Oplopanphesides A-C, Three New Phenolic Glycosides from the Root Barks of Oplopanax horridus

Huang, Wei‐Hua; Zhang, Qingwen; Meng, Lan‐Zhen; Yuan, Chun‐Su; Wang, Chong‐Zhi; Li, Shao‐Ping

doi:10.1248/cpb.59.676

Cited by 14 publications

(18 citation statements)

References 15 publications

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“…Their structures were elucidated by a combination of spectroscopic analyses. Five of them, specifically the two polyynes oplopantriols A and B (Huang et al, 2010) and the three phenolic glycosides, oplopanphesides A, B, and C, are novel compounds (Huang et al, 2011). …”

Section: Introductionmentioning

confidence: 99%

Identification of potential anticancer compounds from Oplopanax horridus

et al. 2013

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Oplopanax horridus is a plant native to North America. Previous reports have demonstrated that this herb has antiproliferative effects on cancer cells but study mostly focused on its extract or fractions. Because there has been limited phytochemical study on this herb, its bioactive compounds are largely unknown. We recently isolated and identified 13 compounds, including six polyynes, three sesquiterpenes, two triterpenoids, and two phenolic acids, of which five are novel compounds. In this study, we systemically evaluated the anticancer effects of compounds isolated from O. horridus. Their antiproliferative effects on a panel of human colorectal and breast cancer cells were determined using the MTS assay. Cell cycle distribution and apoptotic effects were analyzed by flow cytometry. The in vivo antitumor effect was examined using a xenograft tumor model. Among the 13 compounds, strong antiproliferative effects were observed from falcarindiol and a novel compound oplopantriol A. Falcarindiol showed the most potent antiproliferative effects, significantly inducing pro-apoptosis and cell cycle arrest in the S and G2/M phases. The anticancer potential of falcarindiol was further verified in vivo, significantly inhibiting HCT-116 tumor growth in an athymic nude mouse model at 15 mg/kg. We also analyzed the relationship between polyyne structures and their pharmacological activities. We observed that both the terminal hydroxyl group and double bond obviously affected their anticancer potential. Results from this study supplied valuable information for future semi-synthesis of polyyne derivatives to develop novel cancer chemopreventive agents.

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Section: Introductionmentioning

confidence: 99%

Identification of potential anticancer compounds from Oplopanax horridus

et al. 2013

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“…A detailed analysis of 1 H and 13 C NMR spectra of 1 (Table 1) and the literature suggested the presence of a bicyclic tropolone moiety with an isopropenyl group 8 and a 3-hydroxy-3-methylglutaric acid moiety with a C-6 connected glucose. 9 This was confirmed by the two-dimensional NMR experiments described below. Closer examination of HMBC connectivities to carbons 5, 9, 10, and 11 of the tropolone group and COSY connections between H-1 and H-2 and also H-3 and H-4 (Table 1, Figure 1) indicated the presence of a fused sixmembered ring system, for which the seven-spin system was assigned in the following manner.…”

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confidence: 60%

“…The 1 H NMR resonances at δ 2.74, 2.68, 2.63, and 1.34 and the 13 C NMR signals at δ 175.0, 172.5, 70.8, 46.3, 46.0, and 27.9 revealed the existence of a 3-hydroxy-3-methylglutaric acid moiety. 9,11 The HMBC spectrum (Table 1, Figure 1) was then employed to determine how the isopropenyl, fused cyclohexene-tropolone, glucose, and 3-hydroxy-3-methylglutaric acid groups were connected. Correlations from H-13a, H-13b, and CH 3 -14 to C-12 and C-2 confirmed that the isopropenyl group is linked to C-2 of the fused cyclohexene-tropolone unit.…”

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“…Their structures were confirmed by comparison to published spectroscopic data. 9,12 In 1980, the sesquiterpene manicol was isolated from the root bark of the Guyanan tree Dulacia guianensis (Olacaceae). 13 Originally a eudesmane-type structure was assigned to manicol, but on further degradation and derivatization experiments it was found to be inconsistent with the eudesmane skeleton.…”

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Sesquiterpenoid Tropolone Glycosides from Liriosma ovata

Pawar

Grundel

et al. 2015

J. Nat. Prod.

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Two new sesquiterpenoid tropolone glycosides, liriosmasides A (1) and B (2), along with two known compounds, secoxyloganin and oplopanpheside C, were isolated from a methanol extract of the roots of Liriosma ovata. The structures of 1 and 2 were elucidated by spectroscopic methods including 1D and 2D NMR and by high-resolution mass spectrometry involving an ultra-high-performance liquid chromatography-quadrupole-orbital ion trap mass spectrometric (UHPLC-Q-Orbitrap MS) method. Compound 1 showed weak inhibitory activity against HIV RNase H.

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“…Two lupane-type saponins, 3α-hydroxy-lup-20(29)-ene-23, 28-dioic acid-3-O-β-D-glucopyranoside, and 24-nor-3-oxo-lup-20(29)-en-28-oic acid-28-O-α-L-rhamnopyranosyl(1'”→4”)-β-D-glucopyranosyl(1”→6')-β-D-glucopyranoside, as well as a lupane aglycon 3α-hydroxy-lup-20(29)-ene-23,28-dioic acid were isolated from the leaves of OH [13]. Three phenolic glycosides, oplopanphesides A - C were isolated from the root bark of OH [22]. Other isolated and identified compounds include two sesquiterpenes, neroplomacrol and neroplofurol, together with a lignan compound, sesamin from the stem bark of OH [18], and a polyene compound nerolidol from the root bark of OH [19].…”

Section: Chemical Studiesmentioning

confidence: 99%

Chemical and pharmacological studies of Oplopanax horridus, a North American botanical

Calway

Wang

et al. 2011

J Nat Med

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Oplopanax horridus (OH) or Devil's club is an ethnobotanical used by the indigenous people native to the Pacific Northwest. There are three species in the genus Oplopanax, and OH is the only species that is distributed in North America. Compared with the extensive research on OH's “cousin,” American ginseng, there is comparatively little about the chemical makeup and pharmacological effects of OH. Nevertheless, there has been some research over the past few years that shows promise for future usage perspectives of OH. To date, seventeen compounds were isolated and elucidated including polyynes, glycosides, lignans, and polyenes, with most of the attention being paid to the polyynes. GC and HPLC were used to determine the contents of volatile compounds and polyynes in the essential oil and extracts of OH. For the pharmacological studies, antibacterial and anti-diabetes effects of polyynes were reported. Our recent study has focused more on the anticancer effects of OH and the involved mechanisms of action. In this review, we will summarize the research status in the botany, phytochemistry and pharmacology of OH.

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Oplopanphesides A-C, Three New Phenolic Glycosides from the Root Barks of Oplopanax horridus

Cited by 14 publications

References 15 publications

Identification of potential anticancer compounds from Oplopanax horridus

Identification of potential anticancer compounds from Oplopanax horridus

Sesquiterpenoid Tropolone Glycosides from Liriosma ovata

Chemical and pharmacological studies of Oplopanax horridus, a North American botanical

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