Biochemical Systematics and Ecology 26 (1998) 933—934

Short communication

Alkaloids from Dasymaschalon sootepense1

Andrea Sinz!, Rudolf Matusch!,*, Ludger Witte",
Thawatchai Santisuk#, Suttiporn Chaichana$,
Vichai Reutrakul$, Sirichai Wangcharoentrakul%
! Institut fu( r Pharmazeutische Chemie, Philipps-Universita( t, Marburg, D-35032 Marburg, Germany
" Institut fu( r Pharmazeutische Biologie, TU Braunschweig, D-38106 Braunschweig, Germany
# The Herbarium, Royal Forest Department, Bangkok 10900, Thailand
$ Department of Chemistry, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand
% Conservation Science Division, Department of Fine Arts, Ministry of Education, Bangkok 10200, Thailand

Received 9 March 1998; accepted 15 April 1998

Keywords: Dasymaschalon sootepense; Annonaceae; Isoquinoline alkaloids; Gas chromatography-mass

spectrometry

1. Subject and source

Dasymaschalon sootepense (Craib), source: Doi Tung, Chiangrai, Thailand. The

identity was confirmed by Dr P. Kessler, Rijksherbarium Leiden (L). Voucher speci-
men: Coll. T. Santisuk s.n., Thailand, Chiangrai, March 1996 (L 997.104 798).

2. Previous work

A botanical review on the genus Dasymaschalon (Nguyen, 1975) and the isolation of
two novel flavonol glycosides from Dasymaschalon sootepense (Sinz et al., 1998) have
been reported.

* Corresponding author. Tel.: 00 49 6421 285811; fax: 00 49 6421 287052; e-mail: sinz@mailer.uni-
marburg.de
1 Due to circumstances beyond the Publisher’s control, this paper appears in print without author
corrections.

0305-1978/98/$19.00 ( 1998 Elsevier Science Ltd. All rights reserved.

PII: S0 30 5 - 19 7 8( 9 8 )00 0 48 -9
934 A. Sinz et al./Biochemical Systematics and Ecology 26 (1998) 933–934

3. Present study

From the leaves (900 g dr.wt.) of Dasymaschalon sootepense a methanolic extract was
prepared and subjected to column chromatography on silica gel successively eluting with
the solvents n-hexane, CH Cl , methanol and water. The fraction which eluted with
2 2
a mixture of CH Cl : methanol (7 : 3) was separated by preparative HPLC yielding the
2 2
aporphine alkaloids (!)-dicentrine (1; 69 mg; Jackson and Martin, 1966), (!)-
dasymachaline (2; 8 mg; Chan and Toh, 1986) and (!)-N-methyllaurotetanine (3; 34 mg;
Chen et al., 1976). Identification was performed by 1H and 13C-NMR, MS, UV and IR.
The method of gas chromatography-mass spectrometry (GC-MS) was used to tenta-
tively identify five further alkaloids which occured only in trace amounts. These were the
aporphines N-nornuciferine (4; Ohashi et al., 1963; Hesse and Bernhard, 1975; Chen et al.,
1976) and norlaureline (5; Bhakuni et al., 1972) and the tetrahydroprotoberberines
sinactine (6; Madhusudanan et al., 1983), xylopinine (7; Ohashi et al., 1963) and caseadine
(8; Chen et al., 1968).

4. Chemotaxonomic significance

Alkaloids of the isoquinoline type occur in many genera of the Annonaceae (Leboeuf et
al., 1982). It can be noted that the alkaloids of Dasymaschalon sootepense correspond to
those isolated from other members of the Annonaceae. Dasymachalin was isolated only
once previously from Desmos dasymachalus, Annonaceae (Chan and Toh, 1986).

Acknowledgements

The authors thank Dr Paul Kessler, Rijksherbarium Leiden, for identification of the
plant material and BMBF and ASTA Medica AG, Frankfurt/Main, for financial support
(BMBF-project no 0310697). The award of a Senior Research Scholar by the Thailand
Research Fund is also gratefully acknowledged.

References

Bhakuni, D. S., Tewari, S., Dhar, M. M., 1972. Phytochemistry 11, 1819.
Chan, K. C., Toh, H. T., 1986. Phytochemistry 25, 1999.
Chen, C. Y., MacLean, D. B., Manske, R. H. F., 1968. Tetrahedron Lett. (3), 349.
Chen, C. L., Chang, H. M., Cowling, E. B., Huang Hsu, C. Y., Gates, R., 1976. Phytochemistry 15, 1161.
Hesse, M., Bernhard. H. O., 1975. In: Budzikiewicz, H., (Ed.), Progress in Mass Spectrometry, vol. 104, Verlag
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Sinz, A., Matusch, R., Santisuk, T., Chaichana, S., Reutrakul, V., 1998. Phytochemistry, in press.