Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and Their Glycosides

García, Pablo A.; Oliveira, Alaı́de Braga de; Batista, Ronan

doi:10.1002/chin.200735259

Cited by 10 publications

(13 citation statements)

References 86 publications

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“…Other discriminant metabolites were kaurane diterpenoids such as annoglabasin A (methyl‐16 β ‐acetoxy‐19‐al‐ ent ‐kauran‐17‐oate)/annoglabasin B (16 α ‐hydro‐19‐acetoxy‐ ent ‐kauran‐17‐oic acid). These have been principally reported in fruits of Annona glabra , although they may be present in plant species belonging to several families, including mannic acid, a novel dimeric ent ‐kaurane diterpene identified in various Diospyros mannii tissues . The detection of ursanes such as ursa‐12,18‐dien‐3‐ol, 11‐methylgerberinol, and cinnamyl acetate was congruent with their previous identification in fruits of D. kaki and D. blancoi .…”

Section: Discussionsupporting

confidence: 79%

Fruits of wild and semi‐domesticated Diospyros tree species have contrasting phenological, metabolic, and antioxidant activity profiles

et al. 2019

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BACKGROUND In contrast to commercial Diospyros species, Mesoamerican fruit‐producing species are scarcely known, particularly wild species that might harbor desirable traits suitable for breeding. Thus, metabolomic, chemical, and antioxidant profiles of fruits harvested from cultivated Diospyros digyna and wild Diospyros rekoi trees during consecutive winter seasons were obtained. Fruits were harvested in habitats having marked differences in soil quality, climate, and luminosity. RESULTS D. digyna fruits were larger and less acid than D. rekoi fruits, whereas antioxidant activity tended to be higher in D. rekoi fruits. Phenolic, flavonoid, and sugar contents also varied significantly between species. Metabolomic analysis allowed the pre‐identification of 519 and 1665 metabolites in negative and positive electrospray ionization (ESI) modes, respectively. Principal component analysis of the positive ESI data explained 51.8% of the variance and indicated clear metabolomic differences between D. rekoi and D. digyna fruits that were confirmed by direct‐injection ESI mass spectrometry profiles. Twenty‐one discriminating metabolites were detected in fruits of both species; D. digyna fruits differentially accumulated lysophospholipids, whereas discriminating metabolites in D. rekoi fruits were chemically more diverse than those in D. digyna fruits. CONCLUSION Domesticated D. digyna fruits have improved physicochemical fruit traits compared with wild D. rekoi fruits, including larger size and lower acidity. The metabolomic and chemical composition of their respective fruits were also significantly different, which in D. rekoi was manifested as a notable season‐dependent increase in antioxidant capacity. Therefore, wild D. rekoi can be considered as an important genetic resource for the improvement of commercial Diospyros fruit quality. © 2019 Society of Chemical Industry

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Section: Discussionsupporting

confidence: 79%

Fruits of wild and semi‐domesticated Diospyros tree species have contrasting phenological, metabolic, and antioxidant activity profiles

et al. 2019

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“…Kaurane types of cyclized diterpenoids, mostly of the ent-series, are common constituents in traditional herbal remedies. Garcia et al [76] have reviewed in detail the occurrence and biological activities of kaurane diterpenes and their glycosides. Several kaurane diterpenoids are known to inhibit NF-kB signaling and to suppress inflammatory responses.…”

Section: Triptolidementioning

confidence: 99%

Terpenoids: natural inhibitors of NF-κB signaling with anti-inflammatory and anticancer potential

Salminen

Lehtonen

Suuronen³

et al. 2008

Cell. Mol. Life Sci.

372

252

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Traditional medicine has been a fertile source for revealing novel lead molecules for modern drug discovery. In plants, terpenoids represent a chemical defense against environmental stress and provide a repair mechanism for wounds and injuries. Interestingly, effective ingredients in several plant-derived medicinal extracts are also terpenoid compounds of monoterpenoid, sesquiterpenoid, diterpenoid, triterpenoid and carotenoid groups. Inflammatory diseases and cancer are typical therapeutic indications of traditional medicines. Thus folk medicine supports the studies which have demonstrated that plant-derived terpenoid ingredients can suppress nuclear factor-kappaB (NF-kappaB) signaling, the major regulator in the pathogenesis of inflammatory diseases and cancer.We review the extensive literature on the different types of terpenoid molecules, totalling 43, which have been verified both inhibiting the NF-kappaB signaling and suppressing the process of inflammation and cancer. It seems that during evolution, plants have established a terpene-based host defense which also represents a cornucopia of effective therapeutic compounds for common human diseases.

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“…Namely, the 'normal' series are the structures whose fusion between A and B rings occurs in the same way as in steroids, while the structures of the 'enantiomeric' series (denoted as ent) are the corresponding specular images of the normal series. [18] Furthermore, it has been demonstrated that P450 that are key enzymes in plants, catalyze the three steps of oxidation of ent-kaurene to ent-kaurenoic acid in several plant species (CH 3 !CH 2 OH/kaurenol!CHO/ kaurenal!COOH/kaurenoic acid), as well as the oxidation of (À )-kaurenoic acid to the ent-7-α-hydroxykaurenoic acid. [36 -40] Oxidation of ent-7-α-hydroxykaurenoic acid to the ent-7-oxoderivative was detected in an investigation of gibberellin biosynthesis in bacteria.…”

Section: Resultsmentioning

confidence: 99%

A Comprehensive View on (−)‐7‐Oxo‐ent‐kaur‐16‐en‐19‐oic Acid, the Major Constituent of Xylopia sericea Leaves Extract: Complete NMR Assignments, X‐Ray Crystallographic Structure, in Vitro Antimalarial Activity and Cytotoxicity

Gontijo

Nascimento

Borgati

et al. 2019

Chemistry & Biodiversity

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Bioguided fractionation of Xylopia sericea antiplasmodial dichloromethane leaves extract led to the isolation of (−)‐7‐oxo‐ent‐kaur‐16‐en‐19‐oic acid (C20H28O3) that was identified by a combination of 1D and 2D NMR experiments (COSY, HMBC, HSQC, HSQC‐TOCSY, HSQC‐NOESY and NOESY) and by X‐ray crystallography. A feature to be pointed out is its (4R) configuration that was inferred from the NOE experiments (HSQC‐NOESY and NOESY) and X‐ray crystallography. In vitro evaluation of this rare diterpene acid against the chloroquine‐resistant strain Plasmodium falciparum W2 by the PfLDH method showed it disclosed a low antiplasmodial activity and was not cytotoxic to HepG2 cells (CC50 862.6±6.7 μm) by the MTT assay. The unequivocal NMR signals assignments, the X‐ray crystallographic structure, the assessment to the bioactivities and the occurrence this diterpene in X. sericea are reported here for the first time.

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Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and Their Glycosides

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 10 publications

References 86 publications

Fruits of wild and semi‐domesticated Diospyros tree species have contrasting phenological, metabolic, and antioxidant activity profiles

Fruits of wild and semi‐domesticated Diospyros tree species have contrasting phenological, metabolic, and antioxidant activity profiles

Terpenoids: natural inhibitors of NF-κB signaling with anti-inflammatory and anticancer potential

A Comprehensive View on (−)‐7‐Oxo‐ent‐kaur‐16‐en‐19‐oic Acid, the Major Constituent of Xylopia sericea Leaves Extract: Complete NMR Assignments, X‐Ray Crystallographic Structure, in Vitro Antimalarial Activity and Cytotoxicity

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