Diarylheptanoid Sulfates and Related Compounds from <i>Myrica rubra</i> Bark

Yoshimura, Manabu; Yamakami, Saori; Amakura, Yoshiaki; Yoshida, Takashi

doi:10.1021/np300212c

Cited by 19 publications

(8 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fractionation of a methanolic extract of M. salicifolia bark resulted in the isolation of 6 unknown ( 1 – 6 ) and 10 known ( 7 – 16 ) cyclic diarylheptanoids of the sub-group meta-meta cyclophane ( Figure 1 ). The known diarylheptanoids were juglanin B-sulfate ( 7 ) [ 14 , 15 ], myricanol ( 8 ) [ 16 , 17 , 18 , 19 ], myricanone ( 9 ) [ 16 , 19 ], myricanol 5- O -β- d -glucopyranoside ( 10 ) [ 20 ], myricanone 5- O -β- d -glucopyranoside ( 11 ) [ 21 ], myricanol 11- O -β- d -xylopyranoside ( 12 ) [ 22 ], myricanol 5- O -β- d -(6’- O -galloyl)-glucopyranoside ( 13 ) [ 23 ], myricanone 5- O -β- d -(6’- O -galloyl)-glucopyranoside ( 14 ) [ 15 ], myricanol 5- O -α- l -arabinofuranosyl-(1→6)-β- d -glucopyranoside ( 15 ) [ 24 ], and myricanol gentiobiosidse: myricanol 5- O - β - d -glucopranosyl-(1→6)-β- d -glucopyranoside ( 16 ) [ 23 ], respectively. Structure elucidation was done by comprehensive one- and two-dimensional nuclear magnetic resonance (NMR), as well as high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS), sugar hydrolyses, circular dichroism (CD)-analyses, and comparison with published data.…”

Section: Resultsmentioning

confidence: 99%

Diarylheptanoid Glycosides of Morella salicifolia Bark

et al. 2017

View full text Add to dashboard Cite

A methanolic extract of Morella salicifolia bark was fractionated by various chromatographic techniques yielding six previously unknown cyclic diarylheptanoids, namely, 7-hydroxymyricanol 5-O-β-d-glucopyranoside (1), juglanin B 3-O-β-d-glucopyranoside (2), 16-hydroxyjuglanin B 17-O-β-d-glucopyranoside (3), myricanone 5-O-β-d-gluco-pranosyl-(1→6)-β-d-glucopyranoside (4), neomyricanone 5-O-β-d-glucopranosyl-(1→6)-β-d-glucopyranoside (5), and myricanone 17-O-α-l-arabino-furanosyl-(1→6)-β-d-glucopyranoside (6), respectively, together with 10 known cyclic diarylheptanoids. The structural diversity of the diarylheptanoid pattern in M. salicifolia resulted from varying glycosidation at C-3, C-5, and C-17 as well as from substitution at C-11 with hydroxy, carbonyl or sulfate groups, respectively. Structure elucidation of the isolated compounds was achieved on the basis of one- and two-dimensional nuclear magnetic resonance (NMR) as well as high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) analyses. The absolute configuration of the glycosides was confirmed after hydrolysis and synthesis of O-(S)-methyl butyrated (SMB) sugar derivatives by comparison of their 1H-NMR data with those of reference sugars. Additionally, absolute configuration of diarylheptanoid aglycones at C-11 was determined by electronic circular dichroism (ECD) spectra simulation and comparison with experimental CD spectra after hydrolysis.

show abstract

Section: Resultsmentioning

confidence: 99%

Diarylheptanoid Glycosides of Morella salicifolia Bark

et al. 2017

View full text Add to dashboard Cite

show abstract

“…2,3-Digalloyl oregonin was isolated from the 80% acetone extract of Alnus sibirica leaves by column chromatography using Amberlite XAD-2, Sephadex LH-20, MCI-gel, CHP 20P and ODS-B gel with an MPLC system [13]. Diarylheptanoid sulfates were isolated by the combination of size exclusion and reversed-phase chromatography [44,72] or by a sequential application of both together with normalphase chromatography [73]. The AgNO 3 column chromatography of the petroleum ether extract of Alpinia officinarum yielded the highly lipophilic diarylheptanoid 1,7-diphenylhept-3-ene-5-one [74].…”

Section: Isolationmentioning

confidence: 99%

Characterization of diarylheptanoids: An emerging class of bioactive natural products

Alberti

Riethmüller

Béni

2018

Journal of Pharmaceutical and Biomedical Analysis

View full text Add to dashboard Cite

Diarylheptanoids are a class of secondary plant metabolites with a wide variety of bioactivity. Research on their phytochemistry and phytoanalysis is rapidly growing and the number of identified structures bearing the aryl-C-aryl skeleton is at present approaching 500. Historically, the yellow pigment curcumin has been characterized as the first diarylheptanoid and the extensive research on naturally occurring analogues is still ongoing. In this review, studies dealing with the characterization of linear and cyclic derivatives are discussed from the phytoanalytical point of view. Isolation, fractionation and purification strategies from natural sources along with their chromatographic behavior and structural characteristics are discussed. The role of various techniques used for the extraction (such as Soxhlet extraction, sonication, maceration/percolation, microwave-assisted extraction, supercritical carbon dioxide extraction); isolation (liquid-liquid extraction, column chromatographic techniques, preparative thin-layer and high-performance liquid chromatography, centrifugal partition chromatography, counter-current chromatography); separation (thin-layer chromatography, high-performance liquid chromatography, gas chromatography, capillary electrophoresis) and structural characterization (UV/Vis spectroscopy, infrared spectroscopy, X-ray crystallography, mass spectrometry, nuclear magnetic resonance spectroscopy and circular dichroism spectroscopy) are critically reviewed.

show abstract

“…A compound with a close structural relationship to myricanol ( 12a ) in structure, was isolated from Juglans regia and named as juglanin B ( 12ba ) [40]; the structure of this was originally proposed in error [91]. Subsequently, two esters of sulfuric acid such as myricanol 11-sulfate ( 12ab ) and juglanin B 11-sulfate ( 12bb ), and related glycosides ( 12j – n ) were isolated from M. rubra [89]. The juglanin B ( 12ba ) showed cytotoxic activity against human hepatoma Hep G2 cells [40].…”

Section: Isolation Structural Features and Biological Propertiesmentioning

confidence: 99%

Recent Studies on Cyclic 1,7-Diarylheptanoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

Jahng

Park

2018

Molecules

View full text Add to dashboard Cite

Diarylheptanoids are a family of plant secondary metabolites with a 7 carbon skeleton possessing two phenyl rings at the 1- and 7-positions. They can be subdivided into acyclic and cyclic diarylheptanoids where the latter are further divided into meta,meta-bridged biphenyls ([7.0]metacyclophanes) and meta,para-bridged diphenyl ether heptanoids (oxa[7.1]metapara-cyclophanes). Since the isolation of curcumin from the rhizomes of turmeric (Curcuma longa) in 1815 which was named curcumin, a variety of diarylheptanoids have been isolated from a number of plant families such as Aceraceae, Actinidiaceae, Betulaceae, Burseraceae, Casuarinaceae, Juglandaceae, Leguminosae, Myricaceae, and Zingiberaceae. Earlier studies on these diarylheptanoids have been summarized on several occasions, of which the main themes only focus on isolation, structure elucidation, and the biological properties of linear types. Only a few have covered cyclic diarylheptanoids and their chemical synthesis has been covered lastly by Zhu et al. in 2000. The present paper has, therefore, covered recent progress in cyclic diarylheptanoids focusing on the isolation, structural and biological features, and chemical synthesis.

show abstract

Diarylheptanoid Sulfates and Related Compounds from Myrica rubra Bark

Cited by 19 publications

References 13 publications

Diarylheptanoid Glycosides of Morella salicifolia Bark

Diarylheptanoid Glycosides of Morella salicifolia Bark

Characterization of diarylheptanoids: An emerging class of bioactive natural products

Recent Studies on Cyclic 1,7-Diarylheptanoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

Contact Info

Product

Resources

About