Abstract
A new quinic acid ester, 4-O-(3,5-dimethoxy-4-hydroxybenzoyl)quinic acid (1) was isolated, together with 22 known compounds, from the barks and woods of Strychnos lucida. The structure of the new compound was determined by spectroscopic (NMR, MS) and chemical means.
Similar content being viewed by others
References
Bisset NG (1980) Alkaloids of Loganiaceae. In: Phillipson JD, Zenk MH (eds) Indole and biogenetically related alkaloids. Academic Press, New York, Chapter 3
Itoh A, Oya N, Kawaguchi E, Nishio S, Tanaka Y, Kawachi E, Akita T, Nishi T, Tanahashi T (2005) Three secoiridoid glucosides from Strychnos spinosa. J Nat Prod 68:1434–1436
Perry LM (1980) Medicinal plants of East and Southeast Asia. The MIT Press, Massachusetts, p 245
Asai F, Iinuma M, Tanaka T, Matsuura S (1982) Studies on the components of folk medicine, Kaju Ular, in Timor island. Yakugaku Zasshi 102:690–694
Mitsunaga K, Koike K, Fukuda H, Ishii K, Ohmoto T (1991) Ligustrinoside, a new bisiridoid glucoside from Strychnos ligustrina. Chem Pharm Bull 39:2737–2738
Nakamoto K, Otsuka H, Yamasaki K (1988) 7-O-Acetyl loganic acid from Alangium platanifolium var. trilobum. Phytochemistry 27:1856–1858
Bernstein MA, Hall LD (1985) An evaluation of high resolution nuclear magnetic resonance experiments and protocols in the structure elucidation of organic molecules. I. A relatively simple system, brucine. Can J Chem 63:483–490
Verpoorte R, Beek TA, Riegman RLM, Hylands PJ, Bisset NG (1984) Carbon-13 NMR spectroscopy of some Strychnos alkaloids. Part 2. Magn Reson Chem 22:345–348
Goulart MOF, Lima RA, Goulart AE (1984) Flavonoids and alkaloids from Strychnos pseudoquina. J Nat Prod 47:953–957
Thepenier P, Jacquier M-J, Massiot G, Olivier L, Delaude C (1988) Alkaloids from Strychnos staudtii. Phytochemistry 27:657–659
Calis I, Sticher O (1984) Secoiridoid glucosides from Lonicera periclymenum. Phytochemistry 23:2539–2540
Cambie RC, Lal AR, Rickard CEF, Tanaka N (1990) Chemistry of Fijian plants. V. Constituents of Fagraea gracilipes A. Gray. Chem Pharm Bull 38:1857–1861
Damtoft S, Franzyk H, Jensen SR (1997) Iridoid glucosides from Picconia excelsa. Phytochemistry 45:743–750
Abdallah OM (1991) Phenolic glucoside and other constituents of Dipsacus laciniatus. Phytochemistry 30:2805–2806
Kocsis Á, Szabó LF (1993) New bis-iridoids from Dipsacus laciniatus. J Nat Prod 56:1486–1499
Ma W-G, Wang D-Z, Zeng Y-L, Yang C-R (1992) Iridoidal glycosides from Triplostegia grandiflora. Acta Botanica Yunnanica 14:92–96
Zhong X-N, Otsuka H, Ide T, Hirata E, Takeda Y (1999) Hydroquinone diglycoside acyl esters from the leaves of Myrsine seguinii. Phytochemistry 52:923–927
Sakushima A, Coskun M, Maoka T (1995) Hydroxybenzoic acids from Boreava orientalis. Phytochemistry 40:257–261
Matsuda N, Sato H, Yaoita Y, Kikuchi M (1996) Isolation and absolute structures of the neolignan glycosides with the enantiometric aglycones from the leaves of Viburnum awabuki K. Koch. Chem Pharm Bull 44:1122–1123
Lami N, Kadota S, Kikuchi T, Momose Y (1991) Constituents of the roots of Boerhaavia diffusa L. III. Identification of Ca2+ channel antagonistic compound from the methanol extract. Chem Pharm Bull 39:1551–1555
Wang H-B, Mayer R, Rücker G, Neugebauer M (1993) Bisepoxylignan glycosides from Stauntonia hexaphylla. Phytochemistry 34:1621–1624
Nishizawa M, Izuhara R, Kaneko K, Koshihara Y, Fujimoto Y (1988) 5-Lipoxygenase inhibitors isolated from Gardeniae Fructus. Chem Pharm Bull 36:87–95
Wang Y, Hamburger M, Gueho J, Hostettmann K (1992) Cyclohexanecarboxylic-acid derivatives from Psiadia trinervia. Helv Chim Acta 75:269–275
Buckingham J (1994) Dictionary of natural products, vol. 1. Chapman & Hall, London, p. 78
Manthey MK, González-Bello C, Abell C (1997) Synthesis of (2R)-2-bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid. J Chem Soc Perkin Trans 1:625–628
McCord WM (1931) A new method for the preparation of syringic aldehyde. J Am Chem Soc 53:4181–4183
Sefkow M, Kelling A, Schilde U (2001) First efficient synthesis of 1-, 4-, and 5-caffeoylquinic acid. Eur J Org Chem 14:2735–2742
Acknowledgements
Our thanks go to Dr. M. Sugiura (Kobe Pharmaceutical University) for NMR spectra and to Dr. K. Saiki (Kobe Pharmaceutical University) for MS measurements. This research was financially supported by Kobe Pharmaceutical University Collaboration Fund.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Itoh, A., Tanaka, Y., Nagakura, N. et al. A quinic acid ester from Strychnos lucida. J Nat Med 60, 146–148 (2006). https://doi.org/10.1007/s11418-005-0021-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-005-0021-3