Three new C-alkylated flavonoids from Desmodium oblongum

Three new C-alkylated flavonoids, 4′-hydroxy-8-isobutyryl-7-methoxy-6-methyl-flavone (1), 4′,7-dimethoxy-8-isobutyryl-6-methyl-flavone (2), and 4′,7-dimethoxy-8-isobutyryl-flavone (3), together with three know ones luteolin (4), kaemferol (5), and quercetin (6), were isolated from Desmodium oblongum. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compound 1 showed cytotoxicity against NB4, SHSY5Y, and MCF7 cell lines with IC₅₀ values of 8.5, 6.5, and 7.8 μM; compound 2 showed cytotoxicity against SHSY5Y and PC3 cell lines with IC₅₀ values of 5.0 and 6.8 μM; compound 3 displayed cytotoxicity against SHSY5Y and MCF7 cell lines with IC₅₀ values of 6.4 and 9.4 μM, respectively.     

Isoflavanones from Desmodium oxyphyllum and their cytotoxicity

Two new isoflavanones, (3R)-7-hydroxy-4′-methoxy-5-methoxycarbonyl-isoflavanone (1) and (3R)-8-hydroxy-4′-methoxy-7-methoxycarbonyl-isoflavanone (2), together with seven known isoflavanones (3–9) were isolated from Desmodium oxyphyllum of the Leguminosae family. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compound 1 showed good cytotoxicity against NB4 and SHSY5Y cell lines with IC₅₀ values of 3.1 and 2.5 μM; compound 2 exhibited cytotoxicity against PC3 cell lines with a IC₅₀ value of 3.6 μM; compound 4 showed cytotoxicity against A549 and SHSY5Y cell lines with IC₅₀ values of 3.6 and 2.8 μM; and compound 5 displayed cytotoxicity against NB4, SHSY5Y, and MCF7 cell lines with IC₅₀ values of 2.6, 3.8, and 2.8 μM, respectively. Other compounds also showed moderate cytotoxicity for some tested cell lines with IC₅₀ values between 5.4 and 8.8 μM.     

Lecanorosides A and B,two new triterpene glycosides from the sea cucumber Actinopyga lecanora

Two new sulphated triterpene glycosides, lecanorosides A (1) and B (2), along with the known compounds holothurins A (3), A₁ (4), and B (5), were isolated from the sea cucumber Actinopyga lecanora. Their structures were deduced from extensive spectral analysis (NMR and MS) and chemical evidence. Glycosides 1 and 4 showed marginal in vitro cytotoxicity against two human tumour cell lines.     

Ingenine E,a new cytotoxic β-carboline alkaloid from the Indonesian sponge Acanthostrongylophora ingens

A new β-carboline alkaloid ingenine E (4), along with three known metabolites annomontine (1), acanthomine A (2), and 1,2,3,4-tetrahydronorharman-1-one (3) were isolated from the Indonesian marine sponge Acanthostrongylophora ingens. Their structure characterization was unequivocally carried out using one- and two-dimensional NMR spectroscopy, as well as high-resolution mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated toward MCF7, A549, HCT116, PC12, and Hela cancer cell lines. Ingenine E (4) exhibited cytotoxic activity against MCF7, HCT116, and A549 cell lines with IC₅₀ values of 3.5, 0.67, and 2.15 μg/ml.     

C21 steroidal glycosides from Cynanchum taihangense

Two new C₂₁ steroidal glycosides, cynataihosides E (1) and F (2), together with a known one, sublanceoside H₂ (3), were isolated from Cynanchum taihangense. The aglycone of cynataihoside F (2) was also a new compound. Their structures were elucidated on the basis of NMR spectroscopic data, HR-ESI-MS analysis, and chemical evidence. Their cytotoxic activities against three human tumor cell lines (HL-60, THP1, and Caco2) were reported.     

Polygonumnolides C1-C4; minor dianthrone glycosides from the roots of Polygonum multiflorum Thunb

Four new dianthrone glycosides, named polygonumnolides C1-C4 (1–4), were isolated from the dried roots of Polygonum multiflorum Thunb, together with two known emodin dianthrones (5–6). Their hepatotoxicities were evaluated against L-02 cell lines. Compounds 1–4 showed weak hepatotoxicity against L-02 cell lines with IC₅₀ values of 313.05, 205.20, 294.20, and 207.35?μM, respectively.     

Cytotoxic stilbenes from the roots of Paphiopedilum godefroyae

Two new stilbenes, 2-(3′,5′-dimethoxyphenyl)-6-hydroxy-5-methoxybenzofuran (1) and 3′-hydroxy-2,5′-dimethoxystilbene (2), together with seven known stilbenes (3, 5–10) and one flavanone (4), were isolated from the roots of Paphiopedilum godefroyae. Their chemical structures were determined on the basis of their spectroscopic data. These isolated compounds were evaluated for their cytotoxicity against human small cell lung cancer (NCI-H187) cell lines and an arylbenzofuran derivative, 5,6-dimethoxy-2-(3-hydroxy-5-methoxyphenyl)benzofuran (6), was shown to be strongly cytotoxic with an IC₅₀ value of 5.10 μM.     

Cytotoxic lasiodiplodin derivatives from the fungus <Emphasis Type="Italic">Syncephalastrum racemosum</Emphasis>

Chemical investigation of fungal biomass of the fungus Syncephalastrum racemosum led to the isolation of new natural products (3R),(5S)-5-hydroxy-de-O-methyllasiodiplodin (1), 6-oxode-O-methyllasiodiplodin (2), in addition to five known compounds, de-O-methyllasiodiplodin (3), lasiodiplodin (4), (3R),(5R)-5-hydroxy-de-O-methyllasiodiplodin (5), ergosterol (6), and ergosterol peroxide (7). Their structures were elucidated by spectroscopic techniques. The absolute configuration of 1 was determined by a modified Mosher’s method. Compound 1 showed cytotoxicity against cholangiocarcinoma, KKU-M139, KKU-M156, and KKU-M213 cell lines with IC₅₀ values in the range of 14–19 μg/mL, while 3 showed cytotoxicity against KB, BC1, and NCI-H187 cell lines with IC₅₀ values of 12.67, 9.65, and 11.07 μg/mL, respectively.     

Three new elemanolides from the seeds of Vernonia anthelmintica

Three new elemanolides, named vernonilides D (1), E (2), and F (3), along with four known sesquiterpenoids, including two elemanolides (4, 5), a guaianolide (6), and a germacranolide (7) were isolated from the seeds of Vernonia anthelmintica. The structures of them were elucidated based on 1D and 2D NMR experiments and comparison with published data. Cytotoxicity of the compounds against four human tumor cell lines was assayed. 6 showed strongly inhibitory effect against HCT-15 and PC-3 cell lines with IC₅₀ values of 0.56 and 0.69 μM, respectively. The new compounds showed moderate cytotoxicity against four cell lines with IC₅₀ values ranging from 9.1 to 28.1 μM.     

Carotane-type sesquiterpenes from cultures of the insect pathogenic fungus Isaria fumosorosea

Two new carotane-type sesquiterpenes named trichocaranes E (1) and F (2), along with two known ones CAF-603 (3) and trichocarane C (4), were isolated from cultures of the insect pathogenic fungus Isaria fumosorosea. Their structures and relative configurations were elucidated by extensive spectroscopic analysis and X-ray crystallography. Compounds 1–3 showed potent cytotoxic activities against six tumor cell lines MDA, MCF-7, SKOV-3, Hela, A549, HepG2 with IC₅₀ values in a concentration range of 0.1–6.0 μg/ml.     

Two new monoterpenes from Sibiraea laevigata

Two new monoterpenes, 3-(2-oxo-4-methyl-3-pentenyl)furan-5H-2-one (1) and 3-[(2E)-4-hydroxyl-4-methyl-2-pentenyl)]furan-5H-2-one (2), along with eight known compounds (3–10), were isolated from the stalks and infructescence of Sibiraea laevigata. Their structures were elucidated by spectroscopic methods including extensive 1D and 2D NMR techniques. In addition, all of these isolates were evaluated for their cytotoxic and antioxidant activities. The results showed that compounds 5–7 displayed cytotoxicity with IC₅₀ values ranging from 34.8 to 43.2 μg ml^?1 against tumor cell lines. Furthermore, 5 and 9 showed antioxidant activities.     

Monoterpenes and sesquiterpenes from the marine sediment-derived fungus Eutypella scoparia FS46

Eutypellol A (1), the first norsesquiterpenoid of sequicarene family, as well as eutypellol B (2), a rare 7-methyl oxidized 2-carene derivative, and one new natural product 2-(2-hydroxy-4-methylcyclohex-3-enyl)propanoic acid (3), along with eight known terpenoids, were isolated from the marine sediment-derived fungus Eutypella scoparia FS46 collected from the South China Sea. Their structures were established on the basis of extensive spectroscopic analysis. Compounds 1–3 were evaluated for their antibacterial activities against Staphylococcus aureus and cytotoxic activities against MCF-7, NCI-H460, and SF-268 tumor cell lines.     

Three new steroidal saponins from Aspidistra letreae plants and their cytotoxic activities

Three new steroidal saponins, aspiletreins A–C (1–3), together with 2H-chromen-2-one (4), and α-tocopherol (5), were isolated from whole Aspidistra letreae plants collected in Vietnam. Their structures were elucidated by a combination of spectroscopic analyses, including 1D- and 2D-NMR, IR, and HRESIMS, and by comparison with the reported data in the literature. Compounds 1–3 exhibited moderate cytotoxicities against the LU-1, HeLa, MDA-MB-231, HepG2, and MKN-7 human cancer cell lines, with IC₅₀ values ranging from 7.69?±?0.40 to 20.46?±?3.11 µM.

     

Leucanone A and naamine J,glycerol ether lipid and imidazole alkaloid from the marine sponge Leucandra sp.

Chemical investigation on CH₂Cl₂ extract of the marine sponge Leucandra sp. afforded two new compounds named leucanone A (1) and naamine J (2), together with eight known compounds (3–10). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparing with the literature. The cytotoxic activities of the compounds were evaluated against four cancer cell lines, and compound 2 showed mild cytotoxic activities against MCF-7, A549, HeLa, and PC9 cancer cell lines with IC₅₀ values in the range of 20.1–45.3 μM.     

Three minor valepotriate isomers from Valeriana jatamansi and their cytotoxicity

Three new minor valepotriate isomers, jatamanvaltrates Z1 (1), Z2 (2), and Z3 (3), have been isolated from the whole plants of Valeriana jatamansi (syn. Valeriana wallichii.). Their structures were elucidated by extensive spectroscopic analysis, especially 2D NMR and ESI-MS/MSⁿ. All isolated compounds displayed moderate cytotoxicity against the lung adenocarcinoma (A549), metastatic prostate cancer (PC-3 M), colon cancer (HCT-8), and hepatoma (Bel7402) cell lines with IC₅₀ values of 2.8–8.3 μM.     

Cytotoxic triterpenoid saponins from the defatted seeds of Camellia oleifera Abel

Five new oleanane-type triterpenoid saponins, oleiferasaponins D₁–D₅ (1–5), were isolated from the defatted seeds of Camellia oleifera Abel. Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of compounds 1–5 were evaluated against five human tumor cell lines (HCT-116, HepG2, BGC-823, NCI-H1650, and A2780). Compounds 1–2 exhibited cytotoxic activity against five human cancer cell lines, with IC₅₀ values ranging from 3.31 to 10.23 μM. Compounds 3–5 showed moderate cytotoxic activities toward the tested cell lines.     

Three new triterpenoids from Ganoderma theaecolum

Three new triterpenoids (1–3), together with four known triterpenoids (4–7), were isolated from the fruiting bodies of Ganoderma theaecolum. Their structures were elucidated on the basis of their spectroscopic data and chemical evidence. Compounds 4 and 6 exhibited antitumor activities against H460 cells with IC₅₀ values of 22.4 and 43.1 μM, respectively. And the cytotoxic activities of compounds 4 and 5 against MDA-MB-231 cancer cell lines were assayed with IC₅₀ values of 49.1 and 75.8 μM, respectively.     

Terpenoids from the tuber of Cremastra appendiculata

Two new terpenoids including a cadinane sesquiterpene (1), and an ent-kaurane diterpene diglycoside (2), together with a known triterpene containing 32 carbons (3), have been isolated from the ethanolic extract of Cremastra appendiculata. Their structures were established by the spectroscopic methods including the IR, MS, 1D-, and 2D-NMR experiments as ( ? )-cadin-4,10(15)-dien-11-oic acid (1), ( ? )-ent-12β-hydroxykaur-16-en-19-oic acid, 19-O-β-d-xylopyranosyl-(1 → 6)-O-β-d-glucopyranoside (2), and (+)-24,24-dimethyl-25,32-cyclo-5α-lanosta-9(11)-en-3β-ol (3). Compounds 1–3 were evaluated against several human cancer cell lines. Compound 3 showed in vitro-selective cytotoxicity against human breast cancer cell lines (MCF-7) with an IC₅₀ of 3.18 μM, but 1 and 2 were inactive (IC₅₀>10 μg/ml).     

Four new diterpenoids isolated from the Euphorbia rapulum

Four new diterpenoids named 1-epi-9-hydroxydepressin (1), 1-epi-8-hydroxydepressin (2), 2,13,9-trihydroxy-labda-8(17),12(E),14-triene (3) and tagalsin I (4) were isolated from Euphorbia rapulum. The structures of these compounds were elucidated by means of various spectroscopic methods. All the isolated compounds were evaluated for cytotoxic activities against HepG2, MCF-7, and C6 cell lines, and compound 4 showed moderate selective activity against MCF-7 cell line with an IC₅₀ value of 31.8 μM.     

Cytotoxic aspidosperma-type alkaloids from Melodinus axillaris

One new aspidosperma-type alkaloid, melotenine A (1), together with five known ones (2–6), was isolated from the leaves of Melodinus axillaris. Their structures were elucidated by detailed spectroscopic analysis and quantum chemical ECD calculation. The isolated aspidosperma-type alkaloids were evaluated for their cytotoxicity against four human cancer cell lines and melotenine A showed significant cytotoxicity against all cells with IC₅₀ values ranging from 0.6 to 1.5?μM.