Lignans from machilus thunbergii

Shimomura, Hiroko; Sashida, Yutaka; Oohara, Motomu

doi:10.1016/s0031-9422(00)81847-6

Cited by 67 publications

(62 citation statements)

References 7 publications

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“…Compound 1 has the molecular formula C 20 tive of a dihydrobenzofuran lignan [25]. The 1 H NMR data ( suggesting the presence of an (E)-double bond.…”

Section: Resultsmentioning

confidence: 99%

“…Previous chemical investigations on the constituents of this plant have revealed the presence of diterpenes, phorbol esters, cyclopeptides, and courmarino lignans [3 -13]. In continuation of our search for metablites from aerial parts of this plant, four new lignans, curcasinlignan A (1), curcasinlignan B (2), curcasinlignan C (3), and curcasinlignan D (4), together with eight known compounds, (±)-rel-(2α,3β )-7-O-methylcedrusin (5) [14,15], (±)-7R * , 8S * -5-methoxydihydrodehydroconiferyl alcohol (6) [16], dehydrodiisoeugeno1 (7) [17,18], (threo)-1-(4-hydroxy-3-methoxyphenyl)-2-(4-formyl-2-methoxyphenoxy)-propane-1, 3-diol (8) [19], (±)-machilin D (9) [20], (+)-pinoresinol (10) [21], 5 -methoxypropacin (11) [22,23], and hemidesmin-2 (12) [24], were obtained (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

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New Lignans from Jatropha curcas Linn.

Tan

2012

Zeitschrift Für Naturforschung B

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Four new lignans, curcasinlignan A (1), curcasinlignan B (2), curcasinlignan C (3), and curcasinlignan D (4), together with eight known compounds, (±)-rel-(2α,3β )-7-Omethylcedrusin (5), (±)-7R * ,8S * -5-methoxydihydrodehydroconiferyl alcohol (6), dehydrodiisoeugeno1 (7), (threo)-1-(4-hydroxy-3-methoxyphenyl)-2-(4-formyl-2-methoxy-phenoxy)-propane-1,3-diol (8), (±)-machilin D (9), (+)-pinoresinol (10), 5 -methoxypropacin (11), and hemidesmin-2 (12), were isolated from the aerial parts of Jatropha curcas. Their structures were established on the basis of extensive spectroscopic analysis.

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“…Compound 1 has the molecular formula C 20 tive of a dihydrobenzofuran lignan [25]. The 1 H NMR data ( suggesting the presence of an (E)-double bond.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Lignans from Jatropha curcas Linn.

Tan

2012

Zeitschrift Für Naturforschung B

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“…Then, methylene chloride extract, which showed stronger inhibitory activity on topoisomerase I than the other extracts (Table 1), was repeatedly subjected to both silica gel and reverse-phase gel to afford ten lignans (1)(2)(3)(4)(5)(6)(7)(8)(9)(10). By comparison of their 1 H-and 13 C-NMR spectra, MS data, and optical rotation with reported values, their structures were characterized as machilin A (1), 9) erythro-austrobailignan-6 (2), 21,22) meso-monomethyl dihydroguaiaretic acid (3), 23) meso-dihydroguaiaretic acid (4), 24) galbacin (5), 26) machilin F (6), 10) nectandrin A (7), 10,27) nectandrin B (8), 10) (Ϫ)-acuminatin (9) 28) and (7S,8S)-7-(4-hydroxy-3-methoxyphenyl)-1Ј-formyl-3Ј-methoxy-8-methyldihydrobenzofuran (10). 29) Among these lignans described, 2 and 10 were isolated for the first time from this Lauraceae family of the plant kingdom.…”

Section: Resultsmentioning

confidence: 99%

“…8) Lignans, [8][9][10][11][12] alkaloids, 13) flavonoids, 14,15) butanolides 16) and essential oils 17,18) have been reported as components from M. thunbergii, some of which have hepatoprotective activity as antioxidants, 8) antibacterial activity 11,19) and inhibitory activity on nitric oxide synthesis in activated macrophages. 16) In this study, we isolated ten lignans from the bark of the M. thunbergii, and investigated their DNA topoisomerases I and II inhibitory effects and cytotoxicity.…”

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confidence: 99%

Lignans from the Bark of Machilus thunbergii and Their DNA Topoisomerases I and II Inhibition and Cytotoxicity

Lee

Woo

et al. 2004

Biological & Pharmaceutical Bulletin

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DNA topoisomerases are enzymes involved in the relaxation of DNA during a number of critical cellular processes, including replication, recombination and transcription by transiently breaking one or two strands of DNA, passing a single-or double-stranded DNA through the break, and finally resealing the breaking.1-3) Currently, only a camptothecin (CPT) family of compounds as DNA topoisomerase I-directed drugs has been introduced into the clinic to date, 4,5) though many topoisomerase II-directed drugs have been in clinical use for many years.6) DNA topoisomerases have been established as important molecular targets for anticancer drugs.7) During our search for new DNA topoisomerase inhibitors from natural products by activity-guided fractionation, several solvent extracts of more than 100 Korean folk medicines were screened for their DNA topoisomerase I inhibitory activities. Among them, the CH 2 Cl 2 extract of the bark of M. thunbergii showed strong DNA topoisomerase I inhibitory activity (94.1% inhibition at 25 mg/ml), and was subjected to the isolation of compounds with DNA topoisomerase inhibitory activity from the CH 2 Cl 2 extract of the bark of M. thunbergii.The bark of M. thunbergii has been used as a folk medicine for the treatment of leg oedema, abdominal pain and abdominal distension in Korea. 11,19) and inhibitory activity on nitric oxide synthesis in activated macrophages. 16) In this study, we isolated ten lignans from the bark of the M. thunbergii, and investigated their DNA topoisomerases I and II inhibitory effects and cytotoxicity. MATERIALS AND METHODS General ProceduresOptical rotations were measured using a JASCO DIP-1000 (Tokyo, Japan) automatic digital polarimeter. The NMR spectra were recorded on a Bruker 250 MHz (DMX 250) spectrometer using Bruker's standard pulse program. Samples were dissolved in CDCl 3 -d 1 or CD 3 OD-d 4 , and chemical shifts were reported in ppm downfield from TMS. FAB-MS spectra were measured with a VG TRIO 2A mass spectrometer. Stationary phases for column chromatography (Silica gel 60, 70-230 and 270-400 mesh and Lichroprep RP-18 gel, 40-63 mm, Merck) and TLC plates (Silica-gel 60 F 254 and RP-18 F 254 , Merck) were purchased from Merck KGaA (Darmstadt, Germany). Spots were detected under UV radiation and by spraying with 10% H 2 SO 4 , followed by heating. The camptothecin (CPT) and etoposide were purchased from Sigma Chemical Co. (St. Louis, MO, U.S.A.). Supercoiled pBR 322 plasmid DNA and calf thymus topoisomerase I were purchased from MBI Fermentas, Inc. (Hanover, MD, U.S.A.). The human topoisomerase II was purchased from TopoGEN, Inc. (Columbus, OH, U.S.A.). All other chemicals and solvents were of analytical grade, and used without further purification.Plant Material The bark of M. thunbergii was purchased in September 1999 from a folk medicine market, "Yak-ryong-si" in Daegu, Republic of Korea. These materials were confirmed taxonomically by Professor Gi-Hwan Bae, of Chungnam National University, Taejeon, Republic of Korea. A voucher specimen has been de...

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“…7) Lignans, [8][9][10][11] alkaloids, 12) flavonoids, 13,14) butanolides 15) and essential oils 16) have been reported as components from M. thunbergii, some of which have hepatoprotective activity as antioxidants, 7) antibacterial activity 10) and inhibitory activity on nitric oxide synthesis in activated macrophages.…”

Section: )mentioning

confidence: 99%

Meso-dihydroguaiaretic Acid from Machilus thunbergii SIEB et ZUCC., and Its Effects on the Expression of Matrix Metalloproteinase-2, 9 Cause by Ultraviolet Irradiated Cultured Human Keratinocyte Cells (HaCaT)

Moon

Chung

2005

Biological & Pharmaceutical Bulletin

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Ethanol and aqueous extracts of Machilus thunbergii used traditionally for the treatments a wide variety of diseases were screened in vitro for the matrix metalloproteinase (MMP)-9 inhibitor actions. Meso-dihydroguaiaretic acid from the stems bark of Machilus thunbergii showed significant MMP-9 inhibition in human keratinocyte cells cause by ultraviolet irradiation. Here we investigated the effect of meso-dihydroguaiaretic acid, which was isolated from Machilus thunbergii, on UV-induced premature skin aging. We studied the effect of meso-dihydroguaiaretic acid on UV-induced MMP-9 expression in an immortalized human keratinocyte cell line, HaCaT, in vitro. Acute UV irradiation induced MMP-9 expression at both the mRNA and protein levels and meso-dihydroguaiaretic acid suppressed this UV-induced MMP-9 expression in a dose-dependent manner. Taken together, these results show that meso-dihydroguaiaretic acid can prevent the harmful effects of UV that lead to skin aging. Therefore, we suggest that meso-dihydroguaiaretic acid should be viewed as a potential therapeutic agent for preventing and/or treating premature skin aging.Key words Machilus thunbergii; meso-dihydroguaiaretic acid; ultraviolet irradiation; matrix metalloproteinase (MMP)-9Skin connective tissue contains several types of collagen, elastin, fibronectin, proteoglycan, and other extracellular matrix proteins, among which type I collagen is the most abundant. The balance between the synthesis and degradation of extracellular matrix components is important for maintaining a normal connective tissue structure. Moreover, it has been suggested that the most prominent features of photoaged skin are an impairment of collagen fiber and the excessive deposition of abnormal elastin-containing material in the upper and mid-dermis. 1)The matrix metalloproteinases (MMPs) are a family of structurally related zinc-dependent endopeptidases, which are capable of degrading a wide variety of extracellular matrix components.2) MMPs are known to play important roles in tissue remodeling during developmental morphogenesis, angiogenesis, and tissue repair, and in tissue destruction during pathological processes, such as, arthritis, skin aging, tumor invasion, and metastasis. MMPs expression is low in unstimulated skin cells or normal skin tissues, but some MMPs are induced by various extracellular stimuli, e.g., ultraviolet or infrared radiation, growth factors, cytokines, and tumor promoters.3) Recent studies have shown that hairless mouse chronically exposed to ultraviolet B (UV-B) radiation show epidermal hyperplasia, skin wrinkles, and significant enhancement of gelatinase (i.e., MMP-2 and MMP-9) activities. In addition, they have shown that the inhibition of gelatinase activities by a specific MMP inhibitor, suppresses UVB-induced epidermal thickness enhancement and wrinkle formation.4) These results suggest that MMPs are directly involved in the skin photoaging process, and that the inhibition of the activities of MMPs (either directly by a specific inhibitor or indirec...

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Lignans from machilus thunbergii

Cited by 67 publications

References 7 publications

New Lignans from Jatropha curcas Linn.

New Lignans from Jatropha curcas Linn.

Lignans from the Bark of Machilus thunbergii and Their DNA Topoisomerases I and II Inhibition and Cytotoxicity

Meso-dihydroguaiaretic Acid from Machilus thunbergii SIEB et ZUCC., and Its Effects on the Expression of Matrix Metalloproteinase-2, 9 Cause by Ultraviolet Irradiated Cultured Human Keratinocyte Cells (HaCaT)

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