Secoiridoid glucosides

Piperno A, Toscano M and Uccella NA. 2004. The Cannizzaro-like metabolites of secoiridoid glucosides in some olive cultivars. J Sci Food Agric 84(4) 341—349. 

Kuwajima, H., T. Uemura, K. Taka-ishi, K. Inoue, and H. Inouye. A secoiridoid glucoside from Olea euro-paea. Phytochemistry 1988 27(6) 1757-1759. 

OE072 Tsukamoto, H., S. Hisada, and S. OE084 Nishibe. Coumarin and secoiridoid glucosides from bark of Olea europaea and Olea capensis. Chem Pharm Bull 1985 33(1) 396-399. 

Thomas PS, Kanaujia A, Ghosh D, Duggar R, Katiyar CK. Alstonoside, a Secoiridoid Glucoside from Ahtonia scholaris. Indian Journal of Chemistry, sechon B Organic Chemistry Including Medicinal Chemistry 2008 47B(8), 1298-1302. 

Inouye H, Uobe K, Hirai M, Masada Y, Hashimoto K. Studies on Monoterpene Glu-cosides and Related Natural Products. XXX. Gas Chromatography and Gas Chromatography-Mass Spectrometry of Iiidoid and Secoiridoid Glucosides. Journal of Chromatography 1976 118(2) 201-216. 

N.A. Centaurium erythraea Rafn. Secoiridoid glucosides, xanthones, benzophenone, swertiamarin, gentiopicroside.305321-322 323 Antipyretic, antidiabetic. 

Cyclopentanes, Iridoids.—A very useful review of the biosynthesis of the known sweroside-, morroniside-, and oleuropein-type secoiridoid glucosides, together with the biosynthesis of alkaloidal glucosides which can be regarded as secoiridoid... 

Thirty-three known iridoid and secoiridoid glucosides have been analysed by gas chromatography of their trimethylsilyl derivatives. G.c.-m.s. analysis of several representative compounds e.g. 4-CO2H, 4-C02Me, 4-unsubstituted) demonstrated the feasibility of iridoid-containing plant extract analysis and resulted in the identification of secologanoside 11-methyl ester (99 R = H, X = CH2) from Lonicera morrowii the sixth paper in a series of chemotaxonomic studies on iridoids illustrates the need for accurate analysis of minor components. ... 

When the crude secoiridoid glucoside mixture derived from the fruits of Ligustrum vulgare (Oleaceae) was treated with 5% sulfuric acid and then with ammonia, TLC analysis revealed the presence of 12 alkaloid-positive spots (29). No alkaloids were detected in the absence of ammonia. Four of these alkaloids were characterized. One was identical with jasminine (97) the other three isolates were new. 

G. depressa D. Don generally distributed in Nepal at an altitude of 3,000- 3,500 m. From the aerial part of this species mixed iridoid-secoiridoid glucoside, depresteroside (74), iridoid glucoside such as depressoside (75), 3"-glucosyl depresteroside (76) and depressin (77) have been isolated [114-116]. 

In order to explain and confirm the biological activities claimed by the traditional medicine, and to search for new biologically active compounds we studied the antimicrobial, antioxidative, immunomodulatory, antiinflammatory, skin-regenerating and antiviral properties of Fraxinus ornus bark extract and its components. In a parallel detailed phytochemical investigation of the extract we isolated and determined the structures of many hydroxycoumarins, secoiridoid glucosides, caffeoyl esters of phenylethanoid glycosides, lignans and other phenolic compounds. 

Secoiridoid glucosides of oleoside (28) type frequently occur in Oleaceae family. Usually, in Fraxinus species they are present as mono- or diesters of p-hydroxyphenylethanol (29) derivatives. Our phytochemical studies on Fraxinus ornus resulted in the isolation of ligstroside (14), oleuropein (18), framoside (19) and of the new compounds ornoside (15), hydroxyornoside (17), hydroxyframoside A (20a) and hydroxyframoside B (20b) [15-17],... 

Our paper on isolation and structure elucidation of omoside was already in press, when the publications of Tanahashi et al. [18] and Shen et al. [19] appeared in Phytochemistry. Tanahashi and co-authors were the first to report the isolation and structure determination of a novel secoiridoid glucoside from F. insularis, named insularoside, and to assign structure 15 to this compound. Later, Shen et al. described the occurrence of insularoside in Fraxinus uhdei under the name uhdoside [19,20]. 

Therefore, almost simultaneously and independently the secoiridoid glucoside 15 has been isolated from three different Frctxinus species under three different names. Our approach in its structure elucidation provided some additional data and more chemical evidence about this unusual secoiridoid. 

The use of Fraxinus ornus bark in the Bulgarian folk medicine for treatment of inflammation, arthritis and dysentery [1,2] suggests the presence of some active principles with anti-inflammatory activity. Our phytochemical investigations have shown that the bark contains hydroxycoumarins, secoiridoid glucosides, caffeoyl esters of phenylethanoid glycosides and other phenolic compounds [10,14-17,28]. RP-HPLC analysis of commercial samples of Fraxinus ornus bark revealed high esculin (1) content (6-9%) [14]. 

Our investigations revealed the contribution of secoiridoid glucosides to the antiinflammatory action of the extract. 

Table 97.1 Some monomeric iridoid and secoiridoid glucosides, aglucones, and derivatives with their physical constants and plant sources...

Kuwajima H, Marsuuchi K, Takaishi K, Inoue K, Fujita T, Inouye H (1989) A secoiridoid glucoside from Ligustrum japonicum. Phytochemistry 28 1409-1411... 

Tanahashi T, Takenaka Y, Okazaki N, Koge M, Nagakura N, Nishi T (2009) Secoiridoid glucosides and unusual recyclized secoiridoid aglycones from Ligustrum vulgare. Phytochemistry 70 2072-2077... 

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