24-nor-Ursane Type Triterpenoids from the Stems of Rumex japonicus

Jang, Dae Sik; Kim, Jong Min; Kim, Joohwan; Kim, Jin Sook

doi:10.1248/cpb.53.1594

Cited by 28 publications

(13 citation statements)

References 9 publications

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“…This assignment was in agreement with the EI-MS, which revealed three prominent ion fragments at m/z = 264 (C 16 H 24 O 3 ), 246 (264-H 2 O) and 201 (246-COOH) usually resulting from the typical retro-Diels-Alder cleavage of urs-12-enes with a C-17 carboxyl group and a hydroxyl group on ring D or E [12]. The relative trans-configuration of H-2 and H-3 protons in compound 1 was in agreement with the coupling constant (J = 8.5 Hz) between OH-2α and OH-3β compared to that observed in the case of OH-2α and OH-3α (J = 2.4 Hz) [12,13]. The trans-configuration was further supported by the cross peaks between H-3 and H-5, H-5 and H-9, H-9 and (Fig.…”

Section: Resultssupporting

confidence: 88%

“…The IR, 1 H and 13 C NMR spectra of 2 (Table 1) suggested the same skeleton as compound 1 [12]. The 1 H NMR spectrum also revealed the presence of an acetyl group by one additional methyl at δ = 2.02 ppm (s, CH 3 ), supported by signals in the 13 C NMR spectrum at δ = 21.1 (CH 3 ) and 170.3 ppm (C = O) [14].…”

Section: Resultsmentioning

confidence: 74%

“…2), correlations between H-1 (δ = 2.05 ppm) and C-2 (δ = 72.1 ppm), C-3 (δ = 78.2 ppm), C-5 (δ = 49.9 ppm) and C-25 (δ = 13.8 ppm), and between H-3 (δ = 3.75 ppm) and C-23 (δ = 103.8 ppm), C-1 (δ = 46.9 ppm), C-5 (δ = 49.9 ppm), C-2 (δ = 72.1 ppm) and C-4 (δ = 150.4 ppm) indicate the presence of one hydroxyl group at C-2 and the exocyclic methylene group at C-4 thereby confirming the absence of methyl-24 [12]. This assignment was in agreement with the EI-MS, which revealed three prominent ion fragments at m/z = 264 (C 16 H 24 O 3 ), 246 (264-H 2 O) and 201 (246-COOH) usually resulting from the typical retro-Diels-Alder cleavage of urs-12-enes with a C-17 carboxyl group and a hydroxyl group on ring D or E [12]. The relative trans-configuration of H-2 and H-3 protons in compound 1 was in agreement with the coupling constant (J = 8.5 Hz) between OH-2α and OH-3β compared to that observed in the case of OH-2α and OH-3α (J = 2.4 Hz) [12,13].…”

Section: Resultsmentioning

confidence: 81%

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Cytotoxic 24-nor-ursane-type triterpenoids from the twigs of Mostuea hirsuta

Ekon

Bissoue

Fomani

et al. 2015

Zeitschrift Für Naturforschung B

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2α,3β,,12-dien-28-oic acid (1) and 3β-acetoxy-2α,19α-dihydroxy-24-norurs-4(23),12-dien-28-oic acid (2), along with 15 known compounds were isolated from the methanol extract of the twigs of Mostuea hirsuta. While 2-hydroxymethylbenzamide (13) was isolated for the first time from the natural source, compounds 3-12 are reported here for the first time from the genus Mostuea. Their structures were elucidated by means of spectroscopic analyses including 1D-and 2D-NMR spectroscopy, high-resolution mass spectrometric data as well as comparison with data from the literature. Compounds 1, 2, 4-9 and 13 were tested against bacteria, fungi and plant pathogen oomycetes by the paper disk agar diffusion assay resulting in missing to low activities corresponding with minimum inhibitory concentrations (MICs) > 1 mg mL -1 . However, the respective compounds 1, 2, 8, 9 and 13 exhibited moderate cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3, with IC 50 10.6-16.5 μm compared to the standard doxorubicin with IC 50 0.9 μm.

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Section: Resultssupporting

confidence: 88%

Section: Resultsmentioning

confidence: 74%

Section: Resultsmentioning

confidence: 81%

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Cytotoxic 24-nor-ursane-type triterpenoids from the twigs of Mostuea hirsuta

Ekon

Bissoue

Fomani

et al. 2015

Zeitschrift Für Naturforschung B

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“…It has been extensively used for the treatment of constipation, heat phlegm, jaundice, skin disease and uterine hemorrhage in traditional medicine due to presence of anthraquinones, oxanthrones, and flavonoid metabolites (Zee et al 1998;Li et al 2000;Zhou et al 2005;Lee et al 2006;Guo et al 2011). Although, it has potential effects on antibacterial, anti-inflammatory, antioxidant and inhibitory activity against atopic dermatitis and skin disease (Zee et al 1998;Elzaawely et al 2005;Jang et al 2005;Zhou et al 2005;Lee et al 2006;Guo et al 2011;Xie and Yang 2014). Due to the unavailability of chloroplast (cp) information on this important medicinal plant, we sequenced and characterized the complete cp genome of Rumex japonicus Houtt.…”

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confidence: 99%

The complete plastome sequence of Rumex japonicus Houtt.: a medicinal plant

Raman

Cho

Park

2020

Mitochondrial DNA Part B

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Rumex japonicus is a medicinal plant distributed in East Asia. Here, we report and characterize the complete plastid genome sequence of R. japonicus and size is 159,292 bp in length and contains the typical structure and gene content of other angiosperm plastomes, including two inverted repeat regions of 30,629 bp, a large single-copy region of 85,028 bp and a small single-copy region of 13,006 bp. There are 112 unique genes, including 78 protein-coding, 30 tRNAs and 4 rRNAs. We constructed a phylogenetic tree with 14 species and the phylogenetic topologies showed that R. japonicus was closely related to Rheum wittrockii.

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“…양제근의 함유 성분에 대해서는 Jang 등이 줄기에 함유되 어 있는 24-nor-Ursane type triterpenoids를 보고한 바 있으며 3) , Jiang 등 (Fig. 5).…”

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Anti-inflammatory effect of Rumex japonicus HOUTT. in RAW 264.7 cells

Huh¹,

Cho²,

Park³

et al. 2012

The Korea Journal of Herbology

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Objectives : The aim of this study was to authenticate whether fractionated extract of Rumex japonicus HOUTT. (RJ) has anti-inflammatory effects in mouse macrophage, RAW264.7 cells. Methods : Roots of RJ were extracted by methanol for 48hours. The methanol that gained was filtered and freeze dried. The methanol extract was dissolved in water and dichloromethane (DCM). After that, two layers were separated. Ethyl acetate (EA) added to the water layer and separated again. All the layers were filtered and freeze dried and the extracts were tested. Cytotoxic activity of extracts on RAW 264.7 cells was measured using MTS assay. The nitric oxide (NO) production was measured and proinflammatory cytokines and PGE2 were measured by ELISA kit. The levels of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), I κ-B-α and nuclear NF-κB p65 expression were detected by western blot. Results : Our results indicated that DCM and EA extracts of RJ inhibited the LPS-induced NO, PGE2 production and iNOS, COX-2 expression accompanied by an attenuation of TNF-α, IL-1β and IL-6 production in RAW 264.7 cells most effectively. DCM and EA extracts also had suppression effects of LPS-induced NF-κB and MAPKs activation. Conclusions : This results demonstrate that fractionated extract of RJ has anti-inflammatory effects and among the fractioned extract, dichloromethane and ethyl acetate extract have best anti-inflammatory effects.

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24-nor-Ursane Type Triterpenoids from the Stems of Rumex japonicus

Cited by 28 publications

References 9 publications

Cytotoxic 24-nor-ursane-type triterpenoids from the twigs of Mostuea hirsuta

Cytotoxic 24-nor-ursane-type triterpenoids from the twigs of Mostuea hirsuta

The complete plastome sequence of Rumex japonicus Houtt.: a medicinal plant

Anti-inflammatory effect of Rumex japonicus HOUTT. in RAW 264.7 cells

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