2544. Corydaline

Nomenclature

CAS number: 518-69-4
(13S-trans)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-13-methyl-6H-dibenzo[a,g]quinolizine; 2,3,9,10-tetramethoxy-13α-methyl-13aβ-berbine; d-corydaline.
C22H27NO4; mol wt 369.45.
C 71.52%, H 7.37%, N 3.79%, O 17.32%.

Description and references

Alkaloid isolated from many species of Corydalis. Discovery in C. tuberosa: Wackenroder, Kustner's Arch. 8, 423 (1826), as cited in: C. Wehmer, Die Pflanzenstoffe I (G. Fischer, Jena, 1929) p 389. Isoln from Corydalis aurea Willd. and C. solida (L.) Swartz, Fumariaceae: Manske, Can. J. Res. 16B, 81 (1938); Can. J. Chem. 34, 1 (1956). Structure: von Bruchhausen, Stippler, Arch. Pharm. 265, 152 (1927). Synthesis: Sp"ath, Kruta, Ber. 62, 1024 (1929); T. Kametani et al., J. Chem. Soc. Perkin Trans. 1 1977, 1151; M. Cushman, F. W. Dekon, Tetrahedron 1978, 1435; Z. Kiparissides et al., Can. J. Chem. 58, 2770 (1980). Stereochemistry: Bersch, Arch. Pharm. 291, 595 (1958); Jeffs, Experientia 21, 690 (1965). Pharmacology: Berezhinskaya, C.A. 78, 119087j (1973). Toxicity study: R. C. Anderson, K. K. Chen, Fed. Proc. 5, 163 (1946).

Chemical structure

Properties

Prisms from alc, mp 135°. [α]D20 +311° (c = 0.8 in alc). uv max: 396 nm. Sol in chloroform; moderately sol in ether; sparingly sol in methanol, ethanol. Practically insol in water. LD50 in mice (mg/kg): 135.5 ± 12.8 i.v. (Anderson, Chen).

Derivative

Hydrochloride hydrate.
C22H27NO4.HCl.H2O; mol wt 423.93.
C 62.33%, H 7.13%, N 3.30%, O 18.87%, Cl 8.36%.

Properties

Four-sided columns, mp 230-240°.

Derivative

dl-Form.

Properties

mp 135°. Slightly sol in water.

Derivative

dl-Mesocorydaline.

Properties

mp 158°. The (13R-cis)-analog of corydaline. Slightly sol in water.

Derivative

d-Mesocorydaline.

Properties

Rhombic crystals, mp 152°. [α]D20 +82° (c = 1.4); +180° (c = 3 in chloroform).

Derivative

l-Mesocorydaline.

Properties

Rhombic crystals, mp 152°. [α]D20 -85° (c = 1.4); -181° (c = 3 in chloroform).