Bioactive sesquiterpenoids from the rhizomes of Acorus calamus.

Eight new sesquiterpenes (1-8) and one new norsesquiterpene (9) named calamusins A-I were isolated from the ethanol extract of Acorus calamus rhizomes. The absolute configuration of compound 8 was determined by comparing its experimental and calculated ECD spectra. The absolute configurations of the other compounds were determined from their CD spectra. Furthermore, in in vitro assays, compounds 3, 4, 7, and 9 (10 µM) exhibited weak hepatoprotective activities against APAP-induced HepG2 cell damage.

Naphthalenones from a Perenniporia sp. inhabiting the larva of a phytophagous weevil, Euops chinesis.

The new naphthalenone derivatives perenniporides A-D (1-4) were isolated from solid cultures of a fungus Perenniporia sp. inhabiting the larva of Euops chinesis, a phytophagous weevil with high host specificity to the medicinal plant Fallopia japonica. The structures of 1-4 were elucidated primarily by NMR experiments, and 1 was confirmed by X-ray crystallography. The absolute configuration of 1 and 2 was assigned by electronic circular dichroism (ECD) calculations, whereas that of the C-10 tertiary alcohol in 3 was deduced via the CD data of the in situ formed [Rh(2)(OCOCF(3))(4)] complex and supported by the ECD data. Compound 1 showed antifungal activity against five plant pathogens.

Carbazole alkaloids from the stems of Clausena lansium.

Ten new carbazole alkaloids, claulansines A-J (1-10), and seven known analogues (11-17) were isolated from the stems of Clausena lansium. Their structures were established on the basis of extensive spectroscopic analyses, and their absolute configurations were determined by CD experiments and computational methods. Screening results indicated that compounds 1, 6, 8-10, 13, 14, and 17 showed selective neuroprotective effects at the concentration of 10 µM.

Neolignans and sesquiterpenes from cell cultures of Stellera chamaejasme.

Two new neolignans (1, 2) and six sesquiterpenes (3- 8) were isolated from the cell cultures of Stellera chamaejasme. Their structures and absolute configurations were elucidated by extensive spectroscopic and computational methods. Compound 4 exhibited significant protective effects against CCl (4)-induced hepatotoxicity in HepG2 cells, reducing aspartate aminotransferase release by 29.49 % at 10 µM. These compounds have not been isolated from plant material, which implies that in vitro plant cell cultures may offer alternative and effective sources of bioactive natural compounds.

Yaoshanenolides A and B: new spirolactones from the bark of Machilus yaoshansis.

Two novel tricyclic spirolactones bearing long linear alkyl chains, yaoshanenolides A (1) and B (2), formed by Diels-Alder[4 + 2] cycloaddition of a molecule of each butenolide with ß-phellandrene, were isolated from the bark of Machilus yaoshansis. Their structures and absolute configurations were determined by extensive spectroscopic methods, especially 2D NMR and ECD data analysis. The proposed biosynthetic pathway is discussed. Both compounds exhibited nonselective cytotoxic activities against several human cancer cell lines.

A thiopyranchromenone and other chromone derivatives from an Endolichenic fungus, Preussia africana.

The first example of a naturally occurring thiopyranchromenone, preussochromone A (1), and five other new chromone derivatives, preussochromones B-F (2-6), were isolated from solid cultures of an endolichenic fungus, Preussia africana. The structures of 1-6 were established primarily by NMR experiments, and 2 and 4 were further confirmed by X-ray crystallography. The absolute configurations of 1 and 2 were determined by the application of electronic circular dichroism (ECD), whereas those of C-5 in 3, C-6 in 4, and the 6,7-diol in 5 were deduced via the CD data of the in situ formed [Rh2(OCOCF3)4] complex, the modified Mosher method, and Snatzke's method, respectively. Compounds 1 and 3 showed significant cytotoxicity against A549 cells.

Two new terpenoids from endophytic fungus Periconia sp. F-31.

Two new terpenoids, (+)-(3S,6S,7R,8S)-periconone A (1) and (-)-(1R,4R,6S,7S)-2-caren-4,8-olide (2), have been isolated from an endophytic fungus Periconia sp., which was collected from the plant Annona muricata. Their structures were elucidated on the basis of extensive spectroscopic analyses. In the in vitro assays, the two compounds showed low cytotoxic activities against six human tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, A2780 and MCF-7) with IC(50)>10(-5) M.

Indole alkaloids and quassinoids from the stems of Brucea mollis.

Seven new indole alkaloids, bruceollines H-N (1-7), three new quassinoids, yadanziolides T-V (10-12), and four known analogues, bruceolline E (8), bruceolline F (9), bruceine D (13), and yadanziolide B (14), were isolated from an ethanol extract of the stems of Brucea mollis. The absolute configurations of compounds 2 and 5 were determined by comparison of their experimental and calculated ECD spectra. The absolute configuration of the known compound 9 was determined by using Mo2(OAc)4-induced CD analysis for the first time. Compounds 10, 13, and 14 exhibited cytotoxic activities with IC50 values of 3.00-5.81 µM.

Interaction studies of an anticancer alkaloid, (+)-(13aS)-deoxytylophorinine, with calf thymus DNA and four repeated double-helical DNAs.

BACKGROUND: Phenanthroindolizidine alkaloids are a family of plant-derived compounds with significant antineoplastic activity. The specific biomolecular targets of these alkaloids have not yet been clearly identified. (+)-(13aS)-deoxytylophorinine is a new phenanthroindolizidine alkaloid originally extracted from the roots of Tylophora atrofolliculata and Tylophora ovata in our institute. (+)-(13aS)-deoxytylophorinine exerts both in vitro and in vivoanticancer activities. METHODS: The in vivo anticancer effects and toxicity of this compound were investigated in mice, and interactions between this compound and double-helical DNA sequences were studied in detail with circular dichroic spectroscopy and fluorescence spectroscopy. Viscosity measurements were applied to check the interactive mode between this compound and DNA. RESULTS: Potent anticancer effects were observed in vivo. Also, concentration-dependent interactions were observed and this compound seemed to interact in a sequence-specific manner with AT-repeated sequences of double-helical DNA. Such interactions were proved to be intercalating by viscosity measurements. CONCLUSIONS: Anticancer alkaloid (+)-(13aS)-deoxytylophorinine can have sequence-specific interactions with DNA in an intercalating manner.

Anticancer effect and neurotoxicity of S-(+)-deoxytylophorinidine, a new phenanthroindolizidine alkaloid that interacts with nucleic acids.

Phenanthroindolizidine alkaloids are a family of plant-derived compounds with significant antineoplastic activity as well as other effects like antiamebicidal, antiviral, and anti-inflammatory activities. The specific biomolecular targets of these compounds have not yet been clearly identified. S-(+)-Deoxytylophorinidine (CAT) is a new phenanthroindolizidine alkaloid, originally extracted from the roots of Tylophora atrofolliculata and Tylophora ovata. Potent anticancer activity was observed in vitro and in vivo. Neurotoxicity of CAT was also studied and it was far less serious than that of vinblastine. Interactions between this compound and DNA had been studied in detail in our laboratory previously, and we further studied its interactions with RNA.

[Application of circular dichroism to the study of interactions between small molecular compounds and DNA].

Circular dichroism (CD) is an useful technique for monitoring DNA conformation changes resulting from changes in environmental conditions, such as temperature, ionic strength, and pH, and also for the study of the interaction between DNA and ligands (including small molecules and proteins). CD spectroscopy of DNA arises from the asymmetric backbone sugars and by the helical structures often adopted by nucleic acids. By the interpretation of induced circular dichroism (ICD) of ligand signals resulting from the coupling of electric transition moments of the ligand, DNA bases within the asymmetric DNA environment, ligand-DNA interactions, as well as the DNA-binding mode can be assessed. A number of important conclusions have been reported that related to the observed ICD signals resulting from the interactions between intercalators and groove binders with DNA. If short oligonucleotide sequences are used in the study, sequences-specific of binding also can be deduced. CD determination requires smaller amounts of sample, and not limited by the molecular weight or size and can be performed rapidly; though CD is of low resolution, but it's a complement to NMR and X-ray diffraction methods. This review will introduce the characters of the CD spectra of DNA, and its application to the studies of DNA with small molecules; some progress of the studies in our laboratory will also be discussed. CD is expected to be used as a screening method in seeking more DNA-targeted drugs, such as, antineoplastic, antimicrobial and antiviral drugs.

[Xanthones from Tibetan medicine Halenia elliptica and their antioxidant activity].

OBJECTIVE: To investigate the xanthones from Tibetan medicine Halenia elliptica and their antioxidant activity. METHODS: Column chromatography over normal phase silica gel, reversed phase silica gel, Sephadex LH-20, and recrystallization techniques were used to isolate and purify constituents from Halenia elliptica. Infrared spectrometry, mass spectrometry, and nuclear magnetic resonance spectrometry were used to identify the structure of compounds. The antioxidant activity was evaluated by measuring the content of malondialdehyde product in mice liver cell microsomal induced by ferrous-cysteine. RESULTS: Eight xanthones (compound I-VIII) were isolated and identified from the ethyl acetate extract of Halenia elliptica, among which 1,7-dihydroxy-2,3,5-trimethoxyxanthone was a novel compound. Compound I, III at 10 microg/ml and 100 microg/ml could inhibit the production of malondialdehyde in mouse liver microsomes in vitro. CONCLUSION: Eight xanthones were isolated and they have certain antioxidant activity.