Biflavonoids from Lonicera japonica

doi:10.1016/j.phytochem.2005.10.002

Phytochemistry

Volume 66, Issue 23, December 2005, Pages 2740-2744

https://doi.org/10.1016/j.phytochem.2005.10.002 Get rights and content

Abstract

Two biflavonoids, 3′-O-methyl loniflavone [5,5″,7,7″-tetrahydroxy 3′-methoxy 4′,4‴-biflavonyl ether (1)] and loniflavone [5,5″,7,7″,3′-pentahydroxy 4′,4‴-biflavonyl ether (2)] along with luteolin (3) and chrysin (4) were isolated from the leaves of Lonicera japonica. The structures were established on the basis of UV/vis, 1D, 2D NMR (HMQC and HMBC) and ESI-QTOF-MS/MS spectroscopic methods and chemical evidences.

Graphical abstract

Two biflavonoids, 3′-O-methyl loniflavone [5,5″,7,7″-tetrahydroxy 3′-methoxy 4′,4‴-biflavonyl ether] and loniflavone [5,5″,7,7″,3′-pentahydroxy 4′,4‴-biflavonyl ether] along with luteolin and chrysin were isolated and characterized from the leaves of Lonicera japonica.

Introduction

Lonicera (Caprifoliaceae) is a genus of more than 150 species of erect climbing or scrambling shrub distributed chiefly in the sub-tropical and temperate regions of the Northern Hemisphere. Approximately 45 species are known to grow in India and few species are used in indigenous system of medicine as an antipyretic, stomachic and diuretic and in dysentery (Anonymous, 1962, Kirtikar and Basu, 1935). Lonicera japonica Thunb., Japanese honeysuckle, has been used to treat urinary disorders, fever and headache. It has been known as an anti-inflammatory agent in Korea from ancient times and is used widely for upper respiratory tract infections, diabetes mellitus and rheumatoid arthritis (Lee et al., 1998). A number of compounds such as iridoid glycosides, saponins, flavonoids and tannins have been reported from this species (Mehrotra et al., 1988, Kawai et al., 1988a, Kawai et al., 1988b, Machida et al., 2002, Kwak et al., 2003, Son et al., 1992, Son et al., 1994a, Son et al., 1994b). Although the chemical composition of L. japonica from few countries is well documented, there has been no report on the chemical composition from India. We, therefore, report here the isolation and structure elucidation of two new biflavonoids (1 and 2) (Fig. 1) together with luteolin (3) and chrysin (4) from the leaves.

Section snippets

Results and discussion

Dried powdered leaves of L. japonica were extracted with MeOH–H₂O (80:20; v/v) and fractionated successively with hexane, CHCl₃, EtOAc, and n-BuOH. EtOAc extract was subjected to repeated chromatographic purification to yield two new biflavones (1 and 2) along with luteolin (3) and chrysin (4).

Compound 1 was isolated as a yellowish amorphous powder. The presence of paired signals in ¹³C NMR spectrum (Table 1) suggested either a dimer or a mixture of two closely related compounds. However,

General experimental procedures

MPs were determined on a Mettler FP 800 (Central Processor) and were uncorrected. IR spectra were recorded in KBr disks on a Jasco FT-IR-5300, and UV spectra with Specord 200, Analytikjena spectrophotometer. Mass spectra were recorded on QTOF-Micro of Waters Micromass. NMR experiments were performed on Bruker Avance-300 spectrometer. Silica gel (60–120 mesh, MERCK) for Column chromatography, TLC silica gel 60 F₂₅₄ plates and all other chemicals were produced by Merck India Ltd.

Plant material

Leaves of L.

Acknowledgements

Authors are grateful to the Director, IHBT, Palampur for providing necessary facilities and Dr. K.L. Dhar for scientific discussion.

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Phytochemistry

Abstract

Graphical abstract

Introduction

Section snippets

Results and discussion

General experimental procedures

Plant material

Acknowledgements

References (19)

Recent advances in the application of mass spectrometry in food-related analysis

J. Chromatogr. A

Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry

J. Am. Soc. Mass Spectrom.

13C-NMR-Spektren naturlich vorkommender flavonoide

Tetrahedron Lett.

Carbon-13 NMR of flavonoids

Structural and spectroscopic study of 5,7-dihydroxy-flavone and its complex with aluminium

Spectrochim. Acta Part A

Iridoid glucosides from Lonicera japonica Thunb

Chem. Pharm. Bull.

Studies on the saponins of Lonicera japonica Thunb

Chem. Pharm. Bull.

Cited by (86)

The comparative analysis of Lonicerae Japonicae Flos and Lonicerae Flos: A systematical review

Bioactive components and beneficial bioactivities of flowers, stems, leaves of Lonicera japonica Thunberg: A review

The effective components of herbal medicines used for prevention and control of fish diseases

Genus Lonicera: New drug discovery from traditional usage to modern chemical and pharmacological research

Neuroprotective flavonoids of the leaf of Antiaris africana Englea against cyanide toxicity

Evaluation of surface phenomena of magnetic biomass for dye removal via surface modeling

Biflavonoids from Lonicera japonica☆

Abstract

Graphical abstract

Introduction

Section snippets

Results and discussion

General experimental procedures

Plant material

Acknowledgements

J. Chromatogr. A

J. Am. Soc. Mass Spectrom.

Tetrahedron Lett.

Carbon-13 NMR of flavonoids

Structural and spectroscopic study of 5,7-dihydroxy-flavone and its complex with aluminium

Spectrochim. Acta Part A

Iridoid glucosides from Lonicera japonica Thunb

Chem. Pharm. Bull.

Studies on the saponins of Lonicera japonica Thunb

Chem. Pharm. Bull.