden Day Inc., San Francisco, London, Smsterdam, 1966, p . 52. and A. 4. 3 . S. R . JOHSS,J. LAMBERTOS SIOUMIS.d z r s t . J . Chem., 19, 893 11966). and L.’ L ~ Y G EA-atilr, 4. W .SANDERXAAS wzssemciiufien, 54, 249 (1967).
[VOL.
42, s o . 3
5 . -4.C O R R E DA I ~ SILTAand 11. Q. PAIR.%, An. Fac. F a r m . P o r f o , 31, 107 (1971); Cheni. d b s t r . , 78, 132046q (1973).
N. R. F A R K S ~ - Oand R T K. H L. EULER, L l o p d i a , 25, 1% (1962). S. AGURELL,B. HOLMSTEDT, J-E. LISDGREK and R . E . SCHULTES, Acta Clienz Scaiid., 23, 903 (1969). A. D. KINGHORS,S. 8. M.F. BALASDRIS, J . SMOLESSKI and R. H. DOBBERSTEII, J . C i m i n e t o g r . , 157, 365 (1978).
