Evodia

There are several alkaloids in the structure of which are both quinazoline and indole nuclei. Evodiamine (1001 R = H) and rutaecarpine (1002) were both isolated from the seeds of Evodia rutaecarpa about 1916 and synthesized in 1927. They were found subsequently to occur also in Xanthoxylum rhetsa, which in addition yielded rhetsinine (1001 R = OH) (59T(7)257). The plant Hortia arborea afforded two more related alkaloids, hor-tiacine and hortiamine, each characterized by a methoxy group in the benzene ring of the indole portion (60JA5187). 

Several species of Evodia have been stated to contain berberine, but recent workers have failed to confirm this observation. In the Chinese drug, Wou-chou-yu, which is the dried fruit of E. rutcecarpa Benth. and Hook., Asahina and co-workers found two alkaloids, evodiamine and rutascarpine, to which Chen and Chen added a third, wuchuyine, Ci3Hi302N, m.p. 237-5°, [a] f — 60-8°. According to Mayeda, E. 

Evodiamine, the alkaloid from the Chinese drug plant Evodia rutaecarpa Benth. and Hook., has also been called rhetsine and its oxidation product rhetsinine, which is also found in nature, was shown to be the diamide (53). Recently a hypotensive red alkaloid isolated from the Brazilian plant Hortia arborea Engl, was given the name hortiamine. Degradation and synthetic studies have shown it to possess the structure (55). It was found together with another... 

The anti-HP activities of Gosyuyu, a crude extract from the fruit of Evodia rutaecarpa, a Chinese herbal medicine, have also been tested for activity... 

Fig. 9. Two quinolones, l-methyl-2-[(Z)-8-tridecenyl] -(l//)-quinolone and 1-methyl-2-[(Z)-7- tridecenyl]-4-(lZ7)-quinolone isolated from Evodia rutaecarpa, a Chinese herbal medicine used to treat stomach ailments.

Rhetsinine (2), isolated from the hot water extract of Evodia rutae-carpa (family Rutaceae), was found to inhibit aldose reductase with an IC50 value of 24.1 /rM furthermore, the isolate inhibited sorbitol accumulation by 79.3% at 100 This compound could find potential use in the treatment of diabetic complications. Tetramethylpyrazine (3), one of the active components in Qing Huo Yi Hao, displayed strong antioxidant and endothelial protective effects, which can be comparable as Qing Huo Yi Hao this result indicated that some therapeutic potential of Qing Huo Yi Hao for vascular complications of diabetes may be attributed to the presence of tetramethylpyrazine (3). ... 

Kato A, Yasuko H, Goto H, Hollinshead J, Nash RJ, Adachi I. (2009) Inhibitory effect of rhetsinine isolated from Evodia rutaecarpa on aldose reductase activity. Phytomedicine 16 258-261. 

Rutaecarpine (46) is the major alkaloid found in Evodia rutaecarpa (Juss.) Benth., and activities relevant to AD have been identified with the extract and with rutaecarpine. Dehydroevodiamine (47), another alkaloid from the same species, inhibited AChE in vitro, and reversed scopolamine-induced memory impairment in rats and increased cerebral blood flow in vivo in cats, a property which would supplement its usefulness in AD. The structures of (46) and (47) and tacrine (28) have been used as templates for the development of a series of synthetic compounds which have been evaluated for their antiChE activity. These were found to be inhibitory against both AChE and BuChE with A -(2-phenylethyl)-A -[(12Z)-7,8,9,10-tetrahydroazepino [2,l- ]quinazolin-12(6//)-ylidene] amine (48) showing higher affinity for BuChE. 

Park CH, Kim S, Choi W, Novel anticholinesterase and antiamnesic activities of dehydroevodiamine, a constituent of Evodia rutaecarpa, Planta Med... 

Haji A, Momose Y, Takeda R, Increased feline cerebral blood flow induced by dehydroevodiamine hydrochloride from Evodia rutaecarpa, J Nat Prod 57 387-389, 1994. 

There is evidence in literature that alkaloid biology is connected with regulation, stimulation and induction functions. Tsai et al. proved that caffeine levels in the blood, brain and bile of rats decreased when given a treatment of rutaecarpine, an alkaloid from Evodia rutaecarpa (Figure 78). It is known that caffeine has been found to enter the brain by both simple diffusion and saturable carrier-mediated transport . The hepatobiliary excretion of caffeine has also been reported in humans rabbits and rats. ... 

Figure 78. Rutaecarpine, an alkaloid from Evodia rutaecarpa.

H. S. and Kim, Y. K. 2002. Quinolone alkaloids, diacylglycerol acyltransferase inhibitors from the fruits of Evodia rutaecarpa. Planta Medica, 68 1131-1133. 

Ueng, Y. E., Wang, J. J., Lin, L. C., Park, S. S. and Chen, C. F. 2001. Induction of cytochrome P450-dependent monooxygenase in mouse liver and kidney by rutaecarpine, an alkaloid of the herbal drug Evodia rutaecarpa. Life Sciences, 70 207-217. 

Kong, Y. C. Wu chu-yu (Evodia ru-taecarpa) from Pen-ts-ao to action mechanism (the action mechanism of dehydroevodiamine). Scientific basis of traditional Chinese medicine, Y. Lau andj. P. Fowler (eds.) 1982 45—49. Sakamura, F., K. Ogihara, T. Suga, K. Taniguchi, and R. Tanaka. Volatile constituents of Zingiber officinale rhizomes produced by in vitro shoot tip culture. Phytochemistry 1986 25(6) 1333-1335. 

Evodia lepta (Spreng.) Merrill. E. triphylla DC San Ya (root, leaf) Amino acids.55 For arthritis, chickenpox, fever, hemorrhoids, itch, infectious hepatitis. 

Evodia rutaecarpa (Juss.) Berth Wu Zhu Yu (Evodia) (fruit) Alkyl methyl quinolone alkaloids, evodiamine, limonin, evocarpine, rutaecarpine, N-methyl anthranilic acid, evodol, hydroxyevodiamine, N-methylanthranflamide, N,N-dimethyl-5 -methoxytryptamine, dehydroevodiamine.32,33,237 Antiemetic, analgesic, lower blood pressure, antibacterial. 

Takagi S., T. Akiyama, T. Kinoshita, U. Sankawa, and S. Slubata. 1979. Minor basic constituents of evodia fruits. Shoyakugaka Zasshi 33 30-34. 

Ipomoea cairica (L.) Sweet Evodia rutaecarpa (Juss.) Berth Cissampelos pareira L. 

E. sampsoni, E. sieboldiana Evodia rutaecarpa Evodia rutaecarpa Evodia rutaecarpa Eucommia ulmoides... 

S. x tenuifolia, Solidago dahurica, S. pacifica, S. virgaurea, Taraxacum officinale, Vitex nequndo Melilotus alba, M. suaveolens, M. indica, Taraxacum officinale Cephalotaxus wilsoniana Evodia rutaecarpa... 

Dictamnus albus, D. dasycarpus, Evodia rutaecarpa, Poncirus trifoliata Elettaria cardamomum... 

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