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LETTER TO EDITOR
Year : 2020  |  Volume : 3  |  Issue : 3  |  Page : 219-220

Biological activities of bisdesmethoxycurcumin


Ingredients, Laurus Labs Limited, Hyderabad, Telangana, India

Date of Submission04-Dec-2019
Date of Decision18-Jan-2020
Date of Acceptance26-Jan-2020
Date of Web Publication02-Jun-2020

Correspondence Address:
Roopesh Jain
Laurus Labs Ltd., Serene Chambers, Road #7, Banjara Hills, Hyderabad - 500 034, Telangana
India
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Source of Support: None, Conflict of Interest: None


DOI: 10.4103/JNSM.JNSM_65_19

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  Abstract 


Bisdesmethoxycurcumin (about 3%) is one of the three principal forms of Curcuminoids and reported to be more stable than the other two curcuminoids. Considering its pharmacological effects, the objective of this study was to assess antioxidant and anti-inflammatory potential of bisdesmethoxycurcumin. The study revealed that bisdesmethoxycurcumin downregulates tumor necrosis factor alpha-induced nuclear factor-kappa B expression and has highest antioxidant activity among curcuminoids.

Keywords: Bisdesmethoxycurcumin, curcumin, desmethoxycurcumin


How to cite this article:
Jain R. Biological activities of bisdesmethoxycurcumin. J Nat Sci Med 2020;3:219-20

How to cite this URL:
Jain R. Biological activities of bisdesmethoxycurcumin. J Nat Sci Med [serial online] 2020 [cited 2020 Aug 12];3:219-20. Available from: http://www.jnsmonline.org/text.asp?2020/3/3/219/285779




  Brief Introduction Top


Bisdesmethoxycurcumin (also known as Bisdemethoxycurcumin, Curcumin III and BDMC) is a curcuminoid. BDMC (about 3%) is one of the three principal forms of curcuminoids along with curcumin (about 77%) and desmethoxycurcumin (DMC) or demethoxycurcumin (about 17%).[1] Although most of the studies have been carried out on curcumin, other curcuminoids such as DMC and BDMC were also reported to possess various pharmacological effects and health-promoting properties recently.[2] Being a curcuminoid, BDMC is also known to exhibit salient characteristics of the family as an anti-inflammatory and antioxidant agent responsible for pain relief and joint healing. BDMC is the most stable among three curcuminoids,[1] however it is difficult to get its higher concentration in the extract. Laurus Labs developed nature identical and high-pure BDMC (>98%) and tested this compound at reputed lab in the US for different biological activities, i.e., anti-inflammatory (tumor necrosis factor alpha [TNF-α]-induced nuclear factor (NF)-kappa inhibition) and antioxidant (oxygen radical absorbance capacity [ORAC]). Results were encouraging as it showed better activity than curcumin.


  Materials and Methods Top


Curcumin, DMC, and BDMC were provided by Laurus Labs, India. Unless specified, all other reagents were purchased form Sigma. All cells were procured from ATCC, Manassas, Virginia.

Cell culture

Human 293T cells were cultured in Dulbecco's modified eagle medium (DMEM) complete medium (DMEM medium supplemented with 10% fetal bovine serum, L-glutamine, and penicillin-streptomycin-neomycin). Cells were seeded (5 × 105/ml) to a 6 well plate and cultured overnight. The culture medium was replaced by serum-free medium 4 h before addition of TNF-α and samples.

Cell viability assay

Human 293 cells were cultured in serum-free medium for 4 h. Then, TNF-α (50 ng/well), serially diluted samples, and quercetin solutions were added into each well and incubated for 1 h at 37°C with 5% CO2. The bioluminescent ATP assay was used to evaluate the cell viability.

Nuclear factor-kappa B assay

Cells were cultured in serum-free medium for 4 h. Then, TNF-α and serially diluted samples (based on cell viability result) were added into each well and incubated for 1 h at 37°C with 5% CO2. Then, cells were collected, and nuclear proteins were extracted for NF-kappa B activity detection using a NF-kappa detection kit from Active Motif, Inc (Carlsbad, CA).


  Discussion Top


In NF-kappa B testing, human 293 T cells were grown, starved off serum for 4 h, then cocultured with TNF-α (a cytokine involved in systemic inflammation) in the presence or absence of curcumin, DMC, and BDMC for 1 h; cell nuclear proteins were extracted; and their NF-kappa levels were analyzed. As shown in [Table 1], the levels of NF-kappa B for curcumin, DMC and BDMC samples were 79.12, 36.4, and 18.01 μmol QE/g of quercetin activity, respectively.
Table 1: Effects on tumor necrosis factor alpha-induced nuclear factor-kappa activity in human 293 T cells

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Results indicate that BDMC downregulates TNF-α-induced NF-kappa B expression and is more potent than curcumin and DMC as it reaches the same level of protection as quercetin, an antioxidant bench marker used for the assay, with the lowest dose. Curcumin was used at 0.5 mg/ml, as at higher doses it shows cytotoxicity in 293 cells in cell viability assay, while DMC and BDMC were used at 1 mg/ml because there were no obvious signs of cytotoxicity at this dose.

Curcumin, DMC and BDMC were also tested for their antioxidant potential using ORACFN test. The ORACFN of three ingredients was studied at Brunswick Laboratory against different predominant reactive species reported in the body: hydroxyl radicals, peroxyl radicals, peroxynitrite, singlet oxygen, and superoxide anion. [Table 2] provides total ORACFN(degree of the total antioxidant capacity) of curcumin, DMC and BDMC.
Table 2: Antioxidant capacity of ingredients

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BDMC exhibits highest antioxidant activity (6,245,507 μmol/QE/g) among curcuminoids. In this study, we report superior anti-inflammatory and antioxidant potential of BDMC than curcumin and DMC. BDMC was known to exhibit anti-inflammatory and antioxidant activities in previous studies as well.[1],[3] BDMC also reported more potent than curcumin in various pharmacological activities such as antimutagenic, antitumor, suppression of carcinogenesis, nicotine-induced oxidative stress, protection of endothelial and nerve cells from beta amyloid-induced oxidative stress (an established pathway to study neuronal cell death in Alzheimer's disease), preventing alcohol and PUFA-induced oxidative stress, cholesterol, triglycerides, phospholipids and free fatty acids, and carbon tetrachloride-induced hepatotoxicity.[4] BDMC also reported to help in aging and cellular senescence (longevity),[5] allergy,[2] Alzheimer's disease,[6] cardioprotection,[7] chronic kidney conditions,[8] innate immunity,[9] and obesity.[10]

Chemical instability of curcumin limits its usage; it degrades rapidly at physiological pH. BDMC was reported stable to oxidative, alkaline, and acidic degradation when compared with DMC and curcumin.[11] The better stability of BDMC in physiological medium [1],[11] could be a significant factor and opens a door as an ingredient leverages with health benefits.

Financial support and sponsorship

Nil.

Conflicts of interest

There are no conflicts of interest.



 
  References Top

1.
Ramezani M, Hatamipour M, Sahebkar A. Promising anti-tumor properties of bisdemethoxycurcumin: A naturally occurring curcumin analogue. J Cell Physiol 2018;233:880-7.  Back to cited text no. 1
    
2.
Fu M, Fu S, Ni S, Wang D, Hong T. Inhibitory effects of bisdemethoxycurcumin on mast cell-mediated allergic diseases. Int Immunopharmacol 2018;65:182-9.  Back to cited text no. 2
    
3.
Kim AN, Jeon WK, Lee JJ, Kim BC. Up-regulation of heme oxygenase-1 expression through CaMKII-ERK1/2-Nrf2 signaling mediates the anti-inflammatory effect of bisdemethoxycurcumin in LPS-stimulated macrophages. Free Radic Biol Med 2010;49:323-31.  Back to cited text no. 3
    
4.
Anand P, Thomas SG, Kunnumakkara AB, Sundaram C, Harikumar KB, Sung B, et al. Biological activities of curcumin and its analogues (Congeners) made by man and mother nature. Biochem Pharmacol 2008;76:1590-611.  Back to cited text no. 4
    
5.
Li YB, Zhong ZF, Chen MW, Bao JL, Wu GS, Zhang QW, et al. Bisdemethoxycurcumin increases sirt1 to antagonize t-BHP-induced premature senescence in WI38 fibroblast cells. Evid Based Complement Alternat Med 2013;2013:851714.  Back to cited text no. 5
    
6.
Gagliardi S, Franco V, Sorrentino S, Zucca S, Pandini C, Rota P, et al. Curcumin and novel synthetic analogs in cell-based studies of Alzheimer's disease. Front Pharmacol 2018;9:1404.  Back to cited text no. 6
    
7.
Li X, Huo C, Xiao Y, Xu R, Liu Y, Jia X, et al. Bisdemethoxycurcumin protection of cardiomyocyte mainly depends on Nrf2/HO-1 activation mediated by the PI3K/AKT pathway. Chem Res Toxicol 2019;32:1871-9.  Back to cited text no. 7
    
8.
Jin F, Jin Y, Du J, Jiang L, Zhang Y, Zhao Z, et al. Bisdemethoxycurcumin protects against renal fibrosis via activation of fibroblast apoptosis. Eur J Pharmacol 2019;847:26-31.  Back to cited text no. 8
    
9.
Fiala M, Liu PT, Espinosa-Jeffrey A, Rosenthal MJ, Bernard G, Ringman JM, et al. Innate immunity and transcription of MGAT-III and Toll-like receptors in Alzheimer's disease patients are improved by bisdemethoxycurcumin. Proc Natl Acad Sci U S A 2007;104:12849-54.  Back to cited text no. 9
    
10.
Lai CS, Chen YY, Lee PS, Kalyanam N, Ho CT, Liou WS, et al. Bisdemethoxycurcumin inhibits adipogenesis in 3T3-L1 preadipocytes and suppresses obesity in high-fat diet-fed C57BL/6 Mice. J Agric Food Chem 2016;64:821-30.  Back to cited text no. 10
    
11.
Peram MR, Jalalpure SS, Palkar MB, Diwan PV. Stability studies of pure and mixture form of curcuminoids by reverse phase-HPLC method under various experimental stress conditions. Food Sci Biotechnol 2017;26:591-602.  Back to cited text no. 11
    



 
 
    Tables

  [Table 1], [Table 2]



 

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