Diterpenoid glycosides

Toxicity. Atractyloside, a diterpenoid glycoside that occurs naturally in plants, may be present at levels as high as 600 mg/kg of dried plant material. Gonsumption of plants containing atractyloside or carboxyatractyl-oside has caused fatal renal proximal tubule necrosis and/or centrilobular hepatic necrosis in man and farm animals. Although pure atractyloside and crude plant extracts disrupt carbohydrate homeostasis and induce similar pathophysiological lesions in the kidney and liver, it is also possible that the toxicity of atractyloside may be confounded by the presence of other natural constituents in plants. Atractyloside competitively inhibits the adenine nucleoside... 

Hanson JR and de Oliveira BH (1993) Stevioside and related sweet diterpenoid glycosides. Nat Prod Rep 10, 301-309. 

The literature of Cnidara includes 2444 articles comprised of 3744 chemical structures.27 Included within this impressive list is the commercially available diterpenoid glycosides, the pseudopterosins,369,370 with remarkable antiinflammatory and analgesic properties, eleutherobin and the sarcodyctins. Figure 6.6 shows that study within Cnidaria has focused on two orders, that of the soft corals, the Alcyonacea and the Gorgonacea. 

From a taxonomically distinct and still unidentified specie of the Pseudopterogorgia genus, a related series of pseudopterosins containing bicyclic diterpenoid glycosides, 7 seco A-D, were also isolated and their structures elucidated by Look and Fenical [18]. Compounds 7 seco A-D possess potent anti-inflammatory and analgesic activities that are similar to the pseudopterosins, and also show antimicrobial activity towards the bacteria. Staphylococcus aureus. For example 7 seco-A, pseudopterosin exhibited a 69% reduction of inflammation in the mouse ear edema assay at a minimum inhibitory concentration (MIC) of 50 pg/ear. 

Yahara et al. (1988) reported a novel acychc diterpenoid glycoside from polar fractions of the fresh fruits of Capsicum annuum L. vai. fasciculatum. This metabolite was initially named capsianside A. However, in the following publications of these authors with a number of congeners the term capsiansides was substituted by capsianosides. These metabolites were classified into two groups ... 

Fig. 7.9 Examples for acyclic diterpenoid glycosides (above left), cembrenoids (below left), and labdenoids (above and below right) from the Solanaceae...

Unfortunately, two natural compounds discovered in the same year were named corymbosin (i) the diterpenoid glycoside from T. corymbosa mentioned above... 

Rich in diterpenoids and diterpenoid glycosides, including andrographolide, neoandro-grapholide, deoxyandrographolide, isoandro-grapholide, 14-deoxyandrographolide,... 

Ketzinel, S., Rudi, A., Schleyer, M Benayahu, Y, and Kashman, Y. (1996) Sarcodictyn A and two novel diterpenoid glycosides, eleuthosides A and B, from the soft coral Eleutherobia aurea. J. Nat. Prod., 59, 873-875. 

Shin, J. and Fenical, W. (1991a) Fuscosides A-D antiinflammatory diterpenoid glycosides of new structural classes from the Caribbean gorgonian Eunicea jusca. J. Org. Chem., 56, 3153-3158. 

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