7-Feruloylloganin: An Iridoid Glucoside from Stems of Lonicera insularis

Abstract

A new iridoid glucoside, 7-feruloylloganin (1), was isolated from stems of Lonicera insularis, along with six known lignans including (-)-pinoresinol, 9α-hydroxypinoresinol, balanophonin, erythro-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[2-formyl-(E)-vinyl]-2-methoxyphenoxy}-propane-1,3-diol, threo-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[2-formyl-(E)-vinyl]-2-methoxyphenoxy}-propane-1,3-diol and buddlenol A. The structure of 1 was determined by analyses of 2D NMR (¹H-¹H COSY, HMQC and HMBC) and HRFABMS.

References

• 1 Dictionary of Natural Products (Seven-volume set). London; Chapman & Hall 1994
• 2 Bianco A, Passacantilli P. 8-Epiloganin, an iridoid glucoside from Odontites verna .  Phytochemistry. 1981;  20 1873-6
• 3 Garcia J, Chulia A J. 4′-p-Coumaroyl iridoid glucosides from Gentiana pedicellata .  Planta Medica. 1987;  53 101-3
• 4 Garcia J, Chulia A J. Loganin and new iridoid glucosides in Gentiana pedicellata .  Planta Medica. 1986;  52 327-9
• 5 Calis I, Mohamed F L, Sticher O. Loganin, loganic acid and periclymenoside, a new biosidic ester iridoid glucoside from Lonicera periclymenum L. (Caprifoliaceae).  Helvetica Chimica Acta. 1984;  67 160-5
• 6 Rasoanaivo P, Galeffi C, Multari G, Nicoletti M. 7-Caffeoylloganin: an iridoid glucoside from Cassinopsis madagascariensis .  Planta Medica. 1991;  57 486-7
• 7 Calis I, Sticher O. Periclymenosidic acid, a new biosidic ester iridoid glucoside from Lonicera coerulea .  Journal of Natural Products. 1985;  48 108-10
• 8 Abe F, Yamauchi T. 9α-Hydroxypinoresinol, 9α-hydroxymedioresinol and related lignans from Allamanda neriifolia .  Phytochemistry. 1988;  27 575-7
• 9 Marcos M, Jiménez C, Villaverde M C, Riguera R, Castedo L, Stermitz F. Lignans and other constituents from South and Central American Zanthoxylum species.  Planta Medica. 1990;  56 89-91
• 10 Tsulamoto H, Hisada S, Nishibe S. Lignans from bark of Fraxinus mandshurica var. japonica and F. japonica .  Chemical & Pharmaceutical Bulletin. 1984;  32 4482-9
• 11 Khan K A, Shoeb A. A lignan from Lonicera hypoleuca .  Phytochemistry. 1985;  24 628-30
• 12 Murata H, Haruna M, Koube T, Ito K. Balanophonin, a new neo-lignan from Balanophora japonica Makino.  Chemical & Pharmaceutical Bulletin. 1982;  30 1525-7
• 13 Atsushi Y, Shigehiko N, Toshio M, Akira U, Li-Jun W. Phenylethanoid and lignan-iridoid complex glycosides from roots of Buddleja davidii .  Phytochemistry. 1993;  32 421-5
• 14 Della G M, Molinaro A, Monaco P, Previtera L. Neolignans from Arum italicum .  Phytochemistry. 1994;  35 777-9
• 15 Miki K, Sasaya T, Sakakibara A. Lignans of Larix leptolepis .  Phytochemistry. 1980;  19 449-53
• 16 Fang J, Lee C, Cheng Y. Lignans from leaves of Juniperus chinensis .  Phytochemistry. 1992;  31 3659-61
• 17 Houghton P J. Lignans and neolignans from Buddleja davidii .  Phytochemistry. 1985;  24 819-26
• 18 Otsuka H, Kashima N, Nakamoto A. A neolignan glycoside and acylated iridoid glucosides from stem bark of Alangium platanifolium .  Phytochemistry. 1996;  42 1435-8