A New Unusual Iridoid with Inhibition of Activator Protein-1 (AP-1) from the Leaves of <i>Morinda citrifolia </i>L.

Sang, Shengmin; He, Kan; Zhu, Nanqun; Cheng, Xiaofang; Wang, Mingfu; Zheng, Qun Yi; Dong, Zigang; Ghai, Geetha; Rosén, Robert; Ho, Chi Tang

doi:10.1021/ol0156648

Cited by 27 publications

(15 citation statements)

References 13 publications

(17 reference statements)

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“…Of these phenolic compounds the most important reported are anthraquinones (Kamiya et al, 2005;Kim et al, 2005;Pawlus et al, 2005), flavonol glycosides (Sang et al, 2001), iridoid glycosides (Kamiya et al, 2005), Values are given as mean ± SD for groups of six rats in each. * Statistically significant at p \ 0.05.…”

Section: Weight In Gramsmentioning

confidence: 99%

“…* Statistically significant at p \ 0.05. Statistical significance was compared within the groups as follows: a Diabetic rats compared with control rats; b M. citrifolia-treated diabetic rats compared with diabetic rats; c Glyclazide-treated diabetic rats compared with diabetic control rats and triterpenoid (Sang et al, 2001). The main organic acids are caproic acid and caprylic acids (Dittmar, 1993), while the principle alkaloid is xeronine (Heinicke, 1995).…”

Section: Weight In Gramsmentioning

confidence: 99%

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Biochemical evaluation of antihyperglycemic and antioxidative effects of Morinda citrifolia fruit extract studied in streptozotocin-induced diabetic rats

Rao

Subramanian

2008

Med Chem Res

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The hypoglycemic and antioxidative effects of Morinda citrifolia fruit extract were evaluated in streptozotocin (STZ)-induced diabetic rats. The ethanolic extract of Morinda citrifolia fruit at a concentration of 300 mg/kg body weight/rat/ day was orally administered to STZ-induced diabetic rats for a period of 30 days. The elevated levels of blood glucose, glycosylated hemoglobin, blood urea, and serum creatinine in the diabetic rats reverted back to near normal after treatment with the noni fruit extract. Similarly significant decrease in the levels of plasma insulin and hemoglobin were elevated to near normal after treatment with fruit extract, suggesting the antihyperglycemic effect of Morinda citrifolia fruit. Determination of thiobarbituric acid reactive substance (TBARS), hydroperoxides, and both enzymatic and nonenzymatic antioxidants evidenced the antioxidative potential of the extract of noni fruit, which in turn may be responsible for its hypoglycemic potential. Alterations observed in the activities of pathophysiological enzymes such as serum aspartate transaminase (AST), serum alanine transaminase (ALT), and serum alkaline phosphatase (ALP) in the serum of control and experimental groups of rats revealed the tissue protective nature of Morinda citrifolia fruits, and the results of all the biochemical parameters analyzed were comparable with glyclazide, the standard reference drug.

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Section: Weight In Gramsmentioning

confidence: 99%

Section: Weight In Gramsmentioning

confidence: 99%

Biochemical evaluation of antihyperglycemic and antioxidative effects of Morinda citrifolia fruit extract studied in streptozotocin-induced diabetic rats

Rao

Subramanian

2008

Med Chem Res

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“…9) In studies of iridoids from M. citrifolia, asperuloside, 10) asperulosidic acid, 11) 6a-hydroxyadoxoside, 12) 6b,7b-epoxy-8-episplendoside, 12) borreriagenin, 12) citrifolinin B, 12) deacetylasperuloside 12) and dehydromethoxygaertneroside 12) were all isolated from the fruits, while citrifolinin A and citrifolinoside were isolated from the leaves. 13,14) The present paper describes the isolation and characterization of one new anthraquinone, 5,15-dimethylmorindol (1), together with five known anthraquinones, alizarin-1-methylether (2), 15) anthragallol-1,3-dimethylether (3), 16) anthragallol-2-methylether (4), 17) 6-hydroxy-anthragallol-1,3-dimethylether (5) 18) and morindone-5-methylether (6), 19) and one new iridoid, morindacin (7), together with two known iridoids, asuperlosidic acid (8) 20) and deacetylasperulosidic acid (9). (Fig.…”

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confidence: 99%

New Anthraquinone and Iridoid from the Fruits of Morinda citrifolia

et al. 2005

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Morinda citrifolia L. (Rubiaceae), known as "noni", is a small tree that grows widely across Polynesia. The roots, barks, stems, leaves and fruits have been used traditionally as a folk medicine for the treatment of many diseases 1) including diabetes, hypertension 2) and cancer.3) Furthermore, today "noni juice", which is made from the fruits of this plant, is widely drunk for the purported prevention of lifestyle-related diseases such as diabetes, hypertension, cardiopathy and cerebral apoplexy caused by arteriosclerosis. In our previous study of the bioactive constituents of M. citrifolia fruits for the prevention of arteriosclerosis, six lignans were isolated as active components.4) The rubiaceous plant is well-known for its anthraquinone and iridoid constituents. In earlier studies of anthraquinones from M. citrifolia, morenone-1, morenone-2, nordamnacanthal, morindone, rubiadin, rubiadin-1-methyl ether and 7-hydroxy-8-methoxy-2-methylanthraquinone were identified in the root. 9) In studies of iridoids from M. citrifolia, asperuloside, 10) asperulosidic acid, 11) 6a-hydroxyadoxoside, 12) 6b,7b-epoxy-8-episplendoside, 12) borreriagenin, 12) citrifolinin B, 12) deacetylasperuloside 12) and dehydromethoxygaertneroside 12) were all isolated from the fruits, while citrifolinin A and citrifolinoside were isolated from the leaves. 13,14) The present paper describes the isolation and characterization of one new anthraquinone, 5,15-dimethylmorindol (1), together with five known anthraquinones, alizarin-1-methylether (2), 15) anthragallol-1,3-dimethylether (3), 16) anthragallol-2-methylether (4), 17) 6-hydroxy-anthragallol-1,3-dimethylether (5) 18) and morindone-5-methylether (6), 19) and one new iridoid, morindacin (7), together with two known iridoids, asuperlosidic acid (8) 20) and deacetylasperulosidic acid (9). (Fig. 2). From the above results, compound 1 was characterized as 1,6-dihydroxy-5-methoxy-2-methoxymethylanthraquinone. This compound was named as 5,15-O-dimethylmorindol, as it is the 5,15-dimethylether of morindone 15-alcohol.Compound 7, a colorless syrup, gave a molecular formula of C 10 H 14 O 5 by HR-FAB-MS. The IR spectrum of 7 indicated absorption bands due to hydroxyl and lactone functions at 3400 cm Ϫ1 and 1743 cm .27 (C-6)]. The connectivities of the quaternary carbons (C-3, C-8) were deduced by a HMBC experiment (Fig. 3). In the HMBC spectrum, one quaternary carbon signal at H COSY spectra, the planar structure was established. Furthermore, the relative stereostructure of 7 was characterized on the basis of a NOESY From the fruits of Morinda citrifolia L., one new anthraquinone, 5,15-O-dimethylmorindol, together with five known anthraquinones and one new iridoid, morindacin, together with two known iridoids, were isolated. Their structures were elucidated by analysis of spectroscopic data.

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“…Iridoids compose a class of natural compounds which have various biological activities such as antiviral [2], anti-allergic, anti-anaphylactic, analgesic [3], antioxidant [4,5], antimicrobial, antirheumatic, laxative, hypotensive, sedative, antitumor [2,6], immunostimulant [7,9], antimicrobial [10,11] and hepatotoxic [13][14][15]. Others show radical scavenging activity against DPPH, antioxidant activity against β-carotene [12] and significant inhibition of UVB-induced: Activator Protein-1 activity in cell culture [16,17].…”

Section: Introductionmentioning

confidence: 99%

Studies of Trans- and Cis-Xylomollin Molecular Structures Using Molecular Dynamics Simulations

Mahboub

2013

ILCPA

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The present work describes the comparative study of the trans-and the cis-xylomollin structures. We have determined the two bridgehead H 5 and H 9 configurations using simulation calculations for both trans-and cis-distereoisomers. Molecular Dynamic (MD) simulations of the trans-and cis-xylomollin were performed with an efficient program. The geometries, interaction energies, bonds, angles, and the Van der Waals (VDW) interactions were carried out in solution and gas phases. This comparative study shows that the trans-xylomollin acquires the high configuration energy under the AMBER field using MD method. This molecule reaches its high stable configuration state in solution environment. Our MD simulation results are goods and in agreement with those of literature.

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A New Unusual Iridoid with Inhibition of Activator Protein-1 (AP-1) from the Leaves of Morinda citrifolia L.

Cited by 27 publications

References 13 publications

Biochemical evaluation of antihyperglycemic and antioxidative effects of Morinda citrifolia fruit extract studied in streptozotocin-induced diabetic rats

Biochemical evaluation of antihyperglycemic and antioxidative effects of Morinda citrifolia fruit extract studied in streptozotocin-induced diabetic rats

New Anthraquinone and Iridoid from the Fruits of Morinda citrifolia

Studies of Trans- and Cis-Xylomollin Molecular Structures Using Molecular Dynamics Simulations

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