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	<title>lignans &#8211; Science</title>
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	<title>lignans &#8211; Science</title>
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		<title>Sprouted Flaxseed Oil Supercharges Brain Lipids in Mice Despite Losing Some Omega-3</title>
		<link>https://scienmag.com/sprouted-flaxseed-oil-supercharges-brain-lipids-in-mice-despite-losing-some-omega-3/</link>
		
		<dc:creator><![CDATA[Cassandra Pierce]]></dc:creator>
		<pubDate>Mon, 19 Oct 2026 16:15:14 +0000</pubDate>
				<category><![CDATA[Chemistry]]></category>
		<category><![CDATA[alpha-linolenic acid]]></category>
		<category><![CDATA[alpha-linolenic acid reduction during sprouting]]></category>
		<category><![CDATA[brain lipidomics]]></category>
		<category><![CDATA[C57BL/6J mice]]></category>
		<category><![CDATA[DHA]]></category>
		<category><![CDATA[effects of flaxseed oil on mice brain lipids]]></category>
		<category><![CDATA[EPA]]></category>
		<category><![CDATA[flaxseed]]></category>
		<category><![CDATA[flaxseed oil]]></category>
		<category><![CDATA[Food Chemistry: X]]></category>
		<category><![CDATA[germinated versus ungerminated flaxseed oil chemical composition]]></category>
		<category><![CDATA[germination]]></category>
		<category><![CDATA[impact of germination on flaxseed lipid profile]]></category>
		<category><![CDATA[lignans]]></category>
		<category><![CDATA[neural development and brain health from plant-based omega-3s]]></category>
		<category><![CDATA[omega-3 and omega-6 fatty acids balance]]></category>
		<category><![CDATA[omega-3 fatty acids]]></category>
		<category><![CDATA[omega-3 fatty acids in plant oils]]></category>
		<category><![CDATA[phytosterols]]></category>
		<category><![CDATA[role of flaxseed in cardiovascular health]]></category>
		<category><![CDATA[Sprouted flaxseed oil benefits]]></category>
		<category><![CDATA[trade-offs of flaxseed germination process]]></category>
		<guid isPermaLink="false">https://scienmag.com/?p=313664</guid>

					<description><![CDATA[A new mouse study shows that germinating flaxseed before oil extraction lowers its alpha-linolenic acid content but dramatically enriches lignans and sterols, yielding distinct changes in brain lipid composition.]]></description>
										<content:encoded><![CDATA[<p>Flaxseed oil is one of the richest plant sources of alpha-linolenic acid, an essential omega-3 fatty acid that the human body cannot make on its own. Because most people get their long-chain omega-3s, EPA and DHA, from seafood, those with limited access to fish risk falling short of fats that are critical for neural development, cardiovascular protection, and possibly resilience against Alzheimer&#8217;s disease. A new study published in Food Chemistry: X now asks a deceptively simple question: what happens if you let the flaxseed sprout before you press it into oil? The answer, drawn from a detailed chemical characterization and a thirteen-week feeding trial in mice, is a fascinating trade-off between what germination takes away and what it gives back.</p>
<p>The research team, led by Zeqing Huang and Xiuzhu Yu of Northwest A&amp;F University, germinated flaxseed for four days under controlled conditions of darkness, 25 degrees Celsius, and 80 percent relative humidity, then roasted and screw-pressed both germinated and ungerminated seeds into oil. Gas chromatography analysis revealed that germination measurably reshaped the fatty acid profile. Alpha-linolenic acid, the star molecule of flaxseed oil, dropped from 57.17 percent to 53.35 percent of total fatty acids, while linoleic acid, the main omega-6 fatty acid, slipped from 16.14 percent to 15.52 percent. In their place, the relative proportions of palmitic, stearic, and oleic acids rose. The reason is metabolic economics: a germinating seed is an energy-hungry organism, and it burns stored long-chain fatty acids through beta-oxidation to generate acetyl coenzyme A that fuels the construction of new tissues.</p>
<p>But the loss of omega-3 was only half the story. When the researchers quantified the minor components of the oils, germination proved to be a powerful enrichment tool. Total sterols increased, with cycloartenol rising significantly from 25.65 to 33.07 milligrams per kilogram, likely because rapidly dividing cells need sterols as structural building blocks for new membranes. More striking still were the lignans, diphenolic phenolic compounds famous for their antioxidant, anti-inflammatory, and cholesterol-lowering activities. Pinoresinol diglucoside leapt from 2.86 to 32.60 milligrams per kilogram, its free form pinoresinol climbed from 10.11 to 25.10 milligrams per kilogram, and secoisolariciresinol diglucoside, undetectable in the ungerminated oil, appeared at 9.56 milligrams per kilogram. The authors attribute this surge to the shikimate pathway, which germination activates by releasing phosphoenolpyruvate and free amino acids from stored reserves, feeding the biosynthesis of aromatic precursors for lignans.</p>
<p>Why does this matter nutritionally? Accumulating evidence suggests that flaxseed lignans can facilitate the conversion of alpha-linolenic acid into EPA and DHA by up-regulating the elongase and desaturase enzymes of the omega-3 biosynthetic pathway while inhibiting beta-oxidation. That conversion pathway is long and inefficient: alpha-linolenic acid is first desaturated by FADS2, elongated, desaturated again by FADS1 to form EPA, and then, after further elongation and a second FADS2-dependent desaturation to C24:6n-3, trimmed by one round of peroxisomal beta-oxidation to yield DHA. The liver carries out this sequence most effectively, while the brain, testes, and kidneys show far more limited capacity. So a germinated oil with slightly less alpha-linolenic acid but many more lignans could, in principle, deliver equal or better omega-3 nutrition.</p>
<p>To test this, the team ran a thirteen-week dietary intervention in male C57BL/6J mice, dividing them into three groups of twelve. One group received a modified AIN-76A diet based on soybean oil, a second ate the same diet built on ungerminated flaxseed oil, and a third received the germinated flaxseed oil version, each containing roughly 11.7 percent oil by weight. Throughout the trial, body weight, adipose tissue mass, and plasma biochemistry, including triglycerides, total cholesterol, LDL-cholesterol, and HDL-cholesterol, remained normal and statistically indistinguishable across groups. That metabolic stability matters, because it means any differences in tissue fatty acids could be attributed to the oils themselves rather than to obesity, malnutrition, or systemic metabolic disruption.</p>
<p>The tissue results told a clear story about peripheral omega-3 status. In adipose tissue, mice fed either flaxseed oil showed dramatically higher alpha-linolenic acid proportions, around 21 to 23 percent compared with roughly 4 percent in the soybean oil group, and sharply lower linoleic acid. In red blood cells, which integrate dietary fat intake over long periods, the flaxseed oil groups accumulated significantly more alpha-linolenic acid and EPA over the thirteen weeks, while oleic and linoleic acid proportions declined. Crucially, however, DHA and arachidonic acid proportions did not budge in any group. And despite the germinated oil containing less alpha-linolenic acid, tissue levels of alpha-linolenic acid and EPA were essentially identical between the two flaxseed groups, suggesting the lignan-rich oil lost nothing in practical nutritional terms.</p>
<p>The most intriguing part of the study came when the researchers turned to the brain. Using high-performance liquid chromatography coupled with triple quadrupole mass spectrometry, they profiled brain lipids and identified thirty lipid species, with phosphatidylcholines the most abundant class. Principal component analysis showed that the two flaxseed oil groups clustered together and separated from the soybean oil controls, indicating a shared shift in brain lipid composition. Among eighteen EPA- and DHA-containing lipid species examined, several were elevated in the flaxseed-fed mice relative to controls, including DHA-bearing phosphatidylcholines, phosphatidylethanolamines, and other phospholipid classes that are fundamental constituents of neuronal membranes.</p>
<p>One species stood out from the pattern. Phosphatidylinositol 40:6, containing DHA, was significantly higher in the germinated flaxseed oil group than in both the soybean oil and ungerminated flaxseed oil groups, a selective effect that hints the extra lignans may have nudged brain lipid metabolism in a distinct direction. The authors are appropriately cautious about interpretation: the functional consequences of these lipidomic changes remain to be established. Still, the rationale for caring is strong. In experimental hippocampal models, DHA supplementation has been shown to promote neurite growth, synaptic protein expression, and synaptic activity, while deprivation of omega-3 fatty acids during development impairs long-term potentiation, the cellular substrate of learning and memory.</p>
<p>Why did DHA in red blood cells stay flat even as DHA-containing brain phospholipids rose? The authors weigh several mechanisms. Lignan metabolites such as enterolactone have been shown to alter lipid export and fatty acid oxidation proteins in liver cells, and redox-dependent regulation of desaturase activity offers another route. A physiological plateau is also plausible: both flaxseed diets may have supplied enough alpha-linolenic acid that tissue incorporation became insensitive to the modest difference between the oils. Mouse liver studies further suggest the conversion system is nonlinear, with the second delta-6 desaturation step acting as a rate limiter and DHA itself inhibiting FADS2. Because daily food intake was not recorded, the team cannot yet distinguish between greater conversion efficiency and simple substrate sufficiency.</p>
<p>The study&#8217;s practical message is that germination should be evaluated as a whole-system pretreatment rather than judged by any single metric. Four days of sprouting lowered the headline omega-3 number and, as earlier work from the same group showed, reduced oil yield, yet it multiplied the lignan content many times over, enriched sterols, and left tissue omega-3 outcomes essentially intact while producing a unique brain lipidomic signature. For food scientists optimizing germination conditions, the challenge is now to balance alpha-linolenic acid retention, lignan and sterol enrichment, and oil recovery. For the rest of us, the humble flaxseed, given a few days to sprout, may quietly become a more sophisticated functional food than its ungerminated self, one whose benefits reach all the way to the lipids of the brain.</p>
<p><strong>Subject of Research:</strong> Effects of flaxseed germination on oil composition, tissue omega-3 fatty acid profiles, and brain lipidomics in mice</p>
<p><strong>Article Title:</strong> Effects of flaxseed germination on oil composition, tissue n-3 fatty acid profiles, and brain lipidomics in mice</p>
<p><strong>Article References:</strong> Huang, Z., Xu, S., Li, Y., Huang, K., Liu, C., Gao, Y., Li, Q., &amp; Yu, X. (2026). Effects of flaxseed germination on oil composition, tissue n-3 fatty acid profiles, and brain lipidomics in mice. <em>Food Chemistry: X</em>, Article 104654. <a href="https://doi.org/10.1016/j.fochx.2026.104654" rel="noopener noreferrer">https://doi.org/10.1016/j.fochx.2026.104654</a></p>
<p><strong>Image Credits:</strong> AI Generated</p>
<p><strong>DOI:</strong> <a href="https://doi.org/10.1016/j.fochx.2026.104654" rel="noopener noreferrer">10.1016/j.fochx.2026.104654</a></p>
<p><strong>Keywords:</strong> flaxseed, germination, alpha-linolenic acid, omega-3 fatty acids, EPA, DHA, lignans, phytosterols, brain lipidomics, C57BL/6J mice, flaxseed oil, Food Chemistry: X</p>
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		<post-id xmlns="com-wordpress:feed-additions:1">313664</post-id>	</item>
		<item>
		<title>Feeding a flavonoid to trick flax roots into making more anticancer lignan</title>
		<link>https://scienmag.com/feeding-a-flavonoid-to-trick-flax-roots-into-making-more-anticancer-lignan/</link>
		
		<dc:creator><![CDATA[Ophelia Keating]]></dc:creator>
		<pubDate>Sat, 17 Oct 2026 20:17:59 +0000</pubDate>
				<category><![CDATA[Medicine]]></category>
		<category><![CDATA[Science News]]></category>
		<category><![CDATA[biofortification of plant secondary metabolites]]></category>
		<category><![CDATA[competitive]]></category>
		<category><![CDATA[enhancement of anticancer lignan production in plants]]></category>
		<category><![CDATA[European flax species for medicinal compound extraction]]></category>
		<category><![CDATA[flavonoid-mediated pathway rerouting in plants]]></category>
		<category><![CDATA[flax root metabolic engineering]]></category>
		<category><![CDATA[in vitro cultivation techniques for]]></category>
		<category><![CDATA[in vitro plant root culture for medicinal compound synthesis]]></category>
		<category><![CDATA[in vitro root cultures]]></category>
		<category><![CDATA[inhibition]]></category>
		<category><![CDATA[justicidin B]]></category>
		<category><![CDATA[lignans]]></category>
		<category><![CDATA[Linum]]></category>
		<category><![CDATA[metabolic]]></category>
		<category><![CDATA[natural sources of arylnaphthalene lignans]]></category>
		<category><![CDATA[pathways]]></category>
		<category><![CDATA[phenylpropanoid pathway]]></category>
		<category><![CDATA[phytochemical boosting through flavonoid feeding]]></category>
		<category><![CDATA[plant biotechnology]]></category>
		<category><![CDATA[plant secondary metabolite biosynthesis optimization]]></category>
		<category><![CDATA[secondary metabolites]]></category>
		<category><![CDATA[sustainable drug development from plant metabolites]]></category>
		<category><![CDATA[sustainable production of justicidin B]]></category>
		<category><![CDATA[vitexin]]></category>
		<guid isPermaLink="false">https://scienmag.com/?p=301194</guid>

					<description><![CDATA[Exogenous vitexin supplementation significantly boosts justicidin B accumulation in Linum root cultures by rerouting the phenylpropanoid pathway toward lignan biosynthesis.]]></description>
										<content:encoded><![CDATA[<p>Justicidin B is one of those molecules that makes medicinal chemists sit up and pay attention. It belongs to the arylnaphthalene lignans, a family of plant secondary metabolites built from the phenylpropanoid pathway, and decades of pharmacological testing have attributed pronounced anticancer, antiviral, antimicrobial, antioxidant, anti-inflammatory, and antiparasitic activities to it. The catch is supply. Plants make justicidin B only in trace amounts, wild populations of the species that accumulate it are limited in distribution, and extracting enough compound from natural tissues for drug development is neither practical nor sustainable. A new study from researchers working with in vitro root cultures of two European flax relatives, published in Pharmacia, now reports a deceptively simple intervention that significantly boosts justicidin B accumulation: feeding the cultures a flavonoid called vitexin, which appears to reroute the plant&#8217;s own metabolic traffic away from competing pathways and toward lignan biosynthesis.</p>
<p>The two species at the center of the work, Linum austriacum and Linum alpinum, are recognized as some of the richest natural sources of arylnaphthalene lignans. L. austriacum is among the most productive justicidin B-accumulating species known, while L. alpinum, a rare alpine endemic of European mountain regions, has recently emerged as an additional promising source of the same bioactive lignan. Because harvesting wild plants is constrained by the limited range of these species and the low natural abundance of justicidin B, the research team turned to in vitro root cultures, which combine genetic and biochemical stability with rapid growth and the capacity to maintain specialized metabolic pathways under fully controlled conditions. Root cultures are established from aseptically germinated seedlings and maintained on modified Murashige and Skoog medium supplemented with defined auxins and, in the case of L. alpinum, kinetin and casein hydrolysate, subcultured every 30 days to keep biomass development and metabolic state uniform before each experiment.</p>
<p>Understanding why vitexin was chosen requires a look at the architecture of the phenylpropanoid pathway itself. This central metabolic network originates from phenylalanine and proceeds through cinnamic acid, p-coumaric acid, caffeic acid, ferulic acid, and coniferyl alcohol before the sequential formation of pinoresinol, lariciresinol, and secoisolariciresinol, ultimately yielding arylnaphthalene lignans including justicidin B. Crucially, the same pathway also gives rise to flavonoids and numerous other phenolic compounds, so the relative activity of competing branches plays a decisive role in determining which end products accumulate. Flavonoids have traditionally been regarded as terminal products of phenylpropanoid metabolism, but increasing evidence suggests they also participate in metabolic crosstalk and signaling within the network. Vitexin, a naturally occurring C-glycosyl flavone, is a characteristic specialized metabolite of Linum species: it and related mono- and di-C-glycosyl flavones have been identified in the aerial tissues of cultivated flax, and high-resolution mass spectrometry profiling of other Linum species has revealed vitexin among the major detected compounds. Prior work showing that stress-induced accumulation of phenolics, flavonoids including vitexin, and lignans occurs together in Linum cell cultures further supported the close metabolic relationship between the two branches.</p>
<p>Before any supplementation, the researchers first mapped the endogenous accumulation of justicidin B in untreated root cultures of both species over a 30-day cultivation period, quantifying the compound by liquid chromatography coupled with high-resolution electrospray ionization mass spectrometry using an external calibration curve prepared from purified justicidin B. The two species told strikingly different stories. In L. alpinum root cultures, justicidin B was consistently detected and rose gradually from 0.07 micrograms per milligram dry weight on day 5 to a maximum of 0.12 micrograms per milligram dry weight on day 30, with no early accumulation maximum, indicating a slow and progressive trend. In L. austriacum, justicidin B was already present at relatively high levels during early culture development, reaching 1.19 micrograms per milligram dry weight on day 5, then declined to 0.75 on day 20 and bottomed out at 0.58 on day 25, a dip the authors associate with increased biomass development, before partially recovering to 0.72 by day 30. This profile established that justicidin B accumulation in L. austriacum varies with culture age rather than progressing steadily, and it identified day 25 as a suitable intervention point, a phase of reduced endogenous production where the effect of an external supplement could be cleanly evaluated.</p>
<p>The first supplementation experiment applied vitexin at final concentrations of 1, 3, and 5 micromolar to root cultures of both species on cultivation day 25, with harvest after 5 days of treatment on day 30. Each treatment was performed in triplicate, and ethanol-treated cultures were included as solvent controls to distinguish the effects of vitexin from those of the solvent, since stock solutions were prepared in absolute ethanol and diluted with sterile distilled water immediately before use. The ethanol control proved statistically inert in every comparison, confirming that any changes in justicidin B content could be attributed to the flavonoid itself. The results were species-specific in a way that defied a simple concentration-response curve. In L. alpinum, 1 micromolar vitexin produced the highest justicidin B accumulation at 0.14 micrograms per milligram dry weight, roughly a 1.2-fold increase over the untreated control, while higher concentrations of 3 and 5 micromolar yielded contents comparable to controls, indicating that increasing the dose beyond 1 micromolar did not further enhance accumulation in this species.</p>
<p>L. austriacum responded far more dramatically. Supplementation with 1 micromolar vitexin increased justicidin B content to 0.93 micrograms per milligram dry weight, a tendency that fell just short of statistical significance, and 3 micromolar produced 0.86, but the strongest response came at 5 micromolar, where justicidin B reached 1.30 micrograms per milligram dry weight, an approximately 1.8-fold increase over the untreated control that was highly significant. Notably, 3 micromolar did not produce an intermediate response between 1 and 5 micromolar, so vitexin did not induce a simple dose-dependent pattern across the tested range. The authors interpret this as evidence that the effect depends on the metabolic capacity and physiological state of each root culture system, consistent with the known influence of genotype, culture conditions, and treatment optimization on secondary metabolite production in plant in vitro systems.</p>
<p>Because L. austriacum had shown the stronger response, the team extended the work with a prolonged supplementation experiment using higher concentrations and later cultivation stages. Independent sets of cultures were supplemented with 5 or 10 micromolar vitexin on day 30 and harvested on day 35, or supplemented on day 35 and harvested on day 40, again following 5 days of treatment. On day 35, 10 micromolar vitexin significantly increased justicidin B accumulation to 1.45 micrograms per milligram dry weight, approximately 2.4-fold above the untreated control, the strongest effect recorded anywhere in the study. On day 40, however, the picture reversed: 5 micromolar vitexin left justicidin B levels comparable to controls at 1.24 micrograms per milligram dry weight, and 10 micromolar actually produced a slight reduction to 1.01, lower than both the untreated and ethanol-treated controls. This shift demonstrates that the optimal vitexin concentration changes during culture development and that the response is tightly linked to the physiological state of the cultures, with the same dose that strongly supports accumulation at one stage potentially inhibiting the phenylpropanoid pathway at a later one.</p>
<p>The mechanistic hypothesis the authors propose is what makes the study conceptually novel. Vitexin is not a direct biosynthetic precursor of justicidin B, so the observed increases cannot be explained by precursor feeding in the classical sense. Instead, the external supply of vitexin may act through feedback-related modulation of the flavonoid branch of the phenylpropanoid pathway: flooding the cultures with a flavonoid end product may suppress or partially block further metabolic activity toward flavonoid biosynthesis, allowing shared phenylpropanoid intermediates such as coniferyl alcohol to be preferentially directed toward the lignan branch and ultimately toward arylnaphthalene lignan production. In effect, inhibiting a competitive metabolic pathway promotes justicidin B accumulation, exactly as the study&#8217;s title suggests. The cultivation-stage-dependent response in L. austriacum further indicates that this redirection is influenced by the physiological state of the cultures and by the applied concentration, emphasizing the importance of optimizing both treatment timing and dose.</p>
<p>The authors are careful to stress that this mechanism remains hypothetical. Future experiments should include targeted metabolomic profiling of flavonoid and lignan intermediates, expression analysis of key genes involved in both branches, and enzyme activity assays for relevant phenylpropanoid pathway enzymes to clarify whether the increased justicidin B accumulation truly results from redirected metabolic activity toward arylnaphthalene lignan biosynthesis. Such analyses would confirm whether exogenous flavonoid supplementation suppresses flavonoid biosynthesis and promotes justicidin B production at the molecular and enzymatic levels, converting a promising correlation into a demonstrated regulatory interaction.</p>
<p>Even with that caveat, the practical implications are considerable. To the best of current knowledge, this is the first study demonstrating that exogenous supplementation with the flavonoid vitexin can influence justicidin B accumulation in Linum root cultures, introducing a novel strategy for enhancing arylnaphthalene lignan production through flavonoid-mediated regulation of the phenylpropanoid pathway. The findings highlight the importance of species-specific metabolic capacity, vitexin concentration, and treatment timing, with L. austriacum root cultures treated with 10 micromolar vitexin on day 30 delivering the highest fold increase in the study. For a compound with such pronounced pharmacological potential and such limited natural availability, a controlled in vitro system that can be steered toward higher lignan output by a single well-timed flavonoid supplement represents a meaningful step toward sustainable biotechnological production, and it opens a new line of inquiry into how the competing branches of one of plant biology&#8217;s central metabolic networks can be manipulated by the very molecules they produce.</p>
<p><strong>Subject of Research:</strong> Flavonoid-mediated metabolic rerouting enhances anticancer lignan production in Linum root cultures</p>
<p><strong>Article Title:</strong> Inhibition of competitive metabolic pathways promotes lignan accumulation in Linum in vitro root cultures</p>
<p><strong>Article References:</strong> Zarev, Y., Nedelcheva, R., &amp; Ionkova, I. (2026). Inhibition of competitive metabolic pathways promotes lignan accumulation in Linum in vitro root cultures. <em>Pharmacia, 73</em>, Article e206408. <a href="https://doi.org/10.3897/pharmacia.73.e206408" rel="noopener noreferrer">https://doi.org/10.3897/pharmacia.73.e206408</a></p>
<p><strong>Image Credits:</strong> AI Generated</p>
<p><strong>DOI:</strong> <a href="https://doi.org/10.3897/pharmacia.73.e206408" rel="noopener noreferrer">10.3897/pharmacia.73.e206408</a></p>
<p><strong>Keywords:</strong> lignans, justicidin B, Linum, vitexin, phenylpropanoid pathway, plant biotechnology, in vitro root cultures, secondary metabolites, Inhibition, competitive, metabolic, pathways</p>
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		<post-id xmlns="com-wordpress:feed-additions:1">301194</post-id>	</item>
		<item>
		<title>Optical Rotation Gets a Reality Check: Why Methanol Can Mislead Natural Product Chemists</title>
		<link>https://scienmag.com/optical-rotation-gets-a-reality-check-why-methanol-can-mislead-natural-product-chemists/</link>
		
		<dc:creator><![CDATA[]]></dc:creator>
		<pubDate>Fri, 16 Oct 2026 14:37:32 +0000</pubDate>
				<category><![CDATA[Science News]]></category>
		<category><![CDATA[absolute configuration of secondary metabolites]]></category>
		<category><![CDATA[challenges in stereochemical assignment]]></category>
		<category><![CDATA[chiral molecule optical rotation]]></category>
		<category><![CDATA[chiroptical properties in natural products]]></category>
		<category><![CDATA[chiroptical spectroscopy]]></category>
		<category><![CDATA[dispersion]]></category>
		<category><![CDATA[furofuran]]></category>
		<category><![CDATA[furofuran lignans structural analysis]]></category>
		<category><![CDATA[influence of methanol on optical rotation measurements]]></category>
		<category><![CDATA[lignans]]></category>
		<category><![CDATA[natural product chemists]]></category>
		<category><![CDATA[natural products]]></category>
		<category><![CDATA[optical]]></category>
		<category><![CDATA[optical rotatory dispersion]]></category>
		<category><![CDATA[pitfalls]]></category>
		<category><![CDATA[plant secondary metabolites optical properties]]></category>
		<category><![CDATA[potential]]></category>
		<category><![CDATA[rotatory]]></category>
		<category><![CDATA[Scientific Research]]></category>
		<category><![CDATA[solvent effects]]></category>
		<category><![CDATA[solvent effects on optical rotation]]></category>
		<category><![CDATA[stereochemistry]]></category>
		<category><![CDATA[stereochemistry determination]]></category>
		<category><![CDATA[wavelength-dependent optical rotation]]></category>
		<guid isPermaLink="false">https://scienmag.com/?p=285974</guid>

					<description><![CDATA[A systematic study of furofuran lignans shows that optical rotatory dispersion can reliably assign absolute configurations, but only if the solvent is chosen carefully.]]></description>
										<content:encoded><![CDATA[<p>Every chiral molecule interacts with light in a characteristic way. When a beam of left- and right-circularly polarized light passes through a solution of a non-racemic chiral compound, the two components are refracted to different degrees, rotating the plane of polarized light. This optical rotation has been measured by natural product chemists for more than a century, and it remains the single most frequently reported chiroptical property in the literature. Yet a new study published in Frontiers in Natural Products demonstrates that this seemingly simple number can betray chemists when the solvent is wrong, and that a more rigorous wavelength-dependent approach, optical rotatory dispersion, offers a safer path to one of the field&#8217;s most stubborn problems: assigning the absolute configuration of chiral secondary metabolites.</p>
<p>The research, led by Eric Y. Lee, Victor M. S. Sousa, Isabele R. Nascimento, and Joao M. Batista Jr. at the Federal University of São Paulo and São Paulo State University, focused on furofuran lignans, a widespread subclass of plant secondary metabolites built from the central-carbon fusion of two phenylpropanoid units. These molecules share the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane skeleton and exhibit a range of biological activities, including antioxidant, anti-inflammatory, cytotoxic, and antimicrobial effects. Although their relative configurations can be determined efficiently by nuclear magnetic resonance spectroscopy, their absolute configurations have often been assigned in the literature through empirical comparisons of optical rotation values with those of structurally related molecules, a practice the authors describe as risky.</p>
<p>The problem with empirical comparison is fundamental. Optical rotation is simply a signed number that carries no structural information by itself. It is sensitive to solvent, concentration, path length, and temperature, and slight structural changes between related molecules can completely invert the sign of rotation. The only acceptable empirical protocol involves comparing the two enantiomers of the same molecule under identical conditions, and even then the assignment is warranted only if one enantiomer&#8217;s absolute stereochemistry has been secured by independent methods. The golden standard, single-crystal X-ray crystallography, is restricted to high-quality crystals in the solid state, while NMR is intrinsically achiral in isotropic media and requires chiral auxiliaries to differentiate enantiomers.</p>
<p>To overcome these limitations, the team turned to optical rotatory dispersion, the wavelength-dependent version of optical rotation. Instead of recording a single value at the sodium D line of 589 nanometers, they measured specific rotations at six wavelengths: 589, 578, 546, 436, 405, and 365 nanometers. This produces a dispersion curve in the non-resonant region, which can then be compared with density functional theory simulations at the B3LYP/PCM/6-311G++(d,p) level of theory. The comparison of an entire curve rather than a single point provides a far more reliable basis for assigning absolute configuration.</p>
<p>The six lignans studied were isolated from Aristolochia species, including A. gigantea, A. pubescens, A. warmingii, and A. galeata, and their enantiomeric purities had been established previously by chiral HPLC. The researchers measured ORD in three solvents: acetonitrile, chloroform, and methanol. These solvents differ in polarity and hydrogen-bonding capability, properties that can affect molecular conformations, intermolecular interactions, and electronic transitions, all of which influence optical rotation.</p>
<p>The results were striking. For five of the six compounds, the absolute configurations could be unambiguously assigned by comparing experimental and calculated dispersion curves. The dextrorotatory compounds 1, 2, and 3 were assigned as (7S,8R,7′S,8′R), compound 5 as (7S,8R,7′R,8′R), and the levorotatory compounds 4 and 6 as (7R,8S,7′S,8′S). Chloroform emerged as the solvent of choice, providing better dispersion properties, less variation across wavelengths, and improved reproducibility, likely due to lower saturation of the photomultiplier tube detector and smaller conformational perturbation from the less polar medium.</p>
<p>But one compound defied the protocol. Sesamin, measured in methanol, produced calculated dispersion curves that led to the wrong absolute configuration assignment. The theoretical curve for the (7R,8S,7′R,8′S) configuration remained positive in methanol, in contrast to the results in acetonitrile and chloroform and to literature values. When the researchers assigned equal weights to the identified conformers instead of Boltzmann averaging, the curve adopted a negative trend, suggesting problems with the conformational ensemble selection, either from inaccurate geometries or incorrect energy estimations caused by the solvent.</p>
<p>To investigate this anomaly, the team employed molecular dynamics simulations followed by quantum mechanics/molecular mechanics calculations. A cubic box of 50 by 50 by 50 angstroms was filled with a single lignan molecule and 1,600 methanol molecules, and simulations ran for 20 nanoseconds at 300 kelvin and 1 bar. Snapshots taken every 50 picoseconds were subjected to geometry optimization using the two-layer ONIOM method, keeping only solvent molecules within 7 to 8 angstroms of the lignan. Despite this more realistic approach, the theoretical ORD values remained largely positive for the incorrect configuration. The researchers then tested micro-solvation, explicitly including one to four methanol molecules positioned to favor hydrogen-bond interactions with the oxygen atoms of the methylenedioxy and furofuran groups. Even though important structural changes from twisted to flat furofuran moieties were observed, the specific rotation values remained largely positive. The dominant structural factor for sign inversion appeared to be the relative orientation of the dipole moments of the identical aromatic rings, an orientation that seemed to be overestimated when geometry optimizations were performed with implicit solvation.</p>
<p>The findings carry implications far beyond furofuran lignans. Methanol is one of the most common solvents in natural product chemistry, and the authors recommend using it with caution for optical rotation measurements of this class of compounds, especially when absolute configuration assignments are intended. Chloroform is the preferable choice for ORD, as it leads to higher intensities, lower intermolecular interactions, and improved reproducibility. If solubility is an issue, acetonitrile is recommended. The authors also suggest obtaining optical rotation in different solvents for more reliable assignments. Given that empirical comparisons of specific rotation for structurally related molecules remain a common practice in natural product stereochemistry, these results are far-reaching, reinforcing that the solvent environment is not a passive backdrop but an active participant in the chiroptical properties of chiral molecules.</p>
<p><strong>Subject of Research:</strong> Chemistry</p>
<p><strong>Article Title:</strong> Stereochemistry of furofuran lignans from optical rotatory dispersion: potential and pitfalls</p>
<p><strong>Article References:</strong> Lee, E. Y., Sousa, V. M. S., Bernardino, K., Cunha, C. L., Nascimento, I. R., &amp; Batista, J. M., Jr. (2026). Stereochemistry of furofuran lignans from optical rotatory dispersion: potential and pitfalls. <em>Frontiers in Natural Products, 5</em>, Article 1916076. <a href="https://doi.org/10.3389/fntpr.2026.1916076" rel="noopener noreferrer">https://doi.org/10.3389/fntpr.2026.1916076</a></p>
<p><strong>Image Credits:</strong> AI Generated</p>
<p><strong>DOI:</strong> <a href="https://doi.org/10.3389/fntpr.2026.1916076" rel="noopener noreferrer">10.3389/fntpr.2026.1916076</a></p>
<p><strong>Keywords:</strong> stereochemistry, natural products, chiroptical spectroscopy, lignans, solvent effects, furofuran, optical, rotatory, dispersion, potential, pitfalls, scientific research</p>
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		<title>Engineered Sesame Oil Variants Show Skin-Lightening and Wound-Healing Potential</title>
		<link>https://scienmag.com/engineered-sesame-oil-variants-show-skin-lightening-and-wound-healing-potential/</link>
		
		<dc:creator><![CDATA[Alan Morgan]]></dc:creator>
		<pubDate>Mon, 05 Oct 2026 19:49:37 +0000</pubDate>
				<category><![CDATA[Agriculture]]></category>
		<category><![CDATA[anti-inflammatory]]></category>
		<category><![CDATA[antioxidant sesamol in skincare]]></category>
		<category><![CDATA[asarinin]]></category>
		<category><![CDATA[bioactive compounds in sesame oil]]></category>
		<category><![CDATA[cosmetics]]></category>
		<category><![CDATA[engineered sesame oil for skin lightening]]></category>
		<category><![CDATA[inflammation reduction with sesame oil]]></category>
		<category><![CDATA[lignan asarinin for tissue regeneration]]></category>
		<category><![CDATA[lignans]]></category>
		<category><![CDATA[melanin]]></category>
		<category><![CDATA[molecular docking]]></category>
		<category><![CDATA[natural skin whitening agents from sesame oil]]></category>
		<category><![CDATA[sesame oil]]></category>
		<category><![CDATA[sesame oil chemical modification]]></category>
		<category><![CDATA[Sesame oil skincare benefits]]></category>
		<category><![CDATA[sesamol]]></category>
		<category><![CDATA[skin lightening]]></category>
		<category><![CDATA[skin pigmentation inhibitors]]></category>
		<category><![CDATA[sustainable skincare ingredients]]></category>
		<category><![CDATA[traditional medicine to cosmetic applications]]></category>
		<category><![CDATA[tyrosinase]]></category>
		<category><![CDATA[wound healing]]></category>
		<category><![CDATA[wound healing properties of sesame oil]]></category>
		<category><![CDATA[zebrafish]]></category>
		<guid isPermaLink="false">https://scienmag.com/?p=239168</guid>

					<description><![CDATA[Scientists used solid acid catalysis to create sesamol- and asarinin-enriched sesame oils that inhibited melanin production and accelerated wound repair in zebrafish models.]]></description>
										<content:encoded><![CDATA[<p>Sesame oil has been a staple of kitchens and traditional medicine cabinets for thousands of years, but a new study suggests it may be on the verge of a second career in high-end skincare. Researchers report in the Journal of Agriculture and Food Research that a controlled catalytic trick can transform ordinary cold-pressed sesame oil into two chemically distinct functional oils, one enriched in the antioxidant sesamol and the other in the lignan asarinin. In laboratory and zebrafish experiments, these engineered oils displayed markedly different dermatological talents: the sesamol-rich oil proved to be a strikingly effective inhibitor of melanin production, while the asarinin-rich oil excelled at promoting tissue regeneration and calming inflammation after injury.</p>
<p>The team, led by Yuan-Qing Luo of Henan University of Technology and colleagues, started from a well-known chemical paradox. Cold-pressed sesame oil retains abundant lignans, principally sesamin and sesamolin, which lend the oil oxidative stability on the shelf but carry no free phenolic hydroxyl groups and therefore little intrinsic antioxidant or anti-tyrosinase power. Roasting generates the potent antioxidant sesamol by degrading sesamolin, but it also produces an intense aroma that is unwelcome in cosmetic formulations, and industrial refining strips out sesamol and tocopherols altogether. The researchers&#8217; solution was a solid acid-catalyzed in situ conversion, using an oxalic acid-modified mesoporous molecular sieve catalyst added directly to cold-pressed oil at 80 degrees Celsius, selectively converting the endogenous lignans into more active derivatives without creating off-flavors.</p>
<p>By tuning the reaction time, the team produced two bespoke oils. A short 20-minute catalytic treatment yielded a sesamol-rich oil containing 132.25 milligrams of sesamol per 100 grams, while a longer 180-minute treatment produced an asarinin-rich oil with 356.77 milligrams of asarinin per 100 grams. Untreated cold-pressed oil contained neither compound, only its native sesamin and sesamolin. Crucially, gas chromatographic analysis showed that the fatty acid backbone of the oil was essentially untouched: oleic acid and linoleic acid remained at roughly 40 and 44 percent of total fatty acids in all three samples, preserving the emollient and barrier-repair properties that make the oil matrix valuable in cosmetics. Some loss of gamma-tocopherol and phytosterols occurred, apparently through non-selective adsorption onto the mesoporous catalyst, but this was similar in both treated oils.</p>
<p>The first functional test targeted tyrosinase, the copper-containing enzyme that catalyzes the rate-limiting steps of melanin synthesis and stands as the principal drug target for skin-lightening agents. At 1000 micrograms per milliliter, the sesamol-rich oil inhibited tyrosinase by 91.0 percent, statistically indistinguishable from the pharmaceutical benchmark kojic acid at one-tenth the concentration. The untreated oil managed only 2.1 percent inhibition, and the asarinin-rich oil an intermediate 49.3 percent. The pattern pointed squarely at sesamol as the active principle, consistent with earlier work showing sesamol is a potent monophenolase inhibitor with an IC50 of 3.2 micromolar, far exceeding kojic acid&#8217;s 59.72 micromolar, while sesamin and sesamolin lack inhibitory activity against the enzyme.</p>
<p>Molecular docking offered a structural explanation. Using a predicted structure of human tyrosinase, the researchers found that sesamol binds in the hydrophobic catalytic cavity with a favorable energy of minus 5.9 kilocalories per mole, close to arbutin&#8217;s minus 6.2. More tellingly, sesamol&#8217;s phenolic hydroxyl formed a hydrogen bond with Ser375, and its aromatic ring engaged in pi-stacking with His367, while making additional contacts with His180, His202, and His363. Those histidines are not incidental: they coordinate the binuclear copper center that drives tyrosinase&#8217;s catalytic chemistry. Sesamol thus appears to jam the enzyme by perturbing the microenvironment of its dicopper active site, occupying a different subsite from arbutin and raising the possibility of cooperative binding between the two inhibitors.</p>
<p>To test whether the effect survives in a living organism, the team turned to zebrafish embryos, a favorite screening platform for anti-melanogenesis compounds because their optical transparency allows pigment deposition to be watched in real time and their melanin synthesis pathways closely mirror those of humans. After establishing a maximum tolerated concentration of 1 milligram per milliliter, the researchers treated embryos for 45 hours. The sesamol-rich oil reduced cephalic melanin signal by 39.04 percent, approaching the 49.34 percent achieved by the positive control arbutin at five times the concentration. Biochemical assays confirmed the mechanism: melanin protein content fell to 60.35 percent of control levels and tyrosinase activity to 64.55 percent, closely matching the visible depigmentation.</p>
<p>The wound-repair experiments revealed a different division of labor. In a zebrafish skin injury model created by injecting acetic acid into larvae, all three oils accelerated healing, with efficacies of 56 percent for the untreated and sesamol-rich oils and 63 percent for the asarinin-rich oil at 100 milligrams per milliliter, approaching the 69 percent of epidermal growth factor. In a tail fin amputation model, however, the asarinin-rich oil pulled decisively ahead: at 25 milligrams per milliliter it achieved 39 percent tissue regeneration, roughly 44 percent better than the sesamol-rich oil and 56 percent better than untreated oil, nearing the performance of the positive control glycoin.</p>
<p>Anti-inflammatory activity told the opposite story. Using transgenic zebrafish whose neutrophils glow green, the researchers tracked the resolution of inflammation at amputated tail fins, where lingering neutrophils can release toxic granules that damage tissue. At low doses of 5 and 10 milligrams per milliliter, the sesamol-rich oil cleared 56 to 57 percent of wound-site neutrophils, dramatically outperforming both the untreated oil at 34 to 36 percent and the asarinin-rich oil at 37 to 38 percent, and beating the positive control dipotassium glycyrrhizinate&#8217;s 39 percent. At 25 milligrams per milliliter the asarinin-rich oil caught up, reaching 66 percent clearance. The authors attribute these divergent profiles to the lignan chemistry: sesamol is a known suppressor of reactive oxygen species and of pro-inflammatory cytokines such as IL-1 beta, IL-6, and TNF-alpha, while asarinin has been reported to inhibit superoxide-driven inflammatory activation more potently than sesamin.</p>
<p>The study&#8217;s broader significance lies in its demonstration that processing chemistry, not just the source plant, determines what a functional oil can do. Because the fatty acid matrix stayed constant while lignan composition was deliberately reshaped, the researchers could attribute specific bioactivities to specific lignan enrichments, effectively converting a traditional edible oil into a tunable platform for dermocosmetic design. The authors caution that the differential effects cannot yet be pinned on single compounds, since each oil retains a mixture of lignans and minor constituents, and the lipid matrix itself may influence lignan delivery and bioavailability. They also note that the sesamol-rich oil&#8217;s UV absorption at 287 nanometers was 14.4 percent higher than untreated oil, hinting at modest photoprotective value that requires verification in finished formulations. Still, with kojic acid associated with contact dermatitis and sensitization in some users, an edible-oil-derived alternative that approaches its tyrosinase-blocking potency while simultaneously offering wound-repair and anti-inflammatory benefits represents an appealing prospect for the next generation of natural skincare ingredients.</p>
<p><strong>Subject of Research:</strong> Lignan-enriched sesame oils for skin lightening and wound repair</p>
<p><strong>Article Title:</strong> Exploring the Potential of Sesamol/Asarinin-Enriched Sesame Oil in Skin Lightening and Wound Repair</p>
<p><strong>Article References:</strong> Luo, Y.-Q., Li, Z.-Q., Wang, Q., Qin, J.-W., Yu, T., Liu, H.-M., &amp; Yang, J.-C. (2026). Exploring the Potential of Sesamol/Asarinin-Enriched Sesame Oil in Skin Lightening and Wound Repair. <em>Journal of Agriculture and Food Research</em>, Article 103348. <a href="https://doi.org/10.1016/j.jafr.2026.103348" rel="noopener noreferrer">https://doi.org/10.1016/j.jafr.2026.103348</a></p>
<p><strong>Image Credits:</strong> AI Generated</p>
<p><strong>DOI:</strong> <a href="https://doi.org/10.1016/j.jafr.2026.103348" rel="noopener noreferrer">10.1016/j.jafr.2026.103348</a></p>
<p><strong>Keywords:</strong> sesame oil, sesamol, asarinin, tyrosinase, melanin, skin lightening, wound healing, zebrafish, lignans, cosmetics, anti-inflammatory, molecular docking</p>
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