A New Diterpenoid Glucoside and Two New Diterpenoids from the Fruit of Vitex agnus-castus

Ono, M.; Eguchi, Koichi; Konoshita, Masatarou; Furusawa, Chisato; Sakamoto, Junich; Yasuda, Shin; Ikeda, Tsuyoshi; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro

doi:10.1248/cpb.59.392

Cited by 34 publications

(26 citation statements)

References 31 publications

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“…This shows their antioxidant potential effects. Previous studies have confirmed the antioxidant impacts of Met as well as Vit (Ono et al, 2011;Jamilian et al, 2017). Ono et al (2011) reiterate that this antioxidant impact of Vit plant has been attributed to the active component called flavonoid.…”

Section: Discussionmentioning

confidence: 71%

“…Previous studies have confirmed the antioxidant impacts of Met as well as Vit (Ono et al, 2011;Jamilian et al, 2017). Ono et al (2011) reiterate that this antioxidant impact of Vit plant has been attributed to the active component called flavonoid. The compound is portrayed by scholars to have scavenging effect on O -2 and H2O2 as well as NO radicals that are extremely effective in oxidative DNA damage.…”

Section: Discussionmentioning

confidence: 71%

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Therapeutic Potential of Metformin and Vitex Agnus-Castus In Alleviating Cardiac Damage Induced By Hyperandrogenism In Polycystic Ovary Female Rats

2017

Aust. J. Basic & Appl. Sci.

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To Cite This Article: Widad M. Al-Bishri Therapeutic potential of metformin and Vitex agnus-castus in alleviating cardiac damage induced by hyperandrogenism in polycystic ovary female rats Aust. J. Basic & Appl. Sci., 11(14): [129][130][131][132][133][134][135][136][137][138] 2017 This research was aimed at exploring the profound therapeutic impacts of metformin (Met) and Vitex agnus-castus fruit (Vit) on cardiovascular risk factors, which includes dyslipidaemia, hyperhomocysteinemia and hyperleptinemia as well as hypoadiponectinemia. Others are hyperprolactinemia as well as DNA oxidative damage. These factors are generated by hyperandrogenism in Poly-Cystic Ovarian Syndrome (PCOS) female rats. The task involved inducing PCOS in rats using an oral ingestion of letrozole of 1mg/kg once a day for twenty-one days. Rats, which were induced with PCOS, were treated orally with either Met of 70 mg/kg single dose or Vit fruit amounting to 500mg/kg daily for 21 days after PCO induction. The findings indicate that giving rats induced with PCOS Met or Vit significantly ameliorated the increases in hyperandrogenism markers, including androstendione, Dehydroepiandrosterone Sulfate (DHEAS) and total testosterone as well as free testosterone in comparison with PCOS untreated ones. The two agents did modulation of the reduction in the content of serum of apolipoprotein (apo) A. Additionally; they elevated total lipid as well as apo B of rats with PCOS. Furthermore, the findings showed Met or Vit significantly ameliorating the serum hyperhomocysteinemia, hyperleptinemia, hypoadiponectinemia and hyperprolactinemia. There was also the increase in 8-hydroxydeoxyguanosine (8-OHdG) in PCOS rats, when compared to PCOS untreated rats. It became evident that Met and Vit could modulate the increases in the serum cardiac damage markers such as troponine T and alkaline phosphatase (ALP) as well as lactate dehydrogenase (LDH) in the PCOS induced rats. Finally, it became clear through the findings that treating PCOS rats using Vit could yield more efficient results in modulation of most the studied markers compared to Met. Conclusion: Met or Vit can be used to reduce cardiovascular risk. This is as a result of Met and Vit effective showing the ability that they can modulate cardiovascular risk elements in the PCOS induced rats utilised. However; Vit proved to be more potent than Met as far as this therapy went and this explained why Vit fruit is used in managing PCOS related cardiovascular events.

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Section: Discussionmentioning

confidence: 71%

Section: Discussionmentioning

confidence: 71%

Therapeutic Potential of Metformin and Vitex Agnus-Castus In Alleviating Cardiac Damage Induced By Hyperandrogenism In Polycystic Ovary Female Rats

2017

Aust. J. Basic & Appl. Sci.

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“…4. This configuration was supported by some reports on isolation of constituents having the same configuration from congener plants [16][17][18][19]. Since a compound bearing a hemiacetal group generally shows an equilibrium between two stereoisomers, the epimeric ratio varies depending on the solvent and on the temperature [20].…”

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confidence: 65%

Identification of New Diterpenes as Putative Marker Compounds Distinguishing Agnus Castus Fruit (Chaste Tree) from Shrub Chaste Tree Fruit (Viticis Fructus)

et al. 2016

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Agnus Castus Fruit is defined in the European Pharmacopoeia as the dried ripe fruit of Vitex agnus-castus. In Europe it is used as a medicine targeting premenstrual syndrome and climacteric disorder. In Japan, Agnus Castus Fruit is becoming popular as a raw material for over-the-counter drugs and health food products, though its congenic species, Vitex rotundifolia and Vitex trifolia, have been used as Shrub Chaste Tree Fruit in traditional medicines. Therefore, it is important to discriminate these Vitex plants from the viewpoint of regulatory science. Here we tried to identify putative marker compounds that distinguish between Agnus Castus Fruit and Shrub Chaste Tree Fruit. We analyzed extracts of each crude drug by liquid chromatography?mass spectrometry, and performed differential analysis by comparison of each chromatogram to find one or more peaks characteristic of Agnus Castus Fruit. A peak was isolated and identified as an equilibrium mixture of new compounds named chastol (1) and epichastol (1a). The planar structures of 1 and 1a were determined spectroscopically. Their relative configurations were revealed by nuclear Overhauser effect spectroscopy and differential nuclear Overhauser effect-NMR data. Since avoiding contamination from closely related species is needed for the quality control of natural pharmaceuticals, this information will be valuable to establish a method for the quality control of both, Agnus Castus Fruit and Shrub Chaste Tree Fruit products.

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“…During the course of our studies on natural antioxidants from several plant resources, [17][18][19] the antioxidative properties of 9 was evaluated using superoxide anion (O 2 Ϫ ) radical scavenging assay, nitrogen oxide (NO) scavenging assay, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, hydrogen peroxide (H 2 O 2 ) scavenging assay, and metal chelating assay on ferrous ion. Due to the phenolic structure associated with 9, we speculated a potent antioxidant property of this molecule.…”

Section: Four New Iridoid Glucosides From Ajuga Reptansmentioning

confidence: 99%

Four New Iridoid Glucosides from Ajuga reptans

Ono

Furusawa

Ozono

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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NoteAjuga reptans L. (Labiatae) is native to Europe, and has been used as a traditional vulnerary.1) This plant has been reported to contain iridoids, 1,2) diterpenoids, [3][4][5][6][7] ecdysteroids, [8][9][10] and anthocyanins.11) The present paper describes the isolation and structural elucidation of four new iridoid glucosides (1-4) along with four known iridoid glucosides (5-8), one known diterpenoid glycoside (9), one known aliphatic alcohol glycoside (10), and three known ecdysteroids (11-13), as well as the antioxidative activities of 9.Dried whole plants of A. reptans were extracted with methanol (MeOH). This extract was successively subjected to Diaion HP20, silica gel, and Chromatorex octadecyl silica (ODS) column chromatography as well as HPLC using ODS to yield 13 compounds (1-13).Compounds 5-13 were identified as reptoside (5), 12) harpagide (6), 12) 6-epi-acetyl harpagide (7), 13) acetyl harpagide (8), 12) ajugaside A (9), 15) ajugalactone (11), 9) 20-hydroxyecdysone (12), 16) and 20-hydroxyecdysone 3-acetate (13), 16) respectively, based on their physical and spectral data ( Fig. 1).Compound 1, tentatively named ajureptaside A, was obtained as a syrup, and exhibited an [MϩNa] ϩ ion peak at m/z 477 in the positive-ion FAB-MS. (d 99.9, 74.6, 78.0, 71.8, 77.8, 63.0). These 1 H-and 13 C-NMR signals (Tables 1 and 2, respectively) were assigned with the aid of 1 H-1 H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond correlation (HMBC) spectra. The planar structure of 1, which was an iridoid glucopyranoside whose aglycone moiety (Agl) possessed three hydroxyl groups at C-4, C-5, and C-6, one methoxy group at C-3, and one acetoxy group at C-8, could be determined as illustrated in Fig. 2. The relative configurations at C-1, C-3, C-4, C-5, C-6, C-8, and C-9 of Agl were concluded to be S*, R*, R*, S*, R*, S*, and S*, respectively, on the basis of the nuclear Overhauser and exchange spectroscopy (NOESY) spectrum, in which key correlations were observed between H-1 of Agl and H 3 -10 of Agl; H-4 of Agl and H-6 of Agl; and H-4 of Agl and H 3 -10 of Agl, as shown in Fig. 3, and by analysis of the coupling constants (J H-1-H-9 0 Hz; J H-3-H-4 8.0 Hz) between H-1 and H-9; and H-3 and H-4 in the 1 H-NMR spectrum. Acidic hydrolysis of 1 gave D-glucose, which was confirmed by optical rotation using chiral detection in HPLC analysis, and the coupling constant of the signal due to the anomeric proton [d 4.73 (d, Jϭ8.0 Hz)] indicated the mode of glycosidic linkage of the glucopyranosyl group to be b. Consequently, the structure of 1 was concluded to be 8-Oacetyl-4b-hydroxy-3a-methoxy-dihydroharpagide. Four new iridoid glucosides were isolated from the whole plant of Ajuga reptans L. (Labiatae) along with four known iridoid glucosides, one known diterpenoid glycoside, one known aliphatic alcohol glycoside, and three known ecdysteroids. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. The diterpenoid gl...

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A New Diterpenoid Glucoside and Two New Diterpenoids from the Fruit of Vitex agnus-castus

Cited by 34 publications

References 31 publications

Therapeutic Potential of Metformin and Vitex Agnus-Castus In Alleviating Cardiac Damage Induced By Hyperandrogenism In Polycystic Ovary Female Rats

Therapeutic Potential of Metformin and Vitex Agnus-Castus In Alleviating Cardiac Damage Induced By Hyperandrogenism In Polycystic Ovary Female Rats

Identification of New Diterpenes as Putative Marker Compounds Distinguishing Agnus Castus Fruit (Chaste Tree) from Shrub Chaste Tree Fruit (Viticis Fructus)

Four New Iridoid Glucosides from Ajuga reptans

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