Scutia

Morel, A. F., Maldaner, G., Ilha, V., Missau, F., Silva, U. F. and Dalcol, 1.1. 2005. Cyclopeptide alkaloids from Scutia buxifolia reiss and their antimicrobial activity. Phytochemistry, 66 2571-2576. 

The four new cyclopeptide alkaloids (19a)—(19d) isolated from the shrub Ceanothus integerrimus contain a para-bridged fourteen-membered-ring nucleus (19), for which the name phencyclopeptine has been proposed.16 The crude alkaloidal extract from Ceanothus sanguineus17 showed the presence of five major components on composite field-desorption mass spectrometry. H.p.l.c., however, yielded six alkaloids, two of which were isomeric and one of which was a new alkaloid (20). The bark of Scutia buxifolia contains five scutianine alkaloids (B, C, D, E, and H) H is new, and is (21).18 Two new cyclopeptides, sativanines A and B, have been identified as (22) and (23) by m.s.-n.m.r. study.19... 

In 1963 a group of Swiss authors (12) isolated zizyphine from Zizyphus oenoplia and recognized isoleucine and proline as components. Two years later Zbiral etal. (13) proposed a complete structure which was later revised (14). Pais et al. (15) in an earlier preliminary report suggested the structure of pandamine which had been isolated from Panda oleosa. This was confirmed in 1966, and the structure of the similarly constituted pandamine was reported (17). Shortly thereafter Tschesche and co-workers (18) reported the structure of an alkaloid of this type scutianine-A from Scutia buxifolia. Since then the number of cyclopeptide alkaloids of known structure has risen to more than sixty, a figure which Klein and Rapoport had envisioned in 1968 (20). The workers at Gif-sur-Yvette and at Bonn have been in the forefront of these researches but others have made important contributions (19-26). 

An additional 14-membered ring peptide alkaloid, scutianine-B (58 R = = CH2Ph), has been isolated from Scutia buxifoliaP Its structure rests on the typical mass and other spectral data and on the identification of the usual amino-acid fragments obtained by acidic hydrolysis. Amphibine-A, an alkaloid isolated from Ziziphus amphibia, appears to be identical with discarine A [58 R = /i-indolyl-CH2, R = CH(Me)Et] on the basis of comparison with the reported physical, spectral, and chemical properties. ... 

Much of the new work on the larger ring peptide alkaloids continues to emanate from Tschesche and his collaborators. From the Rhamnaceae family, the bark of Scutia buxifolia has been found to contain scutianines A, B, C, D, and F (19) as... 

Boligon AA, Kubica TF, Mario DN, de Bmm TF, Piana M, Weiblen R, et al. Antimicrobial and antiviral activity-guided fractionation from Scutia buxifoUa Reissek extracts. Acta Physiol Plant 2013 35(7) 2229-39. 

Morel AF, Maldaner G, Dha V, MissauF, Silva UF, Dalcol n. Cyclopeptide alkaloids from Scutia buxyblia leiss and their antimicrobial activity. Phytochemistry 2005 66 2571-6. 

Bohgon AA, de Bum TF, Zadra M, Plana M, Alves CFD, Fausto VP, et al. Antimicrobial activity of Scutia buxifoUa against the honeybee pathogen Paenibacillus larvae. J Invertebr Pathol 2013 112(2) 105-7. 

Sources Scutia buxifolia (Rhamnaceae)-stem bark (15,118)... 

Scutianine-B (70) Discaria febrifuga (sb), Melochia tomentosa (r), Scutia buxifolia (r, sb)... 

Tschesche, R., and L. Ammermann Scutianin-C, -D und -E, drei weitere Cyclopep-tidalkaloidc aus Scutia buxifolia Reiss. Chem. Ber., 107, 2274 (1974). 

Tschesche, R., D. Hillebrand, H. Wilhelm, E. Ammermann, and G. Eckhardt Hysodricanin-A, Mauritin-H, Scutianin-F und Aralionin-C, vier weitere Cyclo-peptidalkaloide aus Zizyphus, Scutia und Araliothamnus. Phytochemistry, 16, 1025 (1977). 

Menezes, A.S., M.A. Mostardeiro, N. Zanatta, and A.F. Morel Scutianine-J, a Cyclopeptide Alkaloid Isolated from Scutia buxifolia. Phytochemistry, 38, 783 (1995). 

Merkuza, V.M., M. Gonzalez Sierra, O.A. Mascaretti, E.A. Ruveda, C.-J. Chang, and E. Wenkert Peptide Alkaloids of Discaria longispina and Scutia buxifolia. Phytochemistry, 13, 1279 (1974). 

Tschesche, R., E. Ammermann, and H.-W. Fehlhaber Alkaloide aus Rhamnaceen, X. Scutianin-B, ein weiteres Peptidalkaloid aus Scutia buxifolia Reiss. Tetrahedron Lett., 46, 4405 (1971). 

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