A new dimeric naphthoquinone from<i>Diospyros anisandra</i>

Uc-Cachón, Andrés Humberto; Molina-Salinas, Gloria María; Said‐Fernández, Salvador; Méndez-González, Martha; Cáceres-Farfan, Mirbella; Borges-Argáez, Rocı́o

doi:10.1080/14786419.2012.718770

Cited by 25 publications

(11 citation statements)

References 15 publications

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“…Uc-Cachon et al obtained four naphthoquinones ( 57 , 66 , 67 , 68 ) from a nonpolar extract of Diospyros anisandra S.F. Blake (Ebanaceae).…”

Section: Plant-derived Compounds With Antibacterial Propertiesmentioning

confidence: 99%

“…266 In vivo studies demonstrated that acute bacterial prostatitis induced by E. coli and P. aeruginosa could regress following administration of thymoquinone, improving the general histologic structure and downgraded the degree of inflammation in prostatic tissue. 29,267 Uc-Cachon et al 268 obtained four naphthoquinones (57, 66, 67, 68) from a nonpolar extract of Diospyros anisandra S.F. Blake (Ebanaceae).…”

Section: Phenolic Derivativesmentioning

confidence: 99%

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Ethnobotany and the Role of Plant Natural Products in Antibiotic Drug Discovery

et al. 2020

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The crisis of antibiotic resistance necessitates creative and innovative approaches, from chemical identification and analysis to the assessment of bioactivity. Plant natural products (NPs) represent a promising source of antibacterial lead compounds that could help fill the drug discovery pipeline in response to the growing antibiotic resistance crisis. The major strength of plant NPs lies in their rich and unique chemodiversity, their worldwide distribution and ease of access, their various antibacterial modes of action, and the proven clinical effectiveness of plant extracts from which they are isolated. While many studies have tried to summarize NPs with antibacterial activities, a comprehensive review with rigorous selection criteria has never been performed. In this work, the literature from 2012 to 2019 was systematically reviewed to highlight plant-derived compounds with antibacterial activity by focusing on their growth inhibitory activity. A total of 459 compounds are included in this Review, of which 50.8% are phenolic derivatives, 26.6% are terpenoids, 5.7% are alkaloids, and 17% are classified as other metabolites. A selection of 183 compounds is further discussed regarding their antibacterial activity, biosynthesis, structure−activity relationship, mechanism of action, and potential as antibiotics. Emerging trends in the field of antibacterial drug discovery from plants are also discussed. This Review brings to the forefront key findings on the antibacterial potential of plant NPs for consideration in future antibiotic discovery and development efforts.

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“…Uc-Cachon et al obtained four naphthoquinones ( 57 , 66 , 67 , 68 ) from a nonpolar extract of Diospyros anisandra S.F. Blake (Ebanaceae).…”

Section: Plant-derived Compounds With Antibacterial Propertiesmentioning

confidence: 99%

Section: Phenolic Derivativesmentioning

confidence: 99%

Ethnobotany and the Role of Plant Natural Products in Antibiotic Drug Discovery

et al. 2020

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“…The diversity of the isolated naphthoquinone structures and their differences in terms of mycobacterial activity suggested that the location of the dimeric bond is important for the expression of antituberculosis activity. 74,75 A phytochemical investigation of the root extract of C. greggi yielded two bioactive metabolites identified as the athraquinone chrysophanol (106), active against Bacillus subtilis and Staphylococcus aureus, 76 and discarine B (107), a cyclic dipeptide with moderate antiprotozoal activity against T. cruzi var. tulahuen.…”

Section: ■ Screening the Mayan Pharmacopeiamentioning

confidence: 99%

“…Plumbagin ( 103 ) and its dimers, maritinone ( 104 ) and 3,3′-biplumbagin ( 105 ), were 32 times more potent than rifampicin when tested against the pan-resistant strain of M. tuberculosis , without being toxic to normal cell lines. The diversity of the isolated naphthoquinone structures and their differences in terms of mycobacterial activity suggested that the location of the dimeric bond is important for the expression of antituberculosis activity. , …”

Section: Natural Products From the Yucatan Floramentioning

confidence: 99%

Natural Products from the Yucatecan Flora: Structural Diversity and Biological Activity

2019

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The Yucatan Peninsula possesses a unique climate, geology, landscape, and biota that includes a distinct flora of over 2300 species; of these, close to 800 plants are used in what is known as Mayan traditional medicine, and about 170 are listed as native or endemic. Even though the flora of the Yucatan peninsula has been widely studied by naturalists and biologists, to date, phytochemical and pharmacological knowledge of most of the plants, including the medicinal plants, is limited. Presently, phytochemical studies carried out on plants from the Yucatecan flora have resulted in the identification of a wide variety of natural products that include flavonoids, terpenoids, polyketides, and phenolics with cytotoxic, antiprotozoal, antibacterial, anti-inflammatory, analgesic, antioxidant, and antifungal activities. This review describes the main findings in over 20 years (1992 to 2018) of exploring the natural product diversity of the Yucatecan flora.

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“…These compounds have a highly oxygenated, 6/6/5/6/6‐fused A/B/C/D/E ring system. The related naphthoquinone dimers zeylanone,, zeylanone epoxide, and two shikometabolins, are shown in Figure b. Zeylanone shows antibacterial and antifungal activity . This compound also exhibits cytotoxic activity against cancer cell lines .…”

Section: Figurementioning

confidence: 99%

Total Syntheses of Juglorescein and Juglocombins A and B

et al. 2016

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Total syntheses of juglorescein and juglocombins A and B are reported. The highly oxygenated 6/6/5/6/6-fused pentacyclic ring system of these natural products was constructed through a bioinspired dimerization of 1,4-naphthoquinone. Notably, five new stereogenic centers were constructed in a single step by the dimerization reaction. The epoxide intermediate obtained from the dimerization was successfully converted into juglocombins A and B through photoinduced reduction of the epoxide, dehydration, and conversion of the resultant quinone into a hydroquinone derivative. The same epoxide intermediate was also converted into a dicarboxylic acid, which was transformed into juglorescein through intramolecular lactonization, hydrolysis of the resulting lactone, and removal of the protecting groups. Furthermore, the relative and absolute configurations of juglorescein and juglocombins A and B were determined.

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A new dimeric naphthoquinone fromDiospyros anisandra

Cited by 25 publications

References 15 publications

Ethnobotany and the Role of Plant Natural Products in Antibiotic Drug Discovery

Ethnobotany and the Role of Plant Natural Products in Antibiotic Drug Discovery

Natural Products from the Yucatecan Flora: Structural Diversity and Biological Activity

Total Syntheses of Juglorescein and Juglocombins A and B

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