Identification of a sulfonoquinovosyldiacylglyceride from Azadirachta indica and studies on its cytotoxic activity and DNA binding properties

Chatterjee, Ratna; Singh, Onkar; Pachuau, Lalawmpuii; Malik, Shiba Prasad; Paul, Mausumi; Bhadra, Kakali; Paul, Santanu; Kumar, Gopinatha Suresh; Mondal, Nirup B.; Banerjee, Sukdeb

doi:10.1016/j.bmcl.2010.09.007

Cited by 15 publications

(21 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The glycolipid was characterized (Chatterjee et al . ) as sulfonoquinovosyldiacylglyceride (SQDG, Fig. ) by comparison of its spectroscopic data with those reported in the literature (Sassaki et al .…”

Section: Resultsmentioning

confidence: 80%

“…The compound was crystallized from MeOH and characterized (Chatterjee et al . ) as sulfonoquinovosyldiacylglyceride (SQDG) by the application of spectroscopic analysis, viz. Mass and 1D, 2D NMR spectroscopy.…”

Section: Methodsmentioning

confidence: 99%

“…As a part of our continuous search for bioactive secondary plant metabolites, we could isolate sulfonoquinovosyldiacylglyceride (SQDG) from methanolic extract of mature leaves of A. indica and validated the anticancer activity by DNA binding method (Chatterjee et al . ; Bharitkar et al . ).…”

Section: Introductionmentioning

confidence: 96%

See 2 more Smart Citations

Antibacterial and antiviral evaluation of sulfonoquinovosyldiacylglyceride: a glycolipid isolated from Azadirachta indica leaves

Bharitkar

Bathini

Ojha

et al. 2013

Lett Appl Microbiol

View full text Add to dashboard Cite

Significance and Impact of the Study: The water-soluble metabolite sulfonoquinovosyldiacylglyceride (SQDG) isolated from Azadirachta indica (Neem) possess significant antibacterial as well as anti-HSV activity. The efficacies as well as the solubility factor of SQDG substantiate a greater attention for its use as phytotherapeutic drug for controlling microbial infections as most consumers have better acceptance of phytomedicines than synthetic drugs. AbstractAssessment of antibacterial as well as antiherpes virus activity of sulfonoquinovosyldiacylglyceride (SQDG), a glycolipid, isolated from the leaves of Azadirachta indica has been described. Antimicrobial activity was evaluated against Gram-positive, Gram-negative bacteria and herpes simplex virus. SQDG showed significant inhibitory activity against Salmonella typhi and two isolates of Shigella dysenteriae with MIC values 32 lg ml À1 , while three isolates of Salm. typhi, Escherichia coli and Vibrio cholerae were inhibited at 64 lg ml À1and have shown zone diameter ranging from 6Á2 to 12Á3 mm. The growth kinetics study of SQDG on Salm. typhi and Sh. dysenteriae revealed that the growths were completely inhibited at their MIC values within 24 h of exposure. Interestingly, SQDG inhibits herpes simplex virus (HSV) type 1 and 2 with the EC 50 of 9Á1 and 8Á5 lg ml À1 , compared with acyclovir (2Á2 and 2Á8 lg ml À1 against HSV-1 and HSV-2). The selectivity index (SI) was found to be 12Á4 against HSV-1 and 13Á41 with HSV-2. Furthermore, the expression of proinflammatory cytokines of HSV-infected and SQDG-treated macrophages using ELISA kit revealed that SQDG significantly downregulated the production of TNF-a, IL-1b, IL-12 and IL-6.

show abstract

Section: Resultsmentioning

confidence: 80%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Antibacterial and antiviral evaluation of sulfonoquinovosyldiacylglyceride: a glycolipid isolated from Azadirachta indica leaves

Bharitkar

Bathini

Ojha

et al. 2013

Lett Appl Microbiol

View full text Add to dashboard Cite

show abstract

“…Brahmi et al detected a telomerase inhibitory activity (anticarcinogenic) of SQDGs isolated from the cyanobacterium Microcystis aeruguinosa [58]. In addition, anti-inflammatory activity and anti-proliferative effects on various human (cancer) cell lines are described [59,60,61,62,63,64] as well as a prophylactic effect against Mycobacterium tuberculosum infection is known [44]. As part of a patent, the effect of sulfolipids in inflammatory skin diseases, especially psoriasis is described [65].…”

Section: Discussionmentioning

confidence: 99%

Natural Products from Microalgae with Potential against Alzheimer’s Disease: Sulfolipids Are Potent Glutaminyl Cyclase Inhibitors

et al. 2016

View full text Add to dashboard Cite

In recent years, many new enzymes, like glutaminyl cyclase (QC), could be associated with pathophysiological processes and represent targets for many diseases, so that enzyme-inhibiting properties of natural substances are becoming increasingly important. In different studies, the pathophysiology connection of QC to various diseases including Alzheimer’s disease (AD) was described. Algae are known for the ability to synthesize complex and highly-diverse compounds with specific enzyme inhibition properties. Therefore, we screened different algae species for the presence of QC inhibiting metabolites using a new “Reverse Metabolomics” technique including an Activity-correlation Analysis (AcorA), which is based on the correlation of bioactivities to mass spectral data with the aid of mathematic informatics deconvolution. Thus, three QC inhibiting compounds from microalgae belonging to the family of sulfolipids were identified. The compounds showed a QC inhibition of 81% and 76% at concentrations of 0.25 mg/mL and 0.025 mg/mL, respectively. Thus, for the first time, sulfolipids are identified as QC inhibiting compounds and possess substructures with the required pharmacophore qualities. They represent a new lead structure for QC inhibitors.

show abstract

“…Sulfonoquinovosyldiacylglyceride isolated from neem leaves induced apoptosis in a dosedependent manner with IC 50 8.3 μM against acute lymphoblastic leukaemia (ALL) MOLT-4 cell lines (Chatterjee et al 2010 ). The compound showed signifi cant DNA-binding properties as evidenced by the enhancement of melting temperature and perturbation of the characteristic B-form in CD evidence of calf thymus DNA.…”

Section: Anticancer Activity In Vitro Studiesmentioning

confidence: 98%

Azadirachta indica

Lim¹

2014

Edible Medicinal and Non Medicinal Plants

View full text Add to dashboard Cite

Identification of a sulfonoquinovosyldiacylglyceride from Azadirachta indica and studies on its cytotoxic activity and DNA binding properties

Cited by 15 publications

References 21 publications

Antibacterial and antiviral evaluation of sulfonoquinovosyldiacylglyceride: a glycolipid isolated from Azadirachta indica leaves

Antibacterial and antiviral evaluation of sulfonoquinovosyldiacylglyceride: a glycolipid isolated from Azadirachta indica leaves

Natural Products from Microalgae with Potential against Alzheimer’s Disease: Sulfolipids Are Potent Glutaminyl Cyclase Inhibitors

Azadirachta indica

Contact Info

Product

Resources

About