Semisynthesis of (−)-Rutamarin Derivatives and Their Inhibitory Activity on Epstein–Barr Virus Lytic Replication

Lin, Yongsheng; Wang, Qian; Gu, Qiong; Zhang, Hongao; Jiang, Cheng; Hu, Jinqing; Wang, Yan; Yuan, Yan; Xu, Jing

doi:10.1021/acs.jnatprod.6b00415

Cited by 14 publications

(10 citation statements)

References 25 publications

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“…(+)-Rutamarin is effective in inhibiting EBV DNA replication and virion production with little adverse effect on cell proliferation, and therefore has potential to become a safe and effective drug for the treatment of human diseases associated with EBV infection. 139 A variety of rutamarin derivatives also exhibit similar inhibition of EBV replication. 140…”

Section: Reviewmentioning

confidence: 99%

Epstein-Barr virus (EBV) reactivation and therapeutic inhibitors

2019

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Epstein-Barr virus (EBV) is a ubiquitous human virus which infects almost all humans during their lifetime and following the acute phase, persists for the remainder of the life of the individual. EBV infects B lymphocytes leading to their immortalisation, with persistence of the EBV genome as an episome. In the latent phase, EBV is prevented from reactivating through efficient cytotoxic cellular immunity. EBV reactivates (lytic phase) under conditions of psychological stress with consequent weakening of cellular immunity, and EBV reactivation has been shown to occur in a subset of individuals with each of a variety of cancers, autoimmune diseases, the autoimmune-like disease, chronic fatigue syndrome/myalgic encephalitis and under other circumstances such as being an inpatient in an intensive care unit. Chronic EBV reactivation is an important mechanism in the pathogenesis of many such diseases, yet is rarely tested for in immunocompetent individuals. This review summarises the pathogenesis of EBV infection, EBV reactivation and its role in disease, and methods which may be used to detect it. Known inhibitors of EBV reactivation and replication are discussed, including drugs licensed for treatment of other herpesviruses, licensed or experimental drugs for various other indications, compounds at an early stage of drug development and nutritional constituents such as vitamins and dietary supplements.

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Section: Reviewmentioning

confidence: 99%

Epstein-Barr virus (EBV) reactivation and therapeutic inhibitors

2019

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“…Chalepin (1), isolated from R. graveolens, along with its 28 synthetic analogs were tested for their inhibitory activity on the Epstein-Barr virus (EBV, also known as human herpes virus 4) lytic replication activity [41]. It was noted that most of the synthesized analogs were more active than their parent or precursor, (-)-chalepin (1).…”

Section: Antiviral Activitymentioning

confidence: 99%

Chalepin and Chalepensin: Occurrence, Biosynthesis and Therapeutic Potential

et al. 2021

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Dihydrofuranocoumarin, chalepin (1) and furanocoumarin, chalepensin (2) are 3-prenylated bioactive coumarins, first isolated from the well-known medicinal plant Ruta chalepensis L. (Fam: Rutaceae) but also distributed in various species of the genera Boenminghausenia, Clausena and Ruta. The distribution of these compounds appears to be restricted to the plants of the family Rutaceae. To date, there have been a considerable number of bioactivity studies performed on coumarins 1 and 2, which include their anticancer, antidiabetic, antifertility, antimicrobial, antiplatelet aggregation, antiprotozoal, antiviral and calcium antagonistic properties. This review article presents a critical appraisal of publications on bioactivity of these 3-prenylated coumarins in the light of their feasibility as novel therapeutic agents and investigate their natural distribution in the plant kingdom, as well as a plausible biosynthetic route.

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“…(+)-Rutamarin (30), extracted from Ruta graveolens, has been reported to inhibit EBV lytic DNA replication [175]. Later, 30 was also found to inhibit EBV lytic DNA replication with an IC 50 of 7.0 µM and semi-synthesis of other (−)-rutamarin derivatives, including (−)-chalepin with an IC 50 of 69.9, and it exhibited inhibitory effects on EBV lytic DNA replication [129]. (−)-Chalepin synthesized with 5-ethyl-2-pyridine-ethanol (4m), 4-pyridine-ethanol (4n), and N-(2-hydroxyethyl) phthalimide (4p) by a general procedure exhibited IC 50 values of 1.5, 0.32, and 0.83 µM and SI values of 801, 211, and > 120, respectively.…”

Section: Polyphenols With Potential Anti-herpetic Activitiesmentioning

confidence: 99%

Natural Products and Their Derivatives against Human Herpesvirus Infection

et al. 2021

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Herpesviruses establish long-term latent infection for the life of the host and are known to cause numerous diseases. The prevalence of viral infection is significantly increased and causes a worldwide challenge in terms of health issues due to drug resistance. Prolonged treatment with conventional antiviral drugs is more likely to develop drug-resistant strains due to mutations of thymidine nucleoside kinase or DNA polymerase. Hence, the development of alternative treatments is clearly required. Natural products and their derivatives have played a significant role in treating herpesvirus infection rather than nucleoside analogs in drug-resistant strains with minimal undesirable effects and different mechanisms of action. Numerous plants, animals, fungi, and bacteria-derived compounds have been proved to be efficient and safe for treating human herpesvirus infection. This review covers the natural antiherpetic agents with the chemical structural class of alkaloids, flavonoids, terpenoids, polyphenols, anthraquinones, anthracyclines, and miscellaneous compounds, and their antiviral mechanisms have been summarized. This review would be helpful to get a better grasp of anti-herpesvirus activity of natural products and their derivatives, and to evaluate the feasibility of natural compounds as an alternative therapy against herpesvirus infections in humans.

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Semisynthesis of (−)-Rutamarin Derivatives and Their Inhibitory Activity on Epstein–Barr Virus Lytic Replication

Cited by 14 publications

References 25 publications

Epstein-Barr virus (EBV) reactivation and therapeutic inhibitors

Epstein-Barr virus (EBV) reactivation and therapeutic inhibitors

Chalepin and Chalepensin: Occurrence, Biosynthesis and Therapeutic Potential

Natural Products and Their Derivatives against Human Herpesvirus Infection

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