A Review on Pyranocoumarins and its biological importance
K.P. Beena, G. Sathya Pooja
College of Pharmacy Sri Ramakrishna Institute of Paramedical Sciences 395, Sarojini Naidu Road,
New Siddhapudur, Coimbatore - 641044 Tamilnadu, India.
*Corresponding Author E-mail: beenaakelesh12@gmail.com
ABSTRACT:
Heterocycles occupy a salient place in chemistry due to their wide range of activity in the fields of drug design, photochemistry, agrochemicals, dyes, and so on. Amongst all, Pyranocoumarin scaffold is considered as one of the most promising heterocycles found in natural and synthetic sources and has been shown to possess various biological activities including anti-inflammatory, anti-HIV, antitubercular, anti HBV, anti-dyslipidemic, antiplatelet, anti-inflammatory, antioxidant and antibacterial. Therefore, the objective of this review is to focus on important pyranocoumarin analogs with various biological activities.
Types of Pyranocoumarins:
Linear Type
Angular Type:
Pyranocoumarins and Pharmacological Activity:
Antibacterial Activity:
Coumarins and pyrans are abundant in many important biologically active molecules, synthetic drugs, and drug candidates. The evaluation of chiral pyranocoumarins and 2-amino-4H-chromenes for biological activities and studies on structure−activity relationships are rare and remain as a great challenge.
Seyed Mehdi Razavi et al1 isolated pyranocoumarins from Zosima absinthifolia (Apiaceae) and reported the antibacterial activity against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Salmonella typhi. The MICs of the compounds against the test microorganisms were determined by the Agar dilution method.
Rui Wang et al2 has reported a highly efficient process for the synthesis of optically active pyranocoumarins and 2-amino-4H-chromenes through an organocatalytic Knoevenagel/Michael/cyclization sequence and evaluated preliminary biological studies for the heterocyclic compounds which revealed potent antibacterial activity
Gummudavelly Sandeep et al3 has reported synthesis and biological screening of some novel coumarin derivatives.
Anti- Obesity Activity:
Obesity is well known as a major global health issue and several therapeutic agents have been developed for treating this condition by reducing nutrient absorption or by enhancing thermogenesis and lipid turnover; however, considering the safety of these agents and their adverse side effects, medicinal plants and their active compounds merit investigation for the development of more natural and safer anti-obesity agents.
Naoyuki Taira et al4 evaluated Several types of coumarins from Peucedanum japonicum thunb (PJT) and reported the anti-obesity activity of pteryxin (PTX), as an active compound of PJT. Although all dihydropyranocoumarins used consist of an acetoxy group and a five-carbon acyloxy group, their inhibitory effects on cellular TG accumulation were distinctly different. PCIII had significantly lesser effect on lipid accumulation and gene expression in differentiated 3T3-L1 adipocytes than the other compounds
Deepthi Dongarwar Inamadar et al5 has reported the synthesis of novel 2-Isoxazole substituted Chromenones synthesized by microwave irradiation
The study by Abu Yousuf Hossin et al6 demonstrated that DPCs, such as PCIII and PTX contributed to the beneficial effects of PJT on the development of obesity by converting hypertrophic to hyperplastic obesity and enhancing energy expenditures.
Jacob Jincy et al7 has reported the synthesis of some novel coumarino benzimidazole derivatives and its biological activity
Cytotoxic Activity:
Coumarins constitute a major class of widely distributed O-heterocyclic natural products exhibiting a broad pharmacological profile, including anticancer activity. Naturally occurring pyranocoumarins showed interesting cytotoxic and antitumor-promoting activity.
Prokopios Magiatis et al8 reported that seselin and xanthyletin have been reported to act as DNA-damaging agents,6 and 3’,4’-dihydroxy-3’,4’-dihydroseselin derivatives were found to display significant cytotoxic activity against P-388 lymphocytic leukaemia.
Sanjib Das et al9 has reported the synthesis and pharmacological evaluation of new coumarinoacetamides
Jimmy Yiu-Cheong Wu et al10 isolated pyranocoumarins from Radix peucedani, the dry root of Peucedanum praeruptorum Dunn, through bioassay-guided fractionation. Strong synergistic interactions were demonstrated when pyranocoumarins were combined with common anti-tumour drugs including Doxorubicin, Paclitaxel, Puromycin or Vincristine in MDR KB-V1 cell line, but not in drug-sensitive KB-3-1 cells. Pyranocoumarins increased Doxorubicin accumulation in KB-V1 cells by about 25% after 6 h of incubation. Pyranocoumarins treatment for 24 h down-regulated the expression of P-glycoprotein in KB-V1 cells at both protein and mRNA levels. Pyranocoumarins also transiently reduced the cellular ATP contents in KB-V1 cells in a dose-dependent manner. They suggested that pyranocoumarins could be a potential MDR reversing agent.
Shubhangi S Soman et al11 has reported the synthesis of amino acetyl coumarins and amino acetyl naphthol coumarins and their biological activity
Yue-Lin Song et al12 reported that Angular-type pyranocoumarins from Peucedani Radix (Chinese name: Qian-hu) have exhibited potential for use on treatment of cancer and pulmonary hypertension. Due to the existence of C-3′ and C-4′ chiral centres, compounds belonging to this chemical type commonly exist in enantiomers and/or diastereoisomers, which may elicit distinct activities during their interactions with the human body.
Anti Hyperglycemic and Anti Dyslipidemic Activity:
Diabetes mellitus is multifactorial disease characterized by high level of blood glucose and impaired insulin action. It is an independent risk factor for the development of coronary artery diseases, myocardial infarction, hypertension, and dyslipidemia. Non-insulin dependent diabetes mellitus (NIDDM) accounts for approximately 80–90% of all diabetes cases. The number of diabetics complains are continuously growing with a currently estimated worldwide incidence of about 194 million people and expected to increase to 330 million by 2025. When the carbohydrates are not present in sufficient amount or their metabolism is impaired, fats become the principle source of energy. Fatty acids are mobilized into the general circulation leading to secondary triglyceridemia in which total serum lipids in particular triglycerides as well as the levels of cholesterol and phospholipids increases. This rise is proportional to the severity of the diabetes. Uncontrolled diabetes is manifested by a very high rise in triglycerides and fatty acid levels.
Vijaya Pawar et al13 has reported the synthesis and characterization of novel transition metal complexes of 4-methyl-7-hydroxy-8-formyl coumarin and their biological activities
Atul Kumar et al14 has reported a series of pyranocoumarin derivatives and evaluated in vivo for their anti-hyperglycemic as well as anti-dyslipidemic activities. The design of pyranocoumarin is based on natural products exhibiting promising antidiabetic activity such as Sanggenone C, Luvangetin and Rutamarin. These natural products have coumarin as central nucleus along with pyran or furan scaffolds present in linear arrangements.
Ashok G Gadre et al15 has reported the synthesis and characterization of hydrazones, pyrazoles and pyrazolones form 8-amino-6-chloro coumarin
Ahindra Nag et al16 has demonstrated as simple, eco-friendly and novel procedure for the synthesis of biscoumarins and pyranocoumarins using natural feedstock coconut juice. The major importance of using coconut juice is higher yields, no work-up an no column chromatography
Antiviral Activity:
Boonsong Kongkathip et al17 has reported the isolation of three carbazole derivatives, clauszoline and a pyranocoumarin, clausenidin from the rhizomes and roots of Clausena excavate and demonstrated a lack of cytotoxicity against cancer cell lines.
Arpit Singh et al18 has reported selective recognition of Cd (II) sing coumarin oxirenes
Tian-Shung Wu et al19 has isolated four natural pyranocoumarins clausenidin, clausarin, nordentatin and xanthoxyletin from the medicinal plant Clausena excatava and found that they suppressed hepatitis B virus surface antigen in HepA2 cells. The study also reports the semi-synthesis of several new pyranocoumarin derivatives in excellent yields by using hydrogenation, epoxidation and methylation techniques.
Habeela Jainab et al20 has reported microwave mediated synthesis, characterisation and biological activity of certain new mannich bases of Isatin and Coumarin
Dale L Barnard et al21 has evaluated a series of coumarin and pyranocoumarin analogues in vitro for antiviral efficacy against measles virus (MV)
Hepatoprotective Activity:
Digambar Kumbhar et al22 has reported target oriented selective synthesis of active tyrosinase enzyme inhibitor coumarin core derivatives
Dong-Ming Zhang et al23 has reported isolation of seven new pyranocoumarins belonging to two types of skeletons, clauemarmarins from the stems of Clausena emarginata. Hepatoprotective activities of the isolated coumarins against DL-galactosamine-induced toxicity in WB-F344 cells were evaluated.
Anticancer Activity:
Hyo Jeong Lee et al24 has reported that a 10-herbal traditional formula containing Korean Angelica gigas Nakai exerts potent anti-cancer efficacy and identified decursin and decursinol angelate from Angelica gigas Nakai as novel anti-androgens
Junming Guo et al25 has reported that pyranocoumarin compound decursin from the herb Angelica gigas possesses anti-AR activities distinct from the anti-androgen bicalutamide
Wei Wu et al26 has investigated a data to support decursinol to exert in vivo inhibitory activity against LNCaP/AR-Luc xenograft growth and lung metastasis
He-ping Zeng et al27 has constructed a library of novel 5-hydroxycoumarin and pyranocoumarin derivatives via silica sulfuric acid-catalyzed pechmann reaction and Pd (0) catalyzed Suzuki coupling in tandem and evaluated their antiproliferative activities against breast cancer cells
Anti- Inflammatory Activity:
Salman Khan et al128investigated the neuropathic pain, anti-neuroinflammatory and neuroprotective properties of a pyranocoumarin derivative, anomalin in in vivo and in vitro models. Anomalin remarkably reduced the increase in SNP-induced nuclear factor
Anti- Tubercular Activity:
Ze-Qi Xu et al29 have synthesized pyranocoumarin compounds to embody a novel and unique pharmacophore for anti-TB activity.
Muscle Relaxant Activity:
Toru Okuyama et al30 had compared the relaxant effects of pyranocoumarin compounds, purified from Bai-Hua Qian Hu in isolated rabbit tracheas and pulmonary arteries
CONCLUSION:
In this review, efforts have been made to present the current information about the biological activities of pyranocoumarin analogues. Extensive range of natural sources and new pyranocoumarin analogues are being discovered or synthesized on a regular basis. The reported biological activities including antibacterial, anti-obesity, antivirus, cytotoxic, antihyperglycemic, anti TB, anti-HIV, antifungal activities etc. make them as novel class for therapeutic applications.
CONFLICT OF INTEREST:
The authors have no conflicts of interest regarding this review.
ACKNOWLEDGEMENTS:
The authors would like to thank the Management and The Principal, College of Pharmacy, Sri Ramakrishna Institute of Paramedical Sciences, Coimbatore for their constant support.
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Received on 02.09.2021 Modified on 10.11.2021
Accepted on 15.12.2021 ©AJRC All right reserved
Asian J. Research Chem. 2022; 15(2):176-181.