Boldine

6-dimethoxy-3,7-diethoxyphenanthrene (m.p. 133-134°) (VI), which was prepared synthetically as follows. The anhydrous sodium salt of 

4-methoxy-3-ethoxyphenylacetic acid was condensed with 2-nitrovanillin ethyl ether in the presence of acetic anhydride to yield the stilbenecar- 

The correct structure of laurotetanine (XIII) was determined by Barger 

V-Methyllaurotetanine, C20H23O4N, was obtained from the tertiary phenolic fraction of the alkaloids from L. citrata by Spath and Suominen (28). The alkaloid and its derivatives were amorphous for the greater part. However, the 0-ethyl ether was exhaustively degraded to a nitrogen-free compound which proved to be 3,4,6-trimethoxy-7-ethoxy-l-vinyl-phenanthrene (m.p. 140-141°), identical with a specimen already prepared from laurotetanine (27). The structure of this alkaloid is therefore XV. 

Dicentrine, C20H21O4N, was first isolated from Dicentra pusilla Sieb. and Zucc. by Asahina (29) along with a small amount of protopine, although Heyl (30) had already isolated an alkaloid from D. formosa which was 

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Unlike most alkaloids of the group, glaueine was assigned a formula without the use of the Hofmann degradation process, but since then this process has been applied to glaueine or its derivatives by a number of workers, especially in connection with the investigation of boldine (p. 325) and of laurotetanine (p. 320). 

Asencio M, Delaquerriere B, Cassels BK, Speisky H, Comoy E, Protais P. Biochemical and behavioral effects of boldine and glaucine on dopamine systems. Pharmacol Biochem Behav 1999 62 7-13. 

A bond between carbon and halogen can be cleaved quite easily with light221 One of the few synthetic applications of this reaction is the photo-arylation of aromatic compounds, a sequence employed in the synthesis of alkaloids222,223) as shown for the key step in the synthesis of boldine (2.13) 223>. 

Feinstein E, Kimchi A, Wallach D, Boldin M, Varfolomeev E (1995) Trends Biochem Sci 20 342... 

Boldine, 2,9-diacetyl- Ester hydrolysis Candida lipase 199... 

Boldin, M.P., Mett, I.L., Varfolomeev, E.E., Chumakov, 1., Shemer-Avni, Y., Camonis, J.H. and WaUach, D., 1995, Self-association of the death domain of the p55 tumor necrosis factor (TNF) receptor and Fas/APOl prompts signaling for TNF and Fas/APOl effects. J. Biol. Chem. 270 387-391... 

Boldin, M. P., Goncharov, T. M., Goltsev, Y. V., and WaUach, D., 1996, Involvement of MACH, a novel MORTl/FADD-interacting protease, in Fas/APO-1- and TNF receptor induced cell death. Cell 85 803-815. 

L. Premkumar, A. R. Sawkar, S. Boldin-Adamsky, L. Toker, I. Sihnan, J. W. Kelly, A. H. Futerman, and J. L. Sussman, X-ray structure of human acid-p-glucosidase covalently bound to conduritol-B-epoxide,./. Biol. Chem., 25 (2005) 23815-23819. 

Alkaloids such as boldine, codeine, narceine and morphine are active factors in their receptors. Boldine has morphine-like properties and is active on opioid receptors. It may be used to treat stomach disorders and as metabolic stimulant. As it is similar to morphine, boldine can also be considered in the possible development of treatments for narcotic dependence. Codeine also binds to opiate receptors, and specifically functions to reduce bronchial secretions. Codeine can also be used as a cough suppressant when acting on the centre of the medulla oblongata and as a sedative agent. 

Alkaloids such as boldine, codeine, narceine and morphine are also important in clinical practice. Boldosal and Oxyboldine are good examples of boldine-based drugs with morphine-like properties. 

Tbe aporphines constitute one of the largest groups of isoquinoline alkaloids and have a wide range of physiological activity. For example, bulbocapinine (93) (see Scheme 15) affects the central nervous system and causes catatonia, boldine... 

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