Bioactive constituents from transformed root cultures of Nepeta teydea.

A phytochemical study of an extract from transformed root cultures of Nepeta teydea, induced by Agrobacterium rhizogenes, led to the isolation of the following new compounds: the sesquiterpene (-)-cinalbicol, the diterpene teydeadione (6,11,14-trihydroxy-12-methoxy-abieta-5,8,11,13,15-penten-7-one), a degraded C23-triterpene (teydealdehyde) and three fatty acid esters of lanosta-7,24-dien-3β-ol. The propyl ester of rosmarinic acid was also isolated for the first time from a natural source. In addition, two dehydroabietane diterpenes, eight triterpenes and eighteen known phenolic compounds were obtained.

Biotransformation of an africanane sesquiterpene by the fungus Mucor plumbeus.

Biotransformation of 8β-hydroxy-african-4(5)-en-3-one angelate by the fungus Mucor plumbeus afforded as main products 6α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate and 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate, which had been obtained, together with the substrate, from transformed root cultures of Bethencourtia hermosae. This fact shows that the enzyme system involved in these hydroxylations in both organisms, the fungus and the plant, acts with the same regio- and stereospecificity. In addition another twelve derivatives were isolated in the incubation of the substrate, which were identified as the (2'R,3'R)- and (2'S,3'S)-epoxy derivatives of the substrate and of the 6α- and 1α-hydroxy alcohols, the 8β-(2'R,3'R)- and 8β-(2'S,3'S)-epoxyangelate of 8β,15-dihydroxy-african-4(5)-en-3-one, the hydrolysis product of the substrate, and three isomers of 8β-hydroxy-african-4(5)-en-3-one 2ξ,3ξ-dihydroxy-2-methylbutanoate.

Additional Insights into the Obtusallene Family: Components of Laurencia marilzae.

The obtusallenes are a significant subset of C15-halogenated acetogenins that incorporate 12-membered cyclic ethers. We have recently reported the isolation from Laurencia marilzae of 12-epoxyobtusallene IV (1) and its related α,β-unsaturated carboxylate ester (2), both of special biogenetic relevance. Here we describe the final step of our study, the isolation of three new analogues (3-5), among these, the first bromopropargylic derivative (3) of this class of macrocyclic C15-acetogenins.

Expedient synthesis of C3-symmetric hexasubstituted benzenes via Nicholas reaction/[2 + 2 + 2] cycloaddition. new platforms for molecular recognition.

An expedient methodology to synthesize macrocyclic compounds in one step based on the Nicholas reaction is disclosed. The key step features two intermolecular reactions followed by an intramolecular reaction from the starting dicobalt hexacarbonyl-propargylic complex. The macrocycles obtained were modified through [2 + 2 + 2] cycloaddition, generating two new C3-symmetric hexasubstituted benzene structures suitable for molecular recognition purposes.

2-Amino-N'-phenyl-benzohydrazide.

In the title compound, C(13)H(13)N(3)O, the NNCO unit forms dihedral angles of 35.8 (1) and 84.0 (1)° with the benzene and phenyl rings, respectively.

Disorder in the anionic part of catena-poly[[(pyrazine-2-carboxyl-ato)copper(II)]-μ-pyrazine-2-carboxyl-ato].

The title compound, [Cu(C(5)H(3)N(2)O(2))(0.88)(C(6)H(4)NO(2))(1.12)](n), is characterized by disorder of the anion, resulting from a statistical occupation in a 0.

4',5-Dihy-droxy-7-meth-oxy-flavanone dihydrate.

The title compound, C(16)H(14)O(5)·2H(2)O [systematic name: 5-hy-droxy-2-(4-hy-droxy-phen-yl)-7-meth-oxy-chroman-4-one dihydrate], is a natural phytoalexin flavone isolated from the native chilean species Heliotropium taltalense and crystallizes with an organic mol-ecule and two water mol-ecules in the asymmetric unit. The 5-hy-droxy group forms a strong intra-molecular hydrogen bond with the carbonyl group, resulting in a six-membered ring. In the crystal, the components are linked by O-H⋯O hydrogen bonds, forming a three-dimensional network.

4-[3-(Isonicotino-yloxy)propoxycarbon-yl]pyridinium diiodidoargentate(I).

The structure of the title compound, (C(15)H(15)N(2)O(4))[AgI(2)], consists of an organic 4-[3-(isonicotino-yloxy)propoxycarbon-yl]pyridinium cation which has a gauche-gauche (O/C/C/C-O/C/C/C or GG') conformation and lies on a twofold rotation axis, which passes through the central C atom of the aliphatic chain, and an inorganic [AgI(2)](-) anion. In the complex anion, the Ag(+) cation is bound to two I(-) anions in a linear geometry. The anion was modelled assuming disorder around a crystallographic inversion centre near the location of the Ag(+) cation.

Diaqua-bis-(5-methyl-pyrazine-2-carboxyl-ato-κN,O)cadmium.

In the title compound, [Cd(C(6)H(5)N(2)O(2))(2)(H(2)O)(2)], the Cd(II) ion is coordinated in a severely distorted octa-hedral geometry. The N atoms are cis to each other, while the water O atoms and ligand O atoms are mutually trans. The crystal structure is stabilized by a network of O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds and π-π stacking inter-actions [centroid-centroid distances = 3.

Propane-1,3-diaminium bis-(pyridine-4-carboxyl-ate) monohydrate.

The asymmetric unit of the title compound, C(3)H(12)N(2) (2+)·2C(6)H(4)NO(2) (-)·H(2)O, consists of half of a doubly protonated propane-1,3-diammonium dication, a pyridine-4-carboxyl-ate anion and half of a solvent water mol-ecule; the dication and the solvent water are located on a twofold rotation axis which passes through the central C atom of the dication and the water O atom. The carboxyl-ate group of the anion appears to be delocalized on the basis of the C-O bond lengths. In the crystal, the components are linked by inter-molecular N-H⋯O, N-H⋯N and O-H⋯O hydrogen bonds.

1-[2-(4-Nitrophenyl)-5-(5-phenyl-1,2-oxazol-3-yl)-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one.

The title compound, (I) C(28)H(24)N(4)O(4), is the trans diastereo-isomer of the compound 1-[2-(4-nitro-phen-yl)-6-(5-phenyl-3-isoxazol-yl)-1,2,3,4-tetra-hydro-4-quinolin-yl]-2-pyrrolidinone monohydrate, (II) [Gutierrez et al. (2011 ▶). Acta Cryst.

A monoclinic modification of propane-1,3-diyl bis-(pyridine-3-carboxyl-ate).

In the title compound, C(15)H(14)N(2)O(4), (I), the mol-ecule lies on a twofold rotation axis which passes through the central C atom of the aliphatic chain, giving one half-mol-ecule per asymmetric unit. The structure is a monoclinic polymorph of the triclinic structure previously reported [Brito, Vallejos, Bolte & López-Rodríguez (2010). Acta Cryst.

Nonterpenoid C15 acetogenins from Laurencia marilzae.

Eight new halogenated C(15) acetogenins, 1-8, were isolated from the organic extract of the red alga Laurencia marilzae. The structure elucidation and the assignments of the relative configurations were established by extensive use of spectroscopic studies, particularly 1D and 2D NMR data, while the absolute configurations of compounds 1 and 5 were determined by single-crystal X-ray diffraction analysis. Compounds 1, 2, 4, 5, and 7, along with the previously reported related cyclic ether obtusallene IV (9), were evaluated against six human solid tumor cell lines.

Propane-1,3-diyl bis-(pyridine-3-carboxyl-ate).

The title compound, C(15)H(14)N(2)O(4), has a trans-gauche [O/C/C/C-O/C/C/C] (TG) conformation. The angle between the planes of aromatic rings is 76.4 (3)°.

An orthorhombic polymorph of mulinic acid.

THE TITLE COMPOUND [SYSTEMATIC NAME: (3S,3aS,10bR)-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,10,10a,10b-deca-hydro-endo-epidioxy-cyclo-hepta-[e]indene-3a(1H)-carboxylic acid], C(20)H(30)O(4), is a polymorphic form of a previously reported structure [Loyola et al. (1990 ▶). Tetra-hedron, 46, 5413-5420].

Propane-1,3-diyl bis-(pyridine-4-carboxyl-ate).

The title compound. C(15)H(14)N(2)O(4), (I), has a gauche-gauche (O/C/C/C-O/C/C/C or GG) conformation and is a positional isomer of propane-1,3-diyl bis-(pyridine-3-carboxyl-ate), (II). The mol-ecule of (I) lies on a twofold rotation axis, which passes through the central C atom of the aliphatic chain, giving one half-mol-ecule per asymmetric unit.

Cynaratriol, a sesquiterpene lactone from Centaurea musimomum.

THE TITLE COMPOUND [SYSTEMATIC NAME: 3,8-dihydr-oxy-3-(hydroxy-meth-yl)-9-methyl-6-methyl-enedeca-hydro-azuleno[4,5-b]furan-2(3H)-one], C(15)H(22)O(5), is a sesquiterpene lactone showing the typical tricyclic guaianolide skeleton which has been isolated, together with other related metabolites, from the plant Centaurea musimomum. The present study confirms the mol-ecular structure, assigned by (1)H NMR and MS spectroscopy, as well as the the 11β-hydroxy-methyl, 3β-hydr-oxy and 4α-methyl stereochemistry. The crystal structure is built through a network of O-H⋯O hydrogen bonds involving the three hydroxyl groups that are present in the mol-ecular skeleton.

3-Hydr-oxy-3a,6,8c-trimethyl-perhydro-oxireno[2',3':7,8]naphtho[1,2-b]furan-7(2H)-one.

The title compound, C(15)H(22)O(4), consists of two trans-fused six-membered rings and a trans-fused five-membered γ-lactone. The ep-oxy and hydroxyl groups are α-oriented. The cyclo-hexane rings adopt half-chair and chair conformations and the lactone ring is in an envelope conformation.

1-(3-Phenyl-isoxazol-5-yl)cyclo-hexane-1,2-diol.

In the title compound, C(15)H(17)NO(3), there are two mol-ecules in the asymmetric unit wherein the isoxazole rings make dihedral angles of 16.16 (15) and 16.79 (13)° with the benzene rings, and the cyclo-hexane rings adopt chair conformations.

Ethane-1,2-diyl bis-(pyridine-3-car-box-ylate).

The title compound, C(14)H(12)N(2)O(4), has twofold imposed crystallographic symmetry in the solid state. The asymmetric unit contains one half-mol-ecule. An intra-molecular C-H⋯O hydrogen bond is formed between the carboxyl-ate O group and one H atom of the aromatic ring such that a five-membered ring is formed.

1-Methyl-4-({5-[(4-methyl-phen-yl)sulfan-yl]pent-yl}sulfan-yl)benzene.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(19)H(24)S(2). In both mol-ecules, the aliphatic segment of the ligand is in an all-trans conformation: the -S-(CH(2))(5)-S-bridging chain is almost planar (r.m.

Dimethyl 2,2'-[butane-1,4-diylbis(sul-fanediyl)]dibenzoate.

The title compound, C(20)H(22)O(4)S(2), was synthesized by the reaction of 1,4-dibromo-butene with methyl thio-salicylate. The aliphatic segment of this ligand is in an all-trans conformation. The bridging chain, -S-(CH(2))(4)-S-, is almost planar (r.

(-)-istanbulin a.

9a-hydr-oxy-3,4a,5-trimethyl-4a,6,7,8a,9,9a-hexa-hydro-4H,5H-naphtho[2,3-b]furan-2,8-dione), C(15)H(20)O(4), is a sesquiterpene lactone showing the typical eremophilanolide skeleton, which has been isolated from the plant Senecio candidans collected in the Chilean Magallanes region. The present study confirms the atomic connectivity assigned on the basis of (1)H and (13)C NMR spectroscopy, as well as the relative stereochemistry of the 4α-methyl,5α-methyl,8β-hydr-oxy,10β-H unit. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds involving the hydr-oxy group as donor and the oxo group as acceptor, giving chains along the a axis.