Six New Lanostane Triterpenoids from the Fruiting Body of Tyromyces sambuceus and Antiproliferative Activity.

During the search for secondary metabolites with antiproliferative activity, six new lanostane triterpenoids, tyrosamic acids A-F (1-6) together with ten known compounds (7-16), were isolated from the fruiting body of Tyromyces sambuceus. Their structures were elucidated using MS analyses, extensive 2D-heteronuclear NMR data interpretation and the structure of 3 was further confirmed by single-crystal X-ray data analyses. All lanostane triterpenoids (1-16) possesses a carboxy group at C-20 position and their strength of antiproliferative activity was affected by the presence or absence of a hydroxy group at C-15 position and at the side chain. Four of the compounds (1, 6, 10, 14) showed antiproliferative activities against human cancer cell lines with IC50 values of 16.8-48.3 µM (HL-60).

Phenanthrene and phenylpropanoid constituents from the roots of Cymbidium Great Flower 'Marylaurencin' and their antimicrobial activity.

Two new phenanthrenes, and one new phenylpropanoid, named ephemeranthoquinone C (1), and marylaurencinols C (2) and D (3), were isolated from the roots of Cymbidium Great Flower 'Marylaurencin', respectively. These structures were determined on the basis of 2D NMR experiments. The compounds were tested for antimicrobial activity against Bacillus subtilis, Klebsiella pneumoniae, and Trichophyton rubrum.

Two novel aromatic glucosides, marylaurencinosides D and E, from the fresh flowers of Cymbidium Great Flower 'Marylaurencin'.

Two novel aromatic glucosides, named marylaurencinosides D (1) and E (2), were isolated from the fresh flowers of Cymbidium Great Flower 'Marylaurencin'. In addition, eight known aromatic compounds (3-10) were isolated. These structures were determined on the basis of NMR experiments as well as chemical evidence.

Constituents of Caryopteris incana and their antibacterial activity.

Two new compounds named caryocanolide (1), and caryocanoside A (2), together with nine known compounds (3-11) were isolated from the whole plant of Caryopteris incana. These structures were determined mainly on the basis of 2D nuclear magnetic resonance and high resolution fast atom bombardment mass spectroscopy data. Furthermore, the isolated compounds (1, 2, 4-11) were tested for their antibacterial activity. Compound 1 exhibited moderate antimicrobial activity against Bacillus subtilis with a minimum inhibitory concentration value of 35.7 µM.

Aromatic constituents of Cymbidium Great Flower Marie Laurencin and their antioxidative activity.

Two novel aromatic glucosides, named marylaurecinosides B (1) and C (2), were isolated from Cymbidium Great Flower Marie Laurencin, together with six known aromatic compounds (3-8). These structures were determined on the basis of NMR experiments as well as chemical evidence. All of the isolated compounds (1-8) were tested for antioxidative activity using a superoxide dismutase-like assay.

Aromatic compounds and their antioxidant activity of Acer saccharum.

A new lignan glycoside, 5-(3″,4″-dimethoxy-phenyl)-3-hydroxy-3-(4'-hydroxy-3'-methoxybenzyl)-4-hydroxymethyl-dihydrofuran-2-one 4'-O-α-L: -rhamnopyranoside (1), with seven known compounds, compound 2, koaburside, icariside E(4), cleomiscosin C, cleomiscosin D, scopoletin, and 5'-demethylaquillochin, were isolated from the EtOH extract of the wood of Acer saccharum (Aceraceae). Their structures were determined by 1D and 2D nuclear magnetic resonance (NMR) and mass spectroscopy analysis. All of the isolated compounds, 1-8, were tested for their antioxidant activity in superoxide dismutase (SOD)-like assay.

Ipomotaosides A-D, resin glycosides from the aerial parts of Ipomoea batatas and their inhibitory activity against COX-1 and COX-2.

Four new resin glycosides, namely, ipomotaosides A-D (1-4), were isolated from the dried aerial parts of Ipomoea batatas. The structures of 1-4 were elucidated by analysis of their spectroscopic data and by chemical derivatization and were tested for their anti-inflammatory activity against cyclooxygenase (COX)-1 and -2.

Constituents of the lichen Peltigera dolichorrhiza.

A new aromatic derivative, 5-(3,4-dihydroxyphenyl)-3-methylcyclohex-2-enone (1), and three known compounds, peltigerine, solorinine, and phenyl butanoid, were isolated from the MeOH extract of the lichen Peltigera dolichorrhiza (Peltigeraceae). Their structures were determined by 1D and 2D nuclear magnetic resonance and mass spectroscopy analysis.

Novel abietane diterpenoids and aromatic compounds from Cladonia rangiferina and their antimicrobial activity against antibiotics resistant bacteria.

From Cladonia rangiferina were isolated two novel abietane diterpenoids, hanagokenols A (1) and B (2). Also in this investigation, four known abitetane diterpenoids (3-6), four known labdane diterpenoids (7-10), one known isopimarane diterpenoid (11), and six known aromatic compounds were isolated. These structures were elucidated primarily through extensive NMR experiments. Hanagokenol A (1) was a unique abietane diterpene having an ether linkage between C-6 and C-18 of sugiol. Hanagokenol B (2) is also a unique secoabietane diterpene, having gamma-lactone which occurred by cleavage and subsequently oxidation between C-6/C-7 of 12-hydroxydehydroabietinol. Furthermore, all the isolated compounds (1-17) were tested for the antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE).

Flavonoids from Acacia pennata and their cyclooxygenase (COX-1 and COX-2) inhibitory activities.

Two new flavonoids quercetin 4'-O-alpha-L-rhamnopyranosyl-3-O-beta-D-allopyranoside (1) and apigenin 6-C-[2''-O-(E)-feruloyl- beta-D-glucopyranosyl]-8-C-beta-glucopyranoside (2), along with the known isorhamnetin 3-O-alpha-L-rhamnopyranoside (3), kaempferol 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranoside (4), and isovitexin (5) were isolated from the leaves of Acacia pennata Willd. (Mimosaceae) and tested for their anti-inflammatory activity. Their structures were determined by 1D and 2D NMR and mass spectrometry. They were tested for an inhibitory effect on COX-1 and COX-2, showing 60-90% inhibition at 10(-4) g/mL and 5-14% inhibition at 10(-4) g/mL, respectively.

Abietane diterpenoids from the barks of Cryptomeria japonica.

From the bark of Cryptomeria japonica were isolated sugikurojins I (1) and J (2), and an abietane derivative (3) was obtained for the first time as a natural product. These structures were elucidated primarily through extensive NMR experiments. Sugikurojin I (1) has a unique skeleton incorporating an abietane diterpene and a 1,10-secocadinane sesquiterpene. Sugikurojin J (2) is a peroxyester of hydroxyabietane diterpene and isopimarane acid diterpene. Compound 3 was p-quinone acid, which occurred by cleavage between C-7 and C-8 of sugiol; it was deduced to [4'-isopropyl-1(S),3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2(R)-yl]-acetic acid. Also obtained in this investigation were three known diterpenes (4-6).

A new abietane and two dimeric abietane diterpenes from the black heartwood of Cryptomeria japonica.

Three new diterpenes, sugikurojins A-C (1-3) were isolated from the black heartwood of Cryptomeria japonica. The structure of sugikurojin A was deduced to be 19-hydroxy-6,7-dehydroferruginol on the basis of extensive NMR experiments. Sugikurojin B was a dimer of 6,7-dihydroxyferruginol and 6,7-dehydroferruginol with a 6-O-11' linkage. Sugikurojin C was a dimeric ferruginol with 6-O-7' and 7-O-6' linkages. Also obtained in this investigation were the known compounds formosaninol (4), 15 sesquiterpenes (5-19), 16 diterpenes (20-35), three phenylpropanoids (36-38), and a phenolic compound (39).

New lanostanoids, elfvingic acids A-H, from the fruit body of Elfvingia applanata.

Eight new lanostanoids, 12alpha,15beta-dihydroxy-3,7,11,23-tetraoxolanost-8,(20Z)(22)-dien-26-oic acid (1), 7beta,8beta-epoxy-15beta,20S-dihydroxy-3,12,23-trioxolanost-9(11),16-dien-26-oic acid (2), 7beta,8beta-epoxy-3beta,15beta,20S-trihydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (3), 7beta,8beta-epoxy-2alpha,3beta,15beta,20S-tetrahydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (4), 7beta,8beta-epoxy-3beta,15beta,20S,28-tetrahydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (5), 7beta,8beta-epoxy-3beta,15beta,19,20S-tetrahydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (6), 8beta,15beta,20S-trihydroxy-3,7,12,23-tetraoxolanost-9(11),16-dien-26-oic acid (7), 7alpha,8alpha-epoxy-15beta,23xi-dihydroxy-12-oxo-3,4-secolanost-4(28),9(11),(20Z)(22)-trien-3,26-dioic acid (8), and the methyl ester of 8 (8a) were isolated from the fruit bodies of Elfvingia applanata. Their structures were established primarily by NMR experiments, and their biological activity against Kato III and Ehlrich cells was investigated.