Structure–activity relationships of benzhydrol derivatives based on 1′-acetoxychavicol acetate (ACA) and their inhibitory activities on multiple myeloma cell growth via inactivation of the NF-κB pathway

Misawa, Takashi; Dodo, Kosuke; Ishikawa, Minoru; Hashimoto, Yuichi; Sagawa, M.; Kizaki, Masahiro; Aoyama, Hiroshi

doi:10.1016/j.bmc.2015.02.039

Cited by 7 publications

(5 citation statements)

References 16 publications

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“…Furthermore, previous studies showed that ACA and AEA suppressed the growth of cancer cells by inhibiting nuclear factor-κB (NF-κB) pathway. 19 , 41 – 43 The expression of the anti-apoptotic proteins, such as Bcl-2 44 and Bcl-xL, 45 was regulated by NF-κB. Hence, the induction of apoptosis by ACA, AEA, and AMCA may also be linked to the inactivation of the NF-κB.…”

Section: Discussionmentioning

confidence: 99%

Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1′<em>S</em>-1′-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells

Liew

Azmi

et al. 2017

DDDT

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Nine analogs of 1′S-1′-acetoxychavicol acetate (ACA) were hemi-synthesized and evaluated for their anticancer activities against seven human cancer cell lines. The aim of this study was to investigate the anti-proliferative, apoptotic, and anti-migration effects of these compounds and to explore the plausible underlying mechanisms of action. We found that ACA and all nine analogs were non toxic to human mammary epithelial cells (HMECs) used as normal control cells, and only ACA, 1′-acetoxyeugenol acetate (AEA), and 1′-acetoxy-3,5-dimethoxychavicol acetate (AMCA) inhibited the growth of MDA-MB-231 breast cancer cells with a half-maximal inhibitory concentration (IC50) value of <30.0 μM based on 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay results, and were selected for further investigation. DNA fragmentation assays showed that these three compounds markedly induced apoptosis of MDA-MB-231 cells. Western blot analysis revealed increased expression levels of cleaved PARP, p53, and Bax, while decreased expression levels of Bcl-2 and Bcl-xL were seen after treatment, indicating that apoptosis was induced via the mitochondrial pathway. Moreover, ACA, AEA, and AMCA effectively inhibited the migration of MDA-MB-231 cells. They also downregulated the expression levels of pFAK/FAK and pAkt/Akt via the integrin β1-mediated signaling pathway. Collectively, ACA and its hemi-synthetic analogs, AEA and AMCA are seen as potential anticancer agents following their abilities to suppress growth, induce apoptosis, and inhibit migration of breast cancer cells.

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Section: Discussionmentioning

confidence: 99%

Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1′<em>S</em>-1′-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells

Liew

Azmi

et al. 2017

DDDT

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“…In HL-60 leukemia cancer cells, ACA inhibits myeloma cell growth through inactivation of the NF-kB pathway. The resulting IC 50 value was 2 g/ml [31]. ACA can also be an alternative inhibitor for uPA and FGF2 because it can bind to them through a hydrogen formation pattern [32].…”

Section: Resultsmentioning

confidence: 99%

Systematic Review: Anticancer Potential of Active Compounds from Galangal (Alpinia galanga)

Suciati¹,

Maryati²

2022

Atlantis Highlights in Chemistry and Pharmaceutical Sciences

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Galangal (Alpinia galanga) is a plant that is widely spread in Southeast Asia and is widely used for cooking spices. Research related to the effect of A. galanga on cancer cells has been carried out. The purpose of this systematic review is to examine the potential of A. galanga as an anticancer agent and co-chemotherapy. The literature search was carried out through the Pubmed, Science Direct, Springer Link, DOAJ, and Garuda Portal databases. The keywords used were "Alpinia Galanga and Anticancer", "Alpinia Galanga and Cytotoxicity", "Lengkuas dan Sitotoksik", "Lengkuas dan Kanker", and "Alpinia Galanga and Cancer". Of the 965 articles found at the beginning of the search, 31 articles were obtained which had been filtered and discussed further. The results showed that the ethanolic extract of A. galanga had a cytotoxic effect because it contained antioxidant polyphenols that inhibited cell proliferation by stopping the cell cycle. The most abundant compounds in A. galanga as anticancer agents are 1'-Acetoxychavicol Acetate (ACA) and Galangin. ACA works to inhibit cancer cells by inducing apoptosis through mitochondrial depolarization and DNA fragmentation in the cell cycle phase. Meanwhile, Galangin works as a chemopreventive agent that reduces oxidative stress and inflammation by suppressing the MAPKs pathway.

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“…In addition, the introduction of methoxyl group at C-3 and C-5 (analogues 13-14) also exhibited potent activity. Furthermore, substitution of ester group with long chain carbon such as isobutyryl (11), butyryl (12), cyclohexane (13) and hexanoyl (14) showed higher activity compared to the analogue 5, which has less carbon chain and gave less activity. Next, the contribution of 2'-3' double bond of 1 to the activity was evaluated and as a result, compound 2 was less active than 1.…”

Section: Structural Activity Relationship (Sar) Analysis Of Aca Derivmentioning

confidence: 96%

“…1'-acetoxychavicol acetate (1) and trans-p-coumaryl diacetate (2) were isolated from Alpinia conchigera. In addition to that, the syntheses strategy of ACA derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were outlined in Schemes 1 and 2, respectively.…”

Section: Chemical Compoundsmentioning

confidence: 99%

“…12 Among them, 1'-acetoxychavicol acetate (ACA, 1) was found as the major constituent that exhibited various biological activity, including anti-inflammatory activity, anti-human immunodeficiency virus (HIV) activity, the inhibition of nitric oxide (NO), antimicrobial activity and the inhibition of xanthine oxidase (XO). 13 In the present study, we describe the synthesis and antimicrobial evaluation of ACA analogues against MRSA ( Figure 1). The structural activity relationship of ACA were observed by comparing the inhibition activities with structural features of analogues.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 1ʹ-acetoxychavicol acetate (ACA) analogues and their inhibitory activities against methicillin-resistant Staphylococcus aureus

Anuar¹,

Azmi²,

Hanafiah³

et al. 2020

JPS

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A series of 1ʹ-acetoxychavicol acetate analogues were synthesised and evaluated for their antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) using broth microdilution technique. The minimum inhibitory concentration (MIC) was used to determine whether the compounds had potential as inhibitory agents against the MRSA ATCC 43300, and the compounds with antimicrobial potential (<2000 μg ml–1) were tested for minimum bactericidal concentration (MBC). Based on this assay, compound 1 exhibited potent antimicrobial activity with MIC value of 250 μg ml–1. Meanwhile, compounds 2 and 13 showed the moderate activity with MIC values of 500 μg ml–1, respectively.

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Structure–activity relationships of benzhydrol derivatives based on 1′-acetoxychavicol acetate (ACA) and their inhibitory activities on multiple myeloma cell growth via inactivation of the NF-κB pathway

Cited by 7 publications

References 16 publications

Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1′<em>S</em>-1′-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells

Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1′<em>S</em>-1′-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells

Systematic Review: Anticancer Potential of Active Compounds from Galangal (Alpinia galanga)

Synthesis of 1ʹ-acetoxychavicol acetate (ACA) analogues and their inhibitory activities against methicillin-resistant Staphylococcus aureus

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Structure–activity relationships of benzhydrol derivatives based on 1′-acetoxychavicol acetate (ACA) and their inhibitory activities on multiple myeloma cell growth via inactivation of the NF-κB pathway

Cited by 7 publications

References 16 publications

Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1&prime;<em>S</em>-1&prime;-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells

Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1&prime;<em>S</em>-1&prime;-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells

Systematic Review: Anticancer Potential of Active Compounds from Galangal (Alpinia galanga)

Synthesis of 1ʹ-acetoxychavicol acetate (ACA) analogues and their inhibitory activities against methicillin-resistant Staphylococcus aureus

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Product

Resources

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Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1′<em>S</em>-1′-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells

Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1′<em>S</em>-1′-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells