A new belamcandaquinone from the seeds of Iris bungei Maxim

A novel dimeric 1,4-benzoquinone and resorcinol derivative, Belamcandaquinone N (1), and two known compounds, 3-hydroxyirisquinone (2) and 5-[(Z)-10-heptadecenyl] resorcinol (3), were isolated from the seeds of Iris bungei Maxim. Their structures were elucidated by spectroscopic methods and comparing with literature data of known compounds. These compounds showed remarkable cytotoxic activity against RM-1 cell lines.     

Cytotoxic sesquiterpenoids from the fruits of Lindera communis

A new sesquiterpenoid, namely Linerenone (1), together with three known sesquiterpenoids (2–4), were isolated from the fruits of Lindera communis. Their structures were determined by extensive spectroscopic analysis including 1D, 2D-NMR and HR-MS spectra. Compound 1 showed significant cytotoxic activity against H460, ES2 and DU145 cancer cells with IC₅₀ of 2.1 μg/mL, 2.8 μg/mL and 3.0 μg/mL, respectively.     

Sesquiterpene lactones from Saussurea involucrata

Bioassay-directed separation of the ethyl acetate extract from the aerial parts of Saussurea involucrata (Kar. et Kir. ex Maxim) led to the isolation of three new sesquiterpene lactones sausinlactones A (1), B (2), C (3) and six known ones (4–9). The structures were established by spectroscopic data (UV, IR, HRESIMS, 1D and 2D NMR). CD technique was also employed to determine the absolute configurations of new compounds 1–3. The anti-inflammatory activities of compounds 1–9 and antitumor activities of new compounds 1–3 were tested. The results presented that compounds 5 and 6 were responsible for anti-inflammatory activities, and compounds 1 and 2 showed significant cytotoxic activities against A549 cells.     

A new 1,3-diketofriedelane triterpene from Salacia verrucosa

A new 1,3-diketofriedelane triterpene, 21α-hydroxyfriedelane-1,3-dione (1) together with six known friedelane triterpenes, 30-hydroxyfriedelane-1,3-dione (2), friedelane-1,3-dione (3), 26-hydroxyfriedelane-1,3-dione (4), friedelin (5), 21α-hydroxy-D:A-friedo-olean-3-one (6) and kokoonol (7), were isolated from the stems of Salacia verrucosa (Celastraceae). The structures of these triterpenes were characterized by spectroscopic methods (IR, MS and NMR). Compound 3 was strongly cytotoxic against SW620 cell line, whereas compounds 4 and 6 were moderately active against SW620, HepG2 and KATO-III cancer cell lines.     

New cassane diterpenes from Caesalpinia echinata

An investigation of the ethanolic extract from stems of Caesalpinia echinata Lam (Leguminosae-Caesalpinioideae) led to the isolation of five new cassane diterpenes along with known lambertianic acid. Their structures were determined based on spectroscopic methods. A preliminary study on leishmanicidal activity demonstrated that compounds 1, 2 and 6 were found to inhibit the growth of amastigote-like forms of Leishmania amazonensis without affecting mononuclear cells obtained from human peripheral blood.     

Chemical constituents from Gmelina arborea bark and their antioxidant activity

Gmelina arborea Roxb. is a fast-growing species and is known to have been used in traditional Indian medicine. Chemical constituents from the bark have not been reported, although some chemical constituents from part of this plant (heartwood, leaf, and root) are known. In this study, the bark meal was successively extracted with acetone and methanol. Fractionation of the acetone extract with n-hexane, diethyl ether, and ethyl acetate and subsequent chromatographic separation of the fractions led to the isolation of four compounds. The diethyl ether-soluble fraction yielded tyrosol [2-(4-hydroxyphenyl)ethanol] (1); (+)-balanophonin (2), an 8-5′ neolignan, with opposite optical rotation to known (−)-balanophonin; and gmelinol (3), a known lignan. The ethyl acetate-soluble fraction afforded a new phenylethanoid glycoside to the best of our knowledge, which was identified as (−)-p-hydroxyphenylethyl[5′″-O-(3,4-dimethoxycinnamoyl)-β-d-apiofuranosyl(1′" → 6′)]-β-d-glucopyranoside (4). From the methanol extract, two known compounds, 2,6-dimethoxy-p-benzoquinone (5) and 3,4,5-trimethoxyphenol (6), were isolated and identified. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging assay of the identifi ed compounds indicated that 3,4,5-trimethoxyphenol (6) exhibited moderate activity. Part of this report was presented at the 57th and 58th Annual Meetings of the Japan Wood Research Society, Hiroshima and Tsukuba, August 2007 and March 2008, respectively     

Cytotoxicity of chemical constituents from the stems of Dalbergia parviflora

Three new compounds, dalberpene (1), dalparvinene B (2) and dalparvone B (3), as well as 12 known compounds were isolated from the heartwood of Dalbergia parviflora. Isoflavanone 13 showed strong cytotoxicity against KB, MCF-7 and NCI-H187 cell lines with IC₅₀ values ranging from 3.5 to 5.4 μg/mL and it was inactive against normal cells.     

Irbic acid, a dicaffeoylquinic acid derivative from Centella asiatica cell cultures

3,5-O-dicaffeoyl-4-O-malonilquinic acid (1) (irbic acid) has been isolated for the first time from cell cultures of Centella asiatica and till now it has never been reported to be present in the intact plant. Evidence of its structure was obtained by spectroscopic analyses (MS/NMR). Besides 1, cell cultures produce also the known 3,5-O-dicaffeoylquinic acid, chlorogenic acid, and the triferulic acid 2 (4-O-8′/4′-O-8″-didehydrotriferulic acid). Biological activities were evaluated for compound 1, which showed to have a strong radical scavenging capacity, together with a high inhibitory activity on collagenase. This suggests a possible utilization of this substance as a topical agent to reduce the skin ageing process.     

neo-Clerodane diterpenes from Ajuga ciliata Bunge and their neuroprotective activities

Three new (1–3) and three known (4–6) neo-clerodane diterpenes have been isolated from the whole plants of Ajuga ciliata Bunge. The structures of the new compounds were elucidated as (12S)-1β,6α,19-triacetoxy-18-chloro-4α,12-dihydroxy-neo-clerod-13-en-15,16-olide (1), (12S,2′S)-12,19-diacetoxy-18-chloro-4α,6α-dihydroxy-1β-(2-methylbutanoyloxy)-neo-clerod-13-en-15,16-olide (2), and (12S)-6α,18,19-triacetoxy-4α,12-dihydroxy-1β-tigloyloxy-neo-clerod-13-en-15,16-olide (3), on the basis of spectroscopic data analysis. All the diterpenes were evaluated for the neuroprotective effects against MPP⁺-induced neuronal cell death in dopaminergic neuroblastoma SH-SY5Y cells and compounds 2–5 exhibited moderate neuroprotective effects.     

Oleanene triterpenes from Sedum lineare Thunb

One new olean-13(18)-ene-3,12,19-trione (1), and two known oleanene triterpenes δ-amyrone (2), and δ-amyrine acetate (3) were isolated from the petroleum ether fraction from an alcoholic extract of the whole plant of Sedum linear Thunb. The new compound was characterized by means of spectroscopic methods including 1D, 2D NMR and HR-ESI–MS, and was further confirmed by X-ray diffraction analysis. The known ones were established on the basis of comparing their NMR data with those of the corresponding compounds in the literature. In addition, the inhibitory effects of the compounds isolated on the TNF-α and NO production were examined in vitro.     

Alkaloids from Lycoris aurea and their cytotoxicities against the head and neck squamous cell carcinoma

Phytochemical investigation of the 80% EtOH extract of the bulbs of Lycoris aurea led to the isolation of six new alkaloids, 2-demethyl-isocorydione (1), 8-demethyl-dehydrocrebanine (2), 1-hydroxy-anhydrolycorin-7-one (3), (+)-1,2-dihydroxy-anhydrolycorine N-oxide (4), 5,6-dihydro-5-methyl-2-hydroxyphenanthridine (5), and (+)-8-hydroxy-homolycorine-α-N-oxide (6), and together with two known compounds, isocorydione (7) and anhydrolycorin-7-one (8). Structural elucidation of all the compounds was performed by spectral methods such as 1D and 2D (¹H–¹H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. All the alkaloids were in vitro evaluated for their cytotoxic activities against seven tumor cell lines of the head and neck squamous cell carcinoma and anti-inflammatory activities. Compounds 1, 2, 6, and 7 exhibited significant cytotoxicities against all the tested cell lines. Moreover, alkaloids 1, 2, and 7 possessed selective inhibition of Cox-2 (> 85%).     

Two new pterosin dimers from Pteris mutifida Poir

Two new C₁₄ pterosin dimers, which are a pair of isomers named as bimutipterosins A (1) and B (2), were isolated from the whole plant of Pteris multifida. Their structures have been elucidated on the basis of NMR and MS data. From a biogenetic point of view, these compounds including a cyclobutane basic core should be considered as a [2 + 2] dimerization product of dehydropterosin Q, which was a known compound and also isolated from this plant. This novel type of pterosin dimer was reported here for the first time. Compounds 1 and 2 showed cytotoxicity against HL 60 cell line (human leukemia) with the IC₅₀ values of 12.8 and 26.6 μM, respectively.     

Formylated phloroglucinols from Eucalyptus loxophleba foliage

Two new naturally occurring formylated phloroglucinol compounds (FPCs), a dimer, loxophlebal B (10) and a cyclized FPC, loxophlebene (8) together with eight other formylated phloroglucinols (1–7 and 9) were isolated from the chloroform-methanol (8:2) extract of the leaves of Eucalyptus loxophleba ssp. lissophloia. The structures of new compounds were established by comprehensive spectral analysis and by comparison of their NMR data with those of related compounds in the literature. All the isolated compounds were evaluated for anti-leishmanial activity against promastigotes of Leishmania donovani.     

Antitrypanosomal sesquiterpene lactones from Saussurea costus

In the course of a larger screen of 1800 plant and fungal extracts, the ethyl acetate extract of Saussurea costus roots potently inhibited the growth of Trypanosoma brucei rhodesiense. Subsequent HPLC based activity profiling led to the identification of the sesquiterpene lactones arbusculin B (1), α-cyclocostunolide (2), costunolide (3), and dehydrocostuslactone (4). They were tested for in vitro antitrypanosomal activities and cytotoxicity alongside the structurally related sesquiterpene lactones parthenolide (5), zaluzanin D (6), and eupatoriopicrin (7), and had IC₅₀s between 0.8 and 22 μM. Cytotoxic IC₅₀s were from 1.6 to 19 μM, and selectivity indices from 0.5 to 6.5.     

Dihydroroseoside, a new cyclohexanone glucoside, from the leaves of shirakamba (Betula platyphylla Sukatchev var.japonica Hara)

A new cyclohexanone glucoside (II) and a known cyclohexenone glucoside roseoside [I, (6S, 9S)-6-hydroxy-6-(9--D-glucopyranosyloxy-trans-7-butenyl)-1,5,5-trimethyl-1-cyclohexenone] were isolated from an ethanol extract of shirakamba (Betula platyphylla Sukatchev var.japonica Hara) leaves. The structure ofII was determined to be (6S, 9R)-6-hydroxy-6-(9-O--D-glucopyranosyloxy-trans-7-butenyl)-1, 5,5-trimethyl-1-cyclohexanone by¹H-NMR and¹³C-NMR spectroscopic analyses. It was named dihydroroseoside.     

Identification of Taxus cuspidata Sieb. et Zucc. endophytic fungi-new species, species known and their metabolite

A total of 94 isolates of endophytic fungi were isolated from the bark of 200-yr.-old Taxus cuspidata Sieb. et Zucc.in the primeval forest of the Changbai Mountain Natural Reserve, and 19 species of endophytic fungi were identified, including 10 new recorded-genus-species, 2 new species (Phomopsis Iongiscoleosporu Y. Xiang et Lu An Guo Wu Wen Fang, Coniothyrium macrospoum Y. Xiang J.X. et Lu An Guo Wu Wen Fang), 1 new varied species (Alternaria alternata (Fr.) Keissler var. taxi Y.Xiang et Lu An Guo) and 6 known species of China (Eurotium amstelodomi Mgngin, Eurotium repens de Bary, Botrytis sp.,Penicillium citrinum Thom, Epicoccum nigrium LinK, Fusarium sp.). Through thin layer chromatography (TLC), liquid fermentation metabolite of the strains was determined, and four strains (Alternaria alternata (Fr.) Keissler var. taxi Y. Xiang et Lu An Guo Wu Wen Fang, Botrytis sp., Eurotium amsteloodomi Mgngin, Eurotium repens de Bary) were screened out, whose metabolites reacted positively with the vanillic aldehyde that was one special taxoid developer. Among the four strains, Alternaria alternata (Fr.) Keissler var. taxi Y. Xiang et Lu An Guo, produced one compound largely, which positively reacted with one alkaloids developer-Bismuth potassium iodide. The compound is identified as taxoids type through spectrum analysis. This demonstrates that Alternaria alternata (Fr.) Keissler var. taxiY. Xiang et Lu An Guo can highly produce taxoids largely.     

A new norlignan from Taxodium ascendens

A new norlignan, (2R,3R,4S,5S)-2,4-bis(4-hydroxyphenyl)-3,5-dihydroxy-tetrahydropyran (1), together with 9 known compounds were isolated from the branches and leaves of Taxodium ascendens. Their structures were mainly determined on the basis of MS, IR, 1D and 2D NMR spectral evidences. Methanol extract showed inhibitory activity on carbonic anhydrase II with an IC₅₀ value of 4.27 µg/ml, acetone extract and methanol extract inhibited activity of cathepsin B with IC₅₀ values of 2.12 and 3.71 µg/ml, respectively.     

Iridoids from the roots of Valeriana jatamansi and their neuroprotective effects

Three new iridoids, valeriandoids A–C (1–3), together with three known analogues (4–6), were isolated from the roots of Valeriana jatamansi. Their structures and relative configurations were elucidated by spectroscopic methods (IR, ESIMS, HRESIMS, 1D and 2D NMR) and by comparison of their NMR data with those of related compounds. All the isolated compounds were evaluated for their neuroprotective effects and compounds 1, 3, 4 and 6 showed moderate neuroprotective effects.     

Two new polyols and a new phenylpropanoid glycoside from the basidiomycete Lactarius deliciosus

Two new polyols, 3-hydroxymethyl-2-methylenepentane-1,4-diol (1) and 1-methylcyclohexane-1,2,4-triol (2), and a new phenylpropanoid glycoside, eugenyl 4″-O-acetyl-β-rutinoside (3), together with seven known steroids (5–11) were isolated from the fruiting bodies of the basidiomycete Lactarius deliciosus. The structures of these compounds were elucidated by the analysis of spectroscopic data.     

Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica

A new resveratrol trimer, malaysianol A (1), five known resveratrol oligomers: laevifonol (2), ampelopsin E (3), α-viniferin (4), ε-viniferin (5), diptoindonesin A (6), and bergenin (7) have been isolated from the acetone extract of the stem bark of Dryobalanops aromatica by combination of vacuum and radial chromatography techniques. Their structures were established on the basis of their spectroscopic evidence and comparison with the published data. The cytotoxic activity of the compounds was tested against several cell lines in which compound 4 was found to inhibit strongly the growth of HL-60 cell line.