Anatoly Kalinovsky

• G.B. Elyakova Pacific Institute of Bioorganic Chemistry

Five new non-holostane di- and trisulfated triterpene pentaosides, conicospermiumosides A3-1 (1), A3-2 (2), A3-3 (3), A7-1 (4), and A7-2 (5) were isolated from the Far Eastern sea cucumber Cucumaria conicospermium Levin et Stepanov (Cucumariidae, Dendrochirotida). Twelve known glycosides found earlier in other Cucumaria species were also obtained a...

Four new glycosides of polyhydroxysteroids, ceramasterosides A, B, D, and E (1–4), and two previously known compounds, ceramasteroside C1 (5) and attenuatoside B-I (6), were isolated from an extract of a deep-sea sea star species, the orange cookie star Ceramaster patagonicus. The structures of 1–4 were elucidated by the extensive NMR and ESIMS met...

Ten new decalin polyketides, zosteropenilline M (1), 11-epi-8-hydroxyzosteropenilline M (2), zosteropenilline N (3), 8-hydroxyzosteropenilline G (4), zosteropenilline O (5), zosteropenilline P (6), zosteropenilline Q (7), 13-dehydroxypallidopenilline A (8), zosteropenilline R (9) and zosteropenilline S (10), together with known zosteropenillines G...

Three new monosulfated polyhydroxysteroid glycosides, spiculiferosides A (1), B (2), and C (3), along with new related unsulfated monoglycoside, spiculiferoside D (4), were isolated from an ethanolic extract of the starfish Henricia leviuscula spiculifera collected in the Sea of Okhotsk. Compounds 1–3 contain two carbohydrate moieties, one of which...

Four extracts of the marine-derived fungus Penicillium velutinum J.F.H. Beyma were obtained via metal ions stress conditions based on the OSMAC (One Strain Many Compounds) strategy. Using a combination of modern approaches such as LC/UV, LC/MS and bioactivity data analysis, as well as in silico calculations, influence metal stress factors to change...

Two new steroid 3β,21-disulfates (1, 2) and two new steroid 3β,22- and 3α,22-disulfates (3, 4), along with the previously known monoamine alkaloid tryptamine (5) were found in the ethanolic extract of the Far Eastern slime sea star Pteraster marsippus. Their structures were determined on the basis of detailed analysis of one-dimensional and two-dim...

Six previously unknown triterpene glycosides, pacificusosides L–Q (1–6), and two previously known triterpene glycosides, cucumariosides B1 (7) and A5 (8), were isolated from an alcoholic extract of Pacific sun star, Solaster pacificus. The structures of 1–6 were determined using 1D and 2D NMR, ESIMS, and chemical modifications. Compound 1 is a rare...

Two new cyclopiane diterpenes and a new cladosporin precursor, together with four known related compounds, were isolated from the marine sediment-derived fungus Penicillium antarcticum KMM 4670, which was re-identified based on phylogenetic inference from ITS, BenA, CaM, and RPB2 gene regions. The absolute stereostructures of the isolated cyclopian...

Investigation of the Vietnamese marine sponge Rhabdastrella globostellata led to the isolation of two new polar isomalabaricanes: rhabdastrellosides A (1) and B (2). Their structures and stereochemistry were elucidated with the application of 1D and 2D NMR, HRESIMS, and HRESIMS/MS methods, as well as chemical modifications and GC–MS analysis. Metab...

Seven new monosulfated triterpene glycosides, djakonoviosides A (1), A1 (2), A2 (3), and B1–B4 (4–7), along with three known glycosides found earlier in the other Cucumaria species, namely okhotoside A1-1, cucumarioside A0-1, and frondoside D, have been isolated from the far eastern sea cucumber Cucumaria djakonovi (Cucumariidae, Dendrochirotida)....

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 HRESIMS techniques as well as by chemical transformations. All new compounds have a...

Five new triterpene di-, tri- and tetrasulfated hexaosides (chitonoidosides I (1), J (2), K (3), K1 (4) and L (5)) were isolated from the Far-Eastern sea cucumber Psolus chitonoides, collected near Bering Island (Commander Islands) from a depth of 100–150 m. The structural variability of the glycosides concerned both the aglycones (with 7(8)- or 9(...

Sea stars or starfish (class Asteroidea) and holothurians or sea cucumbers (class Holothuroidea), belonging to the phylum Echinodermata (echinoderms), are characterized by different sets of glycosidic metabolites: the steroid type in starfish and the triterpene type in holothurians. However, herein we report the isolation of eight new triterpene gl...

New steroidal 3β,21-disulfates (2–4), steroidal 3β,22-disulfate (5), and the previously known related steroidal 3β,21-disulfate (1) were isolated from the ethanolic extract of the Far Eastern starfish Pteraster marsippus, collected off Urup Island in the Sea of Okhotsk. The structures of these compounds were determined by intensive NMR and HRESIMS...

Four new triterpene disulfated glycosides, chitonoidosides E1 (1), F (2), G (3), and H (4), were isolated from the Far-Eastern sea cucumber Psolus chitonoides and collected near Bering Island (Commander Islands) at depths of 100–150 m. Among them there are two hexaosides (1 and 3), differing from each other by the terminal (sixth) sugar residue, on...

Six new triterpene tetra-, penta- and hexaosides, chitonoidosides A (1), A1 (2), B (3), C (4), D (5), and E (6), containing one or two sulfate groups, have been isolated from the Far-Eastern sea cucumber Psolus chitonoides, collected near Bering Island (Commander Islands) from the depth of 100–150 m. Three of the isolated compounds (1, 3 and 6) are...

Nine new mono-, di-, and trisulfated triterpene penta- and hexaosides, kurilosides A3 (1), D1 (2), G (3), H (4), I (5), I1 (6), J (7), K (8), and K1 (9) and two desulfated derivatives, DS-kuriloside L (10), having a trisaccharide branched chain, and DS-kuriloside M (11), having hexa-nor-lanostane aglycone with a 7(8)-double bond, have been isolated...

Three new triterpene glycosides, pacificusosides A–C (1–3), and three previously known triterpene glycosides, cucumariosides C1 (4), C2 (5), and A10 (6), were isolated from the alcoholic extract of the Far Eastern starfish Solaster pacificus. The structures of 1–3 were elucidated by extensive NMR and ESIMS techniques and chemical transformations. C...

In continuation of our studies on a Vietnamese collection of a Stelletta sp., sponge we have isolated two new isomalabaricane triterpenoids, stellettins Q and R (1 and 2), and four new isomalabaricane-derived nor-terpenoids, stellettins S-V 3–6, along with previously known globostelletin N. Among them, compound 3 contains an acetylenic fragment, un...

Six new monosulfated triterpene tetra-, penta- and hexaosides, namely, the kurilosides A1 (1), A2 (2), C1 (3), D (4), E (5) and F (6), as well as the known earlier kuriloside A (7), having unusual non-holostane aglycones without lactone, have been isolated from the sea cucumber Thyonidium (= Duasmodactyla) kurilensis (Levin) (Cucumariidae, Dendroch...

Two new natural compounds, sulfated polyhydroxysteroid, microdiscusol G (1), and polyhydroxysteroid bioside, microdiscusoside A (2), along with eight previously known polar steroid substances 3–10, were isolated from the Arctic starfish Asterias microdiscus. The structures of 1 and 2 have been elucidated by extensive 1D and 2D NMR spectroscopy and...

Genomic analysis of the marine bacterium Wenyingzhuangia fucanilytica CZ1127T revealed the presence of four fucoidanase genes fwf1, fwf2, fwf3, fwf4 that belonged to the glycoside hydrolase family 107 (GH107, CAZy), which is located in one gene cluster putatively involved in fucoidan catabolism. Genes encoding two fucoidanases fwf1 and fwf2 were cl...

Thirteen new mono-, di-, and trisulfated triterpene glycosides, quadrangularisosides A–D4 (1−13) have been isolated from the sea cucumber Colochirus quadrangularis, which was collected in Vietnamese waters. The structures of these glycosides were established by 2D NMR spectroscopy and HR-ESI (High Resolution Electrospray Ionization) mass spectromet...

Leptogorgins A–C (1–3), new humulane sesquiterpenoids, and leptogorgoid A (4), a new dihydroxyketosteroid, were isolated from the gorgonian Leptogorgia sp. collected from the South China Sea. The structures were established using MS and NMR data. The absolute configuration of 1 was confirmed by a modification of Mosher’s method. Configurations of d...

Structure of the fucoidan from Sargassum horneri and products of its enzymatic transformation with molecular weight over 20 kDa were investigated. Fucoidan was hydrolyzed by recombinant fucoidanase FFA1 and its fraction of higher molecular weight was fractionated using anion-exchange chromatography, resulting in three sulphated polysaccharides of v...

Four new conjugates, esters of polyhydroxysteroids with long-chain fatty acids (1–4), were isolated from the deep-water Far Eastern starfish Ceramaster patagonicus. The structures of 1–4 were established by NMR and ESIMS techniques as well as chemical transformations. Unusual compounds 1–4 contain the same 5α-cholestane-3β,6β,15α,16β,26-pentahydrox...

Four new polyhydroxylated steroids 1-4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and...

Ten new di-, tri- and tetrasulfated triterpene glycosides, psolusosides B1 (1), B2 (2), J (3), K (4), L (5), M (6), N (7), O (8), P (9), and Q (10), were isolated from the sea cucumber Psolus fabricii collected in the Sea of Okhotsk near the Kurile Islands. Structures of these glycosides were established by two-dimensional (2D) NMR spectroscopy and...

Two novel C19 terpenoids (1, 2) with an unprecedented carbon skeleton (A) were isolated from a Stelletta sp. sponge collected from Vietnamese waters. Their structures and absolute configurations were established by extensive NMR, MS, and ECD analyses together with quantum chemical modeling and biogenetic considerations. The probable pathways of bio...

Five new triterpene glycosides, psolusosides C 3 (1), D 2 (2), D 3 (3), D 4 (4), and D 5 (5), have been isolated from the sea cucumber Psolus fabricii. The structures of these glycosides were elucidated by 2-dimensional nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. All the compounds contain hexasaccharide carbohydra...

Six new polyhydroxylated steroids conjugated with taurine, microdiscusols A-F, were isolated from the alcoholic extract of the Arctic starfish Asterias microdiscus. Three of them have been found to have additional sulfate groups in tetracyclic cores. The structures of new compounds were established by 1D and 2D NMR and HRESIMS techniques. The found...

A triterpene glycoside identified as holothurin A 2 (= echinoside A) was isolated from the extract of the tropical starfish Choriaster granulatus and identified by extensive nuclear magnetic resonance (NMR) spectroscopy and electrospray ionization (ESI) mass spectrometry techniques. The fact of obtaining this typical for tropical sea cucumbers meta...

Seven sulfated triterpene glycosides, psolusosides B (1), E (2), F (3), G (4), H (5), H1 (6), and I (7), along with earlier known psolusoside A and colochiroside D have been isolated from the sea cucumber Psolus fabricii collected in the Sea of Okhotsk. Herein, the structure of psolusoside B (1), elucidated by us in 1989 as a monosulfated tetraosid...

Two new steroid glycosides, linckosides LI (1) and L2 (2), were isolated, along with the previously known echinasteroside C (3) from the ethanolic extract of the Vietnamese blue starfish, Linckia laevigata. The structures of the new compounds were elucidated by spectroscopic methods (mainly 2D NMR) and chemical transformations. Lifetime observation...

New asterosaponin, acanthaglycoside G (1), along with three previously known steroidal oligoglycosides (2‒4), were isolated from the ethanolic extract of the starfish Acanthaster planci, collected off the coast of Vietnam. The structure of 1 was mainly elucidated by extensive NMR and ESIMS techniques as sodium 6-O-{β-D-fucopyranosyl-(1→2)-β-D-quino...

Three new triterpene glycosides, psolusosides C1 (1), C2 (2) and D1 (3) have been isolated from the sea cucumber Psolus fabricii collected in the Sea of Okhotsk in the shallow waters of Onekotan Island (Kurile Islands). Five known glycosides: cladolosides B, M1, P2, isolated earlier from the sea cucumbers of genus Cladolabes and holotoxin A1 with 2...

Four new oxysterols 1–4 along with previously known oxygenated sterols 5–14 were isolated from the sponge Inflatella sp., collected from the Sea of Okhotsk. Structures of 1–4 were elucidated by the detailed NMR spectroscopic and mass-spectrometric analyses as well as by comparison of the corresponding experimental data with those reported in litera...

New marine glycoconjugates—the steroidal glycosides designated as anthenosides V–X (1–3)—and the seven previously known anthenosides E (4), G (5), J (6), K (7), S1 (8), S4 (9), and S6 (10) were isolated from the extract of the tropical starfish Anthenea aspera. The structures of 1–3 were elucidated by extensive NMR and ESIMS techniques. Glycoside 1...

Fucoidans belong to a structurally heterogeneous class of sulfated polysaccharides isolated from brown algae. They have a wide spectrum of biological activities. The complex structures of these polysaccharides hinder structure-activity relationships determination. Fucoidan sulfatases can make useful tools for the determination of the fine chemical...

Eight new triterpene olygoglycosides, cladolosides C4 (1), D1 (2), D2 (3), M (4), M1 (5), M2 (6), N (7) and Q (8), were isolated from the tropical Indo-West Pacific sea cucumber Cladolabes schmeltzii (Sclerodactylidae, Dendrochirotida). Structures of these glycosides were elucidated by 2D NMR spectroscopy and HR ESI mass spectrometry. A novel hexas...

The sea cucumber Cladolabes schmeltzii (Sclerodactylidae, Dendrochirotida) contains diverse glycosides, including several dozen individual compounds. Six new triterpene oligoglycosides, cladolosides O (1), P (2), P1 (3), P2 (4), P3 (5) and R (6), were isolated from this sea cucumber. Their structures were elucidated by 2D NMR spectroscopy and HR ES...

Two new polyhydroxysteroidal glycosides, anthenosides A1 (1) and A2 (2), and one previously known steroidal glycoside anthenoside A (3) were isolated from extract of the tropical starfish Anthenea aspera. Structures of 1–3 were determined by analysis of the spectroscopic data as well as chemical transformations. As a result, the structure of anthen...

The O-polysaccharide was isolated from the lipopolysaccharide of a marine bacterium Pseudomonas glareae KMM 9500T and studied by chemical methods along with 1D and 2D ¹H and ¹³C NMR spectroscopy including ¹H,¹H-TOCSY, ¹H,¹H-COSY, ¹H,¹H-ROESY, ¹H,¹³C-HSQC and ¹H,¹³C-HMBC experiments. The O-polysaccharide was found to consist of linear tetrasaccharid...

New minor triterpene glycoside, cucumarioside D (1) identified earlier as a candidate to new glycoside using LC-ESI QTOF-MS has been isolated from the sea cucumber Eupentacta fraudatrix as individual substance. The structure of the glycoside was elucidated using 2D NMR spectroscopy and MS. The glycoside has non-sulfated pentasaccharide carbohydrate...

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...

Structure and anticancer activity of fucoidan from Sargassum horneri and from products of its enzymatic transformation were investigated. A gene that encodes fucoidanase ffa1 in the marine bacteria F. algae was identified, cloned and the protein (FFA1) was produced in Escherichia coli. The mass of the gene product FFA1 is 111 kDa. Sequence analysis...

Seven new asterosaponins, pentaregulosides A–G (1–7), including two furostane-type steroid oligoglycosides (2, 3), along with four previously known compounds (8–11) were isolated from the ethanolic extract of the starfish Pentaceraster regulus, collected off the coast of Vietnam. The structures of 1–7 were elucidated by extensive NMR and ESIMS tech...

A new unique steroidal glycoside, granulatoside C (1), was isolated from the ethanol extract of the starfish Choriaster granulatus. The structure of 1 was elucidated by extensive NMR and ESI-MS techniques as (20R)-16,21-O-di-(β-D-fucopyranosyl)-24-methyl-cholesta-5,24(28)-diene-3β,7α,16α,21-tetraol (1). This glycoside is unusual one, because combin...

Two new monosulfated triterpene glycosides, magnumosides B3 (1) and B4 (2) and one new disulfated triterpene glycoside, magnumoside C3(3) have been isolated from the tropical Indo-West Pacific sea cucumber Neothynidium (=Massinium) magnum (Phyllophoridae, Dendrochirotida) collected in the Vietnamese shallow waters. The structures of the glycosides...

The first representatives of a new group of manzamine-related alkaloids with a previously unknown skeletal systems, namely, lissodendoric acids A (1) and B (2), were isolated from the sponge Lissodendoryx florida collected from the Sea of Okhotsk. The structures and absolute configurations have been elucidated by extensive spectroscopic analysis to...

We presented the structure of the sulfated polysaccharide moiety and anticancer activity in vitro of the О-deacylated lipopolysaccharide (DPS) isolated from the marine bacterium Poseidonocella pacifica KMM 9010T. The structure of O-polysaccharide was investigated by chemical methods along with ¹H and ¹³C NMR spectroscopy. The O-polysaccharide was b...

A facile synthesis of a set of deuterium-labeled steroid 3,6-diols with different steroid A/B ring fusion, unsaturations, and configurations of hydroxyl groups at C-3 and C-6 is described. Reduction and deuteration, based on deuterium-exchange of the obtained the cholest-4-ene-3,6-dione from cholesterol using sodium borodeuteride and deuterium wate...

Nine new sulfated triterpene glycosides, magnumosides A1 (1), A2 (2), A3 (3), A4 (4), B1 (5), B2 (6), C1 (7), C2 (8) and C4 (9) as well as a known colochiroside B2 (10) have been isolated from the tropical Indo-West Pacific sea cucumber Neothynidium (=Massinium) magnum (Phyllophoridae, Dendrochirotida) collected in the Vietnamese shallow waters. Th...

Seven new triterpene glycosides, erylosides F8 (1), V1 (2), V2 (3), V3 (4), W (5), W1 (6) and W2 (7), were isolated from a Carribean sponge Erylus goffrilleri collected from the Carribean Sea near the Arrecife-Seco reef (Cuba). Structures of the glycosides were determined using ¹H and ¹³C NMR spectroscopy, including 2D NMR procedures (¹H–¹H COSY, ¹...

Two new prenylated flavanones, isomaackiaflavanone A (1), isomaackiaflavanone B (2) and a new prenylated stilbene maackiastilbene (3), along with five known flavanones were isolated from the root bark of Maackia amurensis using repeated column chromatography on silica gel, Sephadex LH-20 and octadecyl silica (ODS-A) sorbents. The structures of the...

Two new minor eremophilane-type sesquiterpene glucosides, alticolosides H (1) and I (2) along with known earlier lignan glucosides (−)-pinoresinol-4′-O-β-d-glucoside, plucheoside D1 and tortoside F were isolated from aerial parts of the endemic Far Eastern species Ligularia alticola Worosch. (Family Asteraceae). Structures of the glycosides were el...

Strain KMM 9513T was isolated from a sediment sample collected from the Sea of Japan seashore and selected due to its ability to inhibit indicator bacterial growth. The strain KMM 9513T has been recently described as a novel species Rheinheimera japonica. This study was undertaken to determine which substances produced by strain KMM 9513T could be...

Marine-derived fungi are very promising source of structurally unique and biologically active secondary metabolites. From the beginning of the twenty-first century, the discovery of new natural compounds from marine fungi has been extensively increased annually.

Six new monosulfated triterpene glycosides, cladolosides I1 (1), I2 (2), J1 (3), K1 (4), K2 (5) and L1 (6) were isolated from the tropical Indo-West Pacific sea cucumber Cladolabes schmeltzii (Cladolabinae, Sclerodactylidae, Dendrochirotida). Structures of these glycosides were elucidated by 2D NMR spectroscopy and mass spectrometry. Four new types...

A new antibiotic complex of six aureolic acids was isolated from the marine sediment-associated strain Streptomyces sp. KMM 9048. Four of the compounds (3–6) were found to be similar but not identical to the known chromomycins A2, A3, demethyl chromomycin A3 and A4. The two remaining compounds, A2–1 (1) and A3–1 (2), were established as novel chrom...

The O-polysaccharide was isolated from the lipopolysaccharide of Cellulophaga algicola and studied by chemical analyses along with ¹H and ¹³C NMR spectroscopy, including 2D ¹H, ¹H COSY, TOCSY, ROESY, ¹Н, ¹³С HSQC, HMBC experiments. It was found that the polysaccharide is built up of branched pentasaccharide repeating units, containing D-mannose (Ma...

Reactions of tryptanthrin with acetone, cyclopentanone, hexan-2-one, 4-methylpentan-2-one, 4-hydroxy-4-methylpentan-2-one, cyclohexanone, and butan-2-one in the presence of potassium carbonate afforded racemic phaitanthrin A and other addition products to the ketone group of tryptanthrin with high yields. Thermal dissociation, some chemical transfo...

Two new sulfated steroidal glycosides were isolated from the EtOH extract of the tropical starfish Pentaceraster regulus. Regulusoside S1 was proposed to be the sodium salt of (24R)-3-O-(2-O-methyl-β-D-xylopyranosyl)-24-ethyl-5α-cholestane-3β,6α,8,15α,16β,29-hexaol 16-O-sulfate. Regulusoside S2 was its analog and contained an additional β-D-xylopyr...

Two unprecedented triterpene glycosides, fallaxosides B1 and D3 with aglycones of new skeletal types were isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The first of these aglycones is formed as result of intramolecular aldol condensation of a precursor having 1,6-diketone functionality, while the second one by pin...

[isolation, structure elucidation and bioactivity of the title steroidal glycosides, cf.

Two polar steroid compounds, taurochenodeoxycholic acid sodium salt (1) and a rare cyclic steroid glycoside luzonicoside A (2), were isolated from the tropical starfish Leiaster sp. and identified by extensive NMR and ESIMS techniques. The isolation of primary bile acid 1 is the first report from a representative of the class Asteroidea and on the...

Three new polyhydroxysteroid glycosides, regulusosides A-C (1-3) along with the previously known five steroid compounds (4-8) were isolated from the tropical starfish Pentaceraster regulus. The structures of compounds 1-3 were established by extensive NMR and ESI-MS techniques. New glycosides have the same aglycon, (24S)-5α-cholestane-3-,5,6-,8,15-...

A new asterosaponin aphelasteroside F (1) was isolated from the ethanolic extract of the Far Eastern starfish Aphelasterias japonica along with the previously known ophidianoside F (2). The structure of 1 was elucidated by extensive use of NMR and ESI-MS techniques, and chemical transformations. Compound 1 contains a new type of asterosaponin carbo...

We presented the structure of the polysaccharide moiety and anticancer activity in vitro of the sulfated lipopolysaccharide isolated from the marine bacterium Cobetia litoralis KMM 3880T. The structure of O-polysaccharide was investigated by chemical methods along with ¹H and ¹³C NMR spectroscopy. The O-polysaccharide was built up of branched trisa...

Four new trisulfated triterpene glycosides, fallaxosides D4 (1), D5 (2), D6 (3) and D7 (4) have been isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The structures of the glycosides have been elucidated by 2D NMR spectroscopy and HRESIMS. All the glycosides have the lanostane aglycones of a rare non-holostane type w...

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 linckii. 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-heptahydroxycholesta...

Two new guaiane derivatives (1 and 2) along with six known sesquiterpenoids (38) were isolated from the gorgonian Menella woodin. Their structures were elucidated by 1D and 2D NMR and HRESIMS data as well as by comparison of their spectra with those in the literature. Relative configurations of asymmetric centers in 1 and 2 were suggested on the b...

Four new triterpene glycosides, fallaxosides C1 (1), C2 (2), D1 (3) and D2 (4) along with the known cucumarioside A3-2 (5) and koreoside A (6) have been isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). Structures of the glycosides have been elucidated by 2D NMR spectroscopy and mass spectrometry. All of the glycoside...

Three new epidithiodiketopiperazines pretrichodermamides D-F (1-3), together with the known N-methylpretrichodermamide B (4) and pretrichodermamide С (5), were isolated from the lipophilic extract of the marine algae-derived fungus Penicillium sp. KMM 4672. The structures of compounds 1-5 were determined based on spectroscopic methods. The absolute...

The unusual non-holostane triterpene glycoside, colochiroside E (1) was isolated from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida). The structure of 1 was established by analysis of ID, 2D NMR and HRESI MS data. Colochiroside E (1) belongs to a rare group of glycosylated 9 beta-H-lanosta-18(16)-lactones and has an unpreceden...

Four new diterpene glycosides, virescenosides R1 (1), R2 (2), R3 (3) and Z (4) were isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Structures of 1–3 were determined as the corresponding biosides having isopimaradiene-type aglycons with additional oxidation and unsaturation p...

Seven eremophilane-type sesquiterpenes (1–7), six cycloartane derivatives (8–13) and α-amyrin acetate (14) were isolated from the leaves of the far-eastern plant Ligularia alticola Worosch. (Family Asteraceae). (4S,5R,8S,10R)-8-Ethoxyeremophil-7(11)-en-12(8)-olide (1), 8α,11-epidioxy-8β-methoxyeremophil-6-ene (2) and 29-norcycloartan-3α-ol (8) have...

The O-polysaccharide was isolated from the lipopolysaccharide of Echinicola pacifica KMM 6172(T) and studied by chemical analyses along with (1)H and (13)C NMR spectroscopy, including (1)H, (1)H COSY, 1D and 2D TOCSY, ROESY, (1)H, (13)С HMQC, HMBC and H2BC experiments. It was found that the polysaccharide is built up of branched pentasaccharide rep...

Four new triterpene glycosides, colochirosides A(1) (1), A(2) (2), A(3) (3) and D (4), have been isolated from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida). Structures of the glycosides have been elucidated by 2D NMR spectroscopy and mass-spectrometry. Colochiroside D (4) has a new type of carbohydrate chain having the only...

A new steroid glycoside, capelloside A (1), was isolated from the ethanolic extract of the starfish Ogmaster capella along with the previously known coscinasteroside B (2). The structures of 1 was elucidated by extensive NMR and ESI-MS techniques as (24S)-24-O-(3-O-methyl-β-D-xylopyranosyl)-5α-cholestane-3β,6β,8,15α,24-pentol 15-O-sulfate (1). Comp...

Four new polyoxygenated sterol derivatives (1-4) along with the compounds (5-7) previously known from other biological sources were isolated from the gorgonian Menella woodin, collected from the Vietnamese waters. Structures of 1-4 were elucidated by the detailed NMR spectroscopic and mass-spectrometric analyses as well as comparison with those rep...

Guaiane sesquiterpenoids (1, 2) were isolated from the gorgonian Menella woodin and their structures elucidated by extensive spectroscopic analysis. A complex approach was used to determine the configurations of the asymmetric centres in these natural products, based on the application of Mosher's method, and the calculation of stable conformations...

Four new triterpene glycosides, colochirosides B-1 (1), B-2 (2), B-3 (3) and C (4) have been isolated from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida). Six known earlier glycosides from representatives of two families of the order Dendrochirotida have also been found in C. robustus. Structures of the glycosides have been el...

Heating of 2,2'-methylenedicyclohexanone diphenylhydrazone in diethylene glycol was shown to result in unexpected formation of a bridged polyheterocyclic compound with a previously unknown skeleton, the structure of which was established by spectral methods and X-ray structural analysis. An explanation has been provided for the peculiar course of t...

The O-specific polysaccharide was isolated from the lipopolysaccharide of a marine bacterium Pseudoalteromonas agarivorans KMM 255(T) and studied by chemical methods along with (1)H and (13)C NMR spectroscopies. The following new structure of the O-specific polysaccharide from P. agarivorans KMM 255(T) containing 2-acetamido-2-deoxy-d-glucose (d-Gl...

Three new sulfated steroid monoglycosides, leptaochotensosides A-C (1-3), and a new sulfated polyhydroxylated steroid (4) were isolated from the alcoholic extract of the Far Eastern starfish Leptasterias ochotensis. The structures of compounds 1-4 were established by extensive nuclear magnetic resonance (NMR) and electrospray ionization mass spectr...