Five new secondary metabolites produced by a marine-associated fungus, Daldinia eschscholzii.

Five new compounds, including a benzopyran ribonic glycoside, daldiniside A (1), two isocoumarin ribonic glycosides, daldinisides B (2) and C (3), and two alkaloids, 1-(3-indolyl)-2R,3-dihydroxypropan-1-one (4) and 3-ethyl-2, 5-pyrazinedipropanoic acid (5), along with five known compounds (6-10), were isolated from the EtOAc extract of the marine-associated fungus, Daldinia eschscholzii. Their structures were elucidated by extensive physicochemical and spectroscopic properties, besides comparison with literature data. The absolute configurations of compounds 1-3 were corroborated by chemical transformation, GC analysis and X-ray crystallographic analysis. Meanwhile, the absolute configuration of compound 4 and the planar structure of compound 6 were also determined based on the X-ray diffraction analysis. The cytotoxicity of compounds 1-10, antifungal and anti-HIV activities of compounds 1-5 and the in vitro assay for glucose consumption of compounds 1-3 were done in the anti-diabetic model, whereas none showed obvious activity.

New norclerodane diterpenoids from the tubers of Dioscorea bulbifera.

Phytochemical investigations of the tubers of Dioscorea bulbifera L. resulted in the isolation of nine norclerodane diterpenoids, including two new compounds, diosbulbins N (1) and P (3), a new naturally occurring compound, diosbulbin O (2), and six known ones, diosbulbins A-D, F and G (4-9). Their structures were established by spectroscopic and chemical methods. The absolute stereochemistry of 1 was determined by a modified Mosher's method, and the absolute configuration of 2 was determined by a single-crystal X-ray diffraction analysis with CuKα irradiation. Compounds 1-3 were evaluated for in vitro cytotoxicity against five human cancer cell lines.

Structure and cytotoxicity of diterpenoids from Isodon adenolomus.

Twelve new diterpenoids, isoadenolins A-L (1-12), and 24 known ones were isolated from the aerial parts of Isodon adenolomus. Their structures were identified using spectroscopic data, and the absolute configurations of 1 and 14 were determined by single-crystal X-ray diffraction. Selected compounds were evaluated for their in vitro cytotoxicity against human tumor HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines. Compounds 9, 13-16, and 21 showed significant inhibitory effects on all five cells, with IC50 values in the range 0.7-9.7 µM.

Cytotoxic triterpene dilactones from the stems of Kadsura ananosma.

Six new triterpene dilactones with a rare rearranged pentacyclic skeleton, longipedlactones K-P (1-6), and seven known analogues (7-13) were isolated from the stems of Kadsura ananosma. Compound 1 was found to possess a unique peroxide bridge between C-1 and C-9 in rings A and B. The structures of these new compounds were established on the basis of spectroscopic data analysis, especially of their 2D NMR spectra. In the evaluation of the in vitro cytotoxicity of these compounds against a small panel of human cancer cell lines, compounds 3, 7, 9, and 13 were found to be the most potent against HL-60 acute leukemia cell.

Nortriterpenoids and lignans from the fruit of Schisandra chinensis.

Phytochemical investigation of the fruit of Schisandra chinensis led to the isolation of a schisanartane nortriterpenoid, schindilactone H (1); an 18-norschiartane bisnortriterpenoid, wuweizidilactone I (2); two tetrahydrofuran-type lignans, schinlignins A and B (18 and 19); and three dibenzyl butane-type lignans, schineolignins A-C (20-22), together with 16 known compounds. The structures of these new compounds were elucidated on the basis of extensive analysis of spectroscopic data.

Chemical constituents from the leaves and stems of Schisandra lancifolia.

A new nortriterpenoid, 20-hydroxymicrandilactone D (1) and a novel lignan glycoside, lancilignanside A (2) were isolated from leaves and stems of Schisandra lancifolia, together with three known nortriterpenoids (3-5) and nine known phenolics (6-14). The structures of new compounds 1 and 2 were determined by detailed analysis of their 1D and 2D NMR spectra, and chemical evidences. In addition, compounds 1-2, 6-7, and 9-11 showed anti-human immunodeficiency virus (HIV)-1 activities with 50% effective concentration (EC(50)) in the range of 3.0-99.0 microg/ml. Compound 12 was not bioactive in this assay with EC(50) more than 200 microg/ml.

Kinsenoside: A Promising Bioactive Compound from Anoectochilus Species.

Kinsenoside is a main active component isolated from plants of the genus Anoectochilus, and exhibits many biological activities and pharmacological effects, including hepatoprotective, anti-hyperglycemic, anti-hyperliposis, anti-inflammatory, vascular protective and anti-osteoporosis effects and so on, which is contributing to its promising potency in disease treatments. This review aims to recapitulate the pharmacological functions of kinsenoside, as well as its source, extraction, identification, quantitative analysis, pharmacokinetics, synthesis and patent information. The data reported in this work can confirm the therapeutic potential of kinsenoside and provide useful information for further new drug development.

Kadcoccinones A-F, New Biogenetically Related Lanostane-Type Triterpenoids with Diverse Skeletons from Kadsura coccinea.

Six new lanostane-related triterpenoids, kadcoccinones A-F (1-6), were isolated from Kadsura coccinea. Compound 3 possesses a novel 6/6/9-fused carbocyclic core containing a rare oxabicyclo[4.3.1]decane system. Compounds 4 and 5 are isomers representing the first example of the 18(13 → 12)-abeo-26-norlanostane triterpenoid. The absolute configurations of 1 and 4-6 were defined by X-ray diffraction and experimental ECD spectra, and that of 3 was elucidated by quantum chemical calculations. The plausible biogenetic pathway of 1-6 is postulated.

Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity.

Coumarin derivatives are an important class of C6-C3 plant metabolites that show a variety of bioactivities. Currently, most clinical anticoagulant agents are coumarins, such as warfarin, dicoumarol and acenocoumarol, and patients taking these drugs must be monitored for adverse reactions. In a search for safe and effective anticoagulant compounds from Chinese herbal medicine, a screening procedure on the whole plant of Ainsliaea fragrans was performed. The phytochemical investigation of this plant afforded five new coumarin derivatives, including a pair of natural 4-hydroxycoumarin enantiomers (1), a pair of coumarin enantiomers with a rare polycyclic pyrano[3-2c] carbon skeleton (2) and a 7-hydroxycoumarin derivative (3), together with 5 known biogenetically related compounds (4-8). Enantioseparation of 1 and 2 produced optically pure compounds 1a, 1b, 2a and 2b. The absolute configurations of the new compounds were confirmed by single-crystal X-ray diffraction analysis. In addition, we evaluated the anticoagulant activity of all isolates via activated partial thromboplastin time (APTT), thrombin time (TT) and prothrombin time (PT) assays in vitro and in vivo. Of note, compound 3 displayed potent anticoagulant activity and no significant hepatic or renal toxicity, which could make it a promising agent for further preclinical evaluation for preventing abnormal blood clotting.

Indole diketopiperazines from endophytic Chaetomium sp 88194 induce breast cancer cell apoptotic death.

Diketopiperazines are important secondary metabolites of the fungi with variety bioactivities. Several species belonging to genus Chaetomium produce compounds of this class, such as chetomin. To identify new antitumor agents, secondary metabolites of fungus Chaetomium sp 88194 were investigated and three new indole diketopiperazines, Chaetocochins G (1), Oidioperazines E (2) and Chetoseminudin E (3), along with two known compounds Chetoseminudins C (4) and N-acetyl-ß-oxotryptamine (5), were obtained. Chaetocochins G and Chetoseminudin E were recrystallized in CHCl3 containing a small amount of MeOH, and their structures with absolute configuration were established by spectroscopic data interpretation and single-crystal X-ray diffraction analysis. The absolute configuration of Oidioperazines E was defined by comparing of experimental and calculated electronic circular dichroism spectra. These isolates were also evaluated the anticancer activity, and Chaetocochins G displayed more potent cytotoxicity in MCF-7 cells than the common chemotherapeutic agent (5-fluorouracil) associated with G2/M cell cycle arrest. More importantly, Chaetocochins G induced cell apoptotic death via caspase-3 induction and proteolytic cleavage of poly (ADP-ribose) polymerase, concomitantly with increased Bax and decreased Bcl-2 expression. Our findings suggested that indole diketopiperazines from endophytic Chaetomium sp 88194 may be potential resource for developing anti-cancer reagents.

Henrischinins A-C: three new triterpenoids from Schisandra henryi.

Three novel triterpenoids, henrischinins A-C (1-3), featuring the unique motif of a 3-one-2-oxabicyclo[3.2.1]-octane, were isolated from the leaves and stems of Schisandra henryi. Their structures were elucidated by spectroscopic methods, and the absolute configuration of 2 was confirmed by a single crystal X-ray diffraction. Compounds 1 and 2 showed weak cytotoxicity against HL-60 cell lines.

Chemical constituents from the aerial parts of Isodon coetsa and their cytotoxicity.

Three new compounds (1-3), including a neolignan, a triterpenoid, and a diterpenoid, together with twenty known compounds (4-23), were isolated from the aerial parts of Isodon coetsa. Their structures and relative configurations were elucidated on the basis of spectroscopic data. Compounds 1, 3, 5-9, 11-13, 16-17, and 19-23 were evaluated for their cytotoxicity against HT-29, BEL-7402, and SK-OV-3 human tumor cell lines. Compound 7 showed significant inhibitory effects on all three types of cells, with IC50 values of 2.52, 3.06, 2.14 µM, respectively.

Schicagenins A-C: three cagelike nortriterpenoids from leaves and stems of Schisandra chinensis.

Schicagenins A-C (1-3), three unprecedented nortriterpenoids characterized with a tetracyclic oxa-cage motif and C(9) side chain, were discovered from the leaves and stems of Schisandra chinensis. Their structures were determined on the basis of extensive spectroscopic analysis, and the absolute stereochemistries were established by single-crystal X-ray diffraction and CD experiments. A plausible biosynthetic pathway of 1-3 was also discussed.