Complementarity of DFT Calculations, NMR Anisotropy, and ECD for the Configurational Analysis of Brevipolides K–O from <i>Hyptis brevipes</i>

Suarez‐Ortiz, Gloria Alejandra; Cerda-Garcı́a-Rojas, Carlos M.; Fragoso‐Serrano, Mabel; Pereda‐Miranda, Rogelio

doi:10.1021/acs.jnatprod.6b00953

Cited by 31 publications

(36 citation statements)

References 46 publications

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“…This compound is structurally similar to hypurticin ( 167 ) that presents an acetoxy group linked to the lactone pyran ring ( Almtorp et al, 1991 ). Later, a series of chemical studies carried out with Hyptis brevipes led to the identification of fifteen new α -pyrones named brevipolides A – F ( 171 – 176 ) ( Deng et al, 2009 ), G – J ( 177 – 180 ) ( Suárez-Ortiz et al, 2013 ) and K – O ( 181 – 185 ) ( Suárez-Ortiz et al, 2017 ). Additionally, the compounds named monticolides A ( 186 ) and B ( 187 ) were obtained from Hyptis monticola Mart.…”

Section: Phytochemistrymentioning

confidence: 99%

Subtribe Hyptidinae (Lamiaceae): A promising source of bioactive metabolites

Bridi

Meirelles

Poser

2021

Journal of Ethnopharmacology

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Ethnopharmacological relevance The subtribe Hyptidinae contains approximately 400 accepted species distributed in 19 genera ( Hyptis , Eriope , Condea , Cantinoa , Mesosphaerum , Cyanocephalus , Hypenia , Hyptidendron , Oocephalus , Medusantha , Gymneia , Marsypianthes , Leptohyptis , Martianthus , Asterohyptis , Eplingiella , Physominthe , Eriopidion and Rhaphiodon ). This is the Lamiaceae clade with the largest number of species in Brazil and high rates of endemism. Some species have been used in different parts of the world mainly as insecticides/pest repellents, wound healing and pain-relief agents, as well as for the treatment of respiratory and gastrointestinal disorders. Aim of the review This review aims to discuss the current status concerning the taxonomy, ethnobotanical uses, phytochemistry and biological properties of species which compose the subtribe Hyptidinae. Materials and methods The available information was collected from scientific databases (ScienceDirect, Pubmed, Web of Science, Scopus, Google Scholar, ChemSpider, SciFinder ACS Publications, Wiley Online Library), as well as other literature sources (e.g. books, theses). Results The phytochemical investigations of plants of this subtribe have led to the identification of almost 300 chemical constituents of different classes such as diterpenes, triterpenes, lignans, α -pyrones, flavonoids, phenolic acids and monoterpenes and sesquiterpenes, as components of essential oils. Extracts, essential oils and isolated compounds showed a series of biological activities such as insecticide/repellent, antimicrobial and antinociceptive, justifying some of the popular uses of the plants. In addition, a very relevant fact is that several species produce podophyllotoxin and related lignans. Conclusion Several species of Hyptidinae are used in folk medicine for treating many diseases but only a small fraction of the species has been explored and most of the traditional uses have not been validated by current investigations. In addition, the species of the subtribe appear to be very promising as alternative sources of podophyllotoxin-like lignans which are the lead compounds for the semi-synthesis of teniposide and etoposide, important antineoplastic agents. Thus, there is a wide-open door for future studies, both to support the popular uses of the plants and to find new biologically active compoun...

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Section: Phytochemistrymentioning

confidence: 99%

Subtribe Hyptidinae (Lamiaceae): A promising source of bioactive metabolites

Bridi

Meirelles

Poser

2021

Journal of Ethnopharmacology

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“…In 2016, Suárez-Ortiz et al [96] isolated and described the absolute configuration of five new compounds named brevipolides K−O from H. brevipes . Taking brevipolide M 36 (Figure 4) as an example, it contains a distinctive THF ring in the structure.…”

Section: Tetrahydrofuransmentioning

confidence: 99%

An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies

Harmalkar

Choi

et al. 2019

Molecules

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Saturated oxygen heterocycles are widely found in a broad array of natural products and other biologically active molecules. In medicinal chemistry, small and medium rings are also important synthetic intermediates since they can undergo ring-opening and -expansion reactions. These applications have driven numerous studies on the synthesis of oxygen-containing heterocycles and considerable effort has been devoted toward the development of methods for the construction of saturated oxygen heterocycles. This paper provides an overview of the biological roles and synthetic strategies of saturated cyclic ethers, covering some of the most studied and newly discovered related natural products in recent years. This paper also reports several promising and newly developed synthetic methods, emphasizing 3–7 membered rings.

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“…Hyptis brevipes Poit. is an invasive plant species belonging to the mint family Lamiaceae [1][2][3][4]. This plant has been reported to originate from tropical America but is now distributed broadly in other tropical areas of the world [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Strategies for the synthesis of brevipolides

Kurniawan¹,

Rosyidah²

2021

Beilstein J. Org. Chem.

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In recent years fifteen 5,6-dihydro-α-pyrone derivatives, bearing either a distinctive cyclopropane or furan ring and named brevipolides A–O (1–15), have been isolated from the invasive plant Hyptis brevipes Poit. Their fascinating structural features, and the potent biological activities, including cytotoxicity against an array of human cancer cell lines and inhibition of the chemokine receptor CCR5, make them attractive synthetic targets. This review article highlights the recent synthetic methodologies and briefly summarizes their biological activities.

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Complementarity of DFT Calculations, NMR Anisotropy, and ECD for the Configurational Analysis of Brevipolides K–O from Hyptis brevipes

Cited by 31 publications

References 46 publications

Subtribe Hyptidinae (Lamiaceae): A promising source of bioactive metabolites

Subtribe Hyptidinae (Lamiaceae): A promising source of bioactive metabolites

An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies

Strategies for the synthesis of brevipolides

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