Cycloartanes and other terpenoids and phenylpropanoids from Monocyclanthus vignei

Achenbach, Hans; Frey, Dieter

doi:10.1016/0031-9422(92)80456-o

Cited by 57 publications

(23 citation statements)

References 40 publications

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“…Surprisingly, some plants commonly used to treat malaria in other East-African countries were selected and collected during the present study, but mainly for other purposes (diseases) than malaria or symptoms associated with. This is the case for Hoslundia opposita which is used against malaria in Tanzania (Achenbach and Frey, 1992;Gessler et al, 1994), as well as Harrisonia abyssinica (Chhabra et al, 1993;Muthaura et al, 2007).…”

Section: Scientific Namementioning

confidence: 97%

Antiplasmodial and cytotoxic activities of medicinal plants traditionally used in the village of Kiohima, Uganda

Lacroix

Prado

Kamoga

et al. 2011

Journal of Ethnopharmacology

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Section: Scientific Namementioning

confidence: 97%

Antiplasmodial and cytotoxic activities of medicinal plants traditionally used in the village of Kiohima, Uganda

Lacroix

Prado

Kamoga

et al. 2011

Journal of Ethnopharmacology

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“…The structures of 1 and 2 were determined by spectroscopic analysis and verified by comparison with lit. values (Gensler et al, 1971;Achenbach and Frey, 1992). Elemicin (1) A solution of KMnO 4 (0.050 mmol) in deionized H 2 O (780 ll) was added to an ice-bath cooled solution of 1 (0.070 mmol) in EtOH/H 2 O (2:1) and stirred for 3 min.…”

Section: Isolation Of Plant Chemical Defenses (1-2)mentioning

confidence: 99%

Structure–activity relationship of chemical defenses from the freshwater plant Micranthemum umbrosum

Lane

Kubanek

2006

Phytochemistry

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“…According to biosynthetic origin, Me-18 of cycloartane-type triterpenes was constantly in β-orientation. [13][14][15][16] The NOE associations via a ROESY spectrum from ring to side chain protons could lead to erroneous configurational conclusions. Generally, H-17 and H-20 are biosynthetically in trans configuration for cycloartane-type triterpenes: H-17 was assigned to be α-orientated according to the ROESY correlation of H-17/ Me-30, H-20 was thus in β-orientation accordingly, consistent with those reported in the literature.…”

mentioning

confidence: 99%

“…Generally, H-17 and H-20 are biosynthetically in trans configuration for cycloartane-type triterpenes: H-17 was assigned to be α-orientated according to the ROESY correlation of H-17/ Me-30, H-20 was thus in β-orientation accordingly, consistent with those reported in the literature. [13][14][15][16] Therefore, the structure of 3 is established as 21-(E)-coumaroyloxy-5α-cycloart-24-ene-3,23-dione.…”

mentioning

confidence: 99%

Inhibitory Effect of Four Triterpenoids from <i>Trichilia connaroides</i> on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW264.7 Cells

Wang

Zhang

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Two new highly rearranged trichiliton-type limonoids (trichilitons G-H, 1-2), and two new cycloartane-type triterpenoids, 21-(E)-coumaroyloxy-5α-cycloart-24-ene-3,23-dione (3) and 21-(E)-feruloyloxy-5α-cycloart-24-ene-3,23-dione (4), were isolated from the stem and bark of Trichilia connaroides. These isolates were elucidated on the basis of detailed spectroscopic analysis, and inhibitory effect of these compounds on lipopolysaccharide-induced nitric oxide production in mouse macrophage RAW264.7 cells was evaluated.Key words Trichilia connaroides; Meliaceae; triterpenoid; nitric oxide production inhibition Trichilia connaroides (WIGHT et ARNOTT) BENTV (Meliaceae), has been used as folk medicine in China for treatment of arthritis, pharyngitis, tonsillitis, and other ailments. 1)Previous chemical investigations on the constituents of T. connaroides led to the discovery of many structurally diverse triterpenoids with complex ring systems, 2-7) which inspired a continuing interest of this plant. Searching for structurally unique and biologically interesting secondary metabolites, we investigated the dichloromethane extract of the stem and bark of this plant. As a result, two new highly rearranged trichiliton-type limonoids (trichilitons G-H, 1-2), and two new cycloartane-type triterpenoids, 21-(E)-coumaroyloxy-5α-cycloart-24-ene-3,23-dione (3) and 21-(E)-feruloyloxy-5α-cycloart-24-ene-3,23-dione (4) were isolated and identificated. Herein we described the isolation, structure elucidation of these compounds, and their inhibitory effects on lipopolysaccharide-induced nitric oxide production in mouse macrophage RAW264.7 cells. Results and DiscussionThe dichloromethane extract of the stem and bark of T. connaroides was chromatographed on MCI, silica gel, and octadecyl silica (ODS) and followed by semi-preparative HPLC to afford four new triterpenoids (1-4) (Fig. 1). The chemical structures of these compounds were determined on the basis of detailed spectroscopic analysis, including high resolutionelectrospray ionization-mass spectrum (HR-ESI-MS), one dimensional (1D)-and 2D-NMR experiments.

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Cycloartanes and other terpenoids and phenylpropanoids from Monocyclanthus vignei

Cited by 57 publications

References 40 publications

Antiplasmodial and cytotoxic activities of medicinal plants traditionally used in the village of Kiohima, Uganda

Antiplasmodial and cytotoxic activities of medicinal plants traditionally used in the village of Kiohima, Uganda

Structure–activity relationship of chemical defenses from the freshwater plant Micranthemum umbrosum

Inhibitory Effect of Four Triterpenoids from <i>Trichilia connaroides</i> on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW264.7 Cells

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