Diterpenes, sesquiterpenes, and a C15-acetogenin from the marine red alga Laurencia mariannensis

In addition to 10 known compounds (7- 16), one new brominated diterpene, 10-hydroxykahukuene B (1), two new sesquiterpenes, 9-deoxyelatol (2) and isodactyloxene A (3), one new brominated C 15-acetogenin, laurenmariallene (4), and two new naturally occurring halogenated sesquiterpenes (5 and 6) that were previously obtained as intermediates in a biomimetic synthetic study of rhodolaureol and rhodolauradiol have been isolated and identified from the organic extract of the marine red alga Laurencia mariannensis. The structures of these compounds were established by spectroscopic methods. The antibacterial and antifungal activities of new compounds 1-4 were evaluated.     

New tricyclic sesquiterpenes from the fermentation broth of Stereum hirsutum

In search for novel metabolites from the culture broth of the mushroom Stereum hirsutum, three new tricyclic sesquiterpenes named hirsutenols A (1), B (2), and C (3) have been isolated. Their structures were assigned on the basis of various spectroscopic studies.     

Humulane-type sesquiterpenoids from the mushroom Lactarius mitissimus

Five new humulane-type sesquiterpenes, mitissimols A (1), B (2), and C (3), and a mixture of mitissimol A oleate (4) and mitissimol A linoleate (5), were isolated from the fruiting bodies of Lactarius mitissimus. Their structures were elucidated on the basis of comprehensive spectroscopic techniques and necessary chemical methods. The relative stereochemistry of 1 was determined by single-crystal X-ray diffraction analysis.     

Two new cytotoxic carbonimidic dichlorides from the nudibranch Reticulidia fungia.

Two new sesquiterpenes, reticulidins A (1) and B (2), containing a rare functional group, N=CCl(2), have been isolated together with known congeners from the nudibranch Reticulidia fungia and their structures elucidated by spectroscopic data. Both 1 and 2 were cytotoxic against KB and L1210 cells.     

Hirsutane sesquiterpenes from the fungus Lentinus connatus BCC 8996

Two new hirsutane sesquiterpenes, connatusins A (1) and B (2), were isolated from the fungus Lentinus connatus BCC 8996. The structures, closely related to hypnophilin, were elucidated on the basis of the spectroscopic data. An X-ray analysis was performed to confirm the structure of 1. Six known compounds were also obtained. Panepoxydone (5), panepoxydione (6), and dihydrohypnophilin (8) exhibited significant antimalarial and cytotoxic activities.     

Suberosols A-D,four new sesquiterpenes with beta-caryophyllene skeletons from a Taiwanese gorgonian coral Subergorgia suberosa

Four new beta-caryophyllene-derived sesquiterpenes alcohols, suberosols A (1), B (2), C (3), and D (4), along with two known beta-caryophyllene-derived sesqueterpene ketones, buddledins C (5) and D (6), were isolated from a Taiwanese gorgonian coral Subergorgia suberosa. The structures of 1-4 were determined on the basis of extensive spectroscopic analyses. Cytotoxicity of these compounds toward various cancer cell lines is also described.     

Xenicane-type diterpenes with cytotoxicity from Xenia florida

Chromatographic investigation of an acetone extract of the octocoral Xenia florida afforded three new xenicane diterpenes, namely, florxenilide A (1), florxenilide B (2), and florxenilide C (3), in addition to seven known xenicane diterpenes and two known cadinene sesquiterpenes. Structures were elucidated through spectroscopic analysis, especially 2D NMR, and chemical derivatization. The absolute configuration of 1 was determined by NOESY, CD, and Mosher's methods. Florxenilides A (1) and B (2) exhibited cytotoxicity against human colon cancer (WiDr) cells at 4.5 and 3.7 muM, respectively.     

New cytotoxic sesquiterpenes from the gorgonian Isis hippuris

Five new suberosane sesquiterpenes, suberosenol A (1), suberosenol B (2), suberosanone (3), suberosenol A acetate (4), and suberosenol B acetate (5), along with the known sesquiterpene subergorgic acid (6), have been isolated from the gorgonian Isis hippuris. The structures of these metabolites were established by spectroscopic and chemical methods. Metabolites 1 and 3-5 were found to exhibit potent cytotoxicity toward P-388, A549, and HT-29 cancer cell lines.     

Sesquiterpenes from cultures of the basidiomycete Conocybe siliginea

Six new tremulane sesquiterpenes, conocenol A-D (2-5), conocenolide A (6), and conocenolide B (7), have been isolated from cultures of the basidiomycete Conocybe siliginea. The structures of 2-7 were elucidated by the analysis of spectroscopic data, including heteronuclear multiple-bond correlation, heteronuclear single-quantum coherence, and (1)H,(1)H correlation spectroscopy, and a comparison with known analogues.     

New sesquiterpenes from Pluchea arabica

Two new sesquiterpenes, godotol A (1) and godotol B (2), were isolated from Pluchea arabica. Their structures were determined by analysis of NMR data. The absolute configurations of 1 and 2 were established by Mosher ester methodology. The godotols displayed weak activity against bacteria and the brine shrimp larvae. They were also inactive in the DPPH antioxidant assay.     

A laurane sesquiterpene and rearranged derivatives from the Chinese red alga Laurencia okamurai Yamada

One new laurane sesquiterpenoid, 3beta-hydroxyaplysin (2), and two novel rearranged sesquiterpenes, laurokamurenes A (3) and B (4), together with three known related compounds, 3alpha-hydroxydebromoaplysin (1), debromoaplysin (6), and laurinterol (7), have been isolated from the Chinese red alga Laurencia okamurai. Their structures, including relative stereochemistry, were determined on the basis of detailed interpretation of 2D NMR spectra and comparison with related known compounds.     

Sesquiterpenoids from Pulicaria canariensis and their cytotoxic activities

Thirteen new sesquiterpenes, pulicanadiene A (1), B (2), and C (3), pulicanone (4), pulicanol (5), pulicanarals A (6), B (7), and C (8), pulicanadienals A (9) and B (10), pulicanadienol (11), and pulioplopanones A (12) and B (13), and seven known compounds, stigmasterol, ergosterol peroxide, calenduladiol, 7,4'-di-O-methyldihydrokaempferol, 5,7-dihydroxy-3,3',4'-trimethoxyflavone, dihydroquercetin 7,3'-dimethyl ether, and 6,15alpha-epoxy-1beta,4beta-dihydroxyeudesmane, were isolated from Pulicaria canariensis. Compound 4a showed cytotoxicity on the human myeloid leukemia cell line HL-60. The cytotoxicity was caused by induction of apoptosis as determined by microscopy of nuclear changes, activation of caspases, and the cleavage of poly(ADP-ribose) polymerase-1.     

Sesquiterpenes and aliphatic diketones from cultures of the basidiomycete Conocybe siliginea

Five new tremulane-type sesquiterpenes, 11,12-dihydroxy-1-tremulen-5-one (1), 11,12-epoxy-12beta-hydroxy-1-tremulen-5-one (2), 5alpha,12-dihydroxy-1-tremulen-11-yl 2(S)-pyroglutamate (3), 2alpha,11-dihydroxy-1(10)-tremulen-5,12-olide (4), and 10beta,11-dihydroxy-5,6- seco-1,6(13)-tremuladien-5,12-olide (5), as well as three new aliphatic diketones, 2,3-dihydroxydodecane-4,7-dione (9 and 10) and 1-hydroxydecane-2,5-dione (11), together with three known sesquiterpene analogues, tremulenediol A (6), conocenol B (7), and conocenolide A (8), were isolated from cultures of the basidiomycete Conocybe siliginea.     

Sesquiterpenes from the Hainan Sponge Dysidea septosa

Five new sesquiterpenes, named lingshuiolides A (1) and B (2), lingshuiperoxide (6), isodysetherin (10), and spirolingshuiolide (12), along with several known related analogues (7- 9, 11, and 13- 15), were isolated from the Hainan marine sponge Dysidea septosa. The structures of new compounds 1, 2, 6, 10, and 12 were determined by detailed analysis of 1D and 2D NMR spectra and by comparison with related model compounds. The absolute configuration of lingshuiolide B (2) was established by using the modified Mosher's method. Spirolingshuiolide (12) represents the first example of a sesquiterpene with a rearranged drimane skeleton. Compounds 7- 9 and 15 exhibited significant inhibitory activity against human protein tyrosine phosphatase 1B (hPTP1B), an enzyme involved in the regulation of insulin signaling. In particular, 15 showed the most potent effect, with an IC 50 value of 1.9 microg/mL.     

Terpenoids from Chloranthus serratus and their anti-inflammatory activities

Seven new terpenoids, including two sesquiterpene dimers (1, 2), two norditerpenoids (3, 4), and three sesquiterpenes (5-7), along with six known sesquiterpene dimers and four known sesquiterpenes were isolated from the whole plant of Chloranthus serratus. Their structures and relative configurations were elucidated on the basis of spectroscopic data analysis. The absolute configuration of 1 was determined by the CD exciton chirality method. These isolates were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells. Compound 2 and two known compounds, shizukaols B and D, showed significant anti-inflammatory activities, with IC(50) values of 0.22, 0.15, and 7.22 μM, respectively.     

New axane and oppositane sesquiterpenes from Teclea nobilis

Two new isomeric axane and oppositane sesquiterpene derivatives, named teclenone A (1) and teclenone B (2), were isolated from the aerial parts of Teclea nobilis. Their structures have been established on the basis of (1)H and (13)C NMR spectral data, notably 2D NMR (1)H-(1)H COSY, (1)H-(13)C HMQC, (1)H-(13)C HMBC, and (1)H-(1)H NOESY experiments. This appears to be the first report of the rare axane and oppositane sesquiterpenes from the plant family Rutaceae.     

Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana

Two new sesquiterpenes, leitneridanin A (1) and leitneridanin B (2), and seven known compounds, lirioresinol B, (-)-pinoresinal, (+)-lariciresinol, quassimarin (3), simalikalactone D (4), 1-methoxycanthinone (5), and 5-methoxycanthinone (6), were isolated from Leitneria floridana. Their structures were identified on the basis of spectral data. In vitro biological evaluation showed that 5 is a potent anti-HIV agent (EC(50) 0.26 g/mL; TI >39) and that 3-6 suppressed the growth of a panel of human tumor cell lines (KB, A-549, HCT-8, CAKI-1, MCF-7, and SK-MEL-2). Compounds 3 and 4 were significantly active, with ED(50) values in the range of 0.26-0.012 g/mL.     

Sesquiterpenes from Ferula penninervis

The ethyl acetate soluble extract of the dried roots of Ferula penninervis gave 17 new sesquiterpenes [15 of the guaiane-type, ferupennins A-O (1-15), and two of the eudesmane-type, 1alpha-hydroxy-2-oxo-5alpha,7beta,11betaH-eudesm-3-en-6alpha,12-olide (16) and penninervin (17)] and nine known sesquiterpenes. The structures of the new compounds were elucidated on the basis of spectroscopic evidence and X-ray analysis. The absolute configuration of ferupennin A (1) was determined by a modified Mosher method.     

Sesquiterpenes and monoterpenes from the bark of Inula macrophylla

Eleven new sesquiterpenes (1--11) and two thymol derivatives (12, 13), along with 12 known sesquiterpenes and monoterpenes, were isolated from the bark of Inula macrophylla. Their structures were determined on the basis of spectral evidence (especially by HREIMS and 2D NMR) as well as chemical transformations. The structure of macrophyllic acid A (1) was confirmed by X-ray analysis, and the absolute configuration of 1 was determined on the basis of the appropriate chemical conversions and the application of a modified Mosher's method.     

Bisabolane-type sesquiterpenes from the aerial parts of Lippia dulcis

Six new bisabolane-type sesquiterpenes, peroxylippidulcines A-C (3-5), peroxyepilippidulcine B (6), and epilippidulcines B (7) and C (8), have been isolated from the aerial parts of Lippia dulcis, along with two known bisabolane-type sesquiterpenes, seven known flavonoids, and a known triterpenoid. The structures of 3-8 were characterized on the basis of NMR, MS, specific rotation, and X-ray crystallographic analysis data and chemical evidence.