Rutecarpine - not all toxins are bad

Rutaecarpine is an indolopyridoquinazolinone alkaloid isolated from Evodia rutaecarpa plant and its related herbs. Among the active components of evodia are quinolone and indoloquinazoline alkaloids, such as evodiamine and rutaecarpine. A significant portion of the analgesic effects of Evodia is attributed to these alkaloids. Among the different effects explained by the different compounds found in Evodia rutaecarpa, Rutaecarpine possesses anti-inflammatory action, larvicidal effects, and positive action to contrast several human diseases.

As example, Prostaglandins (PGs) which have various important biological responses, inducing pain, fever and symptoms associated with inflammatory responses. Nonsteroidal anti-inflammatory drugs reduce pain and inflammatory swelling by blocking PG synthesis at the step of cyclooxygenase (COX).

Rutaecarpine has been shown to have anti-inflammatory action that is related to inhibition of COX-2, as well as other mechanisms. Thanks of these effects this compound remains the most popular and multi-purpose herb traditionally used in China [1, 2] for treatment of headache, abdominal pain, postpartum hemorrhage, dysentery and amenorrhea. Beside of that, rutaecarpine has been shown to have cardiovascular biological effects such as, vasorelaxant, anti-platelet aggregation and anti-inflammatory effects. Furthermore, rutaecarpine has the potential for use as an anti-atherosclerotic agent with a novel mechanism preventing hypoxia-reoxygenation-induced myocardial cell apoptosis via inhibition of NADPH oxidases. Also was shown, that rutaecarpine could be effective in preventing the growth of a variety of cancer cells, including downregulating the estrogen receptor of breast cancer [3].

Among the different positive effects for the human body, rutaecarpine has also different plague control uses. During the recent years, environmental friendly and biodegradable natural insecticides of plant origin have received renewed attention as agents for plagues control. During a screening program for new agrochemicals from Chinese medicinal herbs and local wild plants, the ethanol extract of Evodia rutaecarpa was found to possess larvicidal activity against mosquitoes. [4]. The use of plant extracts/essential oils for insect control has several appealing features, as these are generally biodegradable, less hazardous, and richer in chemicals which explain diverse biological activity [5].

Liu et al. [5] reported the extremely wide applications which possesses the essential oil of E. rutaecarpa possessed strong fumigant toxicity against Tribolium castaneum and Sitophilus zeamais, and three active constituent compounds were isolated from the essential oil [6, 7].

Herb extracts containing two quinolone alkaloids exhibited toxicity to brine shrimp (Artemia salina) [8]. Moreover, three alkaloids rutaecarpine, evodiamine and rhetsinine, which are isolated from E. rutaecarpa by bioassay-guided fractionation, showed insecticidal activity against fruit flies (Drosophila melanogaster).

The previous report of the useful activity for the human body and plague control has to be intended that even if natural toxins are generally produced for predation or defense, not all of them have to be intended as part of a human body antagonist family. In fact, the most of the medicines we use daily, with a very high probability have been firstly extracted from toxic plants or other dangerous organisms.

CAS Registry Number: 84-26-4
CAS Name: 8,13-Dihydroindolo[2,3:3,4]pyrido[2,1-b]quinazolin-5(7H)-one
Molecular Formula: C18H13N3O
Molecular Weight: 287.32
Percent Composition: C 75.24%, H 4.56%, N 14.62%, O 5.57%
SMILES: C1CN2C(=NC3=CC=CC=C3C2=O)C4=C1C5=CC=CC=C5N4

Literature:

1. Jiangsu New Medical College (1977) Dictionary of Chinese Herbal Medicine. Shanghai Science & Technology, Shanghai, pp 737–739
2. Moon, T., Murakami, M., Kudo, I. et al. Inflamm. res. (1999) 48: 621.
3. Jia S, Hu C. Molecules. (2010) 15(3):1873–1881.
4. Liu, Z.L., Liu, Q.Z., Du, S.S. et al. Parasitol Res (2012) 111: 991.
5. Liu ZL, Ho SH J. Stored Prod Res (1999) 35:317–328.
6. Liu ZL, Du SS. E-J Chem (2011) 8:1937–1943.
7. Kim YC, Kim NY, Jeong SJ, Sohn DH, Miyamoto T, Higuchi R. (1998) Planta Med 64:490
8. Miyazawa M, Fujioka J, Ishikawa Y. J Sci Food Agric (2002) 82:1574–1578.
9. Parasitol Res (2012) 111:991–996

Figures

• Figure 1: http://en.chembase.cn/substance-73831.html