Six New Polyhydroxysteroidal Glycosides,Anthenosides S1 – S6, from the Starfish Anthenea sibogae

Six new polyhydroxysteroidal glycosides, anthenosides S1  –  S6 ( 1  –  6 ), along with a mixture of two previously known related glycosides, 7 and 8 , were isolated from the methanolic extract of the starfish Anthenea sibogae. The structures of 1  –  6 were established by NMR and HR‐ESI‐MS techniques as well as by chemical transformations. All new compounds have a 5α‐cholest‐8(14)‐ene‐3α,6β,7β,16α‐tetrahydroxysteroidal nucleus and differ from majority of starfish glycosides in positions of carbohydrate moieties at C(7) and C(16) ( 1  –  4 , 6 ) or only at C(16) ( 5 ). The 4‐O‐methyl‐β‐d ‐glucopyranose residue ( 2 ) and Δ²⁴‐cholestane side chain ( 3 ) have not been found earlier in the starfish steroidal glycosides. The mixture of 7 and 8 slightly inhibited the proliferation of human breast cancer T‐47D cells and decreased the colony size in the colony formation assay.     

Chemical Composition and Allelopathic Potential of Essential Oils from Citharexylum spinosum L. Grown in Tunisia

Citharexylum spinosum L. (Verbenaceae) also known as Citharexylum quadrangulare Jacq . or Citharexylum fruticosum L. is an exotic tree introduced many years ago in Tunisia, specially used as a street and park ornamental tree. Essential oils (EOs) were obtained by hydrodistillation of the different parts (roots, stems, leaves, flowers and fruits; drupes) collected from trees grown in the area of Monastir (Tunisia). In total, 84 compounds, representing 90.1 – 98.4% of the whole oil composition, were identified by GC‐FID and GC/MS analyses. The root EO was distinguished by its high content in monoterpene hydrocarbons (α‐phellandrene; 30.8%) whereas that obtained from stems was dominated by sesquiterpene hydrocarbons (cuparene; 16.4%). The leaf oil was rich in an apocarotenoid derivative (hexahydrofarnesylacetone; 26%) and an aliphatic hydrocarbon (nonadecane; 14.5%). Flowers oil was rich in esters (2‐phenylethyl benzoate; 33.5%). Finally, drupes oil was rich in oxygenated sesquiterpenes (β‐eudesmol; 33.1%). Flowers oil showed a significant phytotoxic effect against lettuce seeds germination, it induces a total inhibition when tested at 1 mg/ml. Root and shoot elongation seemed to be more affected than germination. The inhibition of the shoot length varied from 3.6% to 100% and that of the root from 16.1% to 100%. The highest inhibition of 100% was detected for flower oil tested at 1 mg/ml. Our in vitro studies suggest a possible and new alternative use of C. spinosum EOs in herbicidal formulations, further experiments involving field conditions are necessary to confirm its herbicidal potential.     

Root volatiles in plant–plant interactions II: Root volatiles alter root chemistry and plant–herbivore interactions of neighbouring plants

Volatile organic compounds (VOCs) emitted by plant roots can influence the germination and growth of neighbouring plants. However, little is known about the effects of root VOCs on plant–herbivore interactions of neighbouring plants. The spotted knapweed (Centaurea stoebe) constitutively releases high amounts of sesquiterpenes into the rhizosphere. Here, we examine the impact of C. stoebe root VOCs on the primary and secondary metabolites of sympatric Taraxacum officinale plants and the resulting plant‐mediated effects on a generalist root herbivore, the white grub Melolontha melolontha. We show that exposure of T. officinale to C.stoebe root VOCs does not affect the accumulation of defensive secondary metabolites but modulates carbohydrate and total protein levels in T. officinale roots. Furthermore, VOC exposure increases M. melolontha growth on T. officinale plants. Exposure of T. officinale to a major C. stoebe root VOC, the sesquiterpene (E)‐β‐caryophyllene, partially mimics the effect of the full root VOC blend on M. melolontha growth. Thus, releasing root VOCs can modify plant–herbivore interactions of neighbouring plants. The release of VOCs to increase the susceptibility of other plants may be a form of plant offense.     

Constituents from the Roots of Actinidia chinensis and Their Cytochrome P450 Enzyme Inhibitory Activities

A newly discovered triterpenoid, (2α,3β)‐2,3,23‐trihydroxyurs‐13(18)‐en‐28‐oic acid ( 1 ), along with twelve known compounds ( 2  –  13 ), were isolated from the roots of Actinidia chinensis Planch (Actinidiaceae). Their chemical structures were determined by 1D‐ and 2D‐NMR spectra and mass spectrometry (MS). The crude extracts and six main constituents ( 8  –  13 ) were tested for cytochrome P450 (CYPs) enzyme inhibitory activity. The results showed that, except for compound 8 , compounds 9  –  13 had different inhibitory effects on the cytochrome P450 (CYPs) enzyme, and compound 9 significantly inhibited the catalytic activities of CYP3A4 to < 10% of its control activities.     

Comparative phylogeographies of six species of hinged terrapins (Pelusios spp.) reveal discordant patterns and unexpected differentiation in the P. castaneus/P. chapini complex and P. rhodesianus

Using up to 2117 bp of mitochondrial DNA and up to 2012 bp of nuclear DNA, we analysed phylogeographic differentiation of six widely distributed species of African hinged terrapins (Pelusios spp.) representing different habitat types. Two taxa each live in savannahs or in forests and mesic savannahs, respectively, and the remaining two species occur in intermediate habitats. The species living in forests and mesic savannahs do not enter dry savannahs, whereas the savannah species may occur in dry and wet savannahs and even in semi‐arid steppe regions. We found no obvious correlation between habitat type and phylogeographic pattern: one savannah species (P. rhodesianus) shows phylogeographic structure, i.e. pronounced genetic differences among geographically distinct populations, and the other (P. nanus) not. One species inhabiting forests and mesic savannahs (P. carinatus) has phylogeographic structure, the other (P. gabonensis) not. The same pattern is true for the two ecologically intermediate species, with phylogeographic structure present in P. castaneus and absent in P. chapini. Nuclear evidence suggests that the latter two taxa with abutting and partially overlapping ranges are distinct, while mtDNA is only weakly differentiated. Pelusios castaneus shows pronounced phylogeographic structure, which could reflect Pleistocene range interruptions correlated with the fluctuating forest cover in West and Central Africa. Our results do not support the recognition of an extinct subspecies of P. castaneus for the Seychelles. Pelusios carinatus contains two well supported clades, which are separated by the Congo River. This species is closely related to P. rhodesianus, a taxon consisting of two deeply divergent mitochondrial clades. One of these clades is paraphyletic with respect to P. carinatus, but the two clades of P. rhodesianus are not differentiated in the studied nuclear markers and, again, paraphyletic with respect to P. carinatus. Using mtDNA sequences from the type material of P. rhodesianus, we were able to allocate this name to one of the two clades. However, owing to the confusing relationships of P. rhodesianus and P. carinatus, we refrain from taxonomic decisions.     

Chemotaxonomic Considerations of the n‐Alkane Composition in Pinus heldreichii,P. nigra,and P. peuce

The n‐alkane composition in the leaf cuticular waxes of natural populations of Bosnian pine (Pinus heldreichii), Austrian pine (P. nigra), and Macedonian pine (P. peuce) was compared for the first time. The range of n‐alkanes was wider in P. nigra (C₁₆ – C₃₃) than in P. heldreichii and P. peuce (C₁₈ – C₃₃). Species also diverged in abundance and range of dominant n‐alkanes (P. heldreichii: C₂₃, C₂₇, and C₂₅; P. nigra: C₂₅, C₂₇, C₂₉, and C₂₃; P. peuce: C₂₉, C₂₅, C₂₇, and C₂₃). Multivariate statistical analyses (PCA, DA, and CA) generally pointed out separation of populations of P. nigra from populations of P. heldreichii and P. peuce (which were, to a greater or lesser extent, separated too). However, position of these species on the basis of n‐alkane composition was in accordance neither with infrageneric classification nor with recent molecular and terpene investigations.     

Chemical Composition,Antimicrobial and Cytotoxic Activity of Heracleum verticillatum Pančić and H. ternatum Velen. (Apiaceae) Essential Oils

In this work, the chemical composition, antimicrobial and cytotoxic activity of Heracleum verticillatum Pan?i? and H. ternatum Velen . root, leaf, and fruit essential oils were investigated. The composition was analyzed by GC and GC/MS. Heracleum verticillatum and H. ternatum root oils were dominated by monoterpenes, mostly β‐pinene (23.5% and 47.3%, respectively). Heracleum verticillatum leaf oil was characterized by monoterpenes, mainly limonene (20.3%), and sesquiterpenes, mostly (E)‐caryophyllene (19.1%), while H. ternatum leaf oil by the high percentage of phenylpropanoids, with (Z)‐isoelemicin (35.1%) being dominant constituent. Both fruit oils contained the majority of aliphatic esters, mostly octyl acetate (42.3% in H. verticillatum oil and 49.0% in H. ternatum oil). The antimicrobial activity of the oils was determined by microdilution method against eight bacterial and eight fungal strains. The strongest effect was exhibited by H. verticillatum root oil, particularly against Staphylococcus aureus, Salmonella typhimurium (MICs = 0.14 mg/ml, MBCs = 0.28 mg/ml), and Trichoderma viride (MIC = 0.05 mg/ml, MFC = 0.11 mg/ml). Cytotoxic effect was determined by MTT test against malignant HeLa, LS174, and A549 cells (IC₅₀ = 5.9 – 146.0 μg/ml), and against normal MRC‐5 cells (IC₅₀ > 120.1 μg/ml). The best effect was exhibited by H. verticillatum root oil on A549 cells (IC₅₀ = 5.9 μg/ml), and H. ternatum root oil against LS174 cells (IC₅₀ = 6.7 μg/ml).     

Phenolic Composition,Anti‐Inflammatory,Antioxidant, and Antimicrobial Activities of Alchemilla mollis (Buser) Rothm.

The current study was designed to evaluate the antioxidant, anti‐inflammatory and antimicrobial activities of Alchemilla mollis (Buser ) Rothm . (Rosaceae) aerial parts extracts. Chemical composition was analyzed by spectrophotometric and chromatographic (HPLC) techniques. The antioxidant properties assessed included DPPH^· and ABTS^·+ radical scavenging, β‐carotene‐linoleic acid co‐oxidation assay. Antimicrobial activity was evaluated with disc diffusion and micro dilution method. In order to evaluate toxicity of the extracts, with the sulforhodamine B colorimetric assay L929 cell line (mouse fibroblast) was used. The anti‐inflammatory activities of the potent antioxidant extracts (methanol, 70% methanol, and water extracts) were determined by measuring the inhibitory effects on NO production and pro‐inflammatory cytokine TNF‐α levels in lipopolysaccharide stimulated RAW 264.7 cells. 70% methanol and water extracts which were found to be rich in phenolic compounds (184.79 and 172.60 mg GAE/g extract) showed higher antioxidant activity. Luteolin‐7‐O‐glucoside was the main compound in the extracts. Ethyl acetate and 70% methanol extracts showed higher antibacterial activity against Staphylococcus aureus and Salmonella enteritidis with MIC value of 125 μg/ml. 70% methanol extract potentially inhibited the NO and TNF‐α production (18.43 μm and 1556.22 pg/ml, respectively, 6 h).     

Aroma Profile of Rubus ulmifolius Flowers and Fruits During Different Ontogenetic Phases

The chemical composition of spontaneous volatile emission from Rubus ulmifolius flowers and fruits during different stages of development was evaluated by HS‐SPME‐GC/MS. In total, 155 chemical compounds were identified accounting 84.6 – 99.4% of whole aroma profile of flowers samples and 92.4 – 96.6% for fruit samples. The main constituents were α‐copaene, β‐caryophyllene, germacrene D, (E,E)‐α‐farnesene, 1,7‐octadien‐3‐one,2‐methyl‐6‐methylene, tridecane, (E)‐2‐hexenol acetate, (E)‐3‐hexenol acetate and cyperene. The results give a chemotaxonomic contribution to the characterization of the VOCs emitted from flowers and fruits during their ontogenic development.     

Antiviral Activity of Faramea hyacinthina and Faramea truncata Leaves on Dengue Virus Type‐2 and Their Major Compounds

The defatted fractions of the Faramea hyacinthina and F. truncata (Rubiaceae) leaf MeOH extracts showed in vitro non‐cytotoxic and anti‐dengue virus serotype 2 (DENV2) activity in human hepatocarcinoma cell lineage (HepG2). Submitting these fractions to the developed RP‐SPE method allowed isolating the antiviral flavanone (2S)‐isosakuranetin‐7‐O‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 1 ) from both species and yielded less active sub‐fractions. The new diastereoisomeric epimer pair (2S) + (2R) of 5,3′,5′‐trihydroxyflavanone‐7‐O‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 2a / 2b ) from F. hyacinthina; the known narigenin‐7‐O‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 3 ) from both species; rutin ( 4 ) and quercetin‐4′‐β‐d ‐O‐glucopyranosyl‐3‐O‐rutinoside ( 5 ) from F. hyacinthina, and kaempferol‐3‐O‐rutinoside ( 6 ), erythroxyloside A ( 7 ) and asperuloside ( 8 ) from F. truncata have been isolated from these sub‐fractions. Compounds 4  –  8 are reported for the first time in Faramea spp.     

Comprehensive Research on Essential Oil and Phenolic Variation in Different Foeniculum vulgare Populations During Transition from Vegetative to Reproductive Stage

Chemical composition and antioxidant activity of four fennel populations (England, Spain, Poland and Iran) were investigated during six developmental stages including two vegetative and four reproductive phases. In reproductive phase, the essential oil content of fruits decreased and the maximum content (5.9%) was obtained in immediate fruits. The essential oils were analyzed using GC/MS. trans‐Anethole was the main component of the leaves and the fruits oil. In leaves, it ranged from 41.28% in England at late vegetative stage to 56.6% in Poland population at early vegetative stage. Other major compounds of leaves were limonene, α‐pinene and (Z)‐β‐ocimene. In reproductive phases the trans‐anethole increased dramatically. It varied from 85.25% in immature fruits from Poland to 90.7% in pre‐mature stage from Spain. The highest phenolic content in the extracts at different growth stages obtained 189 mg TAE/g DW at full mature stage of seed in Iran population. The flavonoid of leaves extract ranged from 3 to 7.5 mg QUE/g DW, while in fruits extract varied from 3 to 10.3 mg QUE/g DW. Antioxidant activity of the extracts was evaluated using 1,1‐diphenyl‐2‐picrylhydrazy (DPPH) and β‐carotene model systems. Immature and full mature growth stages of fennel population from Spain indicated the highest activity in quenching of DPPH radical (74.2% and 74.5, respectively). Antioxidant activities of the extracts had high positive correlation with their phenolic contents in all fruit maturity stages. Finally, it might probably be suggested that in fennel the hot and humid condition can lead to increase trans‐anethole, while the hot and dry one can produce higher amount of phenolics and flavonoids.     

Cytotoxic Oleanane‐Type Saponins from the Leaves of Albizia anthelmintica Brongn.

Two new oleanane‐type saponins: β‐d ‐xylopyranosyl‐(1 → 4)‐6‐deoxy‐α‐l ‐mannopyranosyl‐(1 → 2)‐1‐O‐{(3β)‐28‐oxo‐3‐[(2‐O‐β‐d ‐xylopyranosyl‐β‐d ‐glucopyranosyl)oxy]olean‐12‐en‐28‐yl}‐β‐d ‐glucopyranose ( 1 ) and 1‐O‐[(3β)‐28‐oxo‐3‐{[β‐d ‐xylopyranosyl‐(1 → 2)‐α‐l ‐arabinopyranosyl‐(1 → 6)‐2‐acetamido‐2‐deoxy‐β‐d ‐glucopyranosyl]oxy}olean‐12‐en‐28‐yl]β‐d ‐glucopyranose ( 2 ), along with two known saponins: (3β)‐3‐[(β‐d ‐Glucopyranosyl‐(1 → 2)‐β‐d ‐glucopyranosyl)oxy]olean‐12‐en‐28‐oic acid ( 3 ) and (3β)‐3‐{[α‐l ‐arabinopyranosyl‐(1 → 6)‐[β‐d ‐glucopyranosyl‐(1 → 2)]‐β‐d ‐glucopyranosyl]oxy}olean‐12‐en‐28‐oic acid ( 4 ) were isolated from the acetone‐insoluble fraction obtained from the 80% aqueous MeOH extract of Albizia anthelmintica Brongn . leaves. Their structures were identified using different NMR experiments including: ¹H‐ and ¹³C‐NMR, HSQC, HMBC and ¹H,¹H‐COSY, together with HR‐ESI‐MS/MS, as well as by acid hydrolysis. The four isolated saponins and the fractions of the extract exhibited cytotoxic activity against HepG‐2 and HCT‐116 cell lines. Compound 2 showed the most potent cytotoxic activity among the other tested compounds against the HepG2 cell line with an IC₅₀ value of 3.60μm . Whereas, compound 1 showed the most potent cytotoxic effect with an IC₅₀ value of 4.75μm on HCT‐116 cells.     

The selective florivory of Erioscelis emarginata matches its role as a pollinator of Philodendron

Flowers commonly face the dilemma of needing to be attractive to pollinators but unattractive to nectar robbers or florivores. When the pollinator has chewing mouthparts, there is also a considerable risk of the pollinator consuming the flowers. Scant field records indicate that the florivorous beetle Erioscelis emarginata (Mannerheim) (Coleoptera: Scarabaeidae: Cyclocephalini), which pollinates Philodendron spp., feeds selectively on the sterile staminate flowers. Here, the hypothesis was tested that E. emarginata prefers sterile staminate flowers of Philodendron bipinnatifidum Schott and Philodendron melinonii Brongn. ex Regel (Araceae) over fertile flowers. This study also examined whether such a preference exists regardless of the proportion of fertile vs. sterile flowers in each Philodendron species. Analysis of nutritional and defensive compounds plus scanning electron microscopy on each flower type were performed. The feeding preference of florivores for either P. bipinnatifidum or P. melinonii was also examined. In both species, sterile flowers were significantly more consumed than fertile ones. The sterile zone of P. bipinnatifidum was significantly larger than that of P. melinonii, and sterile staminate flowers of both plants were consumed at similar rates. Calcium oxalate was markedly low in sterile flowers, which also presented smaller papillae than the other flowers. This study presents evidence that the balance between pollination and florivory has most likely evolved through a strong feeding preference for less‐defended sterile flowers regardless of the size of the sterile zone.     

Oplopane Sesquiterpenes from Ligularia knorringiana and Their Anti‐Complementary Activity

Three new oplopane sesquiterpenes, knorringianalarins D – F ( 1 – 3 , respectively), and five known analogues ( 4 – 8 , respectively), were isolated from the roots and rhizomes of Ligularia knorringiana. The structures of three new compounds were identified as 4‐acetoxy‐11α,12‐epoxy‐2β‐hydroxy‐3β‐(2‐methylbutyryloxy)‐9α‐(4‐methylsenecioyloxy)oplop‐10(14)‐ene ( 1 ), 3β,4‐diacetoxy‐9α‐(4‐acetoxy‐4‐methylsenecioyloxy)‐11α,12‐epoxy‐8α‐(2‐methylbutyryloxy)oplop‐10(14)‐ene ( 2 ), and (1R,5R,6R,7R,9R)‐5,9,11‐trihydroxy‐4,15‐dinoroplop‐10(14)‐en‐3‐one ( 3 ) based on spectroscopic methods including 1D‐ and 2D‐NMR, mass spectrometry, and CD spectroscopy techniques. All compounds were evaluated for their anti‐complementary activity on the classical pathway of the complement system in vitro. Among which, three oplopane sesquiterpenes ( 3 , 7 , and 8 ) exhibited better anti‐complementary effects with CH₅₀ values ranging from 0.33 to 0.89 mm , which are plausible candidates for developing potent anti‐complementary agents.     

Juniperus phoenicea var. turbinata (Guss.) Parl. Leaf Essential Oil Variability in the Balkans

In the present work, the leaf essential oil from 97 individuals of Juniperus phoenicea var. turbinata (Guss .) Parl . from the Balkan Peninsula was analyzed. The essential oil was dominated by monoterpene hydrocarbons (45.5 – 71.8%), of which α‐pinene was the most abundant in almost all of the samples (38.2 – 55.8%). Several other monoterpenes and sesquiterpenes were also present in relatively high abundances in samples such as myrcene, δ‐3‐carene, β‐phellandrene, α‐terpinyl acetate, (E)‐caryophyllene and germacrene D. Multivariate statistical analysis suggested the existence of three possible chemotypes based on the abundance of the four components. Even though the intrapopulation variability was high, discriminant analysis (DA) was able to separate populations. DA showed high separation between western and eastern populations but also grouped geographically closer populations along the west Balkan shoreline. The potential influence of the climate on the composition of the essential oil was also studied.     

Terpenes as Useful Markers in Differentiation of Natural Populations of Relict Pines Pinus heldreichii,P. nigra,and P. peuce

Comparative analysis of terpene diversity and differentiation of relict pines Pinus heldreichii, P. nigra, and P. peuce from the central Balkans was performed at the population level. Multivariate statistical analyses showed that the composition of needle terpenes reflects clear divergence among the pine species from different subgenera: P. peuce (subgenus Strobus) vs. P. nigra and P. heldreichii (subgenus Pinus). In addition, despite the described morphological similarities and the fact that P. nigra and P. heldreichii may spontaneously hybridize, our results indicated differentiation of their populations naturally growing in the same area. In accordance with recently proposed concept of ‘flavonic evolution’ in the genus Pinus, we assumed that the terpene profile of soft pine P. peuce, defined by high amounts of six monoterpenes, is more basal than those of hard pines P. nigra and P. heldreichii, which were characterized by high content levels of mainly sesquiterpenes. In order to establish precise positions of P. heldreichii, P. nigra and P. peuce within the taxonomic and phylogenetic tree, as well as develop suitable conservation strategies and future breeding efforts, it is necessary to perform additional morphological, biochemical, and genetic studies.     

Phytochemical Composition and Antioxidant Activities of the Essential Oil and Extracts of Satureja subspicata Vis. Growing in Bosnia and Herzegovina

The phytochemical composition and the antioxidant activities of the essential oil, as well as methanol and hot water extracts of endemic Satureja subspicata Vis . growing in Bosnia and Herzegovina (BiH), were described. β‐Caryophyllene, cis‐β‐ocimene, and α‐pinene, identified by GC/MS and GC‐FID, were the dominant oil components. The major compound of both of extracts, identified by HPLC‐DAD, was rosmarinic acid. The analyzed essential oil showed moderate antioxidant activity. In this first report on the extracts of S. subspicata growing in BiH, the obtained results showed a high content of rosmarinic acid, as well as considerable amount of total phenols and flavonoids. Compared to the hot water extract, the methanol extract exhibits higher antioxidant potential, measured by DPPH and FRAP assay (IC₅₀ = 0.45 g/l and 1879.43 equiv. Fe²⁺ μm ), while the hot water extract showed higher potential in inhibition of linoleic acid oxidation (51.7% and 61.5% for 1 and 10 g/l). A good antioxidant potential of the tested extracts indicates their potential use as antioxidants, particularly for lipid protection, and partly explains the justification of the use of this plant in traditional medicine of BiH.     

Four New Steroidal Glycosides,Protolinckiosides A – D,from the Starfish Protoreaster lincki

Four new steroidal glycosides, protolinckiosides A – D ( 1 – 4 , resp.), were isolated along with four previously known glycosides, 5 – 8 , from the MeOH/EtOH extract of the starfish Protoreaster lincki. The structures of 1 – 4 were elucidated by extensive NMR and ESI‐MS techniques as (3β,4β,5α,6β,7α,15α,16β,25S)‐4,6,7,8,15,16,26‐heptahydroxycholestan‐3‐yl 2‐O‐methyl‐β‐d ‐xylopyranoside ( 1 ), (3β,5α,6β,15α,24S)‐3,5,6,8,15‐pentahydroxycholestan‐24‐yl α‐l ‐arabinofuranoside ( 2 ), sodium (3β,6β,15α,16β,24R)‐29‐(β‐d ‐galactofuranosyloxy)‐6,8,16‐trihydroxy‐3‐[(2‐O‐methyl‐β‐d ‐xylopyranosyl)oxy]stigmast‐4‐en‐15‐yl sulfate ( 3 ), and sodium (3β,6β,15α,16β,22E,24R)‐28‐(β‐d ‐galactofuranosyloxy)‐6,8,16‐trihydroxy‐3‐[(2‐O‐methyl‐β‐d ‐xylopyranosyl)oxy]ergosta‐4,22‐dien‐15‐yl sulfate ( 4 ). The unsubstituted β‐d ‐galactofuranose residue at C(28) or C(29) of the side chains was found in starfish steroidal glycosides for the first time. Compounds 1 – 4 significantly decreased the intracellular reactive oxygen species (ROS) content in RAW 264.7 murine macrophages at induction by proinflammatory endotoxic lipopolysaccharide (LPS) from E. coli.