New Sesterterpene Diolyl Butanoate from Rice Straw of Oryza sativa

Yang, Ye-Seul; Chung, Ill‐Min; Kim, Seung Hyun; Ahmad, Ateeque

doi:10.14233/ajchem.2014.17848

Cited by 5 publications

(2 citation statements)

References 3 publications

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“…In the literature review, compounds 5a, 5b, and 5c were not found. A literature survey showed that some of the natural compounds contain sesquiterpene part of compounds 5a-c [47][48].…”

Section: Structure Elucidationmentioning

confidence: 99%

Antimicrobial, Cytotoxic, Antiviral Effects, and Spectroscopic Characterization of Metabolites Produced by Fusarium oxysporum YP9B

Kılıç¹,

Tosun²,

Bozdeveci³

et al. 2021

Rec.Nat.Prod.

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The goal of the work is to determine the bioactive pharmaceutical metabolites produced by the Fusarium oxysporum YP9B isolate. Ten new natural compounds were isolated from the ethyl acetate extract of the F. oxysporum YP9B strain. Their structures were elucidated by spectroscopic methods using 1D and 2D NMR, UV, FT-IR, and mass spectra (LC-QTOF MS and GC-FID/MS). Identified compounds were named as; (1-benzyl-2-methoxy-2-oxoethyl)-2-hydroxy-3-methylbutanoate (1), 2-oxo-8-azatricyclo[9.3.1.13,7]-hexadeca-1(15),3(16),4,6,11,13-hexaen-10-one (2), 2,3-dihydroxypropanoic, hexadecanoic anhydride (3a), 2,3-dihydroxypropanoic (9Z)-octadecenoic anhydride (3b), 2,3-dihydroxy-propanoic (9Z,12Z)-octadecadienoic anhydride (3c), 2,3-dihydroxypropanoic (11Z)-octadecenoic anhydride (4a), 2,3-dihydroxypropanoic, (9E,12E)-octadecadienoic anhydride (4b), 3-hydroxy-1,2,6,10-tetramethylundecyl hexzadecanoate (5a), 3-hydroxy-1,2,6,10-tetramethylundecyl (9E)-octadecaenoate (5b), and 3-hydroxy-1,2,6,10-tetramethylundecyl octadecanoate (5c). Antimicrobial activities of the isolates obtained from the YP9B strain were determined. Cytotoxic and antiviral activities were tested for the isolates against VERO, MCF-7, PC-3, and A549. Compounds 5a-c, 1, and 3a-c showed bacteriostatic activity at low concentrations, and 4a-b and 2 were found to be bactericides. MIC and MBC values against Mycobacterium smegmatis for the compounds 5a-c and 1 were determined to be <0.5 µg/mL and 0.46 µg/mL, respectively. The experimental result showed that compounds 2, 5a-c and 1 have strong cytotoxic (7.51±1.38 and 19.13± 0.68 (µM) IC50) activity. The antiviral activity against HSV type-1 was determined to be 1.25 µM for compounds 4a-c and 0.312 µM for compound 1.

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“…In the literature review, compounds 5a, 5b, and 5c were not found. A literature survey showed that some of the natural compounds contain sesquiterpene part of compounds 5a-c [47][48].…”

Section: Structure Elucidationmentioning

confidence: 99%

Antimicrobial, Cytotoxic, Antiviral Effects, and Spectroscopic Characterization of Metabolites Produced by Fusarium oxysporum YP9B

Kılıç¹,

Tosun²,

Bozdeveci³

et al. 2021

Rec.Nat.Prod.

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“…In particular, plant sesterterpenoids derived from geranylfarnesyl diphosphate (GFDP, C 25 ) are a relatively unexplored subgroup of terpenoids, with only about 190 members characterized to date ( Guo et al., 2021 ). Plant sesterterpenoids are widely distributed in lichens, ferns, and angiosperms, including the three important food crops rice ( Oryza sativa ) ( Yang et al., 2014 ), wheat ( Triticum aestivum ) ( Akihisa et al., 1999 ), and potato ( Solanum tuberosum ) ( Toyoda et al., 1969 ). They show high structural diversity and remarkable biological functions involving anti-inflammatory, cytotoxic, antimicrobial, and antifeedant activities ( Liu et al., 2016 ; Guo et al., 2021 ).…”

Section: Introductionmentioning

confidence: 99%

An extremely promiscuous terpenoid synthase from the Lamiaceae plant Colquhounia coccinea var. mollis catalyzes the formation of sester-/di-/sesqui-/mono-terpenoids

Jin

Luo

et al. 2021

Plant Communications

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Terpenoids are the largest class of natural products with complex structures and extensive bioactivities; their scaffolds are generated by diverse terpenoid synthases (TPSs) from a limited number of isoprenoid diphosphate precursors. Promiscuous TPSs play important roles in the evolution of terpenoid chemodiversity, but they remain largely unappreciated. Here, an extremely promiscuous terpenoid synthase (CcTPS1) of the TPS-b subfamily was cloned and functionally characterized from a leaf-specific transcriptome of the Lamiaceae plant Colquhounia coccinea var. mollis . CcTPS1 is the first sester-/di-/sesqui-/mono-TPS identified from the plant kingdom, accepting C 25 /C 20 /C 15 /C 10 diphosphate substrates to generate a panel of sester-/di-/sesqui-/mono-terpenoids. Engineered Escherichia coli expressing CcTPS1 produced three previously unreported terpenoids (two sesterterpenoids and a diterpenoid) with rare cyclohexane-containing skeletons, along with four sesquiterpenoids and one monoterpenoid. Their structures were elucidated by extensive nuclear magnetic resonance spectroscopy. Nicotiana benthamiana transiently expressing CcTPS1 also produced the diterpenoid and sesquiterpenoids, demonstrating the enzyme’s promiscuity in planta . Its highly leaf-specific expression pattern combined with detectable terpenoid products in leaves of C . coccinea var. mollis and N. benthamiana expressing CcTPS1 suggested that CcTPS1 was mainly responsible for diterpenoid and sesquiterpenoid biosynthesis in plants. CcTPS1 expression and the terpenoid products could be induced by methyl jasmonate, suggesting their possible role in plant–environment interaction. CcTPS1 was localized to the cytosol and may differ from mono-TPSs in subcellular compartmentalization and substrate tolerance. These findings will greatly aid our understanding of plant TPS evolution and terpenoid chemodiversity; they also highlight the enormous potential of transcriptome mining and heterologous expression for the exploration of unique enzymes and natural products hidden in plants.

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