Glycosides triterpenoid

Won SW, Choi JS, Seligmann O, Wagner H. Sterol and triterpenoid glycosides from the roots of Patrinia scabiosaefolia. Phytochemistry 1983 22 1045-1047. 

Saponins occur in Liliaceae such as asparagus, in legumes, spinach, and yams. They are triterpenoid glycosides with soap-like properties. Many are glycosides of steroid alcohols, and all have a bitter taste. Two types are... 

The interaction between Drosophila, yeasts and columnar cacti of the Sonoran Desert has been the subject of much recent interest (37) As a coevolved system, perhaps more is known about this interaction than any other. The chemistry of the cacti (70 spp.) has been postulated to play a significant role in the establishment of this system (38 ), but this was based upon reports of a relatively small number of relatively simple alkaloids, and a small number of terpenoid compounds. Only recently, the diversification of plant compounds has been discovered to be much greater (5). In their section on alkaloids in the above work, BajaJ and McLaughlin report the presence of some thirty-five structures. In addition, I have been able to isolate some sixty triterpenoid glycosides (structures were not determined) and more were detected but not Isolated. 

A laboratory study was undertaken to determine the likelihood that cactus triterpenoid glycosides are important factors in the host-plant choice of desert Drosophila (6 ). 

A feeding experiment was conducted using field concentrations of the aikaloidal fraction and the total triterpenoid glycoside fraction of thirty related species of columnar cacti (most in the Pachycereeae). Survivorship was measured as + or - and indicates successful development, pupation and emergence after eggs were laid by several d, melanogaster or d. mojavensis females. The latter species is a desert fly known to specialize on several species of Pachycereeae the former is a nonspecialized, nondesert species. Heliothis zea larvae were also used in a separate bioassay of toxicity where compounds were added to commercial diet. 

Specific differences in toxicity toward each test species were discovered between the various plant chemical arrays. Table HI lists survivorship for these species for alkaloid-producing cacti. Additionally, data was obtained for 20 species in which alkaloids were not detected. The three insect species showed consistent differences in tolerance toward given plant species, with no clear phylogenetic pattern accounting for this. Insects also responded differently to aikaloidal fractions versus triterpenoid glycoside fractions. Alkaloids were found to be generally not toxic to D. 

Table III. Survivorship of Drosophila and Heliothis Upon Alkaloidal and Triterpenoid Glycoside Extracts of Alkaloid-Producing Columnar Cacti...

We may hypothesize for the present that columnar cacti produce alkaloids as a general deterrent to herbivory, and triterpenoid glycosides and associated hydrolytic glycosidases as a specific toxification mechanism against specialist Drosophila species. Radiation and diversification of triterpenoids may have occurred in response to continued interaction between the cacti and Drosophila This process is dependent upon coevolution with specialized yeasts which may interfere with hydrolysis of triterpenoids or hydrolyze individual compounds selectively. 

Morris, S.A. Northcote, P.T. Andersen, R.J. (1991) Triterpenoid glycosides from the northeastern Pacific marine s prmge Xestospongia vanilla. Can. J. Chem., 69, 1352-64. 

Ophioderma longicaudum [10]. On the contrary, there is no report of steroid or triterpenoid glycosides in the classes Echinoidea and Crinoidea. 

Most of the triterpenoid glycosides isolated so far from holothurians present a sugar chain of two to six monosaccharide units linked to the C-3 of the aglycone, which is usually based on a holostanol skeleton [3p,20S-dihydroxy-5a-lanostano- 18,20-lactone] (1), Fig.(l) [1]. 

This as yet unidentified plant has yielded five triterpenoid glycosides with moderate activity against the 1138 yeast strain, together with two other as yet unidentified active compounds. The major glycoside has been identified as having structure 29. 

Hypoglycemic natural products comprise flavonoids, xanthones, triterpenoids, glycosides, alkyldisulfides, aminobutyric acid derivatives, guanidine, polysaccharides, and peptides (see Wang and Ng, 1999). The mechanisms of actions of these hypoglycemic plants are uncertain. They either enhance the release of insulin or enhance the peripheral utilization of glucose. 

Mogroside V (2) is a cucurbitane-type triterpenoid glycoside isolated from the fhiits of Siraitia grosvenorii (Swingle) C. Jeffrey... 

Cyclocarioside A (46) is a dammarane-type triterpenoid glycoside sweet principle from the leaves of Cyclocarya paliurus (Batal.) Iljinsk (Juglandaceae), a plant used in the People s Republic of China in the treatment for diabetes [81]. Recently, another sweet-tasting principle, cyclocarioside I (47), was isolated from the same plant along with two other compounds with the same dammarane-type triterpenoid aglycone structure [82]. Cyclocarioside I was rated as about 250 times sweeter than sucrose [82]. 

Subsequent to the isolation of the dammarane-type triterpenoid glycosides jujuboside B (112), hodulosides I-V (113-117), hovenoside I, and saponins C2, E, and H (122-125) as sweetness inhibitors from the leaves of Hovenia dulcis Thunb. var. tomentella Makino [139], hodulosides VII-X (118-121) were isolated as sweetness-inhibitory agents [140]. Hodulosides I (113) and II (114) have hovenolactone (151) as their aglycone which is the same compoimd as in saponins E (124) and H (125). Hodulosides Ill-V and VII-X (115-121) are based on two different danunarane-type aglycone structures, however [139,140]. The sweetness-inhibitory potencies of hodulosides are shown in Table 2. The sweetness-inhibitory potency of hoduloside X (121) was not determined [140]. 

Recently, from the stems of Stephanotis lutchuensis var. japonica, an evergreen woody climber growing in forests near the warm coastal areas of Japan, several oleanane-type sweetness-inhibitory triterpenoid glycosides have been isolated, namely, sitakisosides I-IX, XI-XIII, XVI, and XVIII (126-139) [141-143]. Some sitakisosides have a N-sitakisosides VI (131), VII (132), XI, XII, and XIII (135-137) afforded sitakisogenin (152) [142,143], while hydrolysis of sitakisosides II (127)... 

This approach was used to establish the structures of triterpenoid glycosides from Uncaria tomentosa (4, 10, 1 ),Uncaria guaianensis (12), Guettarda platypoda (5, 13), and steroidal glycosides from... 

Although the mechanism of action of the above glycosides has not yet been elucidated, they are likely similar. The hypothesis that also the antiviral effect of triterpenoid glycosides from U. tomentosa, G. platypoda and C. arvensis is probably not mediated by a non-specific detergent-like action on virus particles, is supported by two lines of evidence a) the compounds exhibit different degrees of inhibition towards VSV infection and b) they display a moderate to low inhibition against naked virus infection. 

In addition to Asteroidea and Holothuroidea, the phylum Echinodermata (Greek echinos, spiny derma, skin) comprises the classes Ophiuroidea (brittle stars), Crinoidea (sea lilies and feather stars) and Echinoidea (sea urchins). There is no report of occurrence of steroid or triterpenoid glycosides in sea lilies, feather stars or sea urchins. Brittle stars contain sulfated polyhydroxylated steroids [10-12] and only two sulfated steroidal monoglycosides have been isolated from the brittle star Ophioderma longicaudum [13]. 

Several holothurins are specific for different taxonomic groups of sea cucumbers and structural characteristics of triterpene glycosides have been used to resolve taxonomic problems in the class Holothuroidea [57, 58]. For example, the triterpenoid glycosides distribution has been successfully applied in the reclassification of Stichopus mollis into the genus Australostichopus [59] and in the taxonomy of sea cucumbers belonging to the genus Cucumaria [60]. 

---