• Title/Summary/Keyword: Lignans

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Phytochemical Studies of Phyllanthus debilis

  • Chandrashekar, K.S.;Satyanarayana, D.;Joshi, A.B.;Subrahmanyam, E.V.S.
    • Natural Product Sciences
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    • v.10 no.3
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    • pp.101-103
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    • 2004
  • Two Lignans Phyllanthin and Hypophyllanthin, and a steroid ${\beta}-sitosterol$ has been isolated from the leaves of Phyllanthus debilis and their structures were established by spectral analysis and direct comparison with authentic samples. This is the first report of occurrence of these compound from P.debilis.

Lignans of Rosa multiflora Roots

  • Yeo, Hosup;Chin, Young-Won;Park, Shin-Young;Kim, Jin-Woong
    • Archives of Pharmacal Research
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    • v.27 no.3
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    • pp.287-290
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    • 2004
  • Five known lignans, (+)-pinoresinol (1), (+)-8-hydroxypinoresinol (2), (-)- dehydrodiconiferyl alcohol (3), (+)-trans-dehydrodiconiferyl alcohol (4), and (-)-olivil (5), were isolated from the roots of Rosa multiflora for the first time. Their structures were determined using spectroscopic data.

Modulation of IL-12 and IFN-γ Secretions by Eleutheroside E, Tortoside A, and Syringaresinol from Acanthopanax koreanum Nakai

  • Lyu, Su-Yun;Park, Won-Bong
    • Biomolecules & Therapeutics
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    • v.18 no.2
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    • pp.211-218
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    • 2010
  • Acanthopanax koreanum Nakai (Araliaceae) is a medicinal plant indigenous to Korea. The root and stem barks of Acanthopanax species have been used as a tonic and sedative as well as in the treatment of rheumatism and diabetes. In our study, three lignans, eleutheroside E (EE), tortoside A (TA), and syringaresinol (SY), were isolated from the stem and root of A. koreanum in an effort to study the immunomodulating effect. We treated natural killer cells and dendritic cells with lignans (EE, TA, or SY), and analyzed their cytokine (IL-12 and IFN-${\gamma}$) secretion. EE, TA, or SY markedly enhanced IL-12 secretion in mouse lymphoid (DC1) and myeloid type (DC2.4) dendritic cells after 48 hr of treatment. There were no significant differences in the cytokine stimulatory effects between EE, TA, or SY. Moreover, treatment of EE, TA, or SY significantly induced IFN-${\gamma}$ secretion by human NK cells (NK92MI) confirmed by ELISA assay. This study suggests that lignans from A. koreanum modulate cytokines, and that such modulation may provide the mechanism of action for many of their therapeutic effects.

Analysis of Lignans in Acanthopanax sessiliflorus Fruits and Their Fermented Wine by HPLC

  • Kim, Hye-Min;Kim, Ju-Sun;Cho, Seon-Haeng;Kang, Sam-Sik;Cheoi, Dae-Sung;Lee, Sang-Hyun
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.5
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    • pp.289-292
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    • 2006
  • High performance liquid chromatography (HPLC) was used for the determination of lignans, eleutherosides B and E, in Acanthopanax sessiliflorus fruits and their fermented wine. The lignans were quantified by a reversed-phase system using a gradient of $H_2O$ and acetonitrile as a mobile phase within 20 min. The analysis was successfully carried out within 20 min. The contents of eleutherosides Band E as main active principles of Acanthopanax species were measured in A. sessiliflorus fruits (1.15 and $8.49\;{\mu}g/mg$, respectively), their fermented wine (0.45 and $1.33\;{\mu}g/mg$, respectively) and wine residues (no detection).

Anticholinesterase and Anti-inflammatory Constituents from Beilschmiedia pulverulenta Kosterm

  • Wan Salleh, Wan Mohd Nuzul Hakimi;Ahmad, Farediah;Yen, Khong Heng;Zulkifli, Razauden Mohamed
    • Natural Product Sciences
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    • v.22 no.4
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    • pp.225-230
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    • 2016
  • Phytochemical investigation from the stem bark of Beilschmiedia pulverulenta resulted in the isolation of five lignans, (+)-yangambin (1), (+)-sesartemin (2), (+)-excelsin (3), (+)-sesamin (4), and (+)-syringaresinol (5), together with lupeol (6), lupenone (7), ${\beta}-sitosterol$ (8), and ${\beta}-sitostenone$ (9). Their structures were established by the analysis of their spectroscopic (1D and 2D NMR) and spectrometric (MS) data, as well as by comparison with those reported in the literature. The isolated lignans were tested for their anticholinesterase (AChE: acetylcholine esterase and BChE: butyryl cholineesterase) and anti-inflammatory (COX-2: cyclooxygenase-2 and LOX: lipoxygenase) activities. All the isolated lignans (1 - 5) exhibited significant inhibition activities in AChE/BChE and COX-2/LOX assays with $IC_{50}$ values ranging from $168.8-504.2{\mu}M$ and $21.0-59.4{\mu}M$, respectively.

Diarylbutane-type Lignans from Myristica fragrans (Nutmeg) show the Cytotoxicity against Breast Cancer Cells through Activation of AMP-activated Protein Kinase

  • Le, Thi Van Thu;Nguyen, Phi Hung;Choi, Hong Seok;Yang, Jun-Li;Kang, Keon Wook;Ahn, Sang-Gun;Oh, Won Keun
    • Natural Product Sciences
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    • v.23 no.1
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    • pp.21-28
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    • 2017
  • In our program to search for new AMP-activated protein kinase (AMPK) activators from plants that exert potential anticancer property, we found that an EtOAc extract of Myristica fragrans (nutmeg) activated AMPK enzyme in human breast cancer MCF-7 cells. Two major diarylbutane-type lignans, macelignan and meso-dihydroguaiaretic acid (MDGA), were isolated as active principles from this extract. Treatment of breast cancer cells with two compounds induced cellular apoptosis, evidenced by cleavage of poly-(ADP-ribose) polymerase (PARP) and Ser 15 phosphorylation of p53. Moreover, macelignan and MDGA significantly inhibited the colony formation of MCF-7 breast cancer cells on soft agar. Intraperitoneal injection of macelignan and MDGA (20 mg/kg) suppressed the tumor growth of 4T1 mammary cancer cells. These results indicate that the chemopreventive effects of two major diarylbutane-type lignans from Myristica fragrans (nutmeg) may be associated with induction of apoptosis presumably through AMPK activation.

Development of Simultaneous Analytical Method for Five Lignans in Edible Seeds (종자류 식품에 함유된 5종 리그난의 동시 분석법 개발)

  • Yoonjeong, Kim;Jiye, Pyeon;In-hwan, Baek;Younghwa, Kim
    • The Korean Journal of Food And Nutrition
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    • v.35 no.6
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    • pp.543-551
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    • 2022
  • There has been increased interest in lignans due to their potential effect in reducing the risk of developing several diseases. To evaluate lignan contents, sensitive and accurate methods should be developed for their quantification in food. The present study aimed to validate a liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the quantification of 5 lignans: lariciresinol (Lar), matairesinol (Mat), pinoresinol (Pin), secoisolariciresinol (Seco), and syringaresinol (Syr). The validation included selectivity, linearity, recovery, accuracy, and precision. The method was proved to be specific, with a linear response (R2≥0.99). The limits of detection were 0.040~0.765 ㎍/100 g and the limits of quantification were 0.114~1.532 ㎍/100 g. Recoveries were 90.588~109.053% for black sesame powder. Relative standard deviations of repeatability and reproducibility were below 5%. Total lignan contents of roasted coffee bean, oat, and blacksoy bean were 105.702 ㎍/100 g, 78.965 ㎍/100 g, and 165.521 ㎍/100 g, respectively. These results showed that LC-MS/MS analysis would be effective in producing acceptable sensitivity, accuracy, and precision in five lignan analyses.

Varietal Difference of Lignan Contents and Fatty Acids Composition in Korean Sesame Cultivars (국내 참깨 품종의 리그난 함량 및 지방산 조성)

  • 강명화;오명규;방진기;김동휘;강철환;이봉호
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.45 no.3
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    • pp.203-206
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    • 2000
  • Although lignans of sesame seed, sesamolin and sesamin have been known as possessing an antioxidant activity, it is less known about their contents of the sesame cultivated in Korea. Collections of sesame cultivated in Korea were used for studies on their lignans content of the seed and fatty acids composition of the oil. The sesamin content of sesame seed with white-coat were 370.29 mg/100g seed, while that of sesame seed with black-coat were 246.58mg/100g seed. Also, the sesamolin contents of sesame seed were 202.22 mg/100g seed in white-coat cultivars and 132.68 mg/100g seed in black-coat sesames. Hence, the lignan content of white-coat sesame cultivars was significantly hi임or than that of black-coat ones. Korean sesame cultivars also showed considerably higher sesamin content than sesamolin content in seeds. The correlation between sesamin and sesamolin contents was not recognized in Korean sesame cultivars. The stearic acid of white-coat sesame was significantly higher than that of black-coat one (p<0.05).

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Neuroprotective Lignans from Biota orientalis leaves

  • Yoon, Jeong-Seon;Koo, Kyung-Ah;Ma, Choong-Je;Sung, Sang-Hyun;Kim, Young-Choong
    • Natural Product Sciences
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    • v.14 no.3
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    • pp.167-170
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    • 2008
  • We previously reported that 90% MeOH fraction of Biota orientalis leaves (L.) ENDL. had significant neuroprotective activity against glutamate-induced neurotoxicity in primary cultures of rat cortical cells. In the present study, (-)-savinin (1), (-)-hinokinin (2), dehydroheliobuphthalmin (3) were isolated by bioactivity-guided fractionation from the 90% MeOH fraction. All three lignans had significant neuroprotective activities against glutamate-induced neurotoxicity at the concentrations ranging from 0.1 to 10.0 ${\mu}M$.

Phytochemical Studies on Magnoliae Flos (I) Isolation of Lignans from the Flower Buds of Magnolia biondii

  • Lee, Dong Hwa;Kwon, Soon Youl;Woo, Mi Hee;Lee, Je Hyun;Son, Kun Ho
    • Natural Product Sciences
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    • v.19 no.2
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    • pp.160-165
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    • 2013
  • The 12 compounds were isolated from MeOH extract of Magnolia biondii and their structures were identified as seven lignans, two phenolics, one coumarin, and two flavonoid compounds, respectively. Among these constituents, tiliroside (3), kaempferol-7-methyl ether (4), 4-hydroxybenzoic acid (5), vanilic acid (6), and scopoletin (9) were isolated from Magnolia biondii for the first time.