Investigations of antibacterial activities revealed that the incorporation of longer alkyl chains to the C-6 position in resorcylic acid conferred antibacterial properties against
Staphylococcus ...aureus
and
Bacillus subtilis
. The resultant olivetolic acid (OA) derivatives with
n
-undecyl and
n
-tridecyl side-chains, even those lacking the hydrophobic geranyl moiety from their C-3 positions, exhibited strong antibacterial activities against
B. subtilis
at a MIC value of 2.5 μM. Furthermore, the study demonstrated that the
n
-heptyl alkyl-chain modification at C-6 of cannabigerolic acid (CBGA) effectively enhanced the activity against
B. subtilis
, demonstrating the importance of the alkyl side-chain in modulating the bioactivity. Overall, the findings in this study provided insight into further evaluations of the antibacterial activities, as well as other various biological activities of OA and CBGA derivatives, especially with optimized hydrophobicities at both the alkyl and prenyl side-chain positions of the core skeleton for the discovery of novel drug seeds.
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EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, KILJ, KISLJ, MFDPS, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
2-(2-Phenylethyl)chromones (PECs) are the principal constituents contributing to the distinctive fragrance of agarwood. How PECs are biosynthesized is currently unknown. In this work, we describe a ...diarylpentanoid-producing polyketide synthase (PECPS) identified from Aquilaria sinensis. Through biotransformation experiments using fluorine-labeled substrate, transient expression of PECPS in Nicotiana benthamiana, and knockdown of PECPS expression in A. sinensis calli, we demonstrate that the C
-C
-C
scaffold of diarylpentanoid is the common precursor of PECs, and PECPS plays a crucial role in PECs biosynthesis. Crystal structure (1.98 Å) analyses and site-directed mutagenesis reveal that, due to its small active site cavity (247 Å
), PECPS employs a one-pot formation mechanism including a "diketide-CoA intermediate-released" step for the formation of the C
-C
-C
scaffold. The identification of PECPS, the pivotal enzyme of PECs biosynthesis, provides insight into not only the feasibility of overproduction of pharmaceutically important PECs using metabolic engineering approaches, but also further exploration of how agarwood is formed.
The therapeutic effects of Δ9-tetrahydrocannabinol (Δ9-THC) can be enhanced by modifications of the pentyl moiety at C-3. The engineering of Cannabis sativa olivetolic acid cyclase and tetraketide ...synthase with F24I and L190G substitutions, respectively, in the biosynthesis of Δ9-THC serves as a platform for the generation of resorcylic acids up to 6-undecylresorcylic acid. These results provide insights into the development of THC analogs with chemically distinct acyl moieties at C-3.
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IJS, KILJ, NUK, PNG, UL, UM
New copaene-type and nerolidol-type sesquiterpenoids, 7-hydroxymustakone (
1
) and 15-hydroxynerolidol (
2
), and a 15-norlabdane diterpenoid, kaempcandiol (
3
), together with four known compounds (
...4
–
7
) were isolated from the chloroform extract of
Kaempferia candida
roots and rhizomes. The structures of the new compounds
1
–
3
were elucidated based on 1D and 2D NMR and HRESIMS spectroscopic analyses. The extract of the
K. candida
roots and rhizomes and all isolated compounds
1
–
7
possessed HIV-1 viral protein R (Vpr) inhibitory activities on the TREx-HeLa-Vpr cell line at a 5 μM concentration, without detectable cytotoxicity.
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EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, KILJ, KISLJ, MFDPS, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
In this short review, we focus on some of the subjects, related to J. Cleymans’ pioneering contribution of statistical approaches to the particle production process in heavy-ion collisions. We ...discuss these perspectives from the effects of stochastic processes in collective variables of hydrodynamic description, which is described by a stochastic variational method. In this connection, we stress also the necessity of the inclusion of surface and quantum effects in the study of relativistic heavy-ion reactions.
A new brominated pyrrolactam stylissaol A (1) together with four known analogues, 2-bromoaldisine, aldisine, spongiacidin D, and Z-hymenialdisine, were isolated from the EtOAc extract of marine ...sponge Stylissa massa collected in Myanmar. The absolute configuration at C-10 of 1 was determined as R by the electronic circular dichroism (ECD) data. Among the isolated compounds, 2-bromoaldisine showed anti-Viral Protein R (Vpr) activity against TREx-HeLa-Vpr cells with an effective dose of 10 µM and its potency was comparable to that of positive control damnacanthal.
Two new trihydroxy derivative of Δ8(14),15-isopimarane diterpenoids, shanpanootols G (1) and H (2), along with three known analogues were isolated from the ethyl acetate-soluble extract of Kaempferia ...pulchra rhizomes collected in Shan State of Myanmar. The structures of these compounds including their absolute configurations were elucidated by the combination of one dimensional (1D) and 2D-NMR spectroscopic methods, high resolution mass spectrometric technique, and the experimental and the calculated electronic circular dichroism (ECD) data. The isopimarane diterpenoids (1–5) were tested for their Viral protein R (Vpr) inhibitory activities against TREx-HeLa-Vpr cells. Shanpanootol H (2) and (1R,2S,5S,9R,10S,13R)-1,2-dihydroxypimara-8(14),15-dien-7-one (4) exhibited anti-Vpr activities at the 5 µM treated dose.
Biologically active cannabinoids are derived from cannabigerolic acid (CBGA), which is biosynthesized by aromatic prenyltransferase CsPT4. We exploit the catalytic versatility of CsPT4 to synthesize ...various CBGA analogues, including a geranylated bibenzyl acid, the precursor to bibenzyl cannabinoids of liverwort origin. The synthesized natural and new-to-nature cannabinoids exhibit potent cytotoxicity in human pancreatic cancer cells. CsPT4 can artificially extend the cannabinoid biosynthetic diversity with novel and improved biological activities.
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IJS, KILJ, NUK, PNG, UL, UM
Arginases are bimanganese enzymes involved in many human illnesses, and thus are targets for disease treatments. The screening of traditional medicinal plants demonstrated that an ethanol extract of
...Curcuma comosa
rhizomes showed significant human arginase I and II inhibitory activity, and further fractionation led to the isolation of three known guaiane sesquiterpenoids, alismoxide (
1
), 7α,10α-epoxyguaiane-4α,11-diol (
2
) and guaidiol (
3
). Tests of their inhibitory activities on human arginases I and II revealed that
1
exhibited selective and potent competitive inhibition for human arginase I (IC
50
= 30.2 μM), whereas the other compounds lacked inhibitory activities against human arginases. To the best of our knowledge, this is the first demonstration of human arginase I inhibitory activity by a sesquiterpenoid. Thus,
1
is a primary and specific inhibitory molecule against human arginase I.
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EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, KILJ, KISLJ, MFDPS, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
In this work, a hydrodynamic study of the di-hadron azimuthal correlations for the Au+Au collisions at 200 GeV is carried out. The correlations are evaluated using the ZYAM method for the centrality ...windows as well as the transverse momentum range in accordance with the existing data. Event-plane dependence of the correlation is obtained after the subtraction of contributions from the most dominant harmonic coefficients. In particular, the contribution from the triangular flow, v3, is removed from the proper correlations following the procedure implemented by the STAR collaboration. The resultant structure observed in the correlations was sometimes attributed to the mini-jet dynamics, but the present calculations show that a pure hydrodynamic model gives a reasonable agreement with the main feature of the published data. A brief discussion on the physical content of the present findings is presented.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UILJ, UL, UM, UPCLJ, UPUK, ZAGLJ, ZRSKP
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