Euphormins A and B, New Pyranocoumarin Derivatives from Euphorbia formosana Hayata, and Their Anti-Inflammatory Activity.

Euphormin-A (1) and euphormin-B (2), two new pyranocoumarin derivatives, and forty known compounds (3-42) were isolated from Euphorbia formosana Hayata (Euphorbiaceae). The chemical structures of all compounds were established based on spectroscopic analyses. Several isolates were evaluated for their anti-inflammatory activity. Compounds 1, 2, 10, 18, 25, and 33 significantly inhibited against superoxide anion generation and elastase release by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Furthermore, compounds 25 and 33 displayed the most potent effects with IC50 values of 0.68 ± 0.18 and 1.39 ± 0.12 µM, respectively, against superoxide anion generation when compared with the positive control (2.01 ± 0.06 µM).

Anti-inflammatory triterpenoids from the stems of Microtropis fokienensis.

Three new ursane- and four new oleanane- type triterpenoids 1-7 were isolated, along with six known compounds 8-13, from the methanolic extract of Microtropis fokienensis. All structures were elucidated by mass and NMR spectroscopic methods. The isolates 4-10 and known compounds 14-17 that were previously isolated from this material were evaluated for anti-inflammatory activity based on effects against superoxide anion generation and elastase release by neutrophils in response to fMLP/CB. 11α,30-Dihydroxy-2,3-seco-olean-12-en-2,3-dioic anhydride (7) was the first triterpene anhydride from the genus of Microtropis to have the ring A expanded to a seven-membered ring; it showed significant anti-inflammatory activity against superoxide anion generation and elastase release. Unexpectedly, 30-hydroxy-2,3-seco-lup-20(29)-ene-2,3-dioic acid (17) showed the best effect against superoxide anion generation and elastase release with IC50 values of 0.06±0.01 and 1.03±0.35 µg/mL, respectively. Compound 17 had a dioic acid function, and compound 7 had an anhydride function modification in ring A; both showed promising activity in the target assays.

Cytotoxic triterpenoids from the stems of Microtropis japonica.

Bioassay-guided fractionation of a methanol extract obtained from stems of Microtropis japonica led to the isolation of six new ursane-type triterpenoids (1-6) and a new 2,3-seco-oleanane-type triterpenoid (7), together with seven known compounds. The structures of the new compounds were elucidated using spectroscopic data analysis. Among the known compounds isolated, the main component, 8 (ursolic acid), was active for HL60 cells, and its effects on histone hyperacetylation and the inhibition of histone deacetylase (HDAC) activity were investigated.

New cytotoxic lupane triterpenes from Perrottetia arisanensis.

Eight new lupane triterpenes, including 7beta-cis-coumaroylbetulinic acid (1), 7beta-trans-coumaroylbetulinic acid (2), 7beta-cis-coumaroyl-3-epi-betulinic acid (3), 7beta-trans-coumaroyl-3-epi-betulinic acid (4), 7beta-cis-coumaroylbetulonic acid (5), 7beta-trans-coumaroylbetulonic acid (6), 7beta-hydroxybetulinaldehyde (7) and 28-norlup-20(29)-ene-3alpha,17beta-diol (8), together with fifteen known compounds were isolated from the bioactive methanol extract of the stems of Perrottetia arisanensis. The structures of the new compounds were elucidated by spectroscopic and HR-ESI-MS analysis. All new compounds were evaluated for their cytotoxicity against six human cancer cell lines. Among them, lupane triterpene coumaroyl esters 1-6 showed moderate cytotoxicity with IC (50) values ranging from 3.75 to 21.29 microM. This is the first report for lupane triterpenes with a phenylpropane moiety substituted at C-7.

Acasiane A and B and farnesirane A and B, diterpene derivatives from the roots of Acacia farnesiana.

Four new diterpenes, acasiane A ( 1), acasiane B ( 2), farnesirane A ( 3), and farnesirane B ( 4), along with three known diterpenes ( 5 - 7), two triterpenes ( 8 and 9), and eight flavonoids ( 10 - 17) were isolated from the roots of Acacia farnesiana. The structures and relative configurations of these compounds were determined by various spectroscopic and x-ray analyses. All isolated compounds were evaluated for their in vitro cytotoxic activities against six human cancer cell lines (Hep G2, Hep 3B, MDA-MB-231, MCF-7, A549, and Ca9 - 22) with the MTT method. Betulinic acid ( 8) displayed moderate cytotoxicity (1.70 - 5.74 microg/mL) towards five human cancer cell lines and the flavonoids had slight effects. In addition, 8, diosmetin ( 13), and 3',4',5-trihydroxy-7-methoxyflavone ( 15) slightly inhibited superoxide anion generation or elastase release by human neutrophils, indicating moderate anti-inflammatory activities.

Lupane-type triterpenoids from Microtropis fokienensis and Perrottetia arisanensis and the apoptotic effect of 28-hydroxy-3-oxo-lup-20(29)-en-30-al.

Seven new lupane triterpenoids were isolated from bioactive methanol extracts of Microtropis fokienensis (1- 4) and Perrottetia arisanensis (4-7), along with 18 known compounds. The structures of the new compounds were elucidated on the basis of spectroscopic data analysis. All triterpenoids were evaluated for their in vitro cytotoxicity toward seven human cancer cell lines. Compound 8 (28-hydroxy-3-oxo-lup-20(29)-en-30-al) was among the most cytotoxic substances obtained and was found to induce apoptosis of human leukemia HL60 cells and mediate cleavage of PARP and up-regulation of Bax proteins.

Cytotoxic triterpenoids from the leaves of Microtropis fokienensis.

Five new triterpenoids, microfokienoxanes A-D (1-4) and 3beta,28-dihydroxy-11alpha-methoxyurs-12-ene (5), were isolated and identified from the leaves of Microtropis fokienensis, along with nine known compounds. The structures of the new compounds were elucidated by spectroscopic methods. The compounds obtained in this investigation were evaluated against a small panel of human cancer cell lines for cytotoxicity. Only compounds 3 and 5 exhibited cytotoxicity (IC50 < or = 5 microg/mL) for one or more cell lines.

Three new agarofuran sesquiterpenes reissantins F-H from Reissantia buchananii.

Three new agarofuran sesquiterpenes, reissantins F-H, were isolated from a methanol extract of Reissantia buchananii. Their structures as well as their relative stereochemistry were established on the basis of modern mass and spectroscopic methods. Compounds were assayed for cytotoxicity against HepG2 and Hep3B human liver cancer cell lines.

Antitumor agents. 228. five new agarofurans, Reissantins A-E, and cytotoxic principles from Reissantia buchananii.

Twenty-one compounds, including five new agarofuran sesquiterpenes, reissantins A-E (1-5), were isolated from Reissantia buchananii by means of bioassay-directed fractionation and their structures identified from spectral data. Reissantins A-C are the first reported simple agarofuran sesquiterpenes to contain a 5-carboxy-N-methyl-2-pyridone (CNMP) substituent, which has previously been found only in macroring agarofuran pyridine alkaloids. The major terpenoid components, celastrol (6) and its methyl ester derivative, pristimerin (7), were significantly active against nine cancer cell lines, including A549, MCF-7, HCT-8, KB, KB-VIN, U-87-MG, PC-3, 1A9, and PTX10 cell lines, with ED(50) values ranging from 0.076 to 0.34 microg/mL.