Asimina triloba

Santos Isolated anonaine from A. reticulata L., and A. squamosa L. (custard apple), while from A. triloba L. (Asimina triloba Dun.), Lloyd, and later Fletcher, obtained asiminine, itself amorphous, but yielding crystalline salts. Recently Manske has isolated from this species the crystalline alkaloid anolobine. 

The taxonomic classification of Asimina triloba (L). Dunal. (Adapted from Cronquist, A., An Integrated System of Classification of Flowering Plants, Columbia University Press, New York, 53-55, 1993.)... 

Callaway, M.B. The Paw Paw Asimina triloba, Kentucky State University, Frankfurt, 1-22, 1990. 

Gu, Z.-M., Zhou, D., Lewis, N.J., Wu, J., Johnson, H. A., McLaughlin, J.L., and Gordon, J. Quantitative evaluation of Annonaceous acetogenins in monthly samples of paw paw (Asimina triloba) twigs by liquid chromatography/electrospray ionization/tandem mass spectrometry. Phytochem. Anal., 10, 32, 1999. 

Johnson, H.A., Gordon, J., and McLaughlin, J.L. Monthly variations in biological activity of Asimina triloba, in Progress in New Crops Proceedings of the Third National Symposium, Janick, J., Ed., ASHS, Alexandria, VA, 609, 1996. 

Johnson, H.A., Peterson, R.N., Martin, J.M., Bajaj, R., and McLaughlin, J.L. Evaluation of the biological activity of various North American paw paw (Asimina triloba) germplasms. J. Nat. Prod., 62, (submitted), 1999. 

Ratnayake, S., Rupprecht, J.K., Potter, W.M., and McLaughlin, J.L. Evaluation of various parts of the paw paw tree, Asimina triloba (Annonaceae) as commercial sources of the pesticidal Annonaceous acetogenins. /. Econ. Entomol., 85, 2353, 1992. 

Annona muricata, A. spp., Asimina triloba, Guatteria scadens (Annonaceae) [fruit, leaf]... 

Hydroxy-4-deoxybullatacin (= Bullanin) (alkyl tetrahydrofuran) Asimina triloba (Annonaceae) [stem bark] ETC - NADH-UQOR complex I (20nM)... 

Trilobacin Asimina triloba (Annonaceae) [stem bark] ETC-NADH-UQOR... 

An investigation of the basic components of Asimina triloba Dunal (Anonaceae) yielded seven crystalline alkaloids, among them asimilo-bine, C17H17O2N (mp 177°-179° [aj —213° in CHCI3), which was found in the wood and the root of the tree. 

Woo, M. H., Zeng, L., Ye, Q., et al. (1995) 16,19-c/.v-Murisolin and murisolin a, two novel bioactive monotetrahydrofuran annonaceous acetogenins from Asimina triloba seeds. Bioorg. Med. Chem. Lett., 5, 1135-1140. 

Asimina Triloba Common Names Custardapple, Papaw, Pawpaw... 

Anolobine, CiyHisOsN, was obtained from the bark of Asimina triloba Dunal (96). It is sparingly soluble in methanol and crystallizes well from a mixture of chloroform and methanol and then melts at 262° to a tar with some sintering at a lower temperature [a]o —22.5° (chloroform-methanol). The hydrochloride is sparingly soluble and may serve as a salt for purifying the alkaloid. 

Annonin I (Squamocin) Asimicin Rolliniastatin 1 Rolliniastatin 2 Bullatacin l-srHeell C37H66O7 622.93 622.93 wax 81 -83 wax 73-76 cryst. 69-70 Annona squamosa, Uvaria narum Annona squamosa, Asimina triloba, Rollinia mucosa 120298-30-8 102989-24-2 111056-97-4 121917-13-3 123123-32-0... 

A series of acetate-derived compounds have been reported from plants of the family Annonaceae (Annona cherimolia, A. muricata, A. squamosa, and oth r Annona species Asim-ina triloba, pawpaw Goniothalamus giganteus , and several Rollinia and Uvaria species) (Fig. 5.20) (Alkofahi et al., 1989 Lieb et al., 1990 Nahrstedt, 1985 Rupprecht et al., 1986). Most of these compounds exhibit potent antimicrobial, antiparasitic, cytotoxic, and antitumor activity (Bories et al., 1991). For example, asimicin (36), from the bark of Asimina triloba, is extremely cytotoxic (ED50 <10 p-/ml with several cell cultures) fractionation of the plant material was monitored by the brine shrimp bioassay (Alkofahi et al., 1989). This compound also is toxic to the striped cucumber beetle, Mexican bean beetle, mosquito larvae, blowfly larvae, melon aphid, two spotted spider mite, and the free-living nematode, Caenorabditis elegans (Rupprecht et al., 1986). 

Rupprecht, j. K., C. Chang, J. M. Cassady, J. L. McLaughlin, K. L. Mikolajczak, and D. Weisleder, Asimicin, a new cytotoxic and pesticidal acetogenin from the pawpaw, Asimina triloba (Annonaceae), Heterocycles, 24, 1197-1201 (1986). 

---