Cytotoxic polyoxygenated cyclohexene derivatives from the aerial parts of Uvaria cherrevensis.

Three previously undescribed polyoxygenated cyclohexene derivatives named cherrevenol M (1), cherrevenol N (2), and cherrevenone (3), together with nine related known analogues 4-12 were isolated from the ethyl acetate fraction partitioned from the methanol extract of the aerial parts of Uvaria cherrevensis (Annonaceae). The determination of the structures and their relative configurations of the isolated compounds were established by spectroscopic techniques, electronic circular dichroism (ECD) analysis as well as comparison with the literature data. For cherrevenone (3), the relative and absolute configurations were also confirmed by using X-ray diffraction and ECD techniques, respectively. Compounds isolated except for compounds 8 and 10 were evaluated for their cytotoxic activity and cherrevenone (3) showed moderate cytotoxic activity against all cancerous cell lines except for ASK cell line with ED50 values ranging from 1.04 ±â€¯0.13 to 10.09 ±â€¯4.31 µM.

Polyoxygenated cyclohexene derivatives isolated from Dasymaschalon sootepense and their biological activities.

Six new naturally occurring polyoxygenated cyclohexene derivatives together with eight related known derivatives, two known alkaloids, and two known flavonoid derivatives were isolated from bioassay-guided fractionation of the ethyl acetate extract of the leaves and twigs of Dasymaschalon sootepense. The structure elucidation and determination of absolute configurations were established by various spectroscopic methods, X-ray diffraction techniques as well as comparison with the literature data. Several isolated compounds were evaluated for their cytotoxic, anti-HIV-1 RT and anti-inflammatory activities.

Anti-inflammatory activity of compounds from Boesenbergia longiflora rhizomes.

ETHNOPHARMACOLOGICAL RELEVANCE: The rhizomes of Boesenbergia longiflora (Wall.) Kuntze have been traditionally used in treatment of inflammatory bowel disease, ulcerative colitis, aphthous ulcer and abscess. Our previous study indicated that CHCl3 fractions of Boesenbergia longiflora had potential on anti-inflammatory properties. In the present study, we investigated the active constituents of this plant for anti-inflammatory activity in order to support its traditional use. MATERIAL AND METHODS: The CHCl3 fraction was isolated using chromatographic techniques. Isolated compounds were tested using relevant in vitro anti-inflammatory assays against LPS-induced NO and TNF-α releases as well as their mechanisms in transcription levels in murine macrophage RAW264.7 cells. RESULTS: The isolation of the CHCl3 fraction from Boesenbergia longiflora rhizomes led to the isolation of three new daucane sesquiterpenes, which were identified as 8-hydroxy-dauca-9, 11-diene-7-one (longiferone A; 1), dauca-8, 11-diene-7-one (longiferone B; 2) and dauca-8, 11-diene-7, 10-dione (longiferone C; 3); together with four known flavonoids, six known diarylheptanoids as well as one sterol. The longiferone B (2) and longiferone C (3) showed anti-inflammatory activity against NO release with IC50 values of 21.0 and 31.3µM, respectively. Longiferone B (2) also suppressed the iNOS and COX-2 mRNA expression. Moreover, the flavonoids and diarylheptanoids inhibited NO and TNF-α production in a dose dependent manner. CONCLUSION: This study demonstrated that sesquiterpenes, diarylheptanoids and some methoxyflavonoids found in Boesenbergia longiflora are responsible for anti-inflammatory activity.

Nitric oxide and tumor necrosis factor-alpha inhibitory substances from the rhizomes of Kaempferia marginata.

The ethanol extract of the rhizomes of Kaempferia marginata showed a potent inhibitory effect against lipopolysaccharide (LPS)-induced nitric oxide (NO) and tumor necrosis factor-alpha (TNF-alpha) release in RAW264.7 cells. Moreover, the partition with various organic solvents also inhibited NO production. One new pimarane-type diterpene, 1alpha-acetoxysandaracopimaradien-2alpha-ol (5), along with four known diterpenes (1-4), were isolated from the n-hexane and chloroform layers, respectively. Among these metabolites, compounds 1 and 4 were isolated for the first time from K. marginata. Compounds 1-5 showed significant inhibitory effects on NO production, with IC50 values ranging from 38.6 to 51.9 microM. Furthermore, compound 2 also exhibited significant activity against TNF-alpha release (IC50 = 48.3 microM). These findings may support the use of K. marginata by traditional doctors for treatment of inflammatory-related diseases.

Parviflorals A-F, trinorcadalenes and bis-trinorcadalenes from the roots of Decaschistia parviflora.

Trinorcadalenes, parviflorals A and B (1 and 2), and four bis-trinorcadalenes, parviflorals C-F (3-6), together with the known trinorcadalenes, syriacusins A (7) and C (8), scopoletin (9) and stigmasterol were isolated from roots of Decaschistia parviflora. Their structures were established by spectroscopic techniques. The CD spectra of the bis-trinorcadalenes (3-6) established their absolute configurations at the binaphthyl axis. Further, structure 6 was confirmed by a single-crystal X-ray crystallographic analysis. Compounds 2 and 6 showed antimalarial activity against Plasmodium falciparum with IC50 values of 11.45 and 6.85 µM, respectively. Compounds 1, 5, 7 and 8 also exhibited weak antifungal activity against Candida albicans, with IC50 values in the range of 37.03-197.68 µM. Compounds 1-3 and 5-8 showed weak antimycobacterial activity against Mycobacterium tuberculosis with MIC values in the range of 54.30-192.13 µM. In addition, several of these compounds possessed cytotoxicity towards the cancer cell lines, KB, MCF7 and NCI-H187 with IC50 values in the range of 2.20-90.09 µM.

Anti-HIV-1 and anti-inflammatory lupanes from the leaves, twigs, and resin of Garcinia hanburyi.

Two new lupanes, 2 alpha-acetoxy-3 beta-hydroxy-19 beta-hydrogen-lup-20(29)-en-28-oic acid (2-acetoxyalphitolic acid) ( 1) and 2 alpha-hydroxy-3 beta-acetoxy-19 beta-hydrogen-lup-20(29)-en-28-oic acid (3-acetoxyalphitolic acid) ( 2), together with the known betulinic acid ( 3), betulin ( 4), and stimasterol-3- O- beta- D-glucopyranoside ( 5), were isolated from the leaves and twigs of GARCINIA HANBURYI. Compounds 1- 3 were also isolated from the resin of this plant. The structure of 2 was confirmed by single-crystal X-ray diffraction analysis. All of the lupanes ( 1- 4) displayed anti-HIV-1 activities in the anti-HIV-1 reverse transcriptase (IC (50) values 16.3-116.9 microg/mL) and syncytium assays (EC (50) 5.6-73.6 microg/mL, SI 1.7-3.3). Moreover compounds 1- 4 exhibited anti-inflammatory activity in an ethyl phenylpropiolate (EPP)-induced ear edema model.

Diterpenes, sesquiterpenes, and a sesquiterpene-coumarin conjugate from Jatropha integerrima.

Five new compounds, 2alpha-hydroxyjatropholone (1), 2beta-hydroxyjatropholone (2), 1,5-dioxo-2,3-dihydroxyrhamnofola-4(10),6,11(18),15-tetraene (3), 2-keto-5-hydroxyguai-3,11-diene (4), and a sesquiterpene-coumarin conjugate, jatrophadioxan (5), and nine known compounds have been isolated from the roots of Jatropha integerrima. The structures were established from spectroscopic data, and the relative configuration of 1 was confirmed by X-ray crystallography. Six diterpenes were evaluated for their antiplasmodial, antituberculosis, and cytotoxic activities.

Dichapetalin-type triterpenoids and lignans from the aerial parts of Phyllanthus acutissima.

Chemical investigation of the aerial parts of Phyllanthus acutissima resulted in the isolation of five new dichapetalin-type triterpenoids, acutissimatriterpenes A-E ( 1- 5), and two new lignans, acutissimalignans A ( 6) and B ( 7), along with two known lignans and three known ellagic acid derivatives. The structures of 1- 7 were determined mainly on the basis of spectroscopic methods. The compounds obtained were evaluated for cytotoxic and anti-HIV-1 activities.

Anti-HIV-1 constituents from leaves and twigs of Cratoxylum arborescens.

Two new xanthones, 1,3,8-trihydroxy-2,4-dimethoxyxanthone (1) and 1,7-dihydroxy-2,8-dimethoxyxanthone (2), along with twelve known compounds 3 - 14 were isolated from leaves and twigs of Cratoxylum arborescens. Compound 1, euxanthone (4), betulinic acid (8), lup-20(29)-ene-3beta,30-diol (9), 3beta-hydroxylup-20(29)-en-30-oic acid (10) and 3,4-dihydroxybenzoic acid (11) displayed anti-HIV-1 activities in the syncytium assay using (Delta)(Tat/Rev)MC99 virus and the 1A2 cell line system (EC (50) values between 3.9 and 32.2 microg/mL with TI ranging from 1.5 to 11.7), while 1,3,7-trihydroxy-6-methoxy-4,5-diisoprenylxanthone (3), 4, and 8 - 10 inhibited HIV-1 reverse transcriptase with IC (50) values between 8.7 and 84.9 microg/mL.

Azadirachtin derivatives from seed kernels of Azadirachta excelsa.

Three new azadirachtin derivatives, named azadirachtins O-Q (1-3), along with the known azadirachtin B (4), azadirachtin L (5), azadirachtin M (6) 11alpha-azadirachtin H (7), 11beta-azadirachtin H (8), and azadirachtol (9) were isolated from seed kernels of Azadirachta excelsa. Their structures were established by spectroscopic techniques, and the structure of 3 was confirmed by X-ray analysis. Compounds 1-7 and 9 exhibited toxicity to the diamondback moth (Plutella xylostella) with an LD50 of 0.75-1.92 microg/g body weight, in 92 h.

Synthesis of novel rhinacanthins and related anticancer naphthoquinone esters.

Rhinacanthin-M, -N and -Q, natural products isolated from the medicinal plant Rhinacanthus nasutus, and 39 novel naphthoquinone esters have been synthesized in excellent yield by esterification of naphthoquinone-3-(propan-3'-ols) with benzoic or naphthoic acids. Almost all the naphthoquinone esters that contain a C-3 hydroxy group showed significant cytotoxicities against KB, HeLa, and HepG2 cell lines. In contrast, ester derivatives lacking the C-3 hydroxy group were inactive to the cancer cell lines. Two methyl substituents on the C-2' of propyl chain conferred more potent cytotoxicity than when there is only one or no methyl group. Naphthoate esters exhibited greater cytotoxicity than benzoate esters. Computer modeling has been done to obtain a first look at the mode of action in connection with these observations.

New bioactive prenylflavonoids and dibenzocycloheptene derivative from roots of Dendrolobium lanceolatum.

Two new flavanones (1 and 2), a new flavan (3), and a new rare dibenzocycloheptene derivative (4) together with a known flavan, 4'-hydroxy-2' ',2' 'dimethyl-pyranoflavan (5), were isolated from the roots of Dendrolobium lanceolatum. Their structures were established on the basis of spectral evidence, and an X-ray analysis was performed to confirm the structure of 4. Compounds 1-3 exhibited antimalarial activity with IC50 values of 2.6, 3.3, and 3.1 microg/mL, respectively. Compounds 1-5 showed moderate antimycobacterial activity with MIC values of 6.3, 12.5, 25, 25, and 50 microg/mL, respectively. In addition, 1 showed strong cytotoxicity against cancer cell lines KB, BC, and NCI-H187 with IC50 values of 1.2, 1.6, and 0.6 microg/mL, respectively, while 2 showed moderate cytotoxicity against the NCI-H187 cell line with an IC50 value of 8.1 microg/ mL.

Dioscorealides and dioscoreanone, novel cytotoxic naphthofuranoxepins, and 1,4-phenanthraquinone from Dioscorea membranacea Pierre.

[structure: see text] Commonly used among ingredients in Thai traditional anticancer preparations, the rhizome of Dioscorea membranacea Pierre was found potently cytotoxic and possibly contributed to such a therapeutic effect. Bioassay-guided isolation resulted in two novel cytotoxic naphthofuranoxepins, dioscorealides A (1) and B (2), and a new 1,4-phenanthraquinone, dioscoreanone (3). The structure determination, achieved mainly by means of NMR and CD spectral and X-ray crystallographic analyses, and cytotoxicity are discussed here.

A bioactive triterpenoid and vulpinic acid derivatives from the mushroom Scleroderma citrinum.

A new lanostane-type triterpenoid, (20 S,22 S,23 E)-22- O-acetyl-25-hydroxylanosta-8,23( E)-dien-3-one ( 1), isolated as a new natural product for the first time, methyl 4,4'-dimethoxyvulpinate ( 2), together with the known compound 4,4'-dimethoxyvulpinic acid ( 3) were isolated from the mushroom Scleroderma citrinum. Their structures were determined using spectroscopic and chemical methods, and an X-ray analysis was performed to confirm structure of 1. Compound 1 exhibited significant antiviral activity against Herpes simplex type 1. Compound 3 and two of its derivatives, the dibromo derivative 5 and acetate derivative 6, exhibited activity towards Mycobacterium tuberculosis. In addition, 5 and 6 also showed cytotoxicity against the NCI-H187 cell line.

Pughiinin A, a sesquiterpene from the fungus Kionochaeta pughii BCC 3878.

A novel secondary metabolite, pughiinin A, together with pycnidione, mevalonolactone, and 7-hydroxy-2-methylchromanone, was isolated from the seed fungus Kionochaeta pughii BCC 3878. The chemical structure was established by spectroscopic methods and by single crystal X-ray crystallography. Pughiinin A and pycnidione exhibited in vitro antiplasmodial activity against Plasmodium falciparum (K1 strain). Pycnidione also showed anti-cancer activity against KB and BC cell lines with the IC 50 values of 2.0 and 1.6 microg/mL, respectively.

Antimycobacterial anthraquinone-chromanone compound and diketopiperazine alkaloid from the fungus Chaetomium globosum KMITL-N0802.

Investigation of the fungus Chaetomium globosum KMITL-N0802 led to the isolation of a novel anthraquinone-chromanone compound named chaetomanone along with seven known compounds, ergosterol, ergosteryl palmitate, chrysophanol, chaetoglobosin C, alternariol monomethyl ether, echinuline and isochaetoglobosin D. These compounds were characterized by spectroscopic methods. Chaetomanone and echinulin exhibited activity towards Mycobacterium tuberculosis.