Cestrum parqui

Cestrum laevigatum-. K Cestrum probably referable to this species is sold as a marijuana substitute in Brasil under the name dama da noite or lady of the night (Schultes Hofinann 1980). No psychoactive compounds are known from this species. Cestrum parqui recently appeared in a list of putative Italian psychotropic plants (Festi Alliota 1990). 

Occurrence in the Solanaceae. p-Coumaric acid, caffeic acid, methyl caffeate, and methyl ferulate as well as certain of their 2,3-dihydro derivatives have been identified as constituents of the leaves of Cestrum parqui L Herit. with good phytotoxic activity against different species (D Abrosca et al. 2004). Family-specific phenylpropanoid acids like tropic acid or 2-hydroxytropic acid as acyl moieties of tropane alkaloids are synthesized via phenylalanine -> phenylpyruvic acid (l )-3-phenyllactic acid (Fig. 3.14 Table 3.1 (T5-T7-B)]. Tropic acid may occur as a metabolite of, e.g., hyoscyamine, but the free acid is not synthesized as such (for details see Sect. 3.4). 

Triterpenoid Saponins. A unique occurrence of triterpenoid saponins in a species from the Solanales was reported on two constituents of Cestrum parqui L Herit. leaves (Abdel-Gwad et al. 1997). These compounds were characterized by the aglycone oleanolic acid 3 30-linked to a trioside composed of (i) two glucose units and one xylose and (ii) glucuronic acid, rhamnose, and glucose. 

Outline. Saponins, sometimes termed saponosides, are glycosidic derivatives of steroids or polycyclic triterpenes which - dissolved in water - behave like soaps (lat. sapo ), i.e., produce a stable foam, emulsify fatty oils, and stabilize suspensions. They are able to lower the surface tension of aqueous solutions and to cause haemolysis. This is due to their lyobipolar character which is based on the lipophilic aglycone and the highly hydrophilic carbohydrate moiety. There is only one report on triterpenoid saponins in the Solanaceae (Cestrum parqui L Herit., see Sect. 7.5.1.), whereas steroidal saponins are common metabolites of this family. Saponins do not occur in the Convolvulaceae. 

Digitogenin Cestrum parqui L Herit. C. laevigatum Schltdl. (8)... 

Fig. 7.22 The six most frequent glycoalkaloids of the genus Solanum further solanaceous detections solasonine in Cestrum parqui, solanine in Capsicum annuum, tomatine in Lycianthes ran-tonnetii. Dotted lines separate the structures given together with their trivial names above) from related congeners (below)...

Cestrum parqui Solasodine ligogenin Digalogenin Digitogenin Schreiber 1968 and references therein... 

Abdel-Gwad MM, El-Amin SM, El-Sayed MM, Refahy LA, Sabry WA (1997) MoUusddal saponins from Cestrum parqui. Al-Azar J Pharmaceut Sci 20 80-84 Abe F, Nagafuji S, Okawa M, Kinjo J (2006) Trypanocidal constituents in plants 6. Minor with-anoUdes from the aerial parts of Physalis angulata. Chem Pharm BuU 54 1226-1228... 

Baqai FT, Ali A, Ahmad VU (2001) Two new spirostanol glycosides from Cestrum parqui. Helv Chim Acta 84 3350-3356... 

Bheemasankara Rao C, Suseela K, Subba Rao PV, Gopala Krishna P, Subba Raju GV (1984) Chemical examination of some Indian medicinal plants. Indian 1 Chem 23B 787-788 Bianchi E, Girardi F, Diaz F, Sandoval R, Gonzales M (1963) Components of the leaves and fruit of Cestrum parqui Tigogenin, digalogenin, digitogenin, and ursolic add. 1. Ann Chim (Rome) 53 1761-1778... 

D Abrosca B, DellaGreca M, Fiorentino A, Monaco P, Natale A, Oriano P, ZarreUi A (2005) Structural characterization of phytotoxic of terpenoids from Cestrum parqui. Phytochemistry 66 2681-2688... 

A product from the shrub Cestrum parqui, thought to be responsible for poisoning grazing animals in South America and Australia, is a diterpene glycoside of 2-0-isopentanoyl-3-C-carboxy-D-allose carrying a 3,4-diketo furanoid substituent at 0-4. ... 

Aglycone from Digitalis purpurea, also occurring in free state. Also in D. lanata, D. ciliata and Cestrum parqui. Needles (MeOH). Mp 296° (280-283°). [a]], -81° (CHCI3). 

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