Cytotoxic 19-oxygenated steroids from the South China Sea gorgonian,Pacifigorgia senta

Bioassay guided chemical investigation of the gorgonian Pacifigorgia senta led to the discovery of a new 19-oxygenated steroid, cholesta-5,24-diene-3β,7β,19-triol (1), as well as three known steroids (2–4). The structure of 1 was determined by extensive spectroscopic analysis, including NMR and MS spectra. All of the compounds exhibited cytotoxicities against HepG2, Hep3B, MCF-7/ADR, PC-3 and HCT-116 cell lines, with the IC₅₀ values ranging from 7.0 to 29.7 μM. It is the first report on the chemical constituents of the coral species P. senta.     

Taxanes from the leaves of <Emphasis Type="Italic">Taxus cuspidata</Emphasis>

A new taxane, 13-oxobaccatin III (2), and five known taxanes, 10-deacetyl-13-oxobaccatin III (1), baccatin III (3), 7-epi-10-deacetyltaxol (4), 19-debenzoyl-19-acetyltaxinine M (5), and 5a-decinnamoyltaxagifine (6), were isolated from the leaves of the Japanese yew, Taxus cuspidate. Their structures were established on the basis of the analysis of their spectral data.     

Trichosordarin A,a norditerpene glycoside from the marine-derived fungus Trichoderma harzianum R5

Abstract

A new sordarin derivative, trichosordarin A (1), with a unique norditerpene aglycone was isolated from the culture of a marine-sediment-derived fungal strain, Trichoderma harzianum R5. Its structure and relative configuration were unequivocally identified by a combination of 1D/2D NMR, IR, and mass spectrometric methods. Compound 1 was assayed to be toxic to the marine zooplankton Artemia salina.     

Ascomycotin A,a new citromycetin analogue produced by Ascomycota sp. Ind19F07 isolated from deep sea sediment

A new citromycetin analogue, ascomycotin A (1), together with eight known compounds, wortmannilactone E (2), orcinol (3), orsellinic acid (4), isosclerone (5), (3R,4S)-( ? )-4-hydroxymellein (6), diorcinol (7), chaetocyclinone B (8) and 2,5-dimethoxy-3,6-di(p-methoxypheny1)-1,4-benzoquinone (9), was isolated from the fungal strain Ascomycota sp. Ind19F07, which was isolated from the deep sea sediment of the Indian Ocean. The structures of the compounds were established by spectroscopic data including 1D and 2D NMR and HR-ESI-MS. Compounds (1–9) were evaluated for antibacterial activity.     

A new pregnane steroid from cultures of Aspergillus versicolor

A new pregnane steroid, named aspergillon A (1), together with two known compounds, (22E,24R)-ergosta-5,7,22-trien-3β-ol (2) and (22E, 24R)-ergosta-4,6,8(14),22-tetraen-3-one (3) were isolated from cultures of the tin mine tailings-associated fungus Aspergillus versicolor. The new structure and absolute configuration were determined with the help of extensive spectroscopic analyses and quantum chemical calculations of the electronic circular dichroism (ECD) spectra.     

A new diterpenoid alkaloid from Aconitum hemsleyanum

Abstract

A new C₁₉-diterpenoid alkaloid named hemsleyaline (1), along with fourteen known alkaloids (2-15), were isolated from the roots of Aconitum hemsleyanum Pritz. (Ranunculaceae), a herbal medicine in southwest China. Their structures were established on the basis of extensive spectroscopic analyses. Compound 1 showed mild cholinesterase inhibitory effect with IC₅₀ value of 471?±?9?μM.     

Bioactive furanocoumarins from the stems and leaves of Clausena hainanensis

A new furanocoumarin, clauhainanin A (1), together with seven known furanocoumarins (2–8), were isolated from the stems and leaves of Clausena hainanensis. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with data reported in the literature. All known compounds (2–8) were isolated from C. hainanensis for the first time. All isolated compounds were evaluated for their cytotoxicities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1–8 exhibited significant inhibitory effects with IC₅₀ values ranging from 1.36 to 18.96 μM.     

New ent-kaurane diterpenoid dimer from Pulicaria inuloides

A new naturally occurring ent-kaurane diterpenoid dimer, 15β, 15′β-oxybis (ent-kaur-16-en-19-oic acid) (1) along with six known compounds, 15β-hydroxy-ent-kaur-16-en-19-oic acid (2), 15β-hydroxy-ent-kaur-16-en-19-oate-β-d-glucopyranoside (3), 6-hydroxykaempferol-3, 7-dimethyl ether (4), quercetagetin 3, 7, 3′-trimethyl ether (5), β-sitosterol (6) and β-sitosterol glucoside (daucosterol) (7) were isolated from the aerial parts of Pulicaria inuloides DC. Compounds 2–5 were isolated for the first time from genus Pulicaria. The structures of compounds 1–7 were established on the basis of extensive 1D and 2D NMR spectroscopic techniques in combination with ESI-MS. The antimicrobial activity of the isolated compounds was evaluated against Staphylococcus aureus, Escherichia coli and Candida albicans. Sulphorhodamine B cytotoxic assay against HepG2 (liver cancer) cell line and ABTS antioxidant assay were carried out.     

A new dihydrochalcone glycoside from the stems of Homalium stenophyllum

A new dihydrochalcone glycoside, phloretin-4-O-β-D-glucopyranoside (1), together with seven known flavonoids (2–8), were isolated from the stems of Homalium stenophyllum. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with data reported in the literature. The known compounds (2–8) were isolated from the genus Homalium for the first time. All compounds were evaluated for their antibacterial activities against six pathogenic bacteria in vitro.     

A new Secondary metabolites of the crinoid (Comanthina schlegeli) associated fungus Alternaria brassicae 93

Fungus Alternaria brassicae 93 isolated from crinoid (Comanthina schlegeli), which was collected from the South China Sea. Six compounds were isolated from A. brassicae 93, including one new compound (1), along with five known compounds, ochratoxin A methyl ester (2), cis-4-hydroxym-ellein (3), (R)-7-hydroxymellein (4), trans-2-anhydromevalonic (5) and protocatechuic acid (6). Their structures were determined by spectroscopic methods and comparison with reported data. Cytotoxicity against two human cancer cell lines and antibacterial activity against twelve aquatic bacteria of compound 1 were also tested.     

A New Lycopodine-type Alkaloid from Lycopodium japonicum

A new lycopodine-type alkaloid, 12β-hydroxy-acetylfawcettiine N-oxide (1), together with seven known analogues, acetyllycoposerramine M (2), lycopodine (3), lycoclavine (4), diphaladine A (5), lycoposerramine K (6), 11β-hydroxy-12-epilycodoline (7) and fawcettiine (8), were isolated from Lycopodium japonicum. Their structures were established by mass spectrometry and 1D and 2D NMR techniques. The isolated alkaloids were assayed for their inhibition activities against acetylcholinesterase, but no inhibitory activities for the compounds were detected.     

A bicyclo[3.2.1]octanoid neolignan and toxicity of the ethanol extract from the fruit of <Emphasis Type="Italic">Ocotea heterochroma</Emphasis>

A new bicyclo[3.2.1]octanoid neolignan rel-(7S,8R,1′S,2′R,3′S)-Δ8′-2′-hydroxy-5,1′,3′-trimethoxy-3,4methylenedioxy-7,3′,8,1′-neolignan (1) was isolated from ethanol extract from the fruit of Ocotea heterochroma Mez & Sodiro ex Mez as well as the known compounds β-friedelanol (2), meso-dehydroguaiaretic acid (3), and yangambin (4), whose structures were elucidated on the basis of their comprehensive spectroscopic analysis including 2D NMR data. Lethality bioassay using brine shrimp (Artemia salina Leach) was evaluated with the ethanol extract from the Ocotea heterochroma’s fruit. The toxicity of this extract was greater than the toxicity of those fractions obtained in a first solvent partition (benzene, ethyl acetate, and butanol subfractions) and that of a mixture of acetylated 2′-epimers from the new neolignan 1. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 158–160, March–April, 2009.     

Cytotoxic monoterpenoid indole alkaloids isolated from the barks of Voacanga africana Staph.

A new monoterpenoid indole alkaloid compound (1) and six known monoterpenoid indole alkaloids compounds (2–7) were isolated from the barks of Voacanga africana Staph. The structures were established by spectral analysis as ibogamine-16-carboxylic acid,17,20-didehydro-5,6-dioxo-10-methoxy-methyl ester (1), voacamine (2), vobasine (3), voacangine (4), voacristine (5), 19-epi-voacristine (6) and 19-epi-heyneanine (7). Compound 1 was confirmed by X-ray crystallographic analysis. All of the isolated compounds were evaluated for cytotoxicity against five cell lines (HEPG-2, A375, MDA-MB-231, SH-SY5Y, CT26). Among them, compounds 2 and 6 displayed significant inhibitory activities, compounds 3, 4 and 5 showed moderate inhibitory activities, while compounds 1 and 7 showed no inhibitory activities against the five cell lines.     

A new abietane diterpenoid from the roots of Tripterygium regelii

A new abietane diterpenoid, tripterregeline A (1), together with six known diterpenoids (2–7), were isolated from the roots of Tripterygium regelii. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparison with data reported in the literature. All isolated compounds were evaluated for their cytotoxicities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1–7 showed significant inhibitory effects against various human cancer cell lines with IC₅₀ values ranging from 0.58 to 21.06 μM.     

Chemical constituents from seeds of <Emphasis Type="Italic">Lactuca sativa</Emphasis>

A new flavonol glycoside with a rare structure type, lactucasativoside A (1), was isolated from the seeds of Lactuca sativa, together with three known compounds, japonicin A (2), isoquercitrin (3), and caffeic acid (4). Their structures were established on the basis of extensive spectroscopic analysis. Compound 2 was obtained from the genus Lactuca for the first time.     

A new briarane-type diterpenoid from the South China Sea Gorgonian Dichotella gemmacea

One new briarane-type diterpenoid, dichotellide V (1), along with four known analogues, gemmacolide N (2), dichotellide J (3), junceelin A (4) and junceellolide A (5), was isolated from the South China Sea gorgonian Dichotella gemmacea. All of the isolated compounds (1–5) were established by comprehensive analysis of the spectral data, especially 1D and 2D NMR (HMQC and HMBC) spectra. The cytotoxic activities of these compounds were evaluated.     

One new 19-nor cucurbitane-type triterpenoid from the stems of Momordica charantia

One new 19-nor cucurbitane-type triterpenoid (3β,9β,25-trihydroxy-7β-methoxy-19-nor-cucurbita-5,23(E)-diene) (1), together with other six known cucurbitane-type triterpenoids (2–7), were isolated from the stems of Momordica charantia L. The chemical structure of 1 was elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, COSY and ROESY), MS experiments. Using MTT assay, compound 1 exhibited weak cytotoxicity against HL-60, A-549, and SK-BR-3 cell lines with the IC₅₀ values at 27.3, 32.7 and 26.6 μM, respectively.     

Argininosecologanin,a secoiridoid-derived guanidine alkaloid from the roots of Lonicera insularis

A new secoiridoid-derived guanidine alkaloid, argininosecologanin (1), along with 12 known iridoids and secoiridoids (2–13), was isolated from the roots of Lonicera insularis. The structures of the isolated compounds were established by the spectroscopic analysis and comparison of their spectral data with previously reported data. Compound 1 was assigned as the first secoiridoid-derived guanidine alkaloid isolated as a natural product. A plausible biogenetic pathway for 1 is suggested based on its structural similarity to (E)-aldosecologanin (4).     

Aspergilolide,a steroid lactone produced by an endophytic fungus Aspergillus sp. MBL1612 isolated from Paeonia ostii

A new steroid lactone aspergilolide (1), and nine known compounds helvolic acid (2), verruculogen (3), tryprostatin B (4), 13-oxofumitremorgin B (5), fumitremorgin C (6), demethoxy fumitremorgin C (7), terezine D (8), aszonalenin (9), 12, 13-dihydroxy-fumitremorgin C (10) from cultures of the endophytic fungus Aspergillus sp. MBL1612. Their chemical structures were determined by a series of extensive spectroscopic methods. All of the compounds were isolated from this genus for the first time. The cytotoxicity against five human cancer cell lines of new compound were detected.     

酸枣仁中三萜皂苷的分离和结构研究

从酸枣仁(Zizyphus jujuba Mill. Var. spinosa Hu)中分离得到四个三萜皂苷, 分别鉴定为酸枣仁皂苷G (1, jujuboside G), 酸枣仁皂苷A (2, jujuboside A), 酸枣仁皂苷B (3, jujuboside B)和酸枣仁皂苷A₁ (4, jujuboside A₁). 其中酸枣仁皂苷G与其它酸枣仁皂苷不同, 为新的酮基达玛烷型三萜皂苷. 运用现代波谱技术, 包括二维核磁共振谱和高分辨质谱, 对上述化合物的结构进行了确证.