Inhibitors of Nitric Oxide Production from the Flowers of Angelica furcijuga: Structures of Hyuganosides IV and V

Matsuda, Hisashi; Morikawa, Toshio; Ohgushi, Teruki; Ishiwada, Tomoko; Nishida, Norihisa; Yoshikawa, Masayuki

doi:10.1248/cpb.53.387

Cited by 29 publications

(13 citation statements)

References 46 publications

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“…This compound was isolated previously from Angelica furcijuga [20] but described here for the first time in the genus Duguetia . The 1D and 2D NMR spectra were also used to assign unambiguously the 1 H and 13 C chemical shifts (Table 4).…”

Section: Resultsmentioning

confidence: 95%

Antinociceptive Activity of Ethanol Extract fromDuguetia chrysocarpaMaas (Annonaceae)

Almeida

Araújo

Ribeiro

et al. 2012

The Scientific World Journal

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The ethanol extract from the fruits of Duguetia chrysocarpa was evaluated for its antinociceptive activity in chemical and thermal models of nociception in mice. The intraperitoneal administration of the ethanol extract (100, 200, and 400 mg/kg body weight) showed a dose-dependent inhibition of acetic-acid-induced abdominal writhes. The extract also produced a significant inhibition of both phases of the formalin test in all doses tested and increased the reaction time in hot-plate test at dose of 200 mg/kg. The data obtained suggest that the antinociceptive effect of the extract may be mediated via both peripheral and central mechanisms. The phytochemical investigation yielded the isolation of the benzenoid derivative 3-methoxy-4-ethoxy benzoic acid which is being reported for the first time in this genus.

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Section: Resultsmentioning

confidence: 95%

Antinociceptive Activity of Ethanol Extract fromDuguetia chrysocarpaMaas (Annonaceae)

Almeida

Araújo

Ribeiro

et al. 2012

The Scientific World Journal

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“…The same can be noted for trace component 40 , which is defined as khellactone O -hexoside due to lack of more information. The presence of khellactone glucosides has not been established previously for the genus Phlojodicarpus , however, their presence has been shown in the species Angelica [40] and Peucedanum [41].…”

Section: Resultsmentioning

confidence: 99%

Khellactone Derivatives and Other Phenolics of Phlojodicarpus sibiricus (Apiaceae): HPLC-DAD-ESI-QQQ-MS/MS and HPLC-UV Profile, and Antiobesity Potential of Dihydrosamidin

et al. 2019

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With obesity, the consumption of phenolic-enriched food additives as a part of traditional nutrition avoids the negative implications of eating high-calorie products. This study investigated the new herbal food additive, Phlojodicarpus sibiricus roots and herb, ubiquitously used in Siberia as a spice. Chromatographic techniques such as HPLC-DAD-ESI-QQQ-MS/MS and microcolumn HPLC-UV were the basic instruments for component profiling and quantification, and antiobesity potential was investigated using a differentiated 3T3-L1 adipocytes assay. We found that the roots and herb of P. sibiricus were high-coumarin-containing additives inhibiting triacylglycerol accumulation in 3T3-L1 preadipocytes. Forty-one phenolics were detected in P. sibiricus extracts, and 35 were coumarins, including 27 khellactone derivatives present as esters and glucosides. Total coumarin content varied from 36.16 mg/g of herb to 98.24 mg/g of roots, and from 0.32 mg/mL to 52.91 mg/mL in P. sibiricus preparations. Moreover, Siberian populations of P. sibiricus were characterised by a different HPLC-based coumarin profile. The most pronounced inhibiting effect on triacylglycerol accumulation in 3T3-L1 preadipocytes was shown for dihydrosamidin (khellactone 3′-O-isovaleroyl-4′-O-acetyl ester), which was more active than other khellactone esters and glucosides. The results demonstrated that if used as a food additive Phlojodicarpus sibiricus could be a source of bioactive coumarins of the khellactone group with high antiobesity potential.

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“…In the family of NOS, inducible NOS (iNOS) is specifically involved in pathologic aspects with the overproduction of NO and can be expressed in response to proinflammatory agents such as interleukin-1b, tumor necrosis factor-a, and LPS in various cell types including macrophages. As a part of our studies to characterize the bioactive components of natural medicines, we have investigated various NO production inhibitors, i.e., higher unsaturated fatty acids, 27) polyacetylenes, [28][29][30] coumarins, 28,30,31) flavonoids, 29,32) stilbenes, 33,34) lignans, [35][36][37] sesquiterpenes, [38][39][40][41][42][43][44][45] diterpenes, 46,47) triterpenes, [48][49][50][51] diarylheptanoids, [52][53][54] cyclic peptides, 50) alkaloids, 55,56) and phenylpropanoids. 5,6,37) Continuing of these studies, the effects of the principal constituents from E. expansa on NO production from LPS-activated macrophages were examined, and the results were summarized in Table 2.…”

Section: Inhibitory Effects On No Production In Lps-activated Mouse Pmentioning

confidence: 99%

Structures of New Flavonoids, Erycibenins D, E, and F, and NO Production Inhibitors from Erycibe expansa Originating in Thailand

Morikawa

Matsuda

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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The Convolvulaceae plant, Erycibe expansa, is widely distributed in the Southeast Asian countries and the stems of E. expansa have been used for the treatment of hepatitis, hepatic dysfunction, and hepatosis in Thailand traditional medicine.1) We have reported bioactive constituents from several natural medicines originating in Thailand such as Albizia myriophylla,2) Alpinia galanga, [3][4][5][6] Salacia chinensis, 7-9)Piper chaba, 10) and Thai Zedoary. 11) In the course of our characterization studies on the bioactive constituents from Thai natural medicines, we previously reported three new flavonoids, erycibenins A (4), B (5), and C (6), from the methanolic extract of the dried stems of E. expansa together with 17 constituents (7-23).1) As a continuing study of this natural medicine, we additionally isolated a new flavanol, erycibenin D (1), and two new flavans, erycibenins E (2) and F (3), together with 14 compounds. This paper deals with the isolation and stereostructure elucidation of three new flavonoids and the effects of principal constituents on lipopolysaccharide (LPS)-activated nitric oxide (NO) production in mouse peritoneal macrophages.The methanolic extract from the dried stems of E. expansa was partitioned into a mixture of ethyl acetate (EtOAc) and water to provide the EtOAc-soluble portion and H 2 O-soluble portion as previously described.1) The EtOAc-soluble portion was further subjected to silica gel and ODS column chromatographies and finally HPLC to give erycibenins D (1, 0.00009% from the natural medicine), E (2, 0.00026%), and F (3, 0.00027%) together with two flavans, 5,7-dimethoxy-4Ј-hydroxyflavan 12) (24, 0.00028%), 5,7,4Ј-trimethoxyfla- H COSY) experiment on 1 indicated the presence of three partial structures written in the bold lines (C-2-C-3, C-5-C-6, C-5Ј-C-6Ј) (Fig. 1). In the heteronuclear multiple bond correlations (HMBC) experiment of 1, long-range correlations were observed between the following proton and carbon pairs (H-2 and C-3, 4, 1Ј, 2Ј, 6Ј; H-3 and C-4; H-5 and C-4, 9; H-6 and C-7, 10; H-8 and C-7, 9, 10; H-2Ј and C-2, 4Ј; H-5Ј and C-3Ј; H-6Ј and C-2, 4Ј; 3Ј-OCH 3 and C-3Ј). Next, the relative stereostructure of 1 was elucidated using nuclear Overhauser enhancement spectroscopy (NOESY), which showed NOE correlations between the fol- A new flavanol, erycibenin D, and two new flavans, erycibenins E and F, were isolated from the stems of Erycibe expansa originating in Thailand. The structures of new flavonoids were elucidated on the basis of chemical and physicochemical evidence. In addition, the inhibitory activities of the isolated constituents from E. expansa on lipopolysaccharide-activated nitric oxide production in mouse peritoneal macrophages were examined. Among the principal constituents, two isoflavones, clycosin (IC 50 ‫31؍‬ m mM) and erythrinin B (18 m mM), and two rotenoids, deguelin (26 m mM) and rotenone (27 m mM), were found to show potent inhibitory activity.

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Inhibitors of Nitric Oxide Production from the Flowers of Angelica furcijuga: Structures of Hyuganosides IV and V

Cited by 29 publications

References 46 publications

Antinociceptive Activity of Ethanol Extract fromDuguetia chrysocarpaMaas (Annonaceae)

Antinociceptive Activity of Ethanol Extract fromDuguetia chrysocarpaMaas (Annonaceae)

Khellactone Derivatives and Other Phenolics of Phlojodicarpus sibiricus (Apiaceae): HPLC-DAD-ESI-QQQ-MS/MS and HPLC-UV Profile, and Antiobesity Potential of Dihydrosamidin

Structures of New Flavonoids, Erycibenins D, E, and F, and NO Production Inhibitors from Erycibe expansa Originating in Thailand

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