ChemInform Abstract: New Bisabolane Sesquiterpenes from the Rhizomes of Curcuma xanthorrhiza Roxb. and Their Inhibitory Effects on UVB‐Induced MMP‐1 Expression in Human Keratinocytes.

Park, Ji‐Hae; Jung, Ye‐Jin; Mohamed, Mohamed Antar Aziz; Lee, Tae Hoon; Lee, Chang‐Ho; Han, Dongil; Song, Myoung‐Chong; Kim, Jiyoung; Baek, Nam‐In

doi:10.1002/chin.201436193

Cited by 3 publications

(3 citation statements)

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“…The diversity of their structures is often beyond people’s imagination. In recent years, many new sesquiterpenoids were discovered and possessed a wide variety of bioactivities, such as antidiabetic and anti-inflammatory, anti-aging, antimelanogenesis, antineuroinflammatory, antivirus, antimicrobial, acetylcholinesterase inhibitory activity, , protein tyrosine phosphatase, antifouling, etc. Moreover, the relationships between the structure and bioactivities of sesquiterpenoids have been summarized in several reviews − and revealed that the α,β-unsaturated carbonyl structural groups, including α-methylene-γ-lactones, α,β-unsaturated cyclepentanone, etc., are the active functional groups, which could react as Michael acceptors with nucleophiles by Michael addition and display promising cytotoxity, such as bigelovin, ergolide, kaunial, germacranolide, eudesmane derivative, etc.…”

Section: Resultsmentioning

confidence: 99%

New Apoptosis-Inducing Sesquiterpenoids from the Mycelial Culture of Chinese Edible Fungus Pleurotus cystidiosus

Zheng

Pang

Wang

et al. 2015

J. Agric. Food Chem.

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Two new bisabolane-type sesquiterpenoids, pleuroton A (1) and pleuroton B (2), and three clitocybulol derivatives, clitocybulol D (3), clitocybulol E (4), and clitocybulol F (5), were obtained from the mycelial culture of edible fungus Pleurotus cystidiosus O. K. Mill by repeated column chromatography over RP-18, Sephadex LH-20, and silica gel. Their structures were determined according to nuclear magnetic resonance data, high-resolution electron impact mass spectrometry, and circular dichroism spectra. These new sesquiterpenoids exhibited significant cytotoxicity against two human prostate cancer DU-145 and C42B cells in the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The median inhibitory concentration (IC50) of compounds 1, 2, 3, 4, and 5 was 174, 28, 233, 162, and 179 nM, respectively, against the DU-145 cell and was 104, 52, 163, 120, and 119 nM, respectively, against the C42B cell. Especially, pleuroton B (2) exhibited the strongest cytotoxity among these sesquiterpenoids, which was confirmed by the colony formation assay. Furthermore, pleuroton B (2) could trigger the apoptosis of DU-145 cells through the detection of apoptosis cells using annexin V-FITC staining by flow cytometry, the observation of condensed nuclei in the apoptosis cells, and the western blot analysis for the expression of apoptosis-related proteins Bcl-2, Bak, and Bax. Analysis of structure-activity relationships of these sesquiterpenoids revealed that the unusual functional moiety of pleuroton B should contribute to its significant bioactivity. These results display the pharmacological potential of P. cystidiosus.

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Section: Resultsmentioning

confidence: 99%

New Apoptosis-Inducing Sesquiterpenoids from the Mycelial Culture of Chinese Edible Fungus Pleurotus cystidiosus

Zheng

Pang

Wang

et al. 2015

J. Agric. Food Chem.

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“…Organic and aqueous layers were concentrated to produce residues of the EtOAc fraction (CXE, 901 g), n-BuOH fraction (CXB, 40 g), and H 2 O fraction (CXW, 1.4 kg). Fraction CXE-7, which was obtained by SiO 2 column chromatography (CC) from the rhizome of C. xanthorrhiza (Park et al, 2014) [982 mg, elution volume/ total volume (V e /V t ) 0.24-0.26] was subjected to ODS CC (ϕ 3.5×9 cm) and eluted with MeOH-H 2 O (3:2→5:1, each 6 L) to yield 29 fractions (CXE-7-1 to CXE-7-29). Fraction CXE-7-15 (73 mg, V e /V t 0.19-0.30) was subjected to SiO 2 CC (ϕ 3×13 cm) and eluted with CHCl 3 -MeOH (20:1, 500 mL) to ultimately produce 12 fractions (CXE-7-5-1 to CXE-7-5-12) along with purified compound 1 [CXE-7-15-8, 8.4 mg, V e /V t 0.34-0.39, TLC (SiO 2 F 254 ) R f 0.52, CHCl 3 -MeOH=12:1].…”

Section: Introductionmentioning

confidence: 99%

Inhibition of NO production in LPS-stimulated RAW264.7 macrophage cells with curcuminoids and xanthorrhizol from the rhizome of Curcuma xanthorrhiza Roxb. and quantitative analysis using HPLC

Park

Jung

Shrestha

et al. 2014

J Korean Soc Appl Biol Chem

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Three diarylheptanoids, bisdemethoxycurcumin (1), curcumin (2), and demethoxycurcumin (3), two diarylpentanoids, 3,3'-bis(7,7'-hydroxy-6,6'-methoxyphenyl)-penta-(3E,2'E)-3,2'-dien-1-one (4) and 3,3'-bis(7,7'-hydroxy-6-methoxyphenyl)-penta-(3E,2'E)-3,2'-dien-1-one (5), and a bisabolane sesquiterpene, xanthorrhizol (6), were isolated from the rhizome of Curcuma xanthorrhiza through repeated column chromatography. Silica gel (SiO 2 ), octadecyl silica gel (ODS), and Sephadex LH-20 resins were used. Compounds were identified by spectroscopic methods, including nuclear magnetic resonance, mass spectrometry, and infrared spectroscopy. Compounds 1 (IC 50 : 8.21 µM), 2 (IC 50 : 10.01 µM), 3 (IC 50 : 4.86 µM), and 4 (IC 50 : 2.20 µM) inhibited nitric oxide production in LPS-stimulated RAW264.7 macrophage cells. High performance liquid chromatography was used to determine the content of curcuminoids and xanthorrhizol in C. xanthorrhiza extract to be 0.46±0.08% (1), 10.69±0.18% (2), 2.35±0.06% (3), 0.18±0.05% (4), 0.03±0.01% (5), and 27.47± 2.42% (6).

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“…Curcuminoids and bisabolane-type compounds have major pharmacological effects, including anti-cancer, antioxidant, and anti-inflammatory properties [3][4][5]. Continuing phytochemical studies on C. xanthorrhiza rhizome [6] led to isolation of guaiane sesquiterpenes. These are synthesized from E,E-farnesylpyrophosphate (FPP) by cyclization via a 10-membered ring sesquiterpene, germacrane, to form a bicyclo [5,3,0]decane ring system [7].…”

mentioning

confidence: 99%

Guaiane Sesquiterpenes from the Rhizome of Curcuma xanthorrhiza and Their Inhibitory Effects on UVB-induced MMP-1 Expression in Human Keratinocytes

Park

Mohamed

Thi

et al. 2017

Natural Product Communications

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A new guaiane sesquiterpene, (1R,4S,5S,10R)-10-methyl guaianediol (1), along with five known compounds, 10-methylalismoxide (2), (+)-alismoxide (3), isozedoarondiol (4), zedoarondiol (5), and zedoalactone B (6), were isolated from the rhizomes of Curcuma xanthorrhiza Roxb. Compounds 1-6 were isolated from this plant for the first time. Chemical structures were determined using nuclear magnetic resonance (NMR), electron ionization mass spectrometry (EI/MS), polarimetry, circular dichroism (CD), and infrared spectroscopy (IR). Compounds 3 and 4 decreased MMP-1 expression in UVB-treated human keratinocytes by about 8.9-fold and 7.6-fold at the mRNA level, and by about 9.2-fold and 6.6-fold at the protein level, respectively. Results indicate that the isolated compounds have anti-aging effects by inhibiting MMP-1 expression in skin cells.

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ChemInform Abstract: New Bisabolane Sesquiterpenes from the Rhizomes of Curcuma xanthorrhiza Roxb. and Their Inhibitory Effects on UVB‐Induced MMP‐1 Expression in Human Keratinocytes.

Cited by 3 publications

References 1 publication

New Apoptosis-Inducing Sesquiterpenoids from the Mycelial Culture of Chinese Edible Fungus Pleurotus cystidiosus

New Apoptosis-Inducing Sesquiterpenoids from the Mycelial Culture of Chinese Edible Fungus Pleurotus cystidiosus

Inhibition of NO production in LPS-stimulated RAW264.7 macrophage cells with curcuminoids and xanthorrhizol from the rhizome of Curcuma xanthorrhiza Roxb. and quantitative analysis using HPLC

Guaiane Sesquiterpenes from the Rhizome of Curcuma xanthorrhiza and Their Inhibitory Effects on UVB-induced MMP-1 Expression in Human Keratinocytes

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