Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa1

Morikawa, Toshio; Pan, Yingni; Ninomiya, Kiyofumi; Imura, Katsuya; Matsuda, Hisashi; Yoshikawa, Masayuki; Yuan, Dan; Muraoka, Osamu

doi:10.1016/j.bmc.2010.01.047

Cited by 100 publications

(98 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In fact, several studies reported important activities for verbascoside, including antioxidant and free radical scavenging capacity, neuroprotective, hepatoprotective, analgesic, cytotoxic, antimicrobial, anti-inflammatory and beneficial effects on the cardiovascular system. Most of these activities are also ascribed to isoverbascoside (Fu, Pang, & Wong, 2008;Isacchi et al, 2011;Korkina, 2007;Kostyuk, Potapovich, Suhan, de Luca, & Korkina, 2011;Morikawa et al, 2010). Moreover, it is important to highlight that despite the presence of lower amounts of isoscutellarein derivatives as compared to those of phenylethanoid glycosides, these can also be key components on the ethnopharmacological effects of the plant.…”

Section: Quantification Of Phenolic Compounds In Peelmentioning

confidence: 99%

Phenolic constituents of Lamium album: Focus on isoscutellarein derivatives

Pereira

Domingues

Silva

et al. 2012

Food Research International

View full text Add to dashboard Cite

Lamium album L. is an edible plant which is consumed raw or cooked, in particular in the Mediterranean and surrounding areas. It is also consumed as tea infusions and as a main component of food supplements, because of its pharmacological effects. Despite being consumed by humans for centuries, the chemical composition of L. album L. is far from being understood. In this study, a purified ethanolic extract (PEEL) was prepared and further analyzed by high performance liquid chromatography and electrospray mass spectrometry. Overall, verbascoside accounted for approximately half of the phenolic content of the extract, but this also contained other bioactive phenolic compounds herein detected for the first time in the genus, namely isoscutellarein derivatives. The latter included isoscutellarein-7-O-allosyl(1 →2)glucoside, its O-methyl derivative, three acetyl derivatives of isoscutellarein-Oallosyl glucoside and one acetylated form of O-methylisoscutellarein-7-O-allosyl(1 →2)glucoside. From those, the main isoscutellarein derivative was assigned to isoscutellarein-7-O-(6-O-acetyl-β-allosyl)(1→2)-β-glucoside, as confirmed by NMR. Altogether, isoscutellarein derivatives accounted for almost 30% of PEEL phenolics. Since verbascoside and isoscutellarein derivatives are main components of L. album L. ethanolic extract, their possible association to the health benefits of the plant is discussed.

show abstract

Section: Quantification Of Phenolic Compounds In Peelmentioning

confidence: 99%

Phenolic constituents of Lamium album: Focus on isoscutellarein derivatives

Pereira

Domingues

Silva

et al. 2012

Food Research International

View full text Add to dashboard Cite

show abstract

“…Acid hydrolysis of 1 with 1.0 M hydrochloric acid (HCl) liberated D-glucose, which was identified by HPLC analysis using an optical rotation detector. [3][4][5][6] The 1 Hand 13 C-NMR spectra of 1 (CD 3 OD, Tables 1, 2), which were assigned by various NMR experiments, 19) showed signals assignable to four methylenes [ In the heteronuclear multiple-bond correlation (HMBC) experiment on 1, long-range correlations were observed between the following protons and carbons (1-H and 3-C, 8-C; 3-H and 1-C; 7-H and 8-C, 10-C; 9-H and 8-C; 10-H 2 and 7-C, 8-C; 1Ј-H and 1-C) as shown in Fig. 1.…”

mentioning

confidence: 99%

“…echinacoside, acteoside, and isoacteoside, etc.) 5) were also inhibited this cytotoxicity, we further examined iridoid, phenylpropanoid, and lignan constituents as shown in Table 4. As the result, kankanoside A (9, inhibition: 16.3Ϯ2.0% at 100 mM), mussaenosidic acid (10, 44. , were found to show significant activity.…”

mentioning

confidence: 99%

Iridoid and Acyclic Monoterpene Glycosides, Kankanosides L, M, N, O, and P from Cistanche tubulosa

et al. 2010

Self Cite

View full text Add to dashboard Cite

“…ex BAKER cultivated at Loei province, Thailand were purchased from a Thai traditional drug store in Nakhonsithammarat province, Thailand on Effects on D-GalN-Induced Cytotoxicity in Primary Cultured Mouse Hepatocytes The hepatoprotective effect of the constituents were determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay using primary cultured mouse hepatocytes. [48][49][50][51][53][54][55][56] Hepatocytes were isolated from male ddY mice (30-35 g) by collagenase perfusion method. A cell suspension at 4×10 4 cells in 100 μL William's E medium containing FCS (10%), penicillin G (100 units/mL), and streptomycin (100 μg/mL) was inoculated in a 96-well microplate and precultured for 4 h at 37°C under a 5% CO 2 atmosphere.…”

Section: Methodsmentioning

confidence: 99%

“…Consequently, 30,48-57) As a continuing exploratory study for hepatoprotective agents from medicinal plants, the constituents from the rhizomes of K. parviflora were examined. As shown in Table 4, 5,3′-dihydroxy-3,7,4'-trimethoxyflavone (14, IC 50 =18.4 μM) showed higher activity than silybin (38.8 μM), 49,50,[53][54][55][56] a commercial hepatoprotective agent as a positive control.…”

mentioning

confidence: 99%

Structures of Two New Phenolic Glycosides, Kaempferiaosides A and B, and Hepatoprotective Constituents from the Rhizomes of <i>Kaempferia parviflora</i>

et al. 2012

Self Cite

View full text Add to dashboard Cite

Two new phenolic glycosides, kaempferiaosides A and B were isolated from the rhizomes of Kaempferia parviflora (Zingiberaceae) together with 24 known compounds. Their structures including absolute stereochemistry were elucidated on the basis of chemical and spectroscopic evidence. Among the isolates, 5,3′-dihydroxy-3,7,4′-trimethoxyflavone showed higher activity than silybin, a commercial hepatoprotective agent.Key words Kaempferia parviflora; Zingiberaceae; kaempferiaoside; hepatoprotective activity; Krachai Dum A Zingiberaceae plant, Kaempferia parviflora WALL. ex BAKER, is widely distributed in Thailand and is known as Krachai Dum.1,2) The rhizomes of this plant are tinged with-dark purple to black, and have traditionally been used for the treatment of hypertension, [3][4][5] allergy, 6) gastrointestinal disorders, 7) and impotence. 8,9) The extract of the rhizomes of K. parviflora and its constituents were revealed to exhibit several pharmacological activities, such as antiplasmoidal, antifungal, 2) antiinflammatory, [10][11][12] α-glucosidase inhibitory, 13) and xanthine oxidase inhibitory 1) activities and cytotoxicity of several tumor cell lines 14,15) as well as effect of P-glycoprotein function 16) and modulation of multi-drug resistance in cancer cells. 17)Recently, rhizomes of K. parviflora powder was found to show preventive effect from obesity and its downstream symptoms. 18) By a previous chemical study on K. parviflora, presence of several methoxyflavones and related phenolic constituents have been revealed. 2,5,6,[10][11][12][13][14][15]17,[19][20][21][22] During the course of our characterization studies on Thai natural medicines, [23][24][25][26][27][28][29][30][31][32] two new phenolic glycosides named kaempferiaosides A (1) and B (2) were isolated from the rhizomes of K. parviflora together with 24 known compounds. This paper deals with the structure elucidation of 1 and 2, as well as hepatoprotective effect of the constituents from the rhizomes of K. parviflora on D-galactosamine (D-GalN)-induced cytotoxicity in primary cultured mouse hepatocytes.The dried rhizomes of K. parviflora cultivated at Loei province, Thailand were extracted with methanol to give a methanolic extract (7.10% from the dried rhizomes). The methanolic extract was partitioned into an EtOAc-H 2 O (1 : 1, v/v) mixture to furnish an EtOAc-soluble fraction (3.82%) and an aqueous phase. The aqueous phase was subjected to Diaion HP-20 column chromatography (H 2 O → MeOH) to give H 2 O-and MeOH-eluted fractions (2.04, 1.23%, respectively). As shown in Table 1, the EtOAc-soluble fraction and the MeOH-eluted fraction exhibited hepatoprotective activity, but the H 2 Oeluted fraction lacked the activity. The EtOAc-soluble fraction was subjected to normal-and reversed-phase column chromatographies, and finally HPLC to give 5-hydroxy-7-methoxyflavone 33) (3, 0.113%), 5,7-dimethoxyflavone rel-(5aS, 10bS)-5a,10b-dihydro-1,3,5a,9-tetrahydroxy-8-methoxy-6H-benz[b]

show abstract

Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa1

Cited by 100 publications

References 44 publications

Phenolic constituents of Lamium album: Focus on isoscutellarein derivatives

Phenolic constituents of Lamium album: Focus on isoscutellarein derivatives

Iridoid and Acyclic Monoterpene Glycosides, Kankanosides L, M, N, O, and P from Cistanche tubulosa

Structures of Two New Phenolic Glycosides, Kaempferiaosides A and B, and Hepatoprotective Constituents from the Rhizomes of <i>Kaempferia parviflora</i>

Contact Info

Product

Resources

About