New constituents from Mikania laevigata Shultz Bip. ex Baker

A new phenylpropanoid and two new diterpenes were isolated from the leaves of the plant Mikania laevigata Shultz Bip. ex Baker. The structures of these compounds were established by 1D- and 2D-nuclear magnetic resonance spectroscopic techniques and mass spectrometry data. Taraxerol, lupeol, coumarin, syringaldehyde, trans-melilotoside, cis-melilotoside, adenosine, patuletin 3-O-β-d-glucopyranoside, kaempferol 3-O-β-d-glucopyranoside, quercetin 3-O-β-d-glucopyranoside, methyl 3,5-di-O-caffeoyl quinate, and 3,3′,5-trihydroxy-4′,6,7-trimethoxyflavone were isolated too. In addition, the compounds dihydrocoumarin, spathulenol, caryophyllene oxide, kaurenoic acid, beyerenoic acid, and lupeol acetate were identified by GC-MS.     

Three new Lycopodium alkaloids from Huperzia carinata and Huperzia squarrosa

Eleven Lycopodium alkaloids with lycodine-type, lycopodine-type, and fawcettimine-related skeletons were isolated from the whole plants of Huperzia carinata (Desv. Ex. Poir.) Trevis and Huperzia squarrosa (G. Forst) Trevis (Huperziaceae). Among them, 8,15-dihydrohuperzine A (2), lycocarinatine A (3), and lycoposerramine U N-oxide (11) are new compounds. The structures of these new alkaloids were elucidated on the basis of 2D NMR correlations. Some of these isolated alkaloids were assayed for acetylcholinesterase (AChE) inhibitory activity.     

Terpenoids from the liverwort Chandonanthus hirtellus

A new bicyclogermacrane sesquiterpenoid, two new cembrane diterpenoids and five new dolabellane diterpenoids, along with known terpenoids, have been isolated from the Malaysian liverwort Chandonanthus hirtellus. The structures of the new compounds were established by spectroscopic and chemical methods in addition to X-ray crystallographic studies.     

Emervaridione and varioxiranediol, two new metabolites from the endophytic fungus, Emericella variecolor

Two new compounds, emervaridione and varioxiranediol, together with the three known compounds, stellatic acid, ergosterol and dihydroterrein, were isolated from the endophytic fungus, Emericella variecolor. The structures of emervaridione and varioxiranediol were established from spectroscopic and X-ray crystallographic analysis.     

Amycomycins C and D,new angucyclines from Kitasatospora sp.

Two new angucycline compounds containing O-glycosylated 6-deoxy-α-l-talose were isolated from Kitasatospora sp. The compounds were elucidated based on spectroscopic methods including UV, HR-ESIMS, and NMR. A feeding experiment using alizarin led to the conversion of alizarin to a monoglycosylated product with high efficiency, which allows isolation of the sugar after hydrolysis and determination of the absolute configuration of the sugar.     

Hamigeromycins C-G, 14-membered macrolides from the fungus Hamigera avellanea BCC 17816

Five new 14-membered macrolides, hamigeromycins C-G, together with the previously described compounds, hamigeromycin A and 89-250904-F1 (radicicol analog A), were isolated from the fungus Hamigera avellanea BCC 17816. Hamigeromycins A, C, D, and E are stereoisomers differing from one another in the absolute configurations of the 4′,5′-diol moiety. Hamigeromycins F and G are unusual 5′-keto-analogs, and they are 6′-epimers to each other. The structures and the stereochemistry of the new compounds were deduced by analyses of the NMR spectroscopic and mass spectrometry data in combination with chemical means.     

Crassiflorone, a new naphthoquinone from Diospyros crassiflora (Hien)

A new naphthoquinone, 11-hydroxy-1,9-dimethyl-6H-naphtho[2′,3′:4,5]furo[3,2-c]chromene-6,7,12-trione, named crassiflorone, was isolated from the stem bark of Diospyros crassiflora together with the known compounds plumbagin, cyclocanaliculatin, gerberinol, lupeol, lupenone and betulinic acid. The structures of the compounds were established on the basis of 1D and 2D NMR spectroscopic data, as well as co-TLC with authentic samples. Some of the above compounds exhibited significant antimicrobial activity against bacteria and yeasts.     

The first two ecdysteroids containing a furan ring from Serratula wolffii

Two new ecdysteroids, named serfurosterone A and serfurosterone B, were isolated from a methanol extract of the roots of Serratula wolffii. Spectroscopic methods revealed that these compounds had previously unknown ecdysteroid structures with acetal functions in the side-chains.     

Protease inhibitors from a Slovenian Lake Bled toxic waterbloom of the cyanobacterium Planktothrix rubescens

Three new protease inhibitors, planktopeptin BL1125, planktopeptin BL843 and planktopeptin BL1061 were isolated, along with three known compounds, anabaenopeptin A, anabaenopeptin B and anabaenopeptin F from the hydrophilic extract of Planktothrix rubescens. The planar structure of the new compounds was determined by homonuclear and inverse-heteronuclear 2D NMR techniques as well as high-resolution mass spectrometry. The absolute configuration of the asymmetric centers was studied using Marfey's method for HPLC and by comparison of the acid hydrolysate with authentic samples on a chiral HPLC column. The new peptides were found to be elastase and chymotrypsin inhibitors.     

Thermal degradation products derived from the smoke of Salvia divinorum leaves

Smoking of Salvia divinorum leaves is the most common method for its psychotropic effects. Eleven thermal degradation products, including a new neoclerodane diterpene derivative, were isolated from the smoke of S. divinorum leaves, and their structures were identified by spectroscopic methods. The isolated compounds were evaluated for their binding affinities at the opioid receptors, and salvinorin A is still the most potent kappa opioid receptor agonist.     

A xanthone and a polyketide derivative from the leaves of Cassia obtusifolia (Leguminosae)

A new xanthone, 1,8-dihydroxy-3-methoxy-6-methylxantone and a new polyketide derivative, (4R^∗,5S^∗,6E,8Z)-ethyl-4-((E)-but-1-enyl)-5-hydroxypentdeca-6,8-dienoate, together with 20 known secondary metabolites, including 2 steroids, 4 xanthones, 10 anthraquinones, 2 triterpenoids, 1 fatty ester, and (E)-eicos-14-enoic acid, were isolated from the leaves of Cassia obtusifolia. To the best of our knowledge, the last compound was isolated from a natural source for the first time. The structures of all the compounds were elucidated on the basis of 1D and 2D NMR experiments. Some of the compounds were tested against Salmonella typhi, Staphylococcus aureus, Candida albicans ATCC 9002, and Candida tropicalis, they did not show any activity.     

Orirubenones A, B and C, novel hyaluronan-degradation inhibitors from the mushroom Tricholoma orirubens

Three new compounds, orirubenone A (1), B (2) and C (3) were isolated from the mushroom Tricholoma orirubens. Their structures were determined by spectral analyses. These compounds inhibited hyaluronan-degradation by human skin fibroblasts.     

Trypanocidal labdane diterpenoids from the seeds of Aframomum aulacocarpos (Zingiberaceae)

Two novel labdane type diterpenoids, 8β(17)-epoxy-14,15,16-trihydroxylabd-12(E)-ene (aulacocarpin C) and 15,16-epoxy-14ξ,16ξ-dimethoxylabda-8(17),12-(E)-diene (aulacocarpin D) together with the known aulacocarpin A and B; 14,15-epoxy-8(17),12(E)-labdadien-16-al, coronarin E, and 15,16-epoxy-12β-hydroxy-labda-8(17)-13(16),14-triene were isolated from the seeds of Aframomum aulacocarpos. To the best of our knowledge, the last compound was isolated from a natural source for the first time. Acid hydrolysis of aulacocarpin D led to another new labdane type diterpenoid, 15,16-epoxy-12β-methoxylabda-8(17)-13(16),14-triene. The structures of all compounds were established on the basis of their spectroscopic data. These new compounds exhibit moderate trypanocidal activity.     

Synoxazolidinone C; a bicyclic member of the synoxazolidinone family with antibacterial and anticancer activities

Synoxazolidinone C is a new member of the synoxazolidinone family of compounds which are dibrominated guanidinium 4-oxazolidinones isolated from the sub-Arctic ascidian Synoicum pulmonaria. The compound was isolated along with synoxazolidinones A and B from the same ascidian extract. Spectroscopic methods revealed that the synoxazolidinone C differed from the other synoxazolidinones by an unprecedented bicyclic partial structure, containing an additional pyrrolidine ring. Synoxazolidinone C exhibited both antibacterial and anticancer activities.     

Minor cacospongionolide derivatives from the sponge Fasciospongia cavernosa

Together with the known cacospongionolide, three new related sesterterpenes have been isolated from the sponge Fasciospongia cavernosa, collected from the Northern Adriatic Sea. The structures of the new compounds were proposed on the basis of spectroscopic data.     

Polyisoprenylated acylphloroglucinols and a polyisoprenylated tetracyclic xanthone from the bark of Calophyllum thorelii

Two new polyisoprenylated acylphloroglucinols, thoreliones A and B, and a new polyisoprenylated tetracyclic xanthone, oxy-thorelione A, together with twelve known compounds, were isolated from the bark of Calophyllum thorelii. The new structures were determined using spectroscopic methods and chemical modification. The major compound thorelione A (1) showed moderate cytotoxic activity against MCF-7, HeLa and NCI-H460 cells with IC₅₀ values of 7.4, 9.3 and 10.6 μg/mL, respectively, using the sulforhodamine B assay.     

Overlapping chemical and genetic diversity in Ligularia lamarum and Ligularia subspicata. Isolation of ten new eremophilanes and a new seco-bakkane compound

Root chemicals and DNA sequences were analyzed for Ligularialamarum samples collected in Yunnan and Sichuan Provinces of China and the relationship between the plant and Ligulariasubspicata, its taxonomically closest species, was examined. Both species produce furanoeremophilanes and eremophilan-8-one derivatives as the major components. Eleven new compounds, including a new seco-bakkane compound, were isolated. The two species were found to harbor overlapping intra-specific diversities with respect to the chemicals and the DNA sequences.     

Twelve new compounds from Ligularia melanothyrsa; isolation of melanothyrsins A–E,normelanothyrsin A,and other eremophilane sesquiterpenoids

Twelve new compounds, namely, five melanothyrsins A–E (1α-angeloyloxyeremophilenolides), normelanothyrsin A (1α-angeloyloxynoreremophilenone), and six other eremophilane-type compounds, have been isolated from Ligularia melanothyrsa Hand.-Mazz. (Asteraceae), collected in the Sichuan Province of China. Six of the compounds have a 1α-angeloyloxy moiety, while the other six have no functional group at the C-1 position. The absolute configuration was also determined using CD spectra. This is the first chemical study of compounds isolated from this species.     

Unusual sesquiterpene glucosides from Amaranthus retroflexus

Implementing the phytochemical study of the weed Amaranthus retroflexus, four new sesquiterpene glucosides were isolated from the methanolic extract of the plant. The structures of these metabolites are determined on the basis of the mass spectrometry, and 1D and 2D NMR spectroscopies (DQ-COSY, TOCSY, HSQC, HSQC-TOCSY, HMBC, and NOESY). Two compounds are characterized by a new aglycone and differed from the site of glucosylation. The other two compounds are dimeric diastereoisomers.All the glucoside sesquiterpenes were tested on the wild species Taraxacum officinale to evaluate the role of this weed in the habitat and on the seed of A. retroflexus to verify the potential autotoxic effect of the plant.     

Unusual octalactones from Corynespora cassiicola, an endophyte of Laguncularia racemosa

Chemical investigation of the EtOAc extract of the mangrove-derived endophyte Corynespora cassiicola, isolated from Laguncularia racemosa (Combretaceae), afforded five new secondary metabolites, named coryoctalactones A–E (1–5). The structures of the new compounds were determined on the basis of 1D- and 2D-NMR spectroscopy as well as high-resolution mass spectrometry. The absolute configuration of the side chain in 1–3 and 5 were tentatively deduced based on biogenetic consideration in comparison with xestodecalactones, previously isolated from C. cassiicola. All isolated compounds were evaluated for their antimicrobial, cytotoxic, and antitrypanosomal activities.