Evaluation of five essential oils as bio-fungicides on the control of Pilidiella granati rot in pomegranate

With recent public attention focused on chemical residues in food, the managing of plant disease organisms without the use of conventional chemical fungicides or bactericides can sometimes be a challenge. The main aim of this study was the evaluation of the antifungal activity of the essential oils of Ocimum basilicum, Origanum vulgare, Rosmarinus officinalis, Rosmarinus officinalis ‘Prostrates’, Salvia officinalis and their major constituents (carvacrol, thymol, linalool, eucalyptol) against the fungus Pilidiella granati. The results showed that the essential oil vapour of O. basilicum, S. officinalis, R. officinalis, Rosmarinus officinalis ‘Prostrates’, O. vulgare had fungicidal activities against the mycelial growth and conidia germination of P. granati, the pathogen causing postharvest fruit rots in pomegranate. However, in vivo experiments, only the essential oils of O. vulgare and O. basilicum controlled this fungus effectively with the essential oil of O. vulgare to being more effective at the same rates. Analysis showed a high number of compounds in each essential oil, with carvacrol, eucalyptol, linalool and thymol predominating. Thymol and carvacrol primarily and linalool secondary showed antifungicidal activity against P. granati. These results represent an important step towards the goal using essential oils from O. basilicum, S. officinalis, R. officinalis, R. officinalis ‘Prostrates”, O. vulgare and their constituents carvacrol and thymol to control of the pathogen P. granati of pomegranate.     

Larvicidal property of essential oils against Culex quinquefasciatus Say (Diptera: Culicidae)

Essential oils from 22 aromatic plant species were tested for mortality of the mosquito larvae Culex quinquefasciatus. Lethal concentrations were determined for individual essential oils. Essential oils obtained from Thymus vulgaris, Satureja hortensis and Thymus satureioides plants showed the highest effect, with LC₅₀ found lower than 50 μg/ml (33, 36 and 44 μg/ml, respectively). Analyses showed that majority substances for T. vulgaris were thymol and p-cymene (60.3 and 10.1%, respectively); carvacrol and γ-terpinene for S. hortensis (48.1 and 36.7%, respectively), and borneol and thymol for T. satureioides (30.3 and 32.5%, respectively).The selected essential oils also showed very good effectiveness with respect to mortality and percentage of adult emergence upon short-term exposure in water contaminated with lethal doses of individual oils. While there was 77% adult emergence from the larvae in the control, in T. vulgaris, T. satureoides and S. hortensis there was only 12.3, 15.3 and 16.0% adult emergence, respectively. High antioviposition effectiveness was found in all selected oils. Almost 100% deterrence of female oviposition was determined for all oils in concentrations of 0.02%. Significant differences were seen with tested concentrations of 0.01 and 0.005%, where the oil of T. vulgaris proved most effective (repellency about 99.8 and 62.3%, respectively).     

Emerging cultivation of oregano in Sicily: Sensory evaluation of plants and chemical composition of essential oils

The characterization of the essential oil profile together with the sensory analysis of five samples of oregano, four of which cultivated in different areas of Sicily and one of commercial origin, have been carried out. The Sicilian cultivated samples belong to Origanum vulgare ssp. hirtum (Link) Béguinot (syn. O. heracleoticum L.), the most typical Sicilian oregano species. The essential oils, obtained by hydrodistillation, have been analysed by GC-FID-MS. On the whole, 53 compounds representing more than 98% of the oils have been fully characterized. The four cultivated samples showed a very similar chemical profile, thymol and γ-terpinene being the main compounds followed by p-cymene, α-terpinene, carvacrol and thymol methyl ethers, myrcene and carvacrol. The commercial sample, instead, showed a different profile, with carvacrol largely being the main component (>77%), followed by p-cymene, γ-terpinene and thymol, in that order.According to the chemical composition, the sensory profile of the Sicilian oregano samples proved fairly homogenous, whereas different results were obtained for the commercial sample. Indeed, the intensity of sensory attributes “typical oregano flavour” and off-flavour are similar for the four cultivated samples; instead the commercial sample has less freshness and a lower typical oregano flavour, associated with a higher level of off-flavour.     

New and Rare Carotenoids Isolated from Marine Bacteria and Their Antioxidant Activities

Marine bacteria have not been examined as extensively as land bacteria. We screened carotenoids from orange or red pigments-producing marine bacteria belonging to rare or novel species. The new acyclic carotenoids with a C₃₀ aglycone, diapolycopenedioc acid xylosylesters A–C and methyl 5-glucosyl-5,6-dihydro-apo-4,4′-lycopenoate, were isolated from the novel Gram-negative bacterium Rubritalea squalenifaciens, which belongs to phylum Verrucomicrobia, as well as the low-GC Gram-positive bacterium Planococcus maritimus strain iso-3 belonging to the class Bacilli, phylum Firmicutes, respectively. The rare monocyclic C₄₀ carotenoids, (3R)-saproxanthin and (3R,2′S)-myxol, were isolated from novel species of Gram-negative bacteria belonging to the family Flavobacteriaceae, phylum Bacteroidetes. In this review, we report the structures and antioxidant activities of these carotenoids, and consider relationships between bacterial phyla and carotenoid structures.     

The effects of volatile oils on in vitro potato sprout growth

Summary The effects of 10 volatile oils and their main compounds on potato sprout growth were investigated in vitro. Sprout growth was inhibited especially by the volatile oils fromOriganum onites, Rosa damascena, Carum carvi, Mentha piperita, Echinophora tuneifolia andCoriandrum sativum. The major compound of volatile oils was carvacrol (78.2%) inO. onites, citronellol (46.7%) inR. damascena, S-(+)-carvone (54.9%) inC. carvi, menthol (44.1%) inM. piperita, α phelladrene (45.9%) inE. tuneifolia and linalool (76.5%) inC. sativum. The results showed that some volatile oils rich in monoterpenic compounds such as carvacrol, citronellol, geraniol, nerol and S-(+)-carvone were able to prevent the growth of sprouts and extend the storage-life of the potato tubers.     

Essential oil composition of Hypericum perfoliatum L. and Hypericum tomentosum L. growing wild in Tunisia

The essential oils obtained by hydrodistillation from the aerial parts of Tunisian native Hypericum perfoliatum L. (sect. Drosocarpium Spach.) and Hypericum tomentosum (sect. Adenosepalum Spach.) were analyzed by GC and GC–MS. Thirty-two compounds were identified in the essential oils of H. perfoliatum with α-pinene (13.1%), allo-aromadendrene (11.4%), germacrene-D (10.6%), n-octane (7.3%), α-selinene (6.5%) and β-selinene (5.5%) as main constituents. Sixty-seven components were identified in the oil of H. tomentosum with menthone (17.0%), n-octane (9.9%), β-caryophyllene (5.3%), α-pinene (5.2%), lauric acid (4.1%) and β-pinene (3.7%) as the most abundant components. Both oils were characterized by the presence of many components which could have numerous applications in food, pharmaceutical and perfume industries.     

Chemical composition and anti-fungal properties of the essential oils and crude extracts of Orthosiphon stamineus Benth

The hydrodistilled essential leaves and stems oils of Orthosiphon stamineus Benth were analysed by GC–MS/MS. Sixty nine compounds representing 97.6 and 97.4% of the total leaves and stems oils, respectively were identified, of which β-caryophyllene (24.0 and 35.1%), α-humulene (14.2 and 18.4%), β-elemene (11.1 and 8.5%), 1-octen-3-ol (8.2 and 7.0%), β-bourbonene (3.4 and 3.0%), β-pinene (2.1 and 1.7%), caryophyllene oxide (1.6 and 2.2%), camphene (1.6 and 1.3%) and limonene (1.2 and 1.1%) were the major compounds. Thus, the monoterpenes and sesquiterpenes were the predominant portions of the oils. Essential oils and methanol extract of O. stamineus and the derived fractions of hexane, chloroform, and ethyl acetate were tested for anti-fungal activity, which was determined by disc diffusion and minimum inhibitory concentration (MIC) determination methods. The oils, methanol extract and derived fractions of methanol extract displayed great potential of anti-fungal activity as a mycelial growth inhibitor against the tested phytopathogenic fungi such as Botrytis cinerea, Rhizoctonia solani, Fusarium solani, Colletotricum capsici and Phytophthora capsici, in the range of 49.3–70.3% and minimum inhibitory concentration ranging from 500 to 1000 μg/ml.     

Grain weight changes over time in ancient cereal crops: Potential roles of climate and genetic improvement

Inferences of grain weight (GW) for cereals cultivated in the past could be useful to track early agronomic improvements. Though strongly genetically determined, GW also depends on environmental conditions, such as water availability. In the archaeological context, we can estimate GW and plant water status from grain dimensions and carbon isotope discrimination (Δ¹³C), respectively. In this study we attempted to determine the role of environmental changes on the evolution of GW of naked wheat (Triticum aestivum/durum) and hulled barley (Hordeum vulgare) in the Ebro Depression (NE Spain) during the last four millennia. To that end, we examined charred grains from nine archaeological sites, from the Bronze Age (ca. 1950 BCE) to the end of the Middle Ages (XVth century). Estimated GW in archaeological grains (averaging ca. 19.5 mg for both species) was significantly lower than in present rainfed cereals in the area (ca. 35 mg). In contrast, for both species mean Δ¹³C values in archaeological grains were similar to or even greater than in modern material (16.3‰ and 15.5‰, respectively). Accordingly, we conclude that the most recent increase in GW cannot be attributed to increased water availability, but probably to empirical breeding efforts which would have started not before the beginning of the CE.     

Biomass yield and energy balance of three perennial crops for energy use in the semi-arid Mediterranean environment

Three different lignocellulosic energy crops (a local clone of Arundo donax L., Miscanthus x giganteus Greef et Deu. and Cynara cardunculus L. var. altilis D.C. cv. “Cardo gigante inerme”) were compared over 5 years (2002–2007) for crop yield, net energy yield and energy ratio. In a hilly interior area of Sicily (Italy), two different irrigation treatments (75 and 25% of ETm restoration) and two nitrogen fertilization levels (100 and 50 kg ha⁻¹) were evaluated in a split-plot experiment. In the fourth and fifth years of the field experiment (2005–2007) no fertilizer or irrigation was used.From crop establishment to the third year, above ground dry matter yield increased over all studied factors, in A. donax from 6.1 to 38.8 t ha⁻¹ and in M. x giganteus from 2.5 to 26.9 t ha⁻¹. Fifteen months after sowing, C. cardunculus yielded 24.7 t ha⁻¹ of d.m. decreasing to 8.0 t ha⁻¹ in the third year. In the fourth and fifth years, above ground dry matter yields of all crops decreased, but A. donax and M. x giganteus still maintained high productivity levels in both years. By contrast the yield of C. cardunculus yield fell to less than 1 t ha⁻¹ of d.m. by the fourth year.Energy inputs of A. donax and M. x giganteus were higher in the year of establishment than that of C. cardunculus (34 GJ ha⁻¹ for A. donax and M. x giganteus and 12 GJ ha⁻¹ for C. cardunculus), mainly due to irrigation.Net energy yield showed low or negative values in the establishment year in A. donax and M. x giganteus. In the second and third year, net energy yield of A. donax was exceptionally high (487.2 and 611.5 GJ ha⁻¹, respectively), whilst M x giganteus had lower values (232.2 and 425.9 GJ ha⁻¹, respectively). M x giganteus attained its highest net energy yield in the fourth year (447.2 GJ ha⁻¹). Net energy yield of C. cardunculus reflected energy output of the crop, being high in the first compared to subsequent years (364.7, 277.0 and 119.2 GJ ha⁻¹, respectively for the first, second and third years).A significant effect of the different irrigation treatments was noted on all the studied parameters in all species. Conversely, only A. donax was affected by nitrogen fertilization.     

Growth, yield and mineral content of Miscanthus × giganteus grown as a biofuel for 14 successive harvests

Miscanthus × giganteus, a perennial rhizomatous grass commercially used as a biofuel crop was grown in a field experiment on a silty clay loam soil for 14 years. There were 3 rates of fertilizer nitrogen (N), none (control), 60 kg N ha⁻¹ yr⁻¹ and 120 kg N ha⁻¹ yr⁻¹ as cumulative applications. The crop was harvested in winter and dry matter yield measured. N did not influence yield. Yield, which increased for the first 6 years, decreased in years 7 and 8, but then increased again and was highest in the 10th year averaging 17.7 t ha⁻¹ across all treatments. Differences in total production over the14 years were only 5% between the highest and lowest yielding treatments and averaged 178.9 t ha⁻¹ equivalent to 12.8 t ha⁻¹ yr⁻¹. In the first 10 harvests, 92% of dry matter was stem. Although the study showed N fertilizer was not required, it is considered that an application of 7 kg P ha⁻¹ yr⁻¹ and 100 kg K ha⁻¹ yr⁻¹ would avoid soil reserve depletion. Pesticides were not required every year and the crop can be considered as low input with a high level of sustainability for at least 14 years.     

Selection of fecund and chemically valuable clones of thyme (Thymus) species growing wild in Lithuania

The high infraspecific chemical and morphological polymorphism is characteristic for species of genus thyme (Thymus L.). This characteristic can be subservient to the selection of valuable clones from natural habitats. The objective of the present study was to select valuable Thyme clones from native flora of Lithuania according to the productivity of biomass and chemical composition of essential oils for the cultivation. Two Thymus species, namely large thyme (T. pulegioides L.) and wild thyme (T. serpyllum L.), grow wild in Lithuania and other Baltic States (Latvia and Estonia). Was established that T. pulegioides is more suitable for the cultivation than T. serpyllum, because can grow more dried total biomass (up to 3 times), are higher (2.8 times) and synthesize higher amount of essential oils with significant amounts of such biologically active compounds as the thymol, carvacrol, geraniol or linalool. Four most fecund clones of T. pulegioides (the total biomass of dried plant 29–45 g, the amount of essential oil in whole plant 0.5–0.7%) were selected which accumulate the highest amounts of thymol (up to 26.1%), carvacrol (up to 31.0%), geraniol (up to 45.0%) and linalool (up to 80.3%). The cultivation of these clones enables to get the high yield of biomass and chemically homogeneous herbal raw material of desirable chemical composition for the phytomedicines and phytocosmetics.     

Nocapyrones: α- and γ-Pyrones from a Marine-Derived Nocardiopsis sp.

One new α-pyrone (nocapyrone R (1)), and three known γ-pyrones (nocapyrones B, H and L (2–4)) were isolated from the culture extract of a Nocardiopsis strain collected from marine sediment. Structures of these compounds were determined on the basis of spectroscopic data including NMR and MS. γ-Pyrones 2–4 were found to induce adiponectin production in murine ST-13 preadipocyte cells but the α-pyrone 1 had no activity. The absolute configuration of the anteiso-methyl branching in 4 was determined by HPLC comparison of a degraded product of 4 with standard samples as a 2:3 enantiomeric mixture of (R)- and (S)-isomers.     

First Identification of 12β-Deoxygonyautoxin 5 (12α-Gonyautoxinol 5) in the Cyanobacterium Dolichospermum circinale (TA04) and 12β-Deoxysaxitoxin (12α-Saxitoxinol) in D. circinale (TA04) and the Dinoflagellate Alexandrium pacificum (Group IV) (120518KureAC)

Saxitoxin and its analogues, paralytic shellfish toxins (PSTs), are potent and specific voltage-gated sodium channel blockers. These toxins are produced by some species of freshwater cyanobacteria and marine dinoflagellates. We previously identified several biosynthetic intermediates of PSTs, as well as new analogues, from such organisms and proposed the biosynthetic and metabolic pathways of PSTs. In this study, 12β-deoxygonyautoxin 5 (12α-gonyautoxinol 5 = gonyautoxin 5-12(R)-ol) was identified in the freshwater cyanobacterium, Dolichospermum circinale (TA04), and 12β-deoxysaxitoxin (12α-saxitoxinol = saxitoxin-12(R)-ol) was identified in the same cyanobacterium and in the marine dinoflagellate Alexandrium pacificum (Group IV) (120518KureAC) for the first time from natural sources. The authentic standards of these compounds and 12α-deoxygonyautoxin 5 (12β-gonyautoxinol 5 = gonyautoxin 5-12(S)-ol) were prepared by chemical derivatization from the major PSTs, C1/C2, produced in D. circinale (TA04). These standards were used to identify the deoxy analogues by comparing the retention times and MS/MS spectra using high-resolution LC-MS/MS. Biosynthetic or metabolic pathways for these analogues have also been proposed based on their structures. The identification of these compounds supports the α-oriented stereoselective oxidation at C12 in the biosynthetic pathway towards PSTs.     

Waxy gene haplotypes: Associations with pasting properties in an international rice germplasm collection

Associations between RVA pasting properties and three single nucleotide polymorphism (SNP) sites in the Waxy gene intron 1, exon 6, and exon 10 were determined using rice genotypes of diverse geographic origin. A total of four SNP-haplotypes (combination of SNP alleles) were identified that explained high proportions of the variation in RVA pasting properties (R² = 0.574–0.704). A haplotype containing DNA sequence variation in exon 10 (exon 10 cytosine nucleotide) was exclusively found in high-apparent amylose content (AAC) genotypes with a higher RVA viscosity profile compared to the high AAC genotypes with a different haplotype. The exon 10 SNP explained variances in coolpaste and setback (coolpaste–hotpaste) to 0.642 and 0.499, respectively. Across three haplotypes, which contained exon 10 adenine nucleotide, AAC was correlated with peak, hotpaste, breakdown and setback (coolpaste–hotpaste) at r = −0.85, −0.75, −0.79, and 0.49, respectively. Therefore, the exon 10 SNP differentiates high AAC types with a strong RVA profile and thus can be used by molecular breeding programs focused on quality improvement. Additionally, characterizing genotypes by their functional SNPs allowed us to better understand the relationship between the Waxy gene, its chemical product (i.e., AAC) and the functionality created by the product (i.e., pasting properties).     

Differences in conformational stability of barley alpha-amylase isozymes 1 and 2. Role of charged groups and isozyme 2 specific salt-bridges

Barley alpha-amylase isozymes 1 (AMY1) and 2 (AMY2) have 80% sequence identity but possess different physico-chemical properties. By incubation in the range 37–85 °C T₅₀ is 75.2 °C of AMY1 and 79.2 °C of AMY2. While AMY2 is also most stable in urea at pH 6.7, [urea]₅₀ being 8.2 M compared to 7.9 M for AMY1, AMY1 has highest stability in urea below pH 6 or in the presence of NaCl. Moreover AMY1 is most stable in guanidinium chloride. Charge screening thus destabilises AMY2 but stabilises AMY1. Isozyme sequence comparison suggests that AMY1 lacks four of the 20 salt-bridges identified in the crystal structure of AMY2. The four residues that differ comprise Lys67_AMY2 and Asp267_AMY2, forming salt-bridges on the surface of the catalytic (β/α)₈-barrel (domain A), and Glu96_AMY2 and His344_AMY2 that participate in charged networks between domain A and the small domain B and the C-terminal domain, respectively. Four corresponding AMY2 mimics A68K; D97E; Q269D; N346H were made in AMY1 by site-directed mutagenesis. While D97E and Q269D have slightly improved stability compared to AMY1 wild-type, N346H and, under certain conditions, A68K are destabilised. The four mutants show 22–176% activity (k_cat/K_m) toward 2-chloro-4-nitrophenol β- -maltoheptaoside and amylose DP17 and 43–117% activity for insoluble starch.     

Cytotoxic and Antibacterial Cembranoids from a South China Sea Soft Coral,Lobophytum sp

Chemical examination of a South China Sea soft coral Lobophytum sp. led to the isolation of three new α-methylene-γ-lactone-containing cembranoids, (1R*,3R*,4R*,14R*,7E,11E)-3,4-epoxycembra-7,11,15(17)-trien-16,14-olide (1), (1R*,7S*,14S*,3E,11E)-7-hydroperoxycembra-3,8(19),11,15(17)-tetraen-16,14-olide (2), and (1R*,7S*,14S*,3E,11E)-18-acetoxy-7-hydroperoxycembra-3,8(19),11,15(17)-tetraen-16,14-olide (3), along with eleven known analogues 4–14. The structures of the new compounds were elucidated through extensive spectroscopic analysis, including 1D and 2D NMR data. Compounds 1–3 exhibited moderate cytotoxic activity against the selected tumor cell lines. Moreover, 2 and 3 were found to be moderate inhibitors against the bacteria S. aureus and S. pneumoniae.     

Essential oil and by-products of distillation of bay leaves (Laurus nobilis L.) from Argentina

Preliminary chemical studies were undertaken during one year on plant materials collected in a 40 ha field located in Henderson, Province of Buenos Aires, in order to determine the technical viability of the industrial production of essential oil from bay leaves (Laurus nobilis L., Lauraceae) growing in Argentina. The oils were extracted at a pilot scale plant and analyzed by GC–FID-MS. The apparent density of the plant material used for the distillation ranged from 90 g L⁻¹ to 170 g L⁻¹, depending on the type of material. The quality of the volatile oils obtained complied with market requirements and were in agreement with values reported from other countries. No considerable variations were observed in the chemical composition of the oils throughout the year. Taking in account the composition of the sub-fractions obtained during the distillation process, the quality of the final essential oil can be adjusted by fractional distillation. The occurrence of alcohol terpenes and phenols in the condensed waters (hydrolate) makes them a possible alternative to be used in industry. Moreover, and due to the good energetic and digestibility values obtained, our results showed that the exhausted plant material obtained after distillation could be a putative fibrous feed for ruminants. Both, hydrolate and exhausted plant materials are resources that can enhance added values in new endeavours. This is the first report on bay leaves essential oil production at industrial scale in Argentina.     

Effect of growth stage on the content and composition of the essential oil and phenolic fraction of sweet marjoram (Origanum majorana L.)

The variation in the content and composition of Origanum majorana L. essential oil has been studied. Plant material has been harvested at four phenological stages (early vegetative, late vegetative, budding and full-flowering). Essential oil yield varied from 0.04 to 0.09% reached during the full-flowering stage. Analysis of the essential oils by GC and GC/MS revealed the presence of 38 components represented mainly by oxygenated monoterpenes (64.01–71.4%), monoterpene hydrocarbons (21.73–29.92%) and sesquiterpene hydrocarbons (1.47–4.05%). The main components were terpinen-4-ol (29.13–32.57%), cis-sabinene hydrate (19.9–29.27%), trans-sabinene hydrate (3.5–11.61%), γ-terpinene (2.11–8.20%), bornyl acetate (1.52–2.94%) and linalool (1.05–1.39%). On the other hand, phenolic contents varied from 2.706 to 6.834 mg/g of dry weight obtained during the later vegetative stage. RP-HPLC analysis of the methanolic extract of O. majorana L. dried aerial parts showed the predominance of phenolic acids during the early vegetative stage whereas flavonoids predominate during the other stages of growth. The main phenolic acids identified were trans-2-hydroxycinnamic, rosmarinic, vanillic, chlorogenic, gallic and cinnamic whereas the main flavonoids were amentoflavone, apigenin, quercetin, luteolin, coumarin and rutin. Results obtained showed that later vegetative stage is characterized by the highest contents of bioactive compounds and therefore it could be considered as the best stage for harvesting marjoram plants.     

Field trials of Metarhizium anisopliae var. acridum (Ascomycota: Hypocreales) against oriental migratory locusts, Locusta migratoria manilensis (Meyen) in Northern China

During 2002–2006, nymph bands of Locusta migratoria manilensis (Meyen) were treated by ground and aerial applications in 6000 ha of grasslands and the nearby beach of Yellow river using a soybean oil miscible suspension ULV formulation of Metarhizium anisopliae var. acridum isolate CQMa102. The formulation was also applied in Tianjin, Henan, Hebei, Shandong and Shanxi provinces of Northern China by ground and aerial applications. During field studies, cage tests were carried out in corresponding field plots in order to estimate the mortality accurately. Doses of 3.3×10¹² and 5.0×10¹² conidia ha⁻¹ were equally effective and caused 90% mortality 9–13 days after treatment. In the ground spray trial, 3.3×10¹² conidia ha⁻¹ killed >90% of L. migratoria manilensis 11–15 days after treatment in a wide variety of vegetation and weather conditions. The decline of locust populations was slower where vegetation was taller and denser. In the aerial spray treatment, the final percent survival of locusts was lowered to 10% at 11 and 14 days in the field cage and open field locusts, respectively. Furthermore, the M. anisopliae oil miscible suspension formulation did not appear to harm natural enemies of locusts in the field.     

Neritinaceramides A–E,New Ceramides from the Marine Bryozoan Bugula neritina Inhabiting South China Sea and Their Cytotoxicity

Five new ceramides, neritinaceramides A (1), B (2), C (3), D (4) and E (5), together with six known ceramides (6–11), two known alkyl glycerylethers (12 and 13) and a known nucleoside (14), were isolated from marine bryozoan Bugula neritina, which inhabits the South China Sea. The structures of the new compounds were elucidated as (2S,3R,3′S,4E,8E,10E)-2-(hexadecanoylamino)-4,8,10-octadecatriene-l,3,3′-triol (1), (2S,3R,2′R,4E,8E,10E)-2-(hexadecanoylamino)-4,8,10-octadecatriene-l,3,2′-triol (2), (2S,3R,2′R,4E,8E,10E)-2-(octadecanoylamino)-4,8,10-octadecatriene-l,3,2′-triol (3), (2S,3R,3′S,4E,8E)-2-(hexadecanoylamino)-4,8-octadecadiene-l,3,3′-triol (4) and (2S,3R,3′S,4E)-2-(hexadecanoylamino)-4-octadecene-l,3,3′-triol (5) on the basis of extensive spectral analysis and chemical evidences. The characteristic C-3′S hydroxyl group in the fatty acid moiety in compounds 1, 4 and 5, was a novel structural feature of ceramides. The rare 4E,8E,10E-triene structure in the sphingoid base of compounds 1–3, was found from marine bryozoans for the first time. The new ceramides 1–5 were evaluated for their cytotoxicity against HepG2, NCI-H460 and SGC7901 tumor cell lines, and all of them exhibited selective cytotoxicity against HepG2 and SGC7901 cells with a range of IC₅₀ values from 47.3 μM to 58.1 μM. These chemical and cytotoxic studies on the new neritinaceramides A–E (1–5) added to the chemical diversity of B. neritina and expanded our knowledge of the chemical modifications and biological activity of ceramides.