Three new 3,4-seco-cycloartane triterpenes from Gardenia sootepensis

The plants in the genus Gardenia (Rubiaceae) have long been used as traditional medicines in China. In this study, two new 3,4-seco-cycloartane triterpenes, sootepin J (1) and sootepin K (2), and a novel nor-3,4-seco-cycloartane triterpenes, sootepin L (3), together with two known compounds (4–5), were isolated from the methanolic extract of the leaves and twigs of Gardenia sootepensis. The structures of the new compounds were elucidated by combinations of 1D, 2D NMR experiments and HR-MS data, while the known compounds were identified by comparison of the NMR data with previously published data.     

A new lactam alkaloid from Portulaca oleracea L. and its cytotoxity

A new lactam alkaloid named oleraciamide D (1), indentified as (5R)-4-(3-methoxy-4-hydroxyphenyl)-5-(4-hydroxyphenyl)-5,6-dihydropyridin-2(1H)-one, together with five known compounds, indole-3-aldehyde (2), portulacatone (3), N-trans-feruloyloctopamine (4), N-trans-feruloyl-3′-O-methyldopamine (5) and N-trans-feruloyltyramine (6) were isolated from Potulaca oleracea L. Among them, indole-3-aldehyde (2) was isolated from the medicine for the first time. The structure of the new alkaloid was elucidated via UHPLC-ESI-Q-TOF/MS, 1D NMR and 2D NMR. The five known compounds were established by comparing the ¹H-NMR and ¹³C NMR with the reported literature. Oleraciamide D (1) showed cytotoxicity against SH-SY5Y cells when concentration at 50 uM by CCK-8 method.     

A new arbutin derivative from the leaves of Vaccinium dunalianum wight

A new arbutin derivative, namely dunalianosides J (1), along with six known compounds, arbutin (2), robustaside A (3), 6′-O-caffeoylarbutin (4), dunalianoside D (5), kaempferol 3-O-β-D-glucopyranoside (6) and kaempferol 3-O-β-D-sambubioside (7) were isolated from the leaves of Vaccinium dunalianum Wight (Ericaceae). The structure of 1 was elucidated by extensive 1D and 2D NMR, HR-MS and CD spectroscopic analyses. In which, kaempferol 3-O-β-D-sambubioside (7) was isolated from the genus Vaccinium for the first time.     

A new alloside from <Emphasis Type="Italic">Neocheiropteris palmatopedata</Emphasis>

A new compound, 2,4,6-trihydroxybenzoic acid 4-O-β-D-allopyranoside (1), together with four known compounds, sucrose (2), fructose (3), ecdysterone (4), and β-sitosterol (5) was isolated from the roots of Neocheiropteris palmatopedata (Baker) Christ. The new compound was identified based on extensive spectroscopic studies including HR-ESI-MS, FAB-MS, ¹H NMR, ¹³C NMR, DEPT, ¹H–¹H COSY, HSQC, HMBC, and NOESY spectra, and the known compounds were identified by their spectroscopic data analysis, comparison with reports in the literature, and co-chromatography with authentic standards. Compounds 2, 3, and 5 were obtained from the Neocheiropteris genus for the first time, and 4 was originally isolated from the plant.     

A new anthraquinone and eight constituents from Hedyotis caudatifolia Merr. et Metcalf: isolation,purification and structural identification

Hedyotis caudatifolia Merr. et Metcalf. (HC), a folk medicine in Yao nationalities areas in China, was used to investigate the chemical constituents. Through silica gel and Sephadex LH-20 column chromatography, nine compounds were isolated and purified. By physical and chemical properties, IR, MS (EI-MS, high resolution EI-MS), 1D NMR (¹H NMR, ¹³C NMR) and 2D NMR (HSQC, ¹H–¹H COSY, HMBC), their structures were identified as β-sitosterol (1), stigmasterol (2), scopolin (3), 2-hydroxy-1,7,8-trimethoxyanthracene-9,10-dione (4), oleanolic acid (5), ursolic acid (6), methyl barbinervate (7), β-daucosterol (8) and p-Hydroxybenzoic acid (9). These compounds were isolated from HC for the first time, and 4 a new anthraquinone whose biological activities are worth to be investigated in future. These compounds may contribute to the HC’s pharmacological effects on treating diseases, and may be used as candidates for control index in establishing the quality control standard of HC.     

中国南海裸鳃目软体动物美丽拟皮片鳃(Dermatobranchus orna-tus)及其可能的食源动物柳珊瑚Muricella sp.的化学成分研究

从中国南海的裸鳃目软体动物美丽拟皮片鳃(Dermatobranchus ornatus)中分离得到4个eunicellane型二萜: Ophirin (1), calicophirin B (2), 13-去乙酰氧基 calicophirin B (3)及3-去乙酰基-13-去乙酰氧基calicophirin B (4); 而由同时、同地采集到的柳珊瑚Muricella sp. 中则分离得到calicophirin B (2), 13-去乙酰氧基 calicophirin B (3), astrogorgin (5) 及类似物6. 这些化合物的结构经波谱学实验并与文献报道的数据相对照得以确定, 并首次对Ophirin (1) 的NMR数据进行了全归属. Ophirin (1) 的单晶X衍射实验不但进一步确证了化合物的结构, 而且使这一类化合物的立体结构表述得到修正. 本文是对Dermatobranchus属软体动物化学成分研究的首次报道; 研究提示, 美丽拟皮片鳃能通过选择适当的食物, 并将食物中有用的次生代谢产物转移、富集到身体的特定部位, 使之成为自身的化学防性物质. 美丽拟皮片鳃与Muricella 属柳珊瑚中共同出现的类似化合物支持二者间可能存在的捕食与被捕食的生态学关系.     

A new chromene from the fruiting bodies of Chroogomphus rutilus

A new chromene, acetic acid 2R-(4,8-dimethylnona-3,7-dienyl)-8-hydroxy-2-methyl-2H-chromen-6-yl ester (1), was isolated from the fruiting bodies of Chroogomphus rutilus, together with six known compounds (2–7). The structures of these compounds were identified based on 1D and 2D NMR, including ¹H–¹H COSY, HMQC and HMBC spectroscopic methods. Of these seven compounds, 2 and 3 showed cytotoxicity against HSC-T6, SK-Hep1 and A549 cell lines.     

New furostanol glycosides from Polygonatum multiflorum (L.) All.

The phytochemical investigation of the whole plant of Polygonatum multiflorum resulted in the isolation of two new steroidal glycosides, polmultoside A (4) and polmultoside B (5), along with three known glycosides protobioside (1), protodeltonin (2) and huangjiangsu A (3). The structures of the isolated compounds have been elucidated by extensive 1D (¹H, ¹³C) and 2D (COSY, HSQC, HMBC) NMR spectral data analysis, as well as high-resolution mass determinations.     

New compound from Euphorbia alatavica Boiss

One new compound alatavinol (1), together with five known compounds, kaempferol (2), quercetin (3), laricircsinol (4), secoisolariciresinol (5) and loliolide (6) were isolated from the whole plant of Euphorbia alatavica Boiss. Those compounds were isolated and purified by various column chromatographic methods and their structures were elucidated by spectroscopic (1D, 2D NMR, and HR-MS) chemical analyses. All compounds were isolated for the first time from E. alatavica Boiss, and biochemical pathway of the new compound has been hypothesized. Furthermore, these compounds were evaluated for antioxidant properties based on the DPPH radical scavenging activities. Results showed that IC₅₀ values of compounds 1, 3, 4, 5 and 6 were 25.69, 1.88, 2.87, 11.55 and 17.81 μg/mL, respectively, as compared to the control ascorbic acid (5.34 μg/mL).     

Two new ionone glycosides from the roots of Rehmannia glutinosa Libosch.

Two new ionone glycosides, named frehmaglutoside G (1) and frehmaglutoside H (2), together with six known compounds, rehmapicroside (3), sec-hydroxyaeginetic acid (4), dihydroxy-β-ionone (5), trihydroxy-β-ionone (6), rehmaionoside A (7) and rehmaionoside C (8), were isolated from the 95% EtOH extract of the dried roots of Rehmannia glutinosa Libosch. Their structures were determined on the basis of extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, 1D and 2D NMR (¹H–¹H COSY, HSQC, HMBC and NOESY) methods. The absolute configurations were confirmed via the circular dichroism spectra.     

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.     

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.     

Two new polyacetylene glycosides from the roots of Codonopsis tangshen Oliv.

Two new polyacetylene glycosides, tangshenyne A (1) and tangshenyne B (2), along with six known polyacetylenes were isolated from an 85% MeOH extract of the roots of Codonopsis tangshen Oliv. The chemical structures of the new compounds were determined on the basis of extensive spectroscopic analyses, including UV, IR, 1D and 2D NMR (¹H–¹H COSY, HSQC and HMBC) and HR-ESI-MS.     

New chalcanonol glycoside from the seeds of saw palmetto: antiproliferative and antioxidant effects

A new chalcanonol glycoside dimer, bis-O-[(I-4′) → (II-6′)]-α-hydroxyphloretin-2′-O-β-glucoside (1), in addition to six known compounds, namely ( ? )-epicatechin (2) and ( ? )-epiafzelechin (3), 4-hydroxybenzoic acid (4), protocatechuic acid (5), methylgallate (6), β-sitosterol (7) and β-sitosterol-3-O-glucoside (8), was isolated from the seeds of saw palmetto. The structures of the isolated compounds were established from the analysis of their MS and 1D and 2D NMR spectroscopic data. The antiproliferative activities of the isolated compounds towards PC3, the human prostate cancer cells were investigated. Amongst the isolated compounds, the new compound and the sterolic derivatives showed antiproliferative effects. Screening of the antioxidant effects of the isolated compounds by 2,2′-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid radical assay revealed that the isolated phenolics were active free radical scavengers.     

Two new spongian diterpene analogues isolated from the marine sponge Acanthodendrilla sp

Abstract

Two new marine natural compounds, 3β-acetoxy-15-hydroxyspongia-12-en (1) and 3-methylspongia-3,12-dien-16-one (2), were isolated from the marine sponge Acanthodendrilla sp., collected in Pulau-Pulau. Compounds 1 and 2 represent new chemical entities of the known spongian diterpene family. Compound 1 is a new 3-acetoxyspongia and compound 2 presents an unreported rearranged 3-methylspongia-3-en. Their structures, including relative configurations, were fully elucidated based on 1D and 2D NMR analyses, as well as HRESTOFMS experiments. No significant bioactivities were found for these compounds. This work reports two new chemical structures, compounds 1 and 2, together with the first isolation of spongian diterpenes from Acanthodendrilla genus.     

Indole alkaloids from leaves and stems of <Emphasis Type="Italic">Hunteria zeylanica</Emphasis>

Investigation of the leaves and stems of Hunteria zeylanica resulted in the isolation of one new indole alkaloid, 11-hydroxyrhazimanine (1), and nine known analogs 2–10. Their structures were determined by 1D and 2D NMR analyses. Decarbomethoxydihydrogambirtannin (2), dihydroantirhine (3), and 3-oxomehranine (4) were isolated from Hunteria genus for the first time.     

Isoquinoline alkaloids from <Emphasis Type="Italic">Broussonetia papyrifera</Emphasis> fruits

A new isoquinoline alkaloid, named broussonpapyrine (1), along with three other known isoquinoline alkaloids, namely nitidine (2), oxyavicine (3), and liriodenine (4), were isolated from Broussonetia papyrifera fruits. The structures of these compounds were determined by 1D and 2D NMR, MS techniques, and chemical methods. This is the first report of the isoquinoline alkaloids isolated from this plant. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 83–84, January–February, 2007.     

A new benzofuran from Artemisia halodendron Turcz. ex Bess.

A new benzofuran, methyl (2S,2″S,3′E)-[2-(1″-acetoxypropan-2-yl)-2,3-dihydrobenzofuran-5-yl]acrylate (1), and 13 known compounds (2–14) were isolated from an ethanol extract of Artemisia halodendron Turcz. ex Bess. The chemical structures of these compounds were determined by 1D and 2D NMR (¹H-¹H COSY, HMBC, HMQC and NOESY) and HR-ESI-MS spectra, and results were compared with data from the literature. The effects of compounds 1–14 were measured on NF-κB activation, with compounds 2 and 3 exhibiting inhibitory activities against TNF-α-induced NF-κB reporter gene expression in HeLa cells from 10 to 100 μM.     

A new dihydrofurocoumarin from the fruits of Pandanus tectorius Parkinson ex Du Roi

From the fruit of Pandanus tectorius Parkinson ex Du Roi, one new dihydrofurocoumarin, named pandanusin A (1) and 15 known compounds, including one furanocoumarin (2), two coumarins (3, 4), four lignans (5–8), one neolignan (9), two flavonoids (10, 11), three phenolics (12–14), one monoglyceride (15) and one monosaccharide (16) were isolated by various chromatography methods. Among them, compounds (3–5) were obtained from the Pandanus genus for the first time and compounds (9–14, 16) were reported from this species for the first time. Their structures were elucidated by HR–ESI–MS, NMR 1D and 2D experiments and comparison with previous reported data. The α-glucosidase inhibitory activity of all compounds was measured. The isolated compounds (1–12, 14) showed better α-glucosidase inhibitory activity (IC₅₀ = 42.2, 36.5, 84.7, 73.2, 40.8, 26.7, 76.5, 33.8, 68.1, 14.4, 22.1, 81.5, 43.8 μM, respectively) than the standard drug acarbose (IC₅₀ = 214.5 μM).     

Separation of polar antioxidants from Rhizoma Polygonatum Odorati by high-speed counter-current chromatography with a hydrophilic solvent system

Some highly polar compounds are quality control makers for medicinal herbs. However, investigation of them has been hampered because the existing fractionation steps are difficult and laborious to purify them. Similar situations happen to Rhizoma Polygonatum Odorati, a widely used food supplement and medicinal herb with strong antioxidant activity, and up to date, only ethyl acetate fraction of Rhizoma Polygonatum Odorati has been comprehensively investigated. Here, HSCCC using a hydrophilic solvent system composed of n-butanol–ethanol–2 M ammonium sulfate (1:1:2, v/v/v) was performed to isolate highly polar antioxidants in n–butanol fraction of Rhizoma Polygonatum Odorati, guided by DPPH–HPLC experiment. Afterward, Sephadex LH-20 column chromatography eluted by methanol was selected to eliminate ammonium sulfate and purify co-eluted compounds in HSCCC collected fractions. Finally, nine compounds, including four nucleosides, cytidine (1), uridine (4), guanosine (5), and adenosine (8); two nucleobases, guanine (3), and adenine (6); and three amino acids, tyrosine (2), phenylalanine (7), and tryptophan (9) with purities over 98% were achieved and identified by UV, MS, and ¹H NMR data. Notably, compounds 1–9 were first reported in genus Polygonatum. The results indicated that the proposed method was an efficient approach to isolate and purify highly polar compounds from complex extracts.