In vitro anti-uveal melanoma activity of phenolic compounds from the Egyptian medicinal plant Acacia nilotica

Anti-uveal melanoma activity-guided fractionation of the MeOH extract of Acacia nilotica pods resulted in the isolation of the new compound gallocatechin 5-O-gallate (5) in addition to methyl gallate (1), gallic acid (2), catechin (3), catechin 5-O-gallate (4), 1-O-galloyl-β-D-glucose (6), 1,6-di-O-galloyl-β-D-glucose (7) and digallic acid (8). The structures of the isolated compounds were elucidated on the basis of HRESIMS, NMR spectroscopy and CD data. In addition to uveal melanoma, the antiproliferative activities of the isolated compounds and the related compound epigallocatechin 3-O-gallate (EGCG) were evaluated against cutaneous melanoma, ovarian cancer, glioblastoma and normal retinal pigmented cells.     

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.     

Two new chalcone glycosides from the stems of Entada phaseoloides

Two new chalcone glycosides 4′-O-(6″-O-galloyl-β-d-glucopyranosyl)-2′,4-dihydroxychalcone (1) and 4′-O-(6″-O-galloyl-β-d-glucopyranosyl)-2′-hydroxy-4-methoxychalcone (2) together with one known chalcone glycoside 4′-O-β-d-glucopyranosyl-2′-hydroxy-4-methoxychalcone (3) were isolated from the stems of Entada phaseoloides. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis, including HSQC, HMBC, ¹H–¹H COSY, and chemical evidences. This is the first report of chalcone-type compounds isolated from the genus Entada.     

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.     

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.     

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.     

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.     

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     

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.     

Multihydroxylation of ursolic acid by Pestalotiopsis microspora isolated from the medicinal plant Huperzia serrata

The structural modification of ursolic acid by an endophytic fungus Pestalotiopsis microspora, isolated from medicinal plant Huperzia serrata was reported for the first time. The structure diversity was very important for the SAR study of ursolic acid and its derivatives. Incubation of ursolic acid 1 with P. microspora afforded four metabolites: 3-oxo-15α, 30-dihydroxy-urs-12-en-28-oic acid (2), 3β, 15α-dihydroxy-urs-12-en-28-oic acid (3), 3β, 15α, 30- trihydroxy-urs-12-en-28-oic acid (4) and 3,4-seco-ursan-4,30-dihydroxy-12-en-3,28-dioic acid (5). All products were new compounds and their structures elucidation was mainly based on the spectroscopic data.     

Sesquiterpenoids from Trichoderma atroviride, an endophytic fungus in Cephalotaxus fortunei

Two new sesquiterpenoids, identified as (rel 1S, 3R, 4R, 7R)-3-[5-hydroxy-4-methylpent-3-enyl]-1, 3, 7-trimethyl-2-oxabicyclo [2, 2, 1] heptane (1) and (rel 1S, 3R, 4R, 7R)-3-[3, 4-dihydroxy-4-methylpentyl]-1, 3, 7-trimethyl-2-oxabicyclo [2, 2, 1] heptane (2), were isolated from cultures of Trichoderma atroviride (strain no. S361), an endophytic fungal strain residing in the bark of Cephalotaxus fortunei. The structures of compounds 1 and 2 were elucidated by detailed spectroscopic analyses on the basis of NMR, IR, and MS data. Both compounds 1 and 2 were potent inhibitors on NO production in LPS-stimulated RAW264.7 cells, with IC₅₀ values of 15.3 and 9.1 μM, 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 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.     

囊盘菌(Ascocoryne)挥发性气体成分多样性及其产烃分析

[目的]内生真菌紫胶囊盘菌(菌株NRRL 50072)首次被发现能产生石化燃料类似成分的挥发性有机代谢产物,这为生物质能源的发展开辟了新的途径,但囊盘菌属的真菌是否都具有该类代谢属性需要进一步明确。[方法]通过组织表面消毒分离囊盘菌不同菌株,经最大似然法构建分子系统发育树明确亲缘关系,利用顶空固相微萃取方法结合气质联用技术(HSSPEM-GC-MS),进行挥发性成分测定和分析。[结果]不同囊盘菌菌株均能产生挥发性烃、醇、酯、醛、酮和酸等代谢产物,但产物存在高度的多样性,即使近缘的菌株之间其挥发性产物也存在很大差异。[结论]囊盘菌属真菌可能普遍具有产挥发性烃类的能力,但其代谢产物种类具有菌株专化性。因此,发现或遗传工程创造目标新菌株资源是深入研究和开发利用囊盘菌真菌生物柴油的重要基础。     

Lignans ofChamaecyparis obtusa

Heartwood ofChamaecyparis obtusa contains significant amounts of a dibenzylbutyrolactone lignan, hinokinin (8). This investigation demonstrated that the contents of 8 and a norlignan, hinokiresinol (12), were higher in the heartwood region than in the sapwood, indicating their nature of being heartwood extractives. Eleven lignans — xanthoxylol (1), 7-oxohinokinin (2), savinin (3), dihydrosesamin (4), isoactifolin (5), sesamin (6), piperitol (7), hinokinin (8), pluviatolide (9), haplomyrfolin (10), and rnatairesinol (11) — were isolated from young shoots ofChamaecyparis obtusa cv. Breviramea. Eight lignans (1, 2, 4, 5, 7, 9,10, and11) were isolated from this plant for the first time. Chiral high-performance liquid Chromatographie analysis showed that8, 9, 10, and11, were found to be levorotatory and optically pure (>99% e.e.). Based on the chemical structures of the isolated lignans, possible biosynthetic pathways of8 are discussed.Parts of this report were presented at the 44th annual meeting of the Japan Wood Research Society, Nara, April 1994; the 46th annual meeting of the Japan Wood Research Society, Kumamoto, April 1996; and the 44th Lignin Symposium, Gifu, October 1999     

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.     

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.     

北方型美洲黑杨不同无性系重要性状评价

[目的]为杨树高产低耗高效工业用材新品种选育筛选新种质。[方法]采用布雷金多性状综合评定法和模糊数学隶属函数值法,系统分析和评价北方型美洲黑杨种质生长及光、水分、养分等关键环境资源利用性状。[结果]表明:(1)种源间、种源内无性系间在生长、光合、水分和养分利用方面的差异显著或极显著。(2)总叶面积、成叶速率、暗呼吸速率、氮素转移率、生长旺期水分利用效率与北方型美洲黑杨胸径显著或极显著相关。(3)筛选出M6、Q1、Q5、M5、Q7、Q3、M3、Q9等高产型种质,M6、Q1、Q2、M5、Q5、M3、Q4、M2等高产高光效型种质,Q5、Q1、W9、M5、Q7、M6、M3、W2等高产高水分利用型种质,Q9、Q5、Q3、Q8、Q1、M10、Q7、I5高产高养分利用型种质。其中,Q5、M6、Q1、Q2、Q9等无性系兼具生长和对资源(光、水分和养分)的利用优势。[结论]北方型美洲黑杨遗传变异丰富,为优良种源和种质选择提供了依据;总叶面积、成叶速率、、暗呼吸速率、氮素转移率等5个与生长关系密切的指标可作为种质资源评价的可靠指标;筛选出的优良种质特别是综合表现最优的5个无性系是后续育种工作的有效资源。     

New steroids from Clerodendrum colebrookianum

Five new steroids, colebrin A–E (1–5) were isolated from the aerial parts of Clerodendrum colebrookianum. The structures of the new compounds were elucidated on the basis of spectral evidence.     

A new steroidal saponin with antiinflammatory and antiulcerogenic properties from the bulbs of Allium ampeloprasum var. porrum

A new steroidal saponin was isolated from the bulbs of Allium ampeloprasum var. porrum L. On the basis of chemical evidence, comprehensive spectroscopic analyses and comparison of known compounds, its structure was established as (3β,5α,6β,25R)-6-[(β-d-glucopyranosyl)oxy]-spirostan-3-yl O-β-d-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-d-galactopyranoside (1). Results of the present study indicated that the steroidal saponin showed haemolytic effects in the in vitro assays and demonstrated antiinflammatory activity and gastroprotective property using in vivo models.