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Alkaloids of the genus Turbinicarpus (Cactaceae)
Biochemical Systematics and Ecology 27 (1999) 839}841
Short communication
Alkaloids of the genus Turbinicarpus (Cactaceae) Roman S[ tarha *, AdeH la ChybidziurovaH , Zdenek LacnyH Department of Chemistry, University of Ostrava, Bra& fova 7, 701 03 Ostrava, Czech Republic Central Analytical Laboratory, VS[ B Technical University, 708 00 Ostrava, Czech Republic Received 6 November 1998; accepted 3 December 1998
Keywords: Turbinicarpus; Cactaceae; Cactus alkaloid
1. Subject and source Seven species of Turbinicarpus Buxb. et Backbg. as listed in Table 1 were cultivated by the Cactus Club of Ostrava. Identi"cation of plants was made by their commercial suppliers and by comparison with descriptions (Zachar et al., 1996). Living reference specimens of Turbinicarpus are being maintained in the author's greenhouse, photographic documentation is available on University of Ostrava, Department of Chemistry.
2. Previous study Hordenine was identi"ed in two Turbinicarpus species (Bruhn and Bruhn, 1973).
3. Present study The fresh plants (200}240 g of each specimen) were cut into pieces and immediately homogenized in 400}500 ml 95% ethanol. The slurry was left overnight at 53C. The ethanol solution was "ltered and evaporated to dryness. A crude extract was dissolved in a mixture of 50 ml 0.1 M HCl and 50 ml chloroform. The chloroform phase was
* Corresponding author. E-mail address: [email protected] (R. S[ tarha) 0305-1978/99/$ - see front matter 1999 Elsevier Science Ltd. All rights reserved. PII: S 0 3 0 5 - 1 9 7 8 ( 9 9 ) 0 0 0 1 9 - 8
840
R. S[ tarha et al. / Biochemical Systematics and Ecology 27 (1999) 839}841
Table 1 Percentage of total alkaloid fraction in Turbinicarpus species Alkaloids taxon
b-phenethyl- Tyramine amine
N-methyltyramine
Hordenine
Mescaline
N-methylmescaline
1 2 3 4 5 6 7
1.01$0.12 1.07$0.42 1.04$0.27 1.01$0.21 1.12$0.13 0.98$0.12 1.70$0.15
traces traces 0.13$0.11 traces traces 25.15$1.21 0.51$0.02
43.02$1.86 48.81$2.72 91.69$0.54 92.05$0.71 49.60$0.55 62.11$2.42 42.45$0.45
N 1.26$0.21 traces traces 2.48$0.19 N N
1.02$0.21 0.98$0.24 0.51$0.11 traces 3.27$0.09 1.11$0.13 N
Alkaloids taxon
N,N-dimethyl- O-methylmescaline anhalidine
Anhalinine
Anhalonidine Pellotine
Presence of alkaloids
1. 2. 3. 4. 5. 6. 7.
Traces Traces Traces A 2.89$0.15 Traces A
17.19$1.00 39.57$1.14 0.15$0.08 traces 29.24$0.04 2.88$0.15 2.78$0.31
19.86$1.41 0.52$0.11 2.37$0.12 0.88$0.12 2.44$0.13 N 22.70$1.14
* ** *** * ** *** **
5.46$0.14 2.92$0.25 1.82$0.17 3.08$0.08 0.98$0.18 3.18$0.19 2.59$0.13
2.76$0.42 2.82$0.41 0.55$0.02 2.89$0.46 0.77$0.04 1.92$0.15 1.42$0.30
9.02$0.06 0.41$0.11 0.46$0.08 0.15$0.07 0.36$0.08 N 19.33$0.28
(1) Turbinicarpus schmiedeckianus (Bod) Buxb. et Backbg.; (2) T. schmiedeckianus var. schwarzii (Shurly) Gl. et F.; (3) T. lophophoroides (Werd.) Buxb. et Backbg.; (4) T. schmiedeckianus var. yaviyorus (Frank et Lau) Gl. et F.; (5) T. pseudomacrochele var. krainzianus (Frank) Gl. et F.; (6) T. pseudopectinatus (Backbg.) Gl.et F.; (7) T. schmiedeckianus var. dickisoniae Gl. et F. Presence of alkaloids: * "10}25 mg/10 g; **"25}50 mg/10 g; ***"over 50 mg/10 g of fresh plant; N"not detected.
discarded and the aqueous solution was twice washed with 10 ml chloroform. The aqueous phase was basi"ed to pH 10 with conc. ammonia. The aqueous phase was extracted twice into 30 ml chloroform. Alkaloids were identi"ed by GC (cochromatography with reference compounds on two phases) and by GC-MS. GC was carried out using Carlo Erba Ins. HRGC, glass capillary column, phase DB1 and DB5, 0.25 lm, 30 m, 0.32 mm. Mass spectra were recorded with GC-MS MagnumFinnigan Mat Varian 3400 (EIMS-70 eV).
4. Chemotaxonomic signi5cance Seven b-phenethylamines and four tetrahydroisoquinoline alkaloids were found in species of the cactus genus Turbinicarpus, often in appreciable amounts. The results are summarized in Table 1. b-phenethylamine and tetrahydroisoquinoline derivates are known from many plant families as well as in a number of cactus genera (Smith, 1977; Lundstrom, 1983). However, their presence in the genus Turbinicarpus is novel. The results suggest a potential value for alkaloid pro"les in the taxonomy of Turbinicarpus at the infrageneric level.
R. S[ tarha et al. / Biochemical Systematics and Ecology 27 (1999) 839}841
841
Acknowledgements The authors acknowledge the valuable advice and assistance of R. Peter from the University of Ostrava and J. Kuchyna from DPB Paskov. The research was supported by grant IGS OU 3705.
References Bruhn, J.G., Bruhn, C., 1973. Economic Botany 27, 241. Lundstrom, J., 1983. The Alkaloids 21, 255. Smith, T.A., 1977. Phytochemistry 16, 9. Zachar, M., Stanik, R., Lux,A., Drab, I., 1996. Die Gattung Turbinicarpus, Bratislava.
Short communication
Alkaloids of the genus Turbinicarpus (Cactaceae) Roman S[ tarha *, AdeH la ChybidziurovaH , Zdenek LacnyH Department of Chemistry, University of Ostrava, Bra& fova 7, 701 03 Ostrava, Czech Republic Central Analytical Laboratory, VS[ B Technical University, 708 00 Ostrava, Czech Republic Received 6 November 1998; accepted 3 December 1998
Keywords: Turbinicarpus; Cactaceae; Cactus alkaloid
1. Subject and source Seven species of Turbinicarpus Buxb. et Backbg. as listed in Table 1 were cultivated by the Cactus Club of Ostrava. Identi"cation of plants was made by their commercial suppliers and by comparison with descriptions (Zachar et al., 1996). Living reference specimens of Turbinicarpus are being maintained in the author's greenhouse, photographic documentation is available on University of Ostrava, Department of Chemistry.
2. Previous study Hordenine was identi"ed in two Turbinicarpus species (Bruhn and Bruhn, 1973).
3. Present study The fresh plants (200}240 g of each specimen) were cut into pieces and immediately homogenized in 400}500 ml 95% ethanol. The slurry was left overnight at 53C. The ethanol solution was "ltered and evaporated to dryness. A crude extract was dissolved in a mixture of 50 ml 0.1 M HCl and 50 ml chloroform. The chloroform phase was
* Corresponding author. E-mail address: [email protected] (R. S[ tarha) 0305-1978/99/$ - see front matter 1999 Elsevier Science Ltd. All rights reserved. PII: S 0 3 0 5 - 1 9 7 8 ( 9 9 ) 0 0 0 1 9 - 8
840
R. S[ tarha et al. / Biochemical Systematics and Ecology 27 (1999) 839}841
Table 1 Percentage of total alkaloid fraction in Turbinicarpus species Alkaloids taxon
b-phenethyl- Tyramine amine
N-methyltyramine
Hordenine
Mescaline
N-methylmescaline
1 2 3 4 5 6 7
1.01$0.12 1.07$0.42 1.04$0.27 1.01$0.21 1.12$0.13 0.98$0.12 1.70$0.15
traces traces 0.13$0.11 traces traces 25.15$1.21 0.51$0.02
43.02$1.86 48.81$2.72 91.69$0.54 92.05$0.71 49.60$0.55 62.11$2.42 42.45$0.45
N 1.26$0.21 traces traces 2.48$0.19 N N
1.02$0.21 0.98$0.24 0.51$0.11 traces 3.27$0.09 1.11$0.13 N
Alkaloids taxon
N,N-dimethyl- O-methylmescaline anhalidine
Anhalinine
Anhalonidine Pellotine
Presence of alkaloids
1. 2. 3. 4. 5. 6. 7.
Traces Traces Traces A 2.89$0.15 Traces A
17.19$1.00 39.57$1.14 0.15$0.08 traces 29.24$0.04 2.88$0.15 2.78$0.31
19.86$1.41 0.52$0.11 2.37$0.12 0.88$0.12 2.44$0.13 N 22.70$1.14
* ** *** * ** *** **
5.46$0.14 2.92$0.25 1.82$0.17 3.08$0.08 0.98$0.18 3.18$0.19 2.59$0.13
2.76$0.42 2.82$0.41 0.55$0.02 2.89$0.46 0.77$0.04 1.92$0.15 1.42$0.30
9.02$0.06 0.41$0.11 0.46$0.08 0.15$0.07 0.36$0.08 N 19.33$0.28
(1) Turbinicarpus schmiedeckianus (Bod) Buxb. et Backbg.; (2) T. schmiedeckianus var. schwarzii (Shurly) Gl. et F.; (3) T. lophophoroides (Werd.) Buxb. et Backbg.; (4) T. schmiedeckianus var. yaviyorus (Frank et Lau) Gl. et F.; (5) T. pseudomacrochele var. krainzianus (Frank) Gl. et F.; (6) T. pseudopectinatus (Backbg.) Gl.et F.; (7) T. schmiedeckianus var. dickisoniae Gl. et F. Presence of alkaloids: * "10}25 mg/10 g; **"25}50 mg/10 g; ***"over 50 mg/10 g of fresh plant; N"not detected.
discarded and the aqueous solution was twice washed with 10 ml chloroform. The aqueous phase was basi"ed to pH 10 with conc. ammonia. The aqueous phase was extracted twice into 30 ml chloroform. Alkaloids were identi"ed by GC (cochromatography with reference compounds on two phases) and by GC-MS. GC was carried out using Carlo Erba Ins. HRGC, glass capillary column, phase DB1 and DB5, 0.25 lm, 30 m, 0.32 mm. Mass spectra were recorded with GC-MS MagnumFinnigan Mat Varian 3400 (EIMS-70 eV).
4. Chemotaxonomic signi5cance Seven b-phenethylamines and four tetrahydroisoquinoline alkaloids were found in species of the cactus genus Turbinicarpus, often in appreciable amounts. The results are summarized in Table 1. b-phenethylamine and tetrahydroisoquinoline derivates are known from many plant families as well as in a number of cactus genera (Smith, 1977; Lundstrom, 1983). However, their presence in the genus Turbinicarpus is novel. The results suggest a potential value for alkaloid pro"les in the taxonomy of Turbinicarpus at the infrageneric level.
R. S[ tarha et al. / Biochemical Systematics and Ecology 27 (1999) 839}841
841
Acknowledgements The authors acknowledge the valuable advice and assistance of R. Peter from the University of Ostrava and J. Kuchyna from DPB Paskov. The research was supported by grant IGS OU 3705.
References Bruhn, J.G., Bruhn, C., 1973. Economic Botany 27, 241. Lundstrom, J., 1983. The Alkaloids 21, 255. Smith, T.A., 1977. Phytochemistry 16, 9. Zachar, M., Stanik, R., Lux,A., Drab, I., 1996. Die Gattung Turbinicarpus, Bratislava.