Abstract
O. sanctum L. (O. tenuiflorum) is an important sacred medicinal plant of India known as Holy Basil or Tulsi. The chemical composition of volatile oil is highly complex and comprises high ratio of phenylpropanoids and terpenes, and some phenolic compound or flavonoids such as orientin and vicenin. These minor flavonoids are known to be antioxidant and anticancer in nature. Orientin reported as potential anticancer agent due to anti-proliferative activity on human liver cancer cell line HepG2, but its mechanism of action is not fully explored. In the present work an in-silico structure-activity relationship study on orientin was performed and built a pharmacophore mapping and QSAR model to screen out the potential structurally similar analogues from chemical database of Discovery Studio (DSv3.5, Accelrys, USA) as potential anticancer agent. Analogue fenofibryl glucuronide was selected for in vitro cytotoxic/anticancer activity evaluation through MTT assay. Binding affinity and mode of action of orientin and its analogue were explored through molecular docking studies on quinone oxidoreductase, a potential target of flavonoids. Contrary to the assumption, in vitro results showed only 41% cell death at 202.389 μM concentration (at 96 hrs). Therefore, we concluded that the selected orientin analogue fenofibryl glucuronide was non-cytotoxic/non-anti-carcinogenic up to 100 μg/ml (202.389 μM) concentrations for a long term exposure i.e., till 96 hrs in human cancer cells of HepG2. We concluded that orientin and its analogue fenofibryl glucuronide as pure compound showed no activity or less cytotoxicity activity on liver cancer cell line HepG2.
Keywords: HepG2 cancer cell line, Orientin, Docking, ADMET.
Combinatorial Chemistry & High Throughput Screening
Title:Structure-Activity Relationship Studies on Holy Basil (Ocimum sanctum L.) Based Flavonoid Orientin and its Analogue for Cytotoxic Activity in Liver Cancer Cell Line HepG2
Volume: 19 Issue: 8
Author(s): Pooja Sharma, Om Prakash, Aparna Shukla, Chetan Singh Rajpurohit, Prema G. Vasudev, Suaib Luqman, Santosh Kumar Srivastava, Aditya Bhushan Pant and Feroz Khan
Affiliation:
Keywords: HepG2 cancer cell line, Orientin, Docking, ADMET.
Abstract: O. sanctum L. (O. tenuiflorum) is an important sacred medicinal plant of India known as Holy Basil or Tulsi. The chemical composition of volatile oil is highly complex and comprises high ratio of phenylpropanoids and terpenes, and some phenolic compound or flavonoids such as orientin and vicenin. These minor flavonoids are known to be antioxidant and anticancer in nature. Orientin reported as potential anticancer agent due to anti-proliferative activity on human liver cancer cell line HepG2, but its mechanism of action is not fully explored. In the present work an in-silico structure-activity relationship study on orientin was performed and built a pharmacophore mapping and QSAR model to screen out the potential structurally similar analogues from chemical database of Discovery Studio (DSv3.5, Accelrys, USA) as potential anticancer agent. Analogue fenofibryl glucuronide was selected for in vitro cytotoxic/anticancer activity evaluation through MTT assay. Binding affinity and mode of action of orientin and its analogue were explored through molecular docking studies on quinone oxidoreductase, a potential target of flavonoids. Contrary to the assumption, in vitro results showed only 41% cell death at 202.389 μM concentration (at 96 hrs). Therefore, we concluded that the selected orientin analogue fenofibryl glucuronide was non-cytotoxic/non-anti-carcinogenic up to 100 μg/ml (202.389 μM) concentrations for a long term exposure i.e., till 96 hrs in human cancer cells of HepG2. We concluded that orientin and its analogue fenofibryl glucuronide as pure compound showed no activity or less cytotoxicity activity on liver cancer cell line HepG2.
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Sharma Pooja, Prakash Om, Shukla Aparna, Rajpurohit Singh Chetan, Vasudev G. Prema, Luqman Suaib, Srivastava Kumar Santosh, Pant Bhushan Aditya and Khan Feroz, Structure-Activity Relationship Studies on Holy Basil (Ocimum sanctum L.) Based Flavonoid Orientin and its Analogue for Cytotoxic Activity in Liver Cancer Cell Line HepG2, Combinatorial Chemistry & High Throughput Screening 2016; 19 (8) . https://dx.doi.org/10.2174/1386207319666160709192801
DOI https://dx.doi.org/10.2174/1386207319666160709192801 |
Print ISSN 1386-2073 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5402 |
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