Secoiridoid

Secoiridoid glycosides Jasminum urophyllum SiOj CIS CHCI3 + MeOH + HjO MeOH + H2O Isolation 81... 

Secoiridoids are complex phenols produced from the secondary metabolism of terpenes as precursors of several indole alkaloids (Soler-Rivas and others 2000). They are characterized by the presence of elenolic acid, in its glucosidic or aglyconic form, in their molecular structure. Oleuropein, the best-known secoiridoid, is a heterosidic ester of elenolic acid and 3,4- dihydroxyphenylethanol containing a molecule of glucose, the hydrolysis of which yields elenolic acid and hydroxytyrosol (Soler-Rivas and others 2000). 

Oleuropein (the most abundant bitter principle) and its analog ligstroside, both sec-oiridoid biophenols, were extracted from Hojiblanca black olives (Piperno and others 2004). Secoiridoids are present exclusively in plants of the Oleraceae family (Tripoli and others 2005). Oleuropein is present in high amounts (6000 90 mg/100 g DW) in the leaves of the olive tree (Le Tutour and others 1992), but it is also present in all constituent parts of the fruit peel, pulp, and seed (Servili and others 1999). 

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. 

Griboldi, P., G. Jommi, and L. Verotta. Secoiridoids from Olea europaea. Phytochemistry 1986 25(4) 865-869. Tsukamoto, H., S. Hisada, and S. Nishibe. Lignans from bark of the Olea plants. 11. Chem Pharm Bull 1985 33(3) 1232-1241. 

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. 

Lo Scalzo, R., and M. L. Scarpati. A new secoiridoid from olive wastewaters. J Nat Prod 1993 56(4) 621-623. Montedoro, G., M. Servilli, M. Baldioli, R. Selvaggini, E. Miniati, and A. Macchioni. Simple and hydrolyzable compounds in virgin olive oil. 3. Spectroscopic characterizations of the secoiridoid derivatives. J Agr Food Chem 1993 41(11) 2226-2234. 

Rovellini, P., andN. Cortesi. Identification of three intermediates compounds in the biosynthesis of OE069 secoiridoids as oleoside-type in different anatomic parts of Olea europaea L. by HPLC-electrospray-mass spectrometry. Riv Ital Sostanze Grasse 1998 OE070... 

Tsukamoto, H., S. Hisada, and S. Nishibe. Isolation of secoiridoid gluco-sides from the bark of Olea europaea. Shoyakugaku Zasshi 1985 39(1) 90-92. Fleuriet, A., J. ]. Macheix, C. Andary, and P. Villemur. Identification and determination of verbascoside by high-performance liquid chromatography in the fruit of six cultivars of Olea... 

Frederickson, W. R. Antiviral compositions comprising secoiridoids obtained from Oleaceae. Patent-PCT Int Appl -96 14,064 1996 20 pp. Carmena, R., J. F. Ascaso, G. Camejo, et al. Effect of olive and sunflower oils on low density lipoprotein level, composition, size, oxidation and interaction with arterial proteoglycans. Atherosclerosis 1996 125(2) 243-255. Yaqoob, P., J. A. Knapper, D. H. Webb, C. M. Williams, E. A. News-holme, and P. C. Calder. Effect of olive oil on immune function in middle-... 

Schaufelberger, D. and Hostettmann, K., Analytical and preparative reversed-phase liquid chromatography of secoiridoid glycosides, J. Chromatogr., 346, 396, 1985. 

Taneko, T. et al., Secoiridoid and flavonoid glycosides from Gonocaryum calleryanum. Phytochemistry, 39, 115, 1995. 

Rodriguez, S. et al., Xanthones, secoiridoids and flavonoids from Halenia corniculata. Phytochemistry, 40, 1265, 1995. 

Tan, R.X. et al.. Acyl secoiridoids and antifungal constituents from Gentiana macrophylla. Phytochemistry, 42, 1305, 1996. 

Dinda B, Debnath S, Banik R. Naturally Occurring Iridoids and Secoiridoids. An Update review, Part 4. Qiemical Pharmaceutical Bulletin 2011 59(7) 803-833. 

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. 

Dinda B, Chowdhury DR, Mohanta BC. Naturally Occurring Iridoids, Secoiridoids and Their Bioactivity. Tkn Update Review, Part 3. Chemical Pharmaceuhcal Bulletin 2009 57(8) 765-796. 

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. 

Changwichit K, Khorana N, Suwanborirux K, Waranuch N, Limpeanchob N, Wisui-tiprot W, Suphrom N, Ingkaninan K. Bisindole alkaloids and secoiridoids from Alsto-nia macrophylla Wall, ex G. Don. Fitoterapia 2011 82(6) 798-804. 

In most natural iridoids and secoiridoids, there is an additional oxygenation (hydroxy) at C-1, which is generally involved in the glycoside formation. 

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