Menispermaceae alkaloids

Meniscus surgery, 3 723 Menispermaceae, alkaloids in, 2 75 Menke s disease, 7 709 Menschutkin reaction, 20 490 26 846 Men s colognes/fragrances, 18 356, 359-361 Menstruum process carburization, 4 675 solid solutions of industrial carbides, 4 688-689... 

Menachery MD (1996) The alkaloids of South American Menispermaceae. Alkaloids, Chemical and Biological Perspectives (ed Pelletier SW) Vol 11. Elsevier, Amsterdam, pp 269-302. 

Attention is drawn to reviews which include or are concerned wholly with biosynthesis Menispermaceae alkaloids, morphine alkaloids, and one which surveys the role of anthranilic acid in the biosynthesis of many alkaloid types. An excellent book on alkaloid biosynthesis edited by Mothes and Schiitte has appeared during 1969. ... 

Morphanandienone alkaloids are widely distributed in the families Papaveraceae and Menispermaceae. Alkaloids of this structural type in the Papaveraceae and in the genus... 

There are now known a eonsiderable number of alkaloids containing two distinct woquinoline nuclei, such as emetine and its congeners (p. 394), and in the morphine sub-group, -morphine, dithebainone (p. 255), disinomenine and its pseudo-isomeride (p. 268). The most important collection of such alkaloids is the bisbenzylwoquinoline or biscoclaurine section of which the following two alkaloids, berbamine and oxyacanthine, are examples, but which is typically developed in the Menispermaceas. 

Para, Tube or Bamboo Curare. This variety was packed in sections of bamboo, but this almost traditional information needs modification since tube curare became a commercial article. It is now a viscous, solid or even powdered extract, exported in sealed tins. In view of the relationship established between bebeerine, curine, and tubocurarhie, the active alkaloid of this variety of curare, the suggestion was made, first by Spath, Leithe and Ladeck, and more definitely by King that its botanical source should be sought among the Brazilian Menispermaceae, and as shown later the search for the source of the d-tubocurarine found in this variety of curare has been narrowed down to Chondrodendron tomentosum, or possibly a closely related species liable to be confused with it. 

Alkaloids of the Menispermaceae Coclaurine, Dauricine, Magnoline, Tetrandrine, Bebeerine, etc.. ... 

Fangchinoline (40), a 4> 5-benzylisoquinoline alkaloid isolated from Stephania tetrandra S. Moore (family Menispermaceae), was evaluated to possess significant antihyperglycemic activity studied in streptozotocin (STZ)-induced diabetic ddY mice in a dose-dependent manner the drug reduced the blood glucose level of diabetic mice by 52.7 6.7% when administered in 14 h-fasted diabetic mice at a dose of 1 mg/kg. Blood... 

The arrow poison curare, when produced from Chondrodendron species (Menispermaceae), contains principally the bis-benzyltetrahydroisoquino-line alkaloid tubocurarine (see page 324). Species of Strychnos, especially S. toxifera, are employed in making loganiaceous curare, and biologically active alkaloids isolated from such preparations have been identified as a series of toxiferines, e.g. C-toxiferine (Figure 6.85). The structures appear remarkably complex, but may be envisaged as a combination of two Wieland-Gumlich... 

Cocculus pendulus (Forsk.) Diels (Menispermaceae) afforded (+)-cheratamine (469), C36H34N207, [a]g,s +190° (c 0.33, MeOH). The structure assignment was based on analogy with co-occurring alkaloids, on NOEDS, IR, CD, MS, and on the large UV base shift (552). 

Cocsuline A-oxide (470), C35H34N206, amorphous, mp 182-187°C (MeOH), [a], 5 + 125° (c 0.5, MeOH), was found in Cocculus hirsutus D.C. (Menispermaceae). Sul-furous acid reduction yielded cocsuline (29). The A-oxide appears to be a metabolic product as it was not formed from 29 in vitro under the isolation conditions. It is the first diphenyl ether-linked dibenzodioxin A -Oxide alkaloid and the first A -Oxide from a Cocculus species (557). 

Nortrilobine (500), C34H32N205, mp 177-180°C (MeOH), [a] 5 +216° (c 0.44, CHC13), from Pachygone ovata Miers ex Hook. f. Thoms. (Menispermaceae), is the first bis-secondary dibenzo-p-dioxin bisbenzylisoquinoline alkaloid. It was examined by... 

The new reddish-brown alkaloid grandirubrine (75), as well as the known imerubrine (76), are present in Abuta grandifolia (Menispermaceae).54... 

It is interesting to note that the occurrence of C-7 oxygenated aporphine alkaloids with the C-6a R configuration is limited to the families Annonaceae, Lauraceae, Magnoliaceae, and Menispermaceae. Aporphine alkaloids oxygenated at both C-4 and C-7 have been found in the Annonaceae, but (-)-stephadiolamine /3-A-oxide (48) is the first known alkaloid hydroxyl-ated at both C-4 and C-7 and having a cis relationship between H-6a and H-7. (-)-O-Acetylsukhodianine is the first known example of a naturally occurring 7-acetoxylated aporphine (30). 

Only 3 of the 12 species of Cocculus (Menispermaceae) have been examined for alkaloids and most studies have concerned C. laurifolius, which has yielded the greatest number of alkaloids (see Table I) (57, 55-58, 60, 69-76). The Erythrina-type alkaloids obtained from Cocculus are abnormal in the sense that they contain no oxygen function at C-16, the only exceptions being dihydroerysovine (44), dihydroerysodine (47), and erythroculine (53). Erythroculine is, however, unusual in that it has a methoxycarbonyl group at C-16. The two alkaloids isococculidine (36) and isococculine (37) are of theA2(l)-alkene type rather than the Al(6)-alkene type. 

A novel type of bisbenzylisoquinoline alkaloid containing one fully aromatic isoquinoline system is sciadoline, from Sciadotenia toxifera Kruhoff and A. C. Smith (Menispermaceae), which has been shown to have the structure (54) by spectroscopic studies.65 It is related to cycleanine (43 R1 = R2 = Me) and 7-nor-cycleanine (43 R1 = H, R2 = Me). 

A detailed study of the alkaloidal content of the Formosan Stephania sasakii (Menispermaceae) has led to four new aporphines stesakine (4), dehydrostesakine (5), dehydrocrebanine (6),11 and dehydrophanostenine (7).4 Additionally, dehydro-stephanine (8) has been isolated from S. kwangsiensis.12... 

---