Buxaceae Steroidal Alkaloids

The common box wood, Buxas sempervirens, has long been known for its medicinal properties extracts of the plant (23) were used against various kinds of diseases such as malaria and venereal diseases. The extract was reported to possess an antitubercular property. Steroidal amines were isolated from the plant and their structures, including cyclobuxine D and cyclomicophylline A were clarified (19,20). 

1 Adamovics J A, Cina J A, Hutchinson C R 1979 Minor alkaloids of Camptotheca acuminata. Phytochemistry 18 1085-1086 

2 Aimi N, Shito T, Fukushima K, Itai Y, Aoyama C, Kunisawa K, Sakai S, Haginiwa J, Yamasaki K 1982 Studies on plants containing indole alkaloid glycosides and other constituents of the leaves of Uncaria rhynchophylla Miq. Chem Pharm Bull 30 4046 - 4051 

3 Arisawa M, Gunasekera S P, Cordell G A, Farnsworth N R 1981 Plant anticancer agents. XXL Constituents of Merrilliodendron megacarpum. Planta Med 47 404-407 

4 Arther H R, Hui W H, Ng Y L 1959 An examination of the Rutaceae of Hong Kong. II. The alkaloids nitidine and oxynitidine, from Xanthoxylum nitidum. J Chem Soc 1840-1845 

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The path from squalene (114) to the corresponding oxide and thence to lanosterol [79-63-0] (126), C qH qO, cholesterol [57-88-5] (127), and cycloartenol [469-38-5] (128) (Fig. 6) has been demonstrated in nonphotosynthetic organisms. It has not yet been demonstrated that there is an obligatory path paralleling the one known for generation of plant sterols despite the obvious stmctural relationships of, for example, cycloartenol (128), C qH qO, to cyclobuxine-D (129), C25H42N2O. The latter, obtained from the leaves of Buxus sempervirens E., has apparentiy found use medicinally for many disorders, from skin and venereal diseases to treatment of malaria and tuberculosis. In addition to cyclobuxine-D [2241-90-9] (129) from the Buxaceae, steroidal alkaloids are also found in the Solanaceae, Apocynaceae, and LiUaceae. 

Steroid alkaloids have been isolated from four famihes of terrestrial plant sources (Soianaceae l iliaceae pOijnaceae and Buxaceae) two animal sources (Saiamandra and Phjllobates) and several marine sources. Steroid alkaloids can be classified based on stmcture and fall into a variety of categories. The spirosolanes contain a cholestane skeleton with a C20 spiroaminoketal moiety, as exemplified by the most abundant members of this class, veramine... 

These toxic symptoms possibly explain why such plants are not reported to be used traditionally for AD or related conditions. The Buxaceae is another family known for its steroidal alkaloids and several of these have been investigated as cholinesterase inhibitors. The first such alkaloid... 

Steroidal Alkaloids of the Apocynaceae and Buxaceae and Related Compounds , F. Khuong-Huu and R. Goutarel, in Alkaloids , ed. M. F. Grundon, Royal Society of Chemistry, London, 1977, vol. 7, pp. 268-288. 

A number of our regular authors are not participating this year, and I would like to express my appreciation to Drs. Crout and McCorkindale for their contribution to Volumes 6 and 7 and in particular to Drs. Goutarel and Khuong-Huu for reviewing steroidal alkaloids of the Apocynaceae and Buxaceae since the inauguration of this series of Reports in 1971. In this Volume, all steroidal alkaloids are included in Chapter 14. 

The steroidal alkaloids have a nucleus based on 21, 24, or 27 carbon atoms (Fig. 44). The C21 alkaloids are pregnane-derived with nitrogen inserted at C-3, at C-20, or at both positions. They are characteristic of the Apocynaceae Funtumia and Holarrhena species) and the Buxaceae Buxus species). The Buxaceae also produces C24 alkaloids based on the cycloartane skeleton. The most interesting alkaloids are those in the Solanaceae and the Liliaceae. These are C27 alkaloids, and examples include solasodine and solanidine many derivatives are glycosylated. The alkaloids from the Liliaceae, such as veratramine of the white hellebore (Veratrum album), were formerly used for cardiac... 

Steroidal Alkaloids of the Apocynaceae and Buxaceae and Related Compounds... 

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