Bioactive composition of Reevesia formosana root and stem with cytotoxic activity potential

Chang, Hsueh‐Wei; Lin, Chih‐Wei; Hsiao, Pei-Yu; Peng, Hung-Ti; Lee, Shiow‐Ju; Cheng, Ming‐Jen; Chen, Ih-Sheng

doi:10.1039/c7ra04255h

Cited by 6 publications

(12 citation statements)

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“…The known compounds lincomolide A ( 3 ) [ 24 ], linderanolide B ( 4 ) [ 25 ], isolinderanolide B ( 5 ) [ 25 ], isophilippinolide A ( 6 ) [ 26 ], secosubamolide ( 7 ) [ 27 ], reticuol ( 8 ) [ 28 ], burmanol ( 9 ) [ 29 ], (−)-5,7-dimethoxy-3′,4′-methylenedioxy-flavan-3-ol ( 10 ) [ 30 ], taxifolin ( 11 ) [ 31 ], (−)-yangambin ( 12 ) [ 32 ], (−)-pinoresinol ( 13 ) [ 33 ], (+)-monomethylpinoresinol ( 14 ) [ 34 ], (+)-syringaresinol ( 15 ) [ 33 ], erythro -guaiacylglycerol- β - O -4′-(5′)-methoxylariciresinol ( 16 ) [ 35 ], caryolane-1,9 β -diol ( 17 ) [ 36 ], β -sitosterol ( 18 ) [ 37 ], and cinnamtannin B1 ( 19 ) [ 38 ] were identified by comparisons of physical and spectroscopic data ([α] D , UV, IR, 1 H NMR, and MS) with authentic samples or literature data. Among them, cinnamtannin B1 ( 19 ) (3.6 g) was obtained as the major constituent.…”

Section: Resultsmentioning

confidence: 99%

“…[31], (−)-yangambin(12) [32], (−)-pinoresinol(13) [33], (+)-monomethylpinoresinol(14) [34], (+)-syringaresinol (15)[33], erythro-guaiacylglycerol-β-O-4 -(5 )-methoxylariciresinol (16)[35], caryolane-1,9β-diol (17)[36], β-sitosterol (18)[37], and cinnamtannin B1(19) [38] were identified by comparisons of physical and spectroscopic data ([α] D , UV, IR, 1 H NMR, and MS) with authentic samples or literature data. Among them, cinnamtannin B1(19) (3.6 g) was obtained as the major constituent.…”

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confidence: 99%

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Anti-Inflammatory and Antibacterial Activity Constituents from the Stem of Cinnamomum validinerve

Yang

Hwang

et al. 2020

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One new dibenzocycloheptene, validinol (1), and one butanolide firstly isolated from the natural source, validinolide (2), together with 17 known compounds were isolated from the stem of Cinnamomum validinerve. Among the isolates, lincomolide A (3), secosubamolide (7), and cinnamtannin B1 (19) exhibited potent inhibition on both superoxide anion generation (IC50 values of 2.98 ± 0.3 µM, 4.37 ± 0.38 µM, and 2.20 ± 0.3 µM, respectively) and elastase release (IC50 values of 3.96 ± 0.31 µM, 3.04 ± 0.23 µM, and 4.64 ± 0.71 µM, respectively) by human neutrophils. In addition, isophilippinolide A (6), secosubamolide (7), and cinnamtannin B1 (19) showed bacteriostatic effects against Propionibacterium acnes in in vitro study, with minimal inhibitory concentration (MIC) values at 16 μg/mL, 16 μg/mL, and 500 μg/mL, respectively. Further investigations using the in vivo ear P. acnes infection model showed that the intraperitoneal administration of the major component cinnamtannin B1 (19) reduced immune cell infiltration and pro-inflammatory cytokines TNF-α and IL-6 at the infection sites. The results demonstrated the potential of cinnamtannin B1 (19) for acne therapy. In summary, these results demonstrated the anti-inflammatory potentials of Formosan C. validinerve during bacterial infections.

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confidence: 99%

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Anti-Inflammatory and Antibacterial Activity Constituents from the Stem of Cinnamomum validinerve

Yang

Hwang

et al. 2020

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“…All of the proton signals were assigned to the corresponding carbons through direct 1 H and 13 C correlations in the HSQC spectrum. The spectroscopic data of 1 were closely related to those of reevesiacoumarin [ 18 ], a known lignanoid with a coumarinolignan skeleton, which was previously isolated from the root and stem of Reevesia formosana (Malvaceae). The molecular formula of compound 1 was C 20 H 18 O 8 .…”

Section: Resultsmentioning

confidence: 88%

Coumarinolignans with Reactive Oxygen Species (ROS) and NF-κB Inhibitory Activities from the Roots of Waltheria indica

et al. 2022

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Seven new coumarinolignans, walthindicins A–F (1a, 1b, 2–5, 7), along with five known analogs (6, 8–11), were isolated from the roots of Waltheria indica. The structures of the new compounds are determined by detailed nuclear magnetic resonance (NMR), circular dichroism (CD) with extensive computational support, and mass spectroscopic data interpretation. Compounds were tested for their antioxidant activity in Human Cervical Cancer cells (HeLa cells). Compounds 1a and 6 showed higher reactive oxygen species (ROS) inhibitory activity at 20 μg/mL when compared with other natural compound-based antioxidants such as ascorbic acid. Considering the role of ROS in nuclear-factor kappa B (NF-κB) activation, compounds 1a and 6 were evaluated for NF-κB inhibitory activity and showed a concentration-dependent inhibition in Human Embryonic Kidney 293 cells (Luc-HEK-293).

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“…Monoclonal antibody of Na + /K + ‐ATPase β1 was purchased from Upstate (Upstate, Lake Placid, NY). Ascleposide (Figure A) was isolated from R. formosana and its structure as well as preliminary cytotoxicity in cancer cells were determined in the previous study …”

Section: Methodsmentioning

confidence: 99%

“…Ascleposide, a natural cardenolide isolated from Reevesia formosana , has been identified to display cytotoxic effect in several human cancer cell lines, including castration‐resistant prostate cancer (CRPC) DU‐145, non–small‐cell lung cancer NCI‐H460, hepatocellular carcinoma HepG2, and breast cancer MCF‐7 . However, its anticancer mechanism remains unclear.…”

Section: Introductionmentioning

confidence: 99%

Ascleposide, a natural cardenolide, induces anticancer signaling in human castration‐resistant prostatic cancer through Na⁺/K⁺‐ATPase internalization and tubulin acetylation

et al. 2020

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Background: Cardiac glycosides, which inhibit Na + /K + -ATPase, display inotropic effects for the treatment of congestive heart failure and cardiac arrhythmia. Recent studies have suggested signaling downstream of Na + /K + -ATPase action in the regulation of cell proliferation and apoptosis and have revealed the anticancer activity of cardiac glycosides. The study aims to characterize the anticancer potential of ascleposide, a natural cardenolide, and to uncover its primary target and underlying mechanism against human castration-resistant prostate cancer (CRPC).Methods: Cell proliferation was examined in CRPC PC-3 and DU-145 cells using sulforhodamine B assay, carboxyfluorescein succinimidyl ester staining assay and clonogenic examination. Flow cytometric analysis was used to detect the distribution of cell cycle phase, mitochondrial membrane potential, intracellular Na + and Ca 2+ levels, and reactive oxygen species production. Protein expression was examined using Western blot analysis. Endocytosis of Na + /K + -ATPase was determined using confocal immunofluorescence microscopic examination. Results: Ascleposide induced an increase of intracellular Na + and a potent antiproliferative effect. It also induced a decrease of G1 phase distribution while an increase in both G2/M and apoptotic sub-G1 phases, and downregulated several cell cycle regulator proteins, including cyclins, Cdk, p21, and p27 Cip/Kip proteins, Rb and c-Myc. Ascleposide decreased the expression of antiapoptotic Bcl-2 members (eg, Bcl-2 and Mcl-1) but upregulated proapoptotic member (eg, Bak), leading to a significant loss of mitochondrial membrane potential and activation of both caspase-9 and caspase-3. Ascleposide also dramatically induced tubulin acetylation, leading to inhibition of the catalytic activity of Na + /K + -ATPase. Notably, extracellular high K + (16 mM) significantly blunted ascleposide-mediated effects. Furthermore, ascleposide induced a p38 MAPK-dependent endocytosis of Na + /K + -ATPase and downregulated the protein expression of Na + /K + -ATPase α1 subunit. Wohn-Jenn Leu and Ching-Ting Wang equally contributed to this study. Conclusion: Ascleposide displays antiproliferative and apoptotic activities dependent on the inhibition of Na + /K + -ATPase pumping activity through p38 MAPK-mediated endocytosis of Na + /K + -ATPase and downregulation of α1 subunit, which in turn cause tubulin acetylation and cell cycle arrest. Cell apoptosis is ultimately triggered by the activation of caspase cascade attributed to mitochondrial damage through the downregulation of Bcl-2 and Mcl-1 protein expressions while upregulation of Bak protein levels. The data also suggest the potential of ascleposide in anti-CRPC development. K E Y W O R D S ascleposide, endocytosis, Na+/K+-ATPase α1-subunit, p38 MAPK, tubulin acetylation

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Bioactive composition of Reevesia formosana root and stem with cytotoxic activity potential

Abstract: Three lignanoids and three terpenoids, along with 40 known compounds were isolated from Reevesia formosana.

Cited by 6 publications

References 40 publications

Anti-Inflammatory and Antibacterial Activity Constituents from the Stem of Cinnamomum validinerve

Anti-Inflammatory and Antibacterial Activity Constituents from the Stem of Cinnamomum validinerve

Coumarinolignans with Reactive Oxygen Species (ROS) and NF-κB Inhibitory Activities from the Roots of Waltheria indica

Ascleposide, a natural cardenolide, induces anticancer signaling in human castration‐resistant prostatic cancer through Na⁺/K⁺‐ATPase internalization and tubulin acetylation

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Bioactive composition of Reevesia formosana root and stem with cytotoxic activity potential

Abstract: Three lignanoids and three terpenoids, along with 40 known compounds were isolated from Reevesia formosana.

Cited by 6 publications

References 40 publications

Anti-Inflammatory and Antibacterial Activity Constituents from the Stem of Cinnamomum validinerve

Anti-Inflammatory and Antibacterial Activity Constituents from the Stem of Cinnamomum validinerve

Coumarinolignans with Reactive Oxygen Species (ROS) and NF-κB Inhibitory Activities from the Roots of Waltheria indica

Ascleposide, a natural cardenolide, induces anticancer signaling in human castration‐resistant prostatic cancer through Na+/K+‐ATPase internalization and tubulin acetylation

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Ascleposide, a natural cardenolide, induces anticancer signaling in human castration‐resistant prostatic cancer through Na⁺/K⁺‐ATPase internalization and tubulin acetylation