Phenolic lignans from flower buds of Magnolia fargesii

Miyazawa, Mitsuo; Kasahara, Hiroyuki; Kameoka, Hiromu

doi:10.1016/0031-9422(92)83756-o

Cited by 53 publications

(23 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1). 15,16) Compound 3 was a second metabolite when the reaction mixture was monitored by TLC. Its molecular ion peak (m/z 360 [M] ϩ ) in the EI-MS spectrum was 2 mass units (2H) higher than that of 2, suggesting that 3 is a reduced product of 2.…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of Pinoresinol Diglucoside to Mammalian Lignans by Human Intestinal Microflora, and Isolation of Enterococcus faecalis Strain PDG-1 Responsible for the Transformation of (+)-Pinoresinol to (+)-Lariciresinol

et al. 2003

View full text Add to dashboard Cite

Asian people who are vegetarian or semi-vegetarian show a low incidence of and mortality from hormone-dependent diseases, such as breast and prostate cancers, compared with Western people, whose diets are rich in animal protein and fats.1) Consumption of fiber-rich whole grain food elevates a serum mammalian lignan, enterolactone (ENL).2,3) Furthermore, both very low and very high plasma concentrations of ENL are associated with an increased breast cancer risk, 4) and urinary excretion of mammalian lignans [enterodiol (END) and ENL] is low in patients with breast cancer.5,6) All these findings suggest a close relationship between vegetarian diet, mammalian lignans and hormone-dependent diseases. The origins of END and ENL found in human biological fluids and in feces are plant lignans contained in fibrerich whole grain food, which are transformed by intestinal microflora in the proximal colon. 7,8) Until recently, secoisolariciresinol and matairesinol are the only known precursors of END and ENL. 7-9) Pinoresinol, lariciresinol, syringaresinol, 7-hydoxymatairesinol and arctigenin are newly identified enterolactone precursors, 10,11) and a possible metabolic pathway for pinoresinol (formation of mammalian lignans via lariciresinol and secoisolariciresinol) was proposed based on the biosynthetic pathway of secoisolariciresinol and matairesinol in plants. 10) Pinoresinol diglucoside is a major antihypertensive principle of Tu-Chung (the bark of Eucommia ulmoides), used in traditional Chinese medicine, 12) and pinoresinol is contained in cereals, particularly in whole-grain rye products, 1) olive oil, 13) and in various Picea, Pinus and Abies etc.14) The present study was designed for a better understanding of the metabolism of pinoresinol diglucoside by human intestinal microflora, as well as isolation of the bacterial strains responsible for the respective reactions in the transformation. ResultsTransformation of Pinoresinol Diglucoside (PDG, 1) by a Human Intestinal Bacterial Mixture After anaerobic incubation of pinoresinol diglucoside (1) with a bacterial mixture of human feces, the culture was extracted with nBuOH and the extract was subjected to Diaion HP-20, Sephadex LH-20, preparative thin-layer chromatography (TLC) and RP-18 column chromatography. Fifteen metabolites (2-16) were isolated and identified by electron impact mass (EI-MS), one dimensional (1D) and 2D-NMR, and circular dichroic (CD) spectroscopy.Compound 2 was detected as a major metabolite after 6 h of incubation of 1 with a human fecal suspension. The [a] D 25 value measured in MeOH was ϩ69°. The 1 H-and 13 C-NMR spectra (Table 1) were in good agreement with those reported for (ϩ)-pinoresinol, bearing a (7S,7ЈS,8S,8ЈS)-configuration (Fig. 1). 15,16) Compound 3 was a second metabolite when the reaction mixture was monitored by TLC. Its molecular ion peak (m/z 360 [M] ϩ ) in the EI-MS spectrum was 2 mass units (2H) higher than that of 2, suggesting that 3 is a reduced product of 2. The [a] D 25 value in MeOH was ϩ30°. 17) Compound 3 was deter...

show abstract

Section: Resultsmentioning

confidence: 99%

Biotransformation of Pinoresinol Diglucoside to Mammalian Lignans by Human Intestinal Microflora, and Isolation of Enterococcus faecalis Strain PDG-1 Responsible for the Transformation of (+)-Pinoresinol to (+)-Lariciresinol

et al. 2003

View full text Add to dashboard Cite

show abstract

“…Especially, the absolute configurations of 1 and 2 were determined by circular dichroism (CD) studies and that of 3 by Mosher's esterification method for the first time in this study. Six compounds, previously known structures, were identified as tanegool (4), 15) (ϩ)-dehydrodiconiferyl alcohol (5), 16) and epieudesmin (6), 17) (ϩ)-de-O-methylmagnolin (7), 1) biondinin A (8), 18) and magnone B (9). 19) Three lignans 4-6 were isolated from this plant for the first time.…”

mentioning

confidence: 99%

Two New Stereoisomers of Neolignan and Lignan from the Flower Buds of <i>Magnolia fargesii</i>

Lee

Seo

Jang

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

“…1) This species has been reported to contain many kinds of essential oils, lignans, neolignans, and sesquiterpenes associated with biological activities such as anti-platelet-activating factor (PAF), anti-TNFa, and calcium antagonism. [2][3][4][5][6] During our research program to find antioxidants of plant origin, the chloroform extracts of M. fargesii showed significant activity, thus, the extracts were subjected to detailed laboratory investigation, affording compounds 5-8 as active principles along with inactive compounds, 1-4 and 9-11 ( Fig.…”

mentioning

confidence: 99%

Two New Stereoisomers of Tetrahydrofuranoid Lignans from the Flower Buds of <i>Magnolia fargesii</i>

Lee

Jang

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Phenolic lignans from flower buds of Magnolia fargesii

Cited by 53 publications

References 7 publications

Biotransformation of Pinoresinol Diglucoside to Mammalian Lignans by Human Intestinal Microflora, and Isolation of Enterococcus faecalis Strain PDG-1 Responsible for the Transformation of (+)-Pinoresinol to (+)-Lariciresinol

Biotransformation of Pinoresinol Diglucoside to Mammalian Lignans by Human Intestinal Microflora, and Isolation of Enterococcus faecalis Strain PDG-1 Responsible for the Transformation of (+)-Pinoresinol to (+)-Lariciresinol

Two New Stereoisomers of Neolignan and Lignan from the Flower Buds of <i>Magnolia fargesii</i>

Two New Stereoisomers of Tetrahydrofuranoid Lignans from the Flower Buds of <i>Magnolia fargesii</i>

Contact Info

Product

Resources

About