Miscellaneous Steroidal Alkaloids

Synthetic studies on the Salamander alkaloids have been reviewed.67 The synthesis of 18-amino-steroids that are related to the alkaloid batrachotoxin has been discussed.68 

A new toxic alkaloid, marinobufagin 3-suberoyl-L-glutamine ester (36a), has been isolated from the skin of the poison toad (Bufo americanus). The partial synthesis of the toxin from the ester (36b) was also reported.80 

Keeler, in Effects of Poisonous Plants on Livestock, [Proceedings of the Joint U.S.-Australian Symposium on Poisonous Plants], ed. R. F. Keeler, K. R. Van Kampen, and L. F. James, Academic Press, New York, 1977 (publ. 1978), p. 397 (Chem. Abstr., 1979, 91, 84 358) D. Brown, ibid., p. 409 (Chem. Abstr., 1979, 91, 84 359). 

An elegant stereospecific synthesis of (+)-muscarine (2 R = NMe3) has been achieved by reduction of the epoxide (1) (easily produced from D-mannitol) with sodium bis-(2-methoxyethoxy)aluminium hydride to give predominantly (2 R = OH) on monotosylation, this forms (2 R = OTs). Chromatographic resolution and treatment with trimethylamine yielded (-l-)-muscarine (2 R = NMea).1 

Buffard, J.F.Desconclois, A.Jehanno, J.Provost, R.Tiberghien, 

Forgacs, F.Roquet, F.Godard, and M.Aurousseau, Eur. J. Med. Chem.-Chim. Ther., 1982, 43 (Chem. Abstr., 1982,, 6628). 

Van de Woude, M.Biesemans, L.Van Hove, and J.Mertens, Bull. Soc. Chim. 

10 Yu-Yuan Tang, Chen-An Teng, and Ping-Wen Liang, Chung Ts ao Yao, 1981, 12, 

11 Bing-Wen Liang, Xiao-Qing Hou, Chen-An Deng, You-Yuan Tang, Xue-Bin Wang, 

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Experimental procedures have been described in which the desired reactions have been carried out either by whole microbial cells or by enzymes (1—3). These involve carbohydrates (qv) (4,5) steroids (qv), sterols, and bile acids (6—11) nonsteroid cycHc compounds (12) ahcycHc and alkane hydroxylations (13—16) alkaloids (7,17,18) various pharmaceuticals (qv) (19—21), including antibiotics (19—24) and miscellaneous natural products (25—27). Reviews of the microbial oxidation of aUphatic and aromatic hydrocarbons (qv) (28), monoterpenes (29,30), pesticides (qv) (31,32), lignin (qv) (33,34), flavors and fragrances (35), and other organic molecules (8,12,36,37) have been pubflshed (see Enzyp applications, industrial Enzyt s in organic synthesis Elavors AND spices). 

E) coumarins, (F) quinones, (G) flavonoids, (H) tannins, (I) alkaloids, (J) terpenoids and steroids and (K) miscellaneous and unknowns. Although many of these compounds are secondary products of plant metabolism, several are also degradation products which occur in the presence of microbial enzymes. 

Molecular imprinting [1] is now an established technique for the creation of polymeric matrices with predetermined affinity for particular substrates. The technique has been used for the creation of substrates with affinities for amino acids, peptides, proteins, nucleotides and nucleosides, carbohydrates, various drugs (e.g. opiates, alkaloids, antibiotics, /1-blockers, tranquillisers) and other bioactive compounds (e.g. enkephalin, steroids, corticosteroids), herbicides, pesticides, as well as metal ions and a number of miscellaneous organic compounds [2-5]. 

Budzikiewicz, H., Djerassi, C. and Williams, D.H. (1964) Structure Elucidation of Natural Products by Mass Spectrometry, Vol. 1, Alkaloids Vol. 2, Steroids, Terpenoids, Sugars and Miscellaneous Classes, Holden Day, San Francisco. 

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