Medicinal Foodstuffs. XIV. On the Bioactive Constituents of Moroheiya. (2): New Fatty Acids, Corchorifatty Acids A, B, C, D, E, and F, from the Leaves of Corchorus olitorius L. (Tiliaceae): Structures and Inhibitory Effect on NO Production in Mouse Peritoneal Macrophages.

Yoshikawa, Masayuki; Murakami, Toshiyuki; Shimada, Hiromi; Yoshizumi, Satoshi; Saka, M.; Yamahara, Johji; Matsuda, Hisashi

doi:10.1248/cpb.46.1008

Cited by 58 publications

(24 citation statements)

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“…27 3,6,8,9), two methines (H-5, 7), and three quaternary carbons (C-4, 10, 11). As shown in Figure 3, the 1 H-1 H COSY experiment indicated the presence of two partial structures (C-1-3 and C-5-9), and in the HMBC experiment, long-range correlations were observed between the following proton and carbon pairs (H-5 and C-4; H 2 -12 and C-7, 13; H 3 -13 and C-7, 11, 12; H 3 -14 and C-1, 5, 9, 10; H 3 -15 and C-3-5).…”

Section: Resultsmentioning

confidence: 99%

Structures of New Sesquiterpenes and Hepatoprotective Constituents from the Egyptian Herbal Medicine Cyperus longus

et al. 2004

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Six new sesquiterpenes, cyperusols A(1) (1), A(2) (2), B(1) (3), B(2) (4), C (5), and D (6), together with two monoterpenes and 13 sesquiterpenes were isolated from an Egyptian herbal medicine, the whole plants of Cyperus longus. The stereostructures of the new sesquiterpenes were determined on the basis of chemical and physicochemical evidence. In addition, the principal constituents were found to exhibit inhibitory activity on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.

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Section: Resultsmentioning

confidence: 99%

Structures of New Sesquiterpenes and Hepatoprotective Constituents from the Egyptian Herbal Medicine Cyperus longus

et al. 2004

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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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“…In the family of NOS, inducible NOS is specifically involved in the pathologic aspects with 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, endothelial cells, and smooth muscle cells. As a part of our studies to characterize the bioactive components of natural medicines, we reported various NO production inhibitors, i.e., higher unsaturated fatty acids, 28) poly-acetylenes, 2,29) coumarins, 2) flavonoids, 29,30) stilbenes, 31,32) lignans, 33,34) sesquiterpenes, [35][36][37][38][39][40][41] diterpenes, 42,43) triterpenes, [44][45][46][47] diarylheptanoids, 48,49) cyclic peptides, 46) and alkaloids. 50,51) As a continuation of these studies, the effects of the coumarin constituents from the flowers and leaves of A. furcijuga on NO production from LPS-activated macrophages were examined, and the results are summarized in Table 2.…”

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

confidence: 99%

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

et al. 2005

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The methanolic extract from the flowers of Angelica furcijuga KITAGAWA was found to inhibit nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages. From the methanolic extract, two new glycosides, hyuganosides IV and V, were isolated together with 28 known constituents. The structures of the new constituents were determined on the basis of chemical and physicochemical evidence. Furthermore, the inhibitory effects of 11 coumarin constituents on nitric oxide production were examined. Among them, 3-angeloyl-cis-khellactone (IC 50 ‫28؍‬ m mM), (S)-(؊)-oxypeucedanin (57 m mM), imperatorin (60 m mM), isoepoxypteryxin (53 m mM), and isopteryxin (8.8 m mM) showed inhibitory activity.

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Medicinal Foodstuffs. XIV. On the Bioactive Constituents of Moroheiya. (2): New Fatty Acids, Corchorifatty Acids A, B, C, D, E, and F, from the Leaves of Corchorus olitorius L. (Tiliaceae): Structures and Inhibitory Effect on NO Production in Mouse Peritoneal Macrophages.

Cited by 58 publications

References 0 publications

Structures of New Sesquiterpenes and Hepatoprotective Constituents from the Egyptian Herbal Medicine Cyperus longus

Structures of New Sesquiterpenes and Hepatoprotective Constituents from the Egyptian Herbal Medicine Cyperus longus

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

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

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