Rhodomyrtone, an antibotic from Rhodomyrtus tomentosa

Hamidi, Dachriyanus; Salni,; Sargent, Melvyn V.; Skelton, Brian W.; Soediro, Iwang; Sutisna, Mumu; White, Allan H.; Yulinah, Elin

doi:10.1071/ch01194

Cited by 103 publications

(47 citation statements)

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“…Two compounds (1 and 2) were isolated from the 90% acetonitrile layer of peel, and two (3 and 4) from the seeds. Compound 2 was characterized as an acylphloroglucinol isolated from Rhodomyrtus tomentosa, 12) as previously reported. Compound 3 was identified as an acylphloroglucinol, isomyrtucommulone B. Appendino et al reported that isomyrtucommulone B is an isomer of myrtucommulone B, and was a thermal degradation product of a trimeric acylphloroglucinol, myrtucommulone A.…”

Section: Resultsmentioning

confidence: 91%

Antimicrobial constituents of peel and seeds of camu-camu (Myrciaria dubia)

Kaneshima

Myoda

Toeda

et al. 2017

Bioscience, Biotechnology, and Biochemistry

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Various antimicrobial constituents of camu-camu fruit were isolated. Acylphloroglucinol (compound 1) and rhodomyrtone (compound 2) were isolated from the peel of camu-camu (Myrciaria dubia) fruit, while two other acylphloroglucinols (compounds 3 and 4) were obtained from camu-camu seeds. The structures of the isolated compounds were characterized by spectrophotometric methods. Compounds 1 and 4 were confirmed to be new acylphloroglucinols with different substituents at the C7 or C9 position of 2, and were named myrciarone A and B, respectively. Compound 3 was determined to be isomyrtucommulone B. This is the first report of the isolation of 3 from a natural resource. The antimicrobial activities of compounds 1, 3, and 4 were similar to those of 2, and the minimum inhibitory concentrations were either similar to or lower than that of kanamycin. These results suggest that the peel and seeds of camu-camu fruit could be utilized for therapeutic applications.

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Section: Resultsmentioning

confidence: 91%

Antimicrobial constituents of peel and seeds of camu-camu (Myrciaria dubia)

Kaneshima

Myoda

Toeda

et al. 2017

Bioscience, Biotechnology, and Biochemistry

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“…4 H ‐Chromenes are a core structural feature of an array of fascinating natural products that have intriguing biological activities (Scheme ). For example, rhodomyrtone and rhodomyrtosone B show potent antibiotic activities,7 whereas the dimeric 4 H ‐chromene acylphloroglucinol, myrtucommulone E, serves as a promising α‐glucosidase inhibitor with antibacterial activity 8. These frameworks have become attractive targets in organic synthesis,9, 10 and, despite significant advances having been made, asymmetric methods for their construction are still extremely rare 11…”

Section: Methodsmentioning

confidence: 99%

Iminium–Allenamine Cascade Catalysis: One‐Pot Access to Chiral 4H‐Chromenes by a Highly Enantioselective Michael–Michael Sequence

2010

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“…During the past few years, a number of unusual phloroglucinol derivatives such as rhodomyrtone, 3 rhodomyrtosones, 4 and tomentosones, 5 have been isolated from Rhodomyrtus tomentosa. Among them, rhodomyrtone displayed potent anti-bacterial activity, especially against methicillin-resistant Staphylococcus aureus.…”

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Rhodomyrtals A–D, four unusual phloroglucinol-sesquiterpene adducts from Rhodomyrtus psidioides

et al. 2014

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The genus Rhodomyrtus (Myrtaceae) consists of 17 species, which are native to Asia, Malesia, Melanesia, and Australia. 1,2During the past few years, a number of unusual phloroglucinol derivatives such as rhodomyrtone, 3 rhodomyrtosones, 4 and tomentosones, 5 have been isolated from Rhodomyrtus tomentosa. Among them, rhodomyrtone displayed potent anti-bacterial activity, especially against methicillin-resistant Staphylococcus aureus.6 In our efforts to discover natural products with potential application in wound healing, we have examined the Australian endemic species Rhodomyrtus psidioides (G. Don) Benth. This species, commonly called native guava, is a shrub or small rainforest tree, which grows up to 12 m high, native to eastern Australia.7 Chemical investigations of the leaves of this plant led to the isolation of four novel compounds (1-4) (Fig. 1) that possess two new phloroglucinolcoupled eudesmane skeletons, as well as the known compound eucalyptin A (5). Herein, details of the isolation, structural elucidation, and antibacterial activity of the rhodomyrtals A-D (1-4) are described. .5] as well as an oxygenated carbon at d C 71.3. The aforementioned data suggested a phloroglucinol-coupled sesquiterpenoid for compound 1. The above mentioned functionalities accounted for 7 out of the 9 double-bond equivalents, which indicated the presence of two rings in compound 1. The key HMBC correlations (Fig. 2)

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Rhodomyrtone, an antibotic from Rhodomyrtus tomentosa

Cited by 103 publications

References 0 publications

Antimicrobial constituents of peel and seeds of camu-camu (Myrciaria dubia)

Antimicrobial constituents of peel and seeds of camu-camu (Myrciaria dubia)

Iminium–Allenamine Cascade Catalysis: One‐Pot Access to Chiral 4H‐Chromenes by a Highly Enantioselective Michael–Michael Sequence

Rhodomyrtals A–D, four unusual phloroglucinol-sesquiterpene adducts from Rhodomyrtus psidioides

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