Studies on Lignoids in <i>Lauraceae</i>. II. Studies on Lignans in the Leaves of <i>Machilus Japonica</i> Sieb. et Zucc.

Takaoka, Daisuke; Watanabe, Keiko; Hiroi, Mitsuru

doi:10.1246/bcsj.49.3564

Cited by 31 publications

(17 citation statements)

References 4 publications

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“…(4), 10) (Ϫ)-zuonin-A (5), 11) (ϩ)-acuminatin (6), 12) (Ϫ)-galbacin (7), 13,14) (Ϫ)-galbelgin (8), 15,16) (Ϯ)-galgravin (9), (ϩ)-veraguensin (10), [17][18][19] machilin F (11), 20) (Ϫ)machilusin (12), 21,22) L-tryptophan, pellitorineϭN-(2-methylpropyl)-2E,4E,(9C1)-2,4-decadienamide, elemicin, 1,2,4-trimethoxyphenyl-5-aldehyde, and phytol from the aerial parts of P. futokadsura. In this study, the structural elucidation of the new compounds, futokadsurin A (1), B (2), and C (3), and complete 13 C-and 1 H-NMR assignments of other neolignans were carried out using 1 H-1 H correlation spectroscopy ( 1 H-1 H COSY), heteronuclear single-quantum coherence (HSQC), 1 H-detected heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOESY) experiments.…”

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confidence: 99%

Neolignans from Piper futokadsura and Their Inhibition of Nitric Oxide Production

Konishi

Konoshima

Daikonya

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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From a MeOH extract of the aerial part of Piper futokadsura, the tetrahydrofuran lignans, futokadsurin A [(7S,8S,7'S,8'R)-3,4,3'-trimethoxy-4'-hydroxy-7,7'-epoxylignan], futokadsurin B [(7R,8R,7'R,8'S)-3,4-dimethoxy-3',4'-methylenedioxy-7,7'-epoxylignan], and futokadsurin C [(7R,8R,7'S,8'S)-3,4-methylenedioxy-3',4'-dimethoxy-7,7'-epoxylignan] were isolated, together with nine known neolignans. In addition, L-tryptophan, pellitorine, phytol, elemicin, and 1,2,4-trimethoxyphenyl-5-aldehyde were isolated. The structures of the new compounds were elucidated using spectroscopic methods. These lignans inhibited nitric oxide production by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide and interferon-gamma.

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confidence: 99%

Neolignans from Piper futokadsura and Their Inhibition of Nitric Oxide Production

Konishi

Konoshima

Daikonya

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Dinitrohelianthoidin [21] aromatische Restfraktion befinden sich neben dem bisher seltener in der Natur aufgefundenen R-Nerolidol [17] sowie dem Neolignan (-)-Galbacin [18] weitere Kauran-Derivate: (-)-16a, 17-Epoxykauran [4,19] und (-)-Kaur-16-en-18-oI [11]. (-)-Kaur-15-en-17-ol, das bisher nur partialsynthetisch erhalten wurde [4,20], Rückstand orange-braune, viskose FlUssigkeit.…”

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Inhaltsstoffe vonAristolochia triangularis*

Rüċker¹,

Langmann²,

Siqueira³

1981

Planta Med

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The roots and stems of Aristolochia triangularis Chamisso, a woody climber growing in Brasil, contain fatty acids as well as (-)-kaur-16-en-18-acid, but no aristolochic acids. The following stigmastane type triterpenes have been isolated: stigmast-4-en-3-on, stigmastan-3,6-dion and stigmast -4-en-3,6-dion as well as kaurane diterpenes: (-)-kaur-16-en, (-), kaur-16-en-18-al, (-)-kauran-16alpha-ol-18-al, (-)-16alpha, 17-epoxykauran, (-)-kaur- 16 - en-18-ol and (-)-kaur-15-en-17-ol. In addition sesquiterpenes have been found: (-)-alpha-ylangen, (-)-alpha-copaen, (E)-beta-elemen, gamma-elemen, (E)-(R)-Nerolidol. The lignanes isolated from A. TRIANGULARIS include cubebin, found so far only in Piper cubeba, and galbacin. The new lignans 3,4-dimethoxy-3,4-desmethylendioxycubebin and 3',4'-dimethoxy-3',4'-desmethylendioxycubebin have been identified. For better interpretation of the (1)H-NMR-spectra in relation to the stereochemistry, the 6,6'-dinitro derivates are suitable.

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“…M. japonica is an evergreen tree with yellow-green flowers and oval leaves. A few studies on the chemical composition of this plant have resulted in the identification of lignans [ 2 ] and terpene compounds [ 3 ]. In addition, the biological activities of M. japonica extracts such as insecticidal activity [ 4 ], elastase inhibition activity [ 5 ], and inhibition of matrix metalloproteinase-9 activity [ 6 ] have been investigated; however, all of these activities have been identified from extracts of M. japonica leaves.…”

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confidence: 99%

Flavonoids from Machilus japonica Stems and Their Inhibitory Effects on LDL Oxidation

Joo¹,

Park

et al. 2014

IJMS

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Stems of Machilus japonica were extracted with 80% aqueous methanol (MeOH) and the concentrated extract was successively extracted with ethyl acetate (EtOAc), normal butanol (n-BuOH), and water. Six flavonoids were isolated from the EtOAc fraction: (+)-taxifolin, afzelin, (−)-epicatechin, 5,3'-di-O-methyl-(−)-epicatechin, 5,7,3'-tri-O-methyl-(−)-epicatechin, and 5,7-di-O-methyl-3',4'-methylenedioxyflavan-3-ol. The chemical structures were identified using spectroscopic data including NMR, mass spectrometry and infrared spectroscopy. This is the first report of isolation of these six compounds from M. japonica. The compounds were evaluated for their diphenyl picryl hydrazinyl scavenging activity and inhibitory effects on low-density lipoprotein oxidation. Compounds 1 and 3–6 exhibited DPPH antioxidant activity equivalent with that of ascorbic acid, with half maximal inhibitory concentration (IC50) values of 0.16, 0.21, 0.17, 0.15 and 0.07 mM, respectively. The activity of compound 1 was similar to the positive control butylated hydroxytoluene, which had an IC50 value of 1.9 µM, while compounds 3 and 5 showed little activity. Compounds 1, 3, and 5 exhibited LDL antioxidant activity with IC50 values of 2.8, 7.1, and 4.6 µM, respectively.

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Studies on Lignoids in Lauraceae. II. Studies on Lignans in the Leaves of Machilus Japonica Sieb. et Zucc.

Abstract: From the leaves of Machilus japonica Sieb. et Zucc., four lignans were isolated; they have been found to be (+)-galbacin [1], (+)-galbelgin [2], (−)-licarin-B [4], and a new lignan, machilusin, whose structure can be described as [3a] or [3b].

Cited by 31 publications

References 4 publications

Neolignans from Piper futokadsura and Their Inhibition of Nitric Oxide Production

Neolignans from Piper futokadsura and Their Inhibition of Nitric Oxide Production

Inhaltsstoffe vonAristolochia triangularis*

Flavonoids from Machilus japonica Stems and Their Inhibitory Effects on LDL Oxidation

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