Myrsicorianol, A New Prenylated Benzoic Acid Derivative from <i>Myrsine Coriacea</i>

Amaro-Luis, Juan M.; Koteich-Khatib, Sonia; Carrillo-Rodríguez, Freddy; Bahsas, Ali

doi:10.1177/1934578x0800300304

Cited by 5 publications

(6 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the intervening period, MA-F and its various cometabolites, which can also be obtained from certain other plant sources, have been identified as HB-EGF inhibitors (and hence represent potential anticancer agents), as key elements of formulations for treating halitosis, as antimicrobial agents, and as compounds with notable antileishmanial properties . Given these pronounced activities and the absence of studies on the preparation of any cyclic members of the myrsinoic acid class, we sought to prepare compound 1 .…”

mentioning

confidence: 99%

Synthetic Studies on the Natural Product Myrsinoic Acid F Reveal Biologically Active Analogues

et al. 2018

View full text Add to dashboard Cite

The synthesis of the structure, 1, assigned to the anti-inflammatory natural product myrsinoic acid F is reported together with a means for preparing its Z-isomer 21. While neither of these compounds corresponds to the natural product, both of them are anti-inflammatory agents (as determined using a mouse ear edema assay) with congener 1 being notably more potent than the widely prescribed NSAID indometacin.

show abstract

mentioning

confidence: 99%

Synthetic Studies on the Natural Product Myrsinoic Acid F Reveal Biologically Active Analogues

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Additionally, the presence of two monoprenylated benzoic acid derivatives ( 13 and 14 ) was already reported for the related species Eriodictyon sessilifolium (Figure ). Prenylated benzoic acid derivatives are secondary metabolites, which are not widely distributed in nature . The biological activities of this class of compounds include anti-inflammatory , antifungal , antimicrobial , and antioxidative properties , .…”

Section: Resultsmentioning

confidence: 99%

Identification of Bisprenylated Benzoic Acid Derivatives from Yerba Santa (Eriodictyon ssp.) Using Sensory-Guided Fractionation

Reichelt

Hartmann

Weber

et al. 2010

J. Agric. Food Chem.

View full text Add to dashboard Cite

Due to certain off-flavor problems and lacking bitter masking effects with Yerba Santa (Eriodictyon angustifolium and E. californicum) extracts, which are also described as bitter, herbal, medicinal, phenolic, or astringent, methanolic extracts were fractionated and evaluated for their taste properties using a high temperature liquid chromatography (HTLC)-based approach. The taste-guided fractionation led to the identification of a series of novel bisprenylated benzoic acids (erionic acids A (1), B (2), C (3), D (4), E (5), and F (6) and eriolic acids A (7), B (8), C (9), and D (10), respectively), along with the known flavonoids eriodictyol, homoeriodictyol, hesperetin, and chrysoeriol. The new compounds were isolated in larger amounts for characterization from Narrow Leaf Yerba Santa (E. angustifolium) and California Yerba Santa (E. californicum), respectively, using fast centrifugal partition chromatography (FCPC) and HTLC. The structures were elucidated using one and two-dimensional NMR spectroscopy and high resolution mass spectrometry (HR-MS). For E. californicum, data regarding seasonal and climatic variation of the eriolic acid contents and of the flavonoids were collected. The flavor properties of some of the isolated new compounds were evaluated; they showed strong off-flavor characteristics, such as bitter, astringent, phenolic, or woody, and may contribute to the sensory effects observed for crude Yerba Santa extracts. Erionic acid C (3) was not only able to increase the absolute bitterness but also to extinguish the bitter masking effect of homoeriodictyol in a caffeine solution.

show abstract

“…NMR Analysis. 1 H, 13 C NMR, and 2D NMR spectra were acquired with an Avance III 600 MHz NMR spectrometer (Bruker). The NMR spectra were recorded in DMSO-d 6 referenced to residual solvent signals with resonances at δ H 2.49/δ C 39.5 ppm.…”

Section: ■ Methodsmentioning

confidence: 99%

“…During phytochemical analysis of Campylotropis hirtella , it was revealed that flavonoids with a prenyl group have higher antibacterial activities than the parent compounds, probably because these groups heighten lipophilicity and confer to the molecule a strong affinity for biological membranes . Among plant sources, the prenylated benzoic acid derivatives from Piper species are a source of anti-infective agents − and exhibit antiherbivore activity …”

mentioning

confidence: 99%

Combinatory Biosynthesis of Prenylated 4-Hydroxybenzoate Derivatives by Overexpression of the Substrate-Promiscuous Prenyltransferase XimB in Engineered E. coli

He¹,

Bu²,

Zhou³

et al. 2018

ACS Synth. Biol.

View full text Add to dashboard Cite

Prenylated aromatic compounds are important intermediates in the biosynthesis of bioactive molecules such as 3-chromanols from plants, ubiquinones from prokaryotes and meroterpenoids from sponges. Biosynthesis of prenylated aromatic compounds using prokaryotic microorganisms has attracted increasing attention in the field of synthetic biology. In this study, we demonstrated that the production of 3-geranyl-4-hydroxybenzoic acid (GBA) and a variety of GBA analogues was feasible in a metabolically engineered E. coli by using XimB, a special prenyltransferase involved in the biosynthesis of xiamenmycin A in Streptomyces xiamenensis 318. XimB exhibits broad substrate specificity and can catalyze the transfer reaction of prenyl moieties with different carbon chain lengths to both the natural substrate 4-hydroxybenzoate (4-HBA) and to different substituted 4-HBA derivatives at C-2 and C-3. Feeding 4-HBA to an engineered E. coli equipped with a hybrid mevalonate pathway increased the production of GBA up to 94.30 mg/L. Considerable amounts of other GBA derivatives, compounds 4, 5, 6, 7, and 9, can be achieved by feeding precursors. The plug-and-play design for inserting C, C, and C prenyl diphosphate synthetases under the control of the T7 promoter resulted in targeted production of 3-dimethylallyl, 3-farnesyl-, and 3-geranylgeranyl-4-hydroxybenzoic acid, respectively. Furthermore, the valuable benzopyran xiamenmycin B was successfully produced in E. coli R7-MVA by coexpression of a complete biosynthetic gene cluster, which contains ximBDE.

show abstract

Myrsicorianol, A New Prenylated Benzoic Acid Derivative from Myrsine Coriacea

Cited by 5 publications

References 26 publications

Synthetic Studies on the Natural Product Myrsinoic Acid F Reveal Biologically Active Analogues

Synthetic Studies on the Natural Product Myrsinoic Acid F Reveal Biologically Active Analogues

Identification of Bisprenylated Benzoic Acid Derivatives from Yerba Santa (Eriodictyon ssp.) Using Sensory-Guided Fractionation

Combinatory Biosynthesis of Prenylated 4-Hydroxybenzoate Derivatives by Overexpression of the Substrate-Promiscuous Prenyltransferase XimB in Engineered E. coli

Contact Info

Product

Resources

About