New Glycosides from <i>Ajuga decumbens</i>

Takasaki, Midori; Yamauchi, Isao; Matsushita, Haruna; Konoshima, Takao

doi:10.1021/np980148k

Cited by 43 publications

(41 citation statements)

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“…The chemical structures of the compounds were identified as harpagide (1), 8-O-acetylharpagide (2) (Calis et al 1992), cis-melilotoside (3), trans-melilotoside (4) (Vasänge et al 1997), dihydromelilotoside (5) (Ranarivalo et al 1990) verbascoside (6) (Sticher and Lahloub 1982), galactosylmartynoside (7) (Takasaki et al 1998) and isoorientin (8) (Calis et al 2006) by comparison of their 1D and 2D NMR and MS data with those published previously. Table 1 displays the antiprotozoal activities of the isolated compounds from A. laxmannii.…”

Section: Resultsmentioning

confidence: 99%

“…Some of these species are consumed for the treatment of haemorrhoids and as a wound-healing agent in Anatolian folk medicine (Sezik et al 1992;Yesilada et al 1995). Previous phytochemical studies on Ajuga species have shown the presence of diterpenes, phytoecdysteroids, iridoids, sterol glycosides, flavonoids and phenylethanoid glycosides as the secondary metabolites of the genus (De la Torre et al 1997;Takasaki et al 1998;Akbay et al 2002Akbay et al , 2003Sadati et al 2012;Inomata et al 2013). There is only one report on A. laxmannii (L.) Bentham collected from Bulgaria stating the isolation of a diterpene, a coumarin, a phytoecdysteroid, two iridoid glycosides and an ocoumaric acid derivative (Malakov et al 1998).…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of in vitro antiprotozoal activity of Ajuga laxmannii and its secondary metabolites

Atay

Kırmızıbekmez

Kaiser

et al. 2016

Pharmaceutical Biology

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Context Some Ajuga L. (Lamiaceae) species are traditionally used for the treatment of malaria, as well as fever, which is a common symptom of many parasitic diseases. Objective In the continuation of our studies on the identification of antiprotozoal secondary metabolites of Turkish Lamiaceae species, we have investigated the aerial parts of Ajuga laxmannii. Materials and methods The aerial parts of A. laxmannii were extracted with MeOH. The H 2 O subextract was subjected to polyamide, C 18 -MPLC and SiO 2 CCs to yield eight metabolites. The structures of the isolates were elucidated by NMR spectroscopy and MS analyses. The extract, subextracts as well as the isolates were tested for their in vitro antiprotozoal activities against Plasmodium falciparum, Trypanasoma brucei rhodesiense, T. cruzi and Leishmania donovani at concentrations of 90-0.123 mg/mL. Results Two iridoid glycosides harpagide (1) and 8-O-acetylharpagide (2), three o-coumaric acid derivatives cis-melilotoside (3), trans-melilotoside (4) and dihydromelilotoside (5), two phenylethanoid glycosides verbascoside (6) and galactosylmartynoside (7) and a flavone-C-glycoside, isoorientin (8) were isolated. Many compounds showed moderate to good antiparasitic activity, with isoorientin (8) displaying the most significant antimalarial potential (an IC 50 value of 9.7 mg/mL). Discussion and conclusion This is the first report on the antiprotozoal evaluation of A. laxmannii extracts and isolates. Furthermore, isoorientin and dihydromelilotoside are being reported for the first time from the genus Ajuga.ARTICLE HISTORY

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Evaluation of in vitro antiprotozoal activity of Ajuga laxmannii and its secondary metabolites

Atay

Kırmızıbekmez

Kaiser

et al. 2016

Pharmaceutical Biology

View full text Add to dashboard Cite

show abstract

“…Six known compounds were isolated and determined by comparison of the physical data with those reported in the literature: Two iridoid glycosides, 8-O-acetylharpagide (6) [11] and 8-acetyl-6′-O-(p-coumaroyl) harpagide (7) [12], two phenethyl alcohol glycoside, galactosylmartynoside (8) [13] and 6‴-O-feruloylincanoside D (9) [14], an abietatriene-type diterpene glycoside, ajugaside A (10) [13], and a flavonoid luteolin 7-O-glucoside (11) [15], respectively. All compounds were tested for in vitro α-glucosidase inhibitory activity; compounds 4 and 10 possess α-glucosidase inhibitory effects with IC50 values of 0.377 mM and 0.328 mM, respectively.…”

Section: Introductionmentioning

confidence: 99%

New Iridoid Glucosides from Caryopteris incana (Thunb.) Miq. and Their α-Glucosidase Inhibitory Activities

et al. 2016

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Abstract:In our continued investigations of the plant Caryopteris incana, five new iridoid glucosides 1-5, including two cis-trans-isomers, 3 and 4, along with six known compounds 6-11, were isolated from the n-butyl alcohol (n-BuOH) soluble fraction of whole dried material of Caryopteris incana. Their structures were established by a combination of spectroscopic techniques, including 1D and 2D NMR and high resolution electrospray ionization mass spectroscopy (HR-ESI-MS). Furthermore, all isolates were evaluated for their yeast α-glucosidase inhibitory effects. Among these compounds, 4-8 and 10 exhibited potent inhibition of α-glucosidase.

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“…1,2) Many compounds have been isolated and identified from the whole plant, A. decumbens, [3][4][5][6][7] several of which show anti-tumor activity. 8) Recently, the number of cases of age related illnesses, e.g.…”

mentioning

confidence: 99%

Beneficial Effects of Ajuga decumbens on Osteoporosis and Arthritis

Ono¹,

Fukaya²,

Imai³

et al. 2008

Biological & Pharmaceutical Bulletin

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Ajuga decumbens is a naturally occurring herb in Japan and China. The whole flowering plant of A. decumbens has been used in treatment of hypertension, hemoptysis, carbuncles and joint pain, etc.1,2) Many compounds have been isolated and identified from the whole plant, A. decumbens, [3][4][5][6][7] several of which show anti-tumor activity. 8) Recently, the number of cases of age related illnesses, e.g. osteoporosis and osteoarthritis have been trending upwards. These illnesses seriously affect people's daily lives because bones and joints play an important role in supporting the body during everyday movement.Collagen is one of the important bone and joint composition, and decreases naturally with age. Calcium resorption is caused by this effect. It was reported that A. decumbens upregulates the synthesis of collagen in false aged model rats. 9)Accordingly, we focused on the effects of A. decumbens on bone and joint disease.Post-menopausal osteoporosis is a metabolic bone disease characterized by a decrease of bone mass after menopause. 10)Many factors contribute to the development and maintenance of skeletal mass before and after menopause. 11,12) In fact, bone mass is the end result of a dynamic and complex process called remodeling. This process is characterized by a balance between osteoclast bone resorption and osteoblast bone formation. Estrogen is one of the factors that regulates bone metabolism, therefore, estrogen depletion after menopause causes an imbalance between bone resorption and bone formation.11) In addition, it is reported that NO, synthesized by iNOS, is related to the imbalance between osteoclast bone resorption and osteoblast bone formation. [13][14][15] It is widely known that NO is involved in a diverse array of physiological processes. Furthermore, NO, especially synthesized by iNOS, is related to inflammatory diseases like osteoarthritis and rheumatoid arthritis.14,16) Based on this knowledge, we hypothesized that the inhibition or down-regulation of NO production by iNOS would provide a new form of treatment for the prevention of inflammatory bone diseases and bone metabolic disease. MATERIALS AND METHODS AnimalsEight to ten-week-old female ddY mice and eight-week-old male LEW/SsN rats were obtained from SLC (Shizuoka, Japan). The mice and rats were housed under a 12 h/12 h light/dark cycle in a temperature and humidity-controlled room. They were allowed food and water ad libitum. After a week to adapt to the lighting conditions, healthy animals were used in a variety of experiments. All experimental procedures were approved by the Committee for Ethics and Animal Experimentation, Matsuura Yakugyo Co., Ltd. Preparation of Plant ExtractsThe whole plant A. decumbens (200 g) was grown in China and a voucher specimen (HS050601) was placed in our laboratory. The dried A. decumbens was refluxed with 70% aqueous ethanol for 30 min. The alcoholic extract was then concentrated to 50 g. The concentrate was freeze-dried, finally producing 20 g (i.e., 10% yield) of a dark brown, A. decumbens extr...

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New Glycosides from Ajuga decumbens

Cited by 43 publications

References 18 publications

Evaluation of in vitro antiprotozoal activity of Ajuga laxmannii and its secondary metabolites

Evaluation of in vitro antiprotozoal activity of Ajuga laxmannii and its secondary metabolites

New Iridoid Glucosides from Caryopteris incana (Thunb.) Miq. and Their α-Glucosidase Inhibitory Activities

Beneficial Effects of Ajuga decumbens on Osteoporosis and Arthritis

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