Phloroglucinol derivatives and a chromone glucoside from the leaves of Myrtus communis

Tanaka, Naonobu; Jia, Yuyu; Niwa, Kanji; Imabayashi, Kiyoshi; Tatano, Yutaka; Yagi, Hideki; Kashiwada, Yoshiki

doi:10.1016/j.tet.2017.11.044

Cited by 13 publications

(13 citation statements)

References 23 publications

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“…Our biosynthetic proposal for hyperireflexolides A and B ( 1 and 3 ), which asserts their meroterpenoid and PPAP origin, is outlined in Scheme 1. Acylphloroglucinol 13 is an aromatic polyketide commonly invoked in the biosynthesis of PPAPs, and it is the aglycone component of a recently isolated glycoside [9] . Di‐prenylation of 13 at C8 (hyperireflexolide numbering) gives the dearomatized β‐acid 15 , which could undergo single electron oxidation at C10 to form the stabilized β‐diketo radical 16 .…”

Section: Resultsmentioning

confidence: 99%

Intramolecular Tricarbonyl‐Ene Reactions and α‐Hydroxy‐β‐Diketone Rearrangements Inspired by the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols

et al. 2022

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Structurally unique natural products pose biosynthetic puzzles whose solution can inspire new chemical reactions. Herein, we propose a unified biosynthetic pathway towards some complex meroterpenoids-the hyperireflexolides, biyoulactones, hybeanones and hypermonones. This hypothesis led to the discovery of uncatalyzed, intramolecular carbonyl-ene reactions that are spontaneous at room temperature. We also developed an anionic cascade reaction featuring an α-hydroxy-β-diketone rearrangement and an intramolecular aldol reaction to access four distinct natural product scaffolds from a common intermediate.

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Section: Resultsmentioning

confidence: 99%

Intramolecular Tricarbonyl‐Ene Reactions and α‐Hydroxy‐β‐Diketone Rearrangements Inspired by the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols

et al. 2022

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“…The available literature concerning Myrtaceae also reports the existence of products that are not classifiable as acylphloroglucinol oligomers, and are hence not included in this review. Particularly, monomers of either acylphloroglucinol (e.g., callisalignene A–C [25], xanchryone A–D [55], operculatol A–B [56]) or syncarpic acid (e.g., myrtucommulone K [35,57], callistiviminene A–O [58]), and flavonoids conjugated to a syncarpic acid residue (e.g., kunzeanones A–C [59], myrtocummunines A–D [51]).…”

Section: Structures and Chemical Propertiesmentioning

confidence: 99%

Structures and Bioactive Properties of Myrtucommulones and Related Acylphloroglucinols from Myrtaceae

et al. 2018

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Myrtaceae are a group of plants that include a number of renowned species used in ethnomedicine in many areas worldwide. Their valuable therapeutic properties have stimulated a fruitful research activity addressed to the identification of the bioactive components of their extracts yielding a great diversity of terpenes; polyphenols; and other exclusive products. Among the latter, starting with the discovery of myrtucommulone A from myrtle (Myrtus communis), a series of structurally-related acylphloroglucinol compounds have been characterized from several species that represent the basic active principles to be considered in view of possible drug development. Aspects concerning chemical and biological properties of these products are reviewed in the present paper.

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“…Drynaria fortunei rhizomes [22] Inhibitory activity on triglyceride accumulation (inhibited PPARγ, C/EBPα and aP2 expression by 50%, 43% and 37% at 10 mM) [22] Undulatoside A 6 -O-gallate Myrtus communis leaves [48] Corymbosin K3…”

Section: -O-(6 -Galloyl)-β-dglucopyranosyl-5hydroxychromonementioning

confidence: 99%

Naturally Occurring Chromone Glycosides: Sources, Bioactivities, and Spectroscopic Features

et al. 2021

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Chromone glycosides comprise an important group of secondary metabolites. They are widely distributed in plants and, to a lesser extent, in fungi and bacteria. Significant biological activities, including antiviral, anti-inflammatory, antitumor, antimicrobial, etc., have been discovered for chromone glycosides, suggesting their potential as drug leads. This review compiles 192 naturally occurring chromone glycosides along with their sources, classification, biological activities, and spectroscopic features. Detailed biosynthetic pathways and chemotaxonomic studies are also described. Extensive spectroscopic features for this class of compounds have been thoroughly discussed, and detailed 13C-NMR data of compounds 1–192, have been added, except for those that have no reported 13C-NMR data.

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Phloroglucinol derivatives and a chromone glucoside from the leaves of Myrtus communis

Cited by 13 publications

References 23 publications

Intramolecular Tricarbonyl‐Ene Reactions and α‐Hydroxy‐β‐Diketone Rearrangements Inspired by the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols

Intramolecular Tricarbonyl‐Ene Reactions and α‐Hydroxy‐β‐Diketone Rearrangements Inspired by the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols

Structures and Bioactive Properties of Myrtucommulones and Related Acylphloroglucinols from Myrtaceae

Naturally Occurring Chromone Glycosides: Sources, Bioactivities, and Spectroscopic Features

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