AUCUBIN

Structure

2D structure of AUCUBIN
2D structure
Drag to rotate, scroll to zoom
3D model

Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 91458

Names and identifiers

Name

AUCUBIN

IUPAC name

(2S,3R,4S,5S,6R)-2-(((1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

SMILES

C1=CO[C@H]([C@H]2[C@@H]1[C@@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

General information

Molecular formula

C15H22O9

Molecular weight

346.33 g/mol

Monoisotopic mass

346.1264 Da

Classification

Pathway:
Superclass:
Class:
Glycoside:
Yes

Chemical classification: NPClassifier (Kim et al., 2021)

Plants with the compound

Plant Plant part Amount Reference
Ajuga reptans L. - -
Jim Duke's personal files.
Galium aparine L. aerial parts -
Ergun, F., Sener, B. (1986). Hplc determination of iridoids found in some Galium species. Gazi Univ Eczacilik Fak Derg, 3(1), 59-63
Galium verum L. subsp. verum aerial parts -
Ergun, F., Sener, B. (1986). Hplc determination of iridoids found in some Galium species. Gazi Univ Eczacilik Fak Derg, 3(1), 59-63
Linaria vulgaris Mill. subsp. vulgaris flower -
Sticher, O. (1971). Isolation of antirrinoside from Linaria vulgaris. Phytochemistry, 10(8), 1974-1975 doi:10.1016/s0031-9422(00)86487-0
Linaria vulgaris Mill. subsp. vulgaris leaf -
Sticher, O. (1971). Isolation of antirrinoside from Linaria vulgaris. Phytochemistry, 10(8), 1974-1975 doi:10.1016/s0031-9422(00)86487-0
Plantago lanceolata L. - -
Andrzejewska-golec, E., Swiatek, L. (1984). Chemotaxonomic investigations on the genus Plantago. I. analysis of iridoid fractions. Herba Pol, 30(1), 9-16
Plantago lanceolata L. - -
Darrow, K., Bowers, M.D. (1997). Phenological and population variation in iridoid glycosides of Plantago laceolata (Plantaginaceae). Biochem Syst Ecol, 25(1), 1-11 doi:10.1016/s0305-1978(96)00090-7
Plantago lanceolata L. - -
Hazanagy, A. (1970). Recent results with plantaginis folium (plantain leaves). Herba Hung, 9(2), 57-63
Plantago lanceolata L. aerial parts -
Adamczyk, M., Ratz, H., Hose, S., Marchesan, M., Paper, D.H., Franz, G., Wolfheuss, E., Engel, J. (1998). Quantitative determination of the iridoid glycosides aucubin and catalpol in Plantago lanceolata L. extracts by hptlc and hplc. J Planar Chromatogr Mod Tlc, 11(5), 374-378
Plantago lanceolata L. aerial parts -
Handjieva, N., Saadi, H., Evstatieva, L. (1991). Iridoid glucosides from Plantago altissima L., Plantago lanceolata L., Plantago atrata Hoppe and Plantago argentea Chaix. Z Naturforsch Ser C, 46(9/10), 963-965 doi:10.1515/znc-1991-9-1041
Plantago lanceolata L. flower -
Hazanagy, A. (1970). Recent results with plantaginis folium (plantain leaves). Herba Hung, 9(2), 57-63
Plantago lanceolata L. leaf -
Darrow, K., Bowers, M.D. (1997). Phenological and population variation in iridoid glycosides of Plantago laceolata (Plantaginaceae). Biochem Syst Ecol, 25(1), 1-11 doi:10.1016/s0305-1978(96)00090-7
Plantago lanceolata L. leaf -
Duff, R.B., Bacon, J.S.D., Mundie, C.M., Farmer, V.C., Russell, J.D., Forrester, A.R. (1965). Catalpol and methylcatalpol: naturally occurring glycosides in Plantago and Buddleia species. Biochem J, 96, 1 doi:10.1042/bj0960001
Plantago lanceolata L. leaf -
Hazanagy, A. (1970). Recent results with plantaginis folium (plantain leaves). Herba Hung, 9(2), 57-63
Plantago lanceolata L. root -
Hazanagy, A. (1970). Recent results with plantaginis folium (plantain leaves). Herba Hung, 9(2), 57-63
Plantago lanceolata L. seed -
Raszeja, W., Gill, S. (1973). Aucubin content of seeds of the Plantago genus. Rozpr Wydz 3 Nauk Mat-Przyr Gdansk Tow Nauk, 9, 195-200
Plantago major L. - 3700 ppm
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Plantago major L. leaf 10000 ppm
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Plantago major L. seed -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Plantago maritima L. subsp. serpentina (All.) Arcang. - -
Andrzejewska-golec, E., Swiatek, L. (1984). Chemotaxonomic investigations on the genus Plantago. I. analysis of iridoid fractions. Herba Pol, 30(1), 9-16
Plantago media L. subsp. media - -
Andrzejewska-golec, E., Swiatek, L. (1984). Chemotaxonomic investigations on the genus Plantago. I. analysis of iridoid fractions. Herba Pol, 30(1), 9-16
Plantago media L. subsp. media leaf -
Saadi, H., Handjieva, N., Popov, S., Evstatieva, L. (1990). Iridoids from Plantago media. Phytochemistry, 29(12), 3938-3939 doi:10.1016/0031-9422(90)85366-n
Plantago media L. subsp. media seed -
Raszeja, W., Gill, S. (1973). Aucubin content of seeds of the Plantago genus. Rozpr Wydz 3 Nauk Mat-Przyr Gdansk Tow Nauk, 9, 195-200
Scrophularia canina L. - -
Berdini, R., Bianco, A., Guiso, M., Marini, E., Nicoletti, M., Passacantilli, P., Right, G. (1991). Isolation and partial synthesis of 7,8-dehydro-6-beta,10-dihydroxy-11-noriridomyrmecin, a methylcyclopentanoid monoterpene from Scrophularia canina. J Nat Prod, 54(5), 1400-1403 doi:10.1021/np50077a027
Scrophularia nodosa L. - -
Weinges, K., Vondereltz, H. (1978). Natural products from medicinal plants. xxiii. iridoid glycosides from Scrophularia nodosa. Justus Liebigs Ann Chem, 1968
Verbascum blattaria L. - -
Grabias, B., Swiatek, L. (1987). Iridoid glucosides in Verbascum genus. Herba Pol, 33(4), 225-232
Verbascum phlomoides L. - -
Grabias, B., Swiatek, L. (1987). Iridoid glucosides in Verbascum genus. Herba Pol, 33(4), 225-232
Verbascum phlomoides L. flower -
Osvath, K., Papay, V., Toth, L. (1982). Constituents of the flowers of Verbascum phlomoides L. and their therapeutical application. Herba Hung, 21(2/3), 141-147
Verbascum phlomoides L. flower -
Swiatek, L., Adamczyk, U. (1983). Content of glycosides of the aucubin type in crude drug from Verbascum flowers. Farm Pol, 39(5), 275-277
Verbascum phlomoides L. leaf -
Ksotecka-madalska, O., Rymkiewicz, A. (1974). Aucubin in certain species of the Scrophulariaceaex family. Acta Pol Pharm, 31, 221
Verbascum phlomoides L. stem -
Ksotecka-madalska, O., Rymkiewicz, A. (1974). Aucubin in certain species of the Scrophulariaceaex family. Acta Pol Pharm, 31, 221
Veronica anagallis-aquatica L. subsp. anagallis-aquatica - -
Su, B.N., Yang, L., Gao, K., Jia, Z.J. (2000). Aquaticol, a bis-sesquiterpene and iridoid glucosides from Veronica anagallis-aquatica. Planta Med, 66(3), 281-283 doi:10.1055/s-2000-8564
Veronica anagallis-aquatica L. subsp. anagallis-aquatica aerial parts -
Lahloub, M.F., Zaghloul, M.G., Afifi, M.S., Sticher, O. (1993). Iridoid glucosides from Veronica anagallis-aquatica. Phytochemistry, 33(2), 401-405 doi:10.1016/0031-9422(93)85528-y
Veronica chamaedrys L. subsp. chamaedrys - -
Swiatek, L., Druzynski, J. (1968). Aucubin content in medicinal plants of the Veronica genus. Acta Pol Pharm, 25, 597-600
Veronica chamaedrys L. subsp. chamaedrys aerial parts -
Swiatek, L., Broda, B., Frej, E. (1971). Chemical composition of Veronica chamaedrys herb. Acta Pol Pharm, 28, 189-194
Veronica persica Poir. - -
Komai, K., Noguchi, H., Hamada, M. (1991). Isolation of iridoid glycoside from Veronica persica and analysis of biological activity. Zasso Kenkyu, 36(4), 324-328 doi:10.3719/weed.36.324
Veronica persica Poir. aerial parts -
Lahloub, M.F., Saad, H.E.A., Halim, A.F. (1991). Iridoid glucosides from aerial parts of Veronica persica Poir. in lam. growing in Egypt. Mansoura J Pharm Sci, 7(3), 390-401 doi:10.1055/s-2006-961103
Veronica polita Fr. aerial parts -
Tomassini, L., Brkic, D., Serafini, M., Nicoletti, M. (1995). Constituents of Veronica hederifolia and Veronica polita. Fitoterapia, 66(4), 382