Chemistry and Bioactivity of Briaranes from the South China Sea Gorgonian Dichotella gemmacea.

Seven new briarane diterpenoids, gemmacolides AZ-BF (-), were isolated together with eight known analogues (-) from the South China gorgonian . Their structures were elucidated based on detailed spectroscopic analysis and a comparison with reported data. In an in vitro bioassay, these compounds exhibited different levels of growth inhibition activity against A549 and MG63 cells, giving continuous evidences about the biological contribution of functional groups at C-2, C-12, C-13, and C-16.

Crystal structures of (1,4,7,10-tetra-aza-cyclo-dodecane-κ(4) N)bis-(tri-cyano-methanido-κN)nickel and (1,4,7,10-tetra-aza-cyclo-dodecane-κ(4) N)(tri-cyano-methanido-κN)copper tri-cyano-methanide.

The structures of two mononuclear transition-metal complexes with tri-cyano-methanide (tcm(-)) and 1,4,7,10-tetra-aza-cyclo-dodecane (cyclen) ligands, [Ni(C4N3)2(C8H20N4)], (I), and [Cu(C4N3)(C8H20N4)](C4N3), (II), are reported. In the neutral complex (I), the nickel cation is coordinated by one cyclen ligand and two monodentate N-bound tcm(-) anions in a distorted octa-hedral geometry. The tcm(-) ligands are mutually cis.

Briarane diterpenoids from the gorgonian Dichotella gemmacea.

Seven new briarane diterpenoids, gemmacolides AS-AY (1-7), were isolated together with ten known analogues (8-17) from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data and comparison with reported data. The absolute configuration of compounds was determined based on electronic circular dichroism (ECD) experiments and genetic correlations as well.

Briarane diterpenes from the South China Sea gorgonian coral, Junceella gemmacea.

Four new briarane diterpenoids, junceellolides M-P (1-4), were isolated together with seven known analogs (5-11) from the South China Sea gorgonian, Junceella gemmacea. The structures of these compounds were elucidated by detailed spectroscopic analysis and comparison with the reported data. The absolute configuration of compounds 1-3 were determined based on an ECD experiment, while the absolute configuration of compound 4 was genetically determined.

Bis(dicyanamido-κN)[tris-(3-amino-propyl)amine-κ(4) N]nickel(II).

In the title complex, [Ni(C2N3)2(C9H24N4)], the Ni(II) atom is coordinated in a distorted octa-hedral geometry by one tris-(3-amino-prop-yl)amine (tris-apa) ligand and two dicyanamide (dca) ligands [one of them disordered in a 0.681 (19):0319 (19) ratio]. Inter-molecular N-H⋯N hydrogen bonds involving the N atoms of the dca anions and the tris-apa amine H atoms result in the formation of a three-dimensional network.

Tumor cell growth inhibitory activity and structure-activity relationship of polyoxygenated steroids from the gorgonian Menella kanisa.

Fourteen new polyoxygenated steroids (6, 9, 14-18, 20-23, 25-27) having carbon skeletons of cholestane, ergostane, and 24-norcholestane, were isolated together with thirteen known analogues (1-5, 7, 8, 10-13, 19, 24) from the South China Sea gorgonian Menella kanisa. The structures of the new compounds were elucidated by detailed analysis of spectroscopic data and comparisons with reported data. This is the first report of chemical investigation on the title gorgonian.

Chemistry and tumor cell growth inhibitory activity of 11,20-epoxy-3Z,5(6)E-diene briaranes from the South China Sea gorgonian Dichotella gemmacea.

Eighteen new 11,20-epoxy-3Z,5E-dien briaranes, gemmacolides AA-AR (1-18), were isolated together with three known analogs, dichotellides F (19) and I (20), and juncenolide C (21), from the South China Sea gorgonian Dichotella gemmacea. The structures of the compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was determined based on the ECD experiment.

Steroids glycosylated with both D- and L-arabinoses from the South China Sea gorgonian Dichotella gemmacea.

Three new 19-hydroxy steroidal glycosides, namely, junceellosides E-G (2-4), were isolated together with the known analogue junceelloside C (1) from the South China Sea gorgonian Dichotella gemmacea. The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. These glycosides are found to have sugar moieties of both β-l- and β-d-arabinopyranoses by HPLC analysis of their thiocarbamoyl-thiazolidine derivatives and those of authentic d- and l-arabinoses, leading to the structure revision of junceelloside C (1).

Sinularosides A and B, bioactive 9,11-secosteroidal glycosides from the South China Sea soft coral Sinularia humilis Ofwegen.

Two new 9,11-secosteroidal glycosides, namely, sinularosides A and B (1, 2), together with the known pregnene glycoside 3β-(β-xylopyranosyloxy)-5α-pregna-20-ene (3), were isolated from the South China Sea soft coral Sinularia humilis Ofwegen. The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. This is the first report of 9,11-secosteroidal glycosides from a soft coral and from nature.

New bioactive sulfated alkenes from the sea cucumber Apostichopus japonicus.

Two new alkene sulfates, (5Z)-dec-5-en-1-yl sulfate (4) and (3E)-dec-3-en-1-yl sulfate (5), together with three known sulfated alkanes, 2,6-dimethylheptyl sulfate (1), octyl sulfate (2), and decyl sulfate (3), were isolated from the sea cucumber Apostichopus japonicus. The structures of the new compounds 4 and 5 were elucidated by spectroscopic analysis, including ¹H-, ¹³C-, and 2D-NMR, ESI-MS, and HR-ESI-MS. Compounds 2 and 3 were isolated from natural sources for the first time.

Bioactive (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids from the South China Sea gorgonian Dichotella gemmacea.

Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N-S (1-6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7-10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data in combination with the comparison with reported data. The absolute configuration of 1 was determined by a TDDFT calculation of its solution ECD spectrum, affording the determination of absolute configuration of other analogues by simply comparing their ECD spectra with that of 1.

Solubility of disodium 5'-guanylate heptahydrate in aqueous methanol mixtures.

The solubility of disodium 5'-guanylate heptahydrate (5'-GMPNa2) in binary aqueous methanol solvent mixtures with the temperature ranging from 278.15 to 323.15K was measured by a dynamic method with a laser monitoring observation technique.

Bioactive 11,20-epoxy-3,5(16)-diene briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea.

Seven new briarane diterpenoids, gemmacolides G-M (1-7), were isolated together with two known analogues, juncin O and junceellolide C, from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by detailed analysis of spectroscopic data and comparison with reported data. In an in vitro bioassay, these compounds exhibited different levels of growth inhibition activity against A549 and MG63 cells.

A novel sulfated holostane glycoside from sea cucumber Holothuria leucospilota.

A new sulfated holostane glycoside, leucospilotaside B (1), together with the two related structurally known compounds holothurin B(2) (2) and holothurin B (3), was isolated from sea cucumber Holothuria leucospilota collected from the South China Sea. The structure of 1 was elucidated by spectral analysis (1H-, 13C-, and 2D-NMR, ESI-MS, and HR-ESI-MS) and chemical methods. The compounds 1-3 possess the same disaccharide moiety, but were different in the side chains of the triterpene aglycone.

Bis(2,2'-bipyridyl dioxide-κN,N')bis-(tricyano-methanido)cobalt(II) dihydrate.

In the title compound, [Co(C(4)N(3))(2)(C(10)H(8)N(2)O(2))]·2H(2)O, a novel tricyano-methanide complex, the Co(II) atom is located on an inversion center and has a distorted octa-hedral coordination with two 2,2'-bipyridyl dioxide (dpdo) mol-ecules and two trans tricyano-methanide (tcm) anions. The equatorial plane is formed by the four O atoms of the two chelating dpdo ligands, with one N atom of each of the two tcm ligands occupying an apical position. There is a disordered solvent water mol-ecule in the asymmetric unit (occupancy ratio 0.

Antifungal active triterpene glycosides from sea cucumber Holothuria scabra.

To study the new antifungal active triterpene glycosides of sea cucumber Holothuria scabra. Triterpene glycosides from Holothuria scabra were separated and purified by silica gel chromatography, reversed-phase silica gel chromatography and RP-HPLC. Their structures were elucidated on the basis of spectral data and chemical evidence.

Bis(2,2'-bipyridine N,N'-dioxide)bis-(tri-cyano-methanido)manganese(II).

In the title complex, [Mn(C(4)N(3))(2)(C(10)H(8)N(2)O(2))(2)], the Mn(II) atom lies on an inversion center and is coordinated by two 2,2'-bipyridine N,N'-dioxide (dpdo) mol-ecules and two tricyano-methanide (tcm) ligands to form a distorted octa-hedral geometry. Weak inter-molecular C-H⋯O or C-H⋯N hydrogen bonds, involving either the O atom of the dpdo mol-ecule and the pyridyl H atom, or the N atom of the tcm anion and the pyridyl H atom, result in the formation of a three-dimensional network structure.

Bis(2,2':6',2''-terpyridine)cobalt(II) bis-(tricyano-methanide).

The title complex, [Co(C(15)H(11)N(3))(2)](C(4)N(3))(2), is built up from discrete [Co(terpy)(2)](2+) cations (terpy is 2,2':6',2''-terpyridine) and [C(CN)(3)](-) anions. In the cation, the Co(II) atom is coordinated by two terpy mol-ecules, giving a distorted octa-hedral geometry. The tricyano-methanide anions are not directly coordinated to the Co(II) atom, but some weak C-H⋯N hydrogen bonds involving the terminal N atoms of the tricyaomethanide ions and the terpyridine H atoms link anions and cations building a three-dimensional network.

Antifungal triterpene glycosides from the sea cucumber Bohadschia marmorata.

Four new holostan-type triterpene glycosides, marmoratoside A ( 1), 17 alpha-hydroxy impatienside A ( 2), marmoratoside B ( 3), 25-acetoxy bivittoside D ( 4), together with two known triterpene glycosides, impatienside A ( 5) and bivittoside D ( 6), were isolated from the sea cucumber Bohadschia Marmorata Jaeger. On the basis of spectroscopic analyses, including two-dimensional NMR techniques, and chemical reactions, the structures of the new triterpene glycosides were elucidated. Compounds 1, 2, 5, and 6 exhibited significant antifungal activity against six strains (0.

Argusides B and C, two new cytotoxic triterpene glycosides from the sea cucumber Bohadschia argus Jaeger.

Two new triterpene glycosides, argusides B and C (1 and 2, resp.), have been isolated from the sea cucumber Bohadschia argus Jaeger collected in the South China Sea. Their structures have been established by spectral analysis (2D-NMR and ESI-MS) and chemical evidence.

Argusides D and E, two new cytotoxic triterpene glycosides from the sea cucumber Bohadschia argus Jaeger.

Two new triterpene glycosides, argusides D and E (1 and 2, resp.), have been isolated from the sea cucumber Bohadschia argus Jaeger collected in the South China Sea. Their structures have been established by spectral analysis (ESI-MS, and 1D- and 2D-NMR) and chemical evidence.

catena-Poly[[(2,2':6',2''-terpyridine-κN,N',N'')(tricyano-methanido-κN)nickel(II)]-μ-tricyano-methanido].

In the title complex, [Ni(C(4)N(3))(2)(C(15)H(11)N(3))](n), each of the two different Ni(II) atoms is coordinated by one 2,2':6'2''-terpyridine (terpy) and three tricyano-methanide ligands in a distorted octa-hedral geometry. The Ni(II) atoms are linked to each other, forming an infinite chain parallel to (10). π-π Stacking inter-actions of terpy mol-ecules between adjacent chains (centroid-centroid distance = 3.

Arguside A: a new cytotoxic triterpene glycoside from the sea cucumber Bohadschia argus Jaeger.

A new holostane-based triterpene glycoside, arguside A (1), was isolated from the sea cucumber Bohadschia argus, collected in the South China Sea. The structure of the new compound was elucidated by spectroscopic and mass-spectrometric analyses, in combination with chemical transformations. Compound 1 exhibited significant cytotoxicity against different human tumor cell lines, being more active towards HCT-116 cells (IC50 = 0.

A new cytotoxic lanostane-type triterpene glycoside from the sea cucumber Holothuria impatiens.

A new lanostane-type triterpene glycoside, impatienside A (1), was isolated from the sea cucumber Holothuria impatiens, together with a structurally related, known compound, bivittoside D (2). Their structures were elucidated by in-depth spectroscopic and mass-spectrometric methods, including (1)H-, (13)C-, and 2D-NMR, ESI-MS, and HR-ESI-MS experiments, as well as by chemical evidence. Compounds 1 and 2 possess the same hexasaccharide moieties, but differ slightly in their holostane-type triterpene aglycone.

Diaquabis[5-(pyrazin-2-yl-kappaN(1))-1H-tetrazolato-kappaN(1)]manganese(II) and diaquabis[5-(pyrazin-2-yl-kappaN(1))-1H-tetrazolato-kappaN(1)]zinc(II).

The two new title complexes, [Mn(C5H3N6)2(H2O)2] and [Zn(C5H3N6)2(H2O)2], are isomorphous. In both compounds, the metal atom is located on an inversion center and is coordinated by four N atoms from two 5-(pyrazin-2-yl)-1H-tetrazolate anions in the basal plane and by two O atoms of water ligands in the apical positions to form a distorted octahedral geometry. Intermolecular hydrogen-bond interactions between the uncoordinated N atoms of the tetrazolate anions and the H atoms of the water molecules lead to the formation of a three-dimensional network.