Iridoid and megastigmane glycosides from Phlomis aurea

From the leaves of Phlomis aurea, two new iridoids of unique structures named 3-epiphlomurin (1) and phlomurin (2), a new megastigmane glucoside phlomuroside (3) and a new benzyl alcohol glycoside having the structure benzyl alcohol-O-beta-xylopyranosyl-(1-->2)-beta-glucopyranoside (4) have been isolated together with four known iridoids auroside, lamiide, 8-epiloganin and ipolamiide, two known phenolic glycosides acteoside (verbascoside) and syringin, one known phenylethanoid glycoside 2-phenylethyl-O-beta-xylopyranosyl-(1-->2)-beta-glucopyranoside, one known lignan liriodendrin and three known flavonoids chrysoeriol-7-O-beta-glucopyranoside, acacetin-7-O-beta-glucopyranoside and luteolin-7-O-beta-glucopyranoside. The structures of the isolated compounds were verified by means of mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectral analyses.     

A New Phenolic Glycoside from Chloranthus multistachys(Chloranthaceae)

A new phenolic glycoside, named syringic acid-4-O-α-L-rhamnopyranoside (1), together with three known compounds were isolated from the MeOH extract of the whole plants of Chloranthus multistachys. Their structures were elucidated on the basis of extensive spectroscopic. To the best of our knowledge, the three known compounds, 1β,4β-dihydroxy-5α, 8β(H)-eudesm-7 (11) Z-en-8, 12-olide (2), 1β, 4α-dihydroxy-5α, 8β(H)-eudesm-7 (11) Z-en 8, 12-olide (3), and (–) (7S,8R) dihydrodehydrodiconifery alcohol (4) were all isolated from this plant for the first time.     

Coumaroyl triterpene lactone, phenolic and naphthalene glycoside from stem bark of Diospyros angustifolia

From the ethanolic extract of stem bark of D. angustifolia three new compounds, a coumaroyl triterpene lactone, diospyrosooleanolide (1), a phenolic glycoside, diospyrososide (2) and a naphthalene glycoside, diospyrosonaphthoside (3) were isolated along with five known compounds (4-8). The structures of these compounds were established on the basis of spectroscopic and chemical evidences.     

Phenolic glycosides and ionone glycoside from the stem of Sargentodoxa cuneata

Four phenolic glycosides, cuneatasides A-D (1-4), and one ionone glycoside cuneataside E (5), together with seven known phenolic compounds (6-12) were isolated from the water-soluble constituents of the stem of Sargentodoxa cuneata (Sargentodoxaceae). Their structures were elucidated by spectroscopic analysis. In vitro tests for antimicrobial activity showed compounds 1 and 2 to possess significant activity against two Gram-positive organisms, Staphylococcus aureus and Micrococcus epidermidis.     

Coixlachryside A: A new lignan glycoside from the roots of Coix lachryma-jobi L. var. ma-yuen Stapf.

A new lignan glycoside, 1-[3,6-(4,4⿲-dihydroxy-3,3⿲-dimethoxy-δ-truxinyl)-β-fructofuranosyl]-α-glucopyranoside (1), named coixlachryside A, together with nine known simple phenolic compounds (3⿿11) were isolated from the roots of Coix lachryma-jobi var. ma-yuen using various chromatographic methods. Their chemical structures were determined based on the spectroscopic data interpretation, particularly circular dichroism (CD), 1D and 2D NMR data including HSQC and HMBC.     

Phenolic glycosides from Phagnalon rupestre

Analysis of the butanol-soluble fraction from the methanolic extract of the aerial parts of Phagnalon rupestre (Asteraceae) has led to the isolation of seven phenolic compounds. Three have been identified on the basis of their NMR spectra as new natural compounds: the lignan 7,7'-bis-(4-hydroxy-3,5-dimethoxyphenyl)-8,8'-dihydroxymethyl-tetrahydrofuran-4-O-beta-glucopyranoside (1), the prenylhydroquinone glycoside 1-O-beta-glucopyranosyl-1,4-dihydroxy-2-(3'-hydroxy-3'-methylbutyl) benzene (2) and the acetophenone glycoside 12-O-beta-glucopyranosyl-9beta,12-dihydroxytremetone (3). The known flavonoids apigenin-7-O-beta-glucoside, luteolin-7-O-beta-glucoside, luteolin-7-O-beta-glucuronide and the acetophenone picein were also isolated.     

多穗金栗兰中一个新的酚苷

从多穗金粟兰(Chloranthus multistachys)全株的甲醇提取物中分离得到1个新的酚苷,通过波谱技术鉴定其结构为丁香酸-4-O-a-L-鼠李吡喃糖苷(1).同时还首次从该植物中分离得到两个已知倍半萜内酯和一个已知木脂素:1β,4β-二羟基-5a,8β-二氢-7(11)Z-桉叶烯-8,12-内酯(2),lβ,4a-二羟基-5a,8β-二氢-7(11)Z-桉叶烯-8,12-内酯(3),(-)-(7S,8R)-dihydrodehydrodiconifery alcohol(4).     

Two new hemiterpene glycosides and one new phenolic glycoside from the roots of Securidaca inappendiculata Hassk

Two new hemiterpene glycosides, named as securiterpenoside B (1), and securiterpenoside C (2), and one new phenolic glycoside, named as securiphenoside A (3) were isolated from the roots of Securidaca inappendiculata Hassk. Their structures were elucidated on the basis of 1D and 2D NMR data and HRESIMS and comparisons with published data. Moreover, compounds 1–3 were evaluated for cytotoxicities against A549 (Lewis lung cancer), Hela (human cervical cancer) and MCF-7 (human breast cancer) cell lines.     

怒茶素--怒江山茶的一个新黄酮甙

用葡聚糖凝胶和树脂层析技术从云南省昆明地区产怒江山茶（Ｃａｍｅｌｌｉａ ｓａｌｕｅｎｅｎｓｉｓ Ｓｔａｐｆ ｅｘ Ｂｅａｎ）的鲜叶中分离到１１个酚类化合物,其中１０个分别鉴定为已知的槲皮素类黄酮化合物及原花色素类化合物。另１个为新的黄酮甙,经光谱与化学方法测定,其化学结构为槲皮素－３－Ｏ－β－Ｄ－木吡喃糖基（１→２）－α－Ｌ－鼠李吡喃糖基（１→６）－β－Ｄ－葡萄吡喃糖甙,命名为怒茶素。     

Bioactive aristolactams from Piper umbellatum

Four alkaloids named piperumbellactams A-D (1-4) were isolated from branches of Piper umbellatum together with known N-hydroxyaristolam II (5), N-p-coumaroyl tyramine (6), 4-nerolidylcatechol (7), N-trans-feruloyltyramine, E-3-(3,4-dihydroxyphenyl)-N-2-[4-hydroxyphenylethyl]-2-propenamide, beta-amyrin, friedelin, apigenin 8-C-neohesperidoside, acacetin 6-C-beta-d-glucopyranoside, beta-sitosterol, its 3-O-beta-d-glucopyranoside and its 3-O-beta-d-[6'-dodecanoyl]-glucopyranoside. Glycosidase inhibition, antioxidant and antifungal activities of these compounds were evaluated. Compounds 1-3 showed moderate alpha-glucosidase enzyme inhibition with IC50 values 98.07+/-0.44, 43.80+/-0.56 and 29.64+/-0.46, respectively. In DPPH radical scavenging assay, compounds 2, 3 and 6 showed potent inhibitory activity while compounds 4, 5 and 7 showed potent antifungal activity.     

Newbouldiaquinone A: A naphthoquinone-anthraquinone ether coupled pigment, as a potential antimicrobial and antimalarial agent from Newbouldia laevis

The study of the chemical constituents of the roots of Newbouldia laevis (Bignoniaceae) has resulted in the isolation and characterization of a naphthoquinone-anthraquinone coupled pigment named newbouldiaquinone A (1) together with 14 known compounds: apigenin, chrysoeriol, newbouldiaquinone, lapachol, 2-methylanthraquinone, 2-acetylfuro-1,4-naphthoquinone, 2,3-dimethoxy-1,4-benzoquinone, oleanolic acid, canthic acid, 2-(4-hydroxyphenyl)ethyl triacontanoate, newbouldiamide, 5,7-dihydroxydehydroiso-alpha-lapachone, beta-sitosterol, and beta-sitosterol glucopyranoside. The structure elucidation of the isolated compounds was established based on spectroscopic studies, notably of the 2D NMR spectra. The antimalarial activity of compound (1) against Plasmodium falciparum in vitro shows moderate chemo suppression of parasitic growth. Its antimicrobial activity against a wide range of microorganisms was 13- and 24-fold more active against Candida gabrata and Enterobacter aerogens than the reference antibiotics nystatin and gentamycin.     

Glycosides from Dicliptera riparia

The dimeric monoterpenoid glycoside, dicliripariside A, and two flavonoid glycosides, dicliriparisides B and C, together with six known compounds, beta-sitosterol, 2,5-dimethoxy-p-benzoquinone, vanillic acid, daucosterol, lugrandoside and poliumonside, were isolated from the aqueous ethanol extract of the whole plants of Dicliptera riparia Nees. Their structures were determined based on analyses of spectroscopic data.     

Steroidal and phenolic constituents of Lilium speciosum.

Phytochemical examination of the fresh bulbs of Lilium speciosum forma vestale has led to the isolation of a new phenolic glycoside and a new steroidal saponin. The respective structures of the new compounds have been shown by spectral analysis to be 6'-O-feruloylsucrose and (25R,26R)-26-methoxyspirost-5-en-3 beta-o1 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside. Several known phenolic glycosides and saponins have also been isolated and identified.     

Haplophytin-A and B: the alkaloidal constituents of Haplophyllum acutifolium.

During the phytochemical investigation of Haplophyllum acutifolium, two alkaloids named haplophytin-A (1) and B (2) have been obtained. In addition, some known constituents: flindersine (3), kusunokinin (4), beta-sitosterol, oleanolic acid, cholesterol and hexadecanoic acid, have also been obtained. The known constituents have never been obtained from this source. The structures of all the isolated constituents were elucidated by spectroscopic means. However, the structures of constituents 1 and 2 were further confirmed through HMBC technique.     

Lanosterol and tetranorlanosterol glycosides from the bulbs of Muscari paradoxum

Three tetranorlanostane glycosides, named lucilianosides C-E, and three lanostane glycosides, named scillasaponins E-G, together with a known lanostane glycoside, were isolated from the MeOH extract of Muscari paradoxum (Liliaceae) bulbs, as confirmed by detailed analysis of their 1H, 13C, and two-dimensional NMR spectroscopic data, and by the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HSC-2 human oral squamous cell carcinoma cells.     

Acylated iridoid glucosides from Veronica anagallis-aquatica

Three new (1-3) and four known iridoid glucosides (4-7) as well as a known phenylethanoid glycoside (8) were isolated from the aerial parts of Veronica anagallis-aquatica and their structures were determined as 6'-O-benzoyl-8-epiloganic acid named aquaticoside A (1), 6'-O-p-hydroxybenzoyl-8-epiloganic acid named aquaticoside B (2), 6'-O-benzoyl-gardoside named aquaticoside C (3), veronicoside (4), catalposide (5), verproside (6), verminoside (7) and martynoside (8) on the basis of 1D and 2D NMR spectral analysis.     

Chemical constituents from the root of Damnacanthus officinarum Huang

The present phytochemical investigation on Damnacanthus officinarum Huang led to the isolation of a new anthraquinone glycoside named digiferruginol-11-O-β-gentiobioside, along with six known compounds, including anthraquinone glycosides, iridoid glycoside and etc. In the study, compounds (2–7) were isolated for the first time from D. officinarum Huang and Damnacanthus genus. The found of compounds (1–4, 6 and 7) indicate a close relationship between D. officinarum Huang and Morinda officinalis, which may be as chemotaxonomic markers for the tribe Morindeae     

In vivo anti-inflammatory and antinociceptive activity evaluation of phenolic compounds from Sideritis stricta

An acetone extract obtained from aerial parts of S. stricta Boiss. & Heldr. apud Bentham, its fractions and phenolic compounds were investigated for their in vivo anti-inflammatory and antinociceptive activities. For the anti-inflammatory activity and for the antinociceptive activity assessment, carrageenan-induced hind paw edema and p-benzoquinone-induced abdominal constriction tests were used, respectively. The acetone extract of the plant and its phenolic fraction exhibited potent inhibitory activity against both bioassay models in mice. From the active phenolic fraction a well-known phenylethanoid glycoside, verbascoside (acteoside) (1), and two flavonoid glycosides, isoscutellarein 7-O-[6"'-O-acetyl-beta-D-allopyranosyl-(1-->2)]-beta-D-glucopyranoside (2) and isoscutellarein 7-O-[6"'-O-acetyl-beta-D-allopyranosyl-(1-->2)]-6"-O-acetyl-beta-D-glucopyranoside (3), were isolated. During phytochemical studies we also isolated a methoxyflavone, xanthomicrol (4), from the non-polar fraction. The structures of the isolated compounds were established by spectroscopic evidence (UV, IR, 1D- and 2D-NMR, MS). Although antinociceptive and anti-inflammatory activities of the phenolic components were found not significant in the statistical analysis, compounds 1 to 3 showed a notable activity without inducing any apparent acute toxicity as well as gastric damage. Furthermore, a mixture of flavonoid glycosides (2 + 3) exhibited a significant inhibitory effect in both models at a higher dose.     

朝鲜蓟叶中的酚性糖苷化合物

从朝鲜蓟（Cynara scolymus）叶中分离得到2个酚性糖苷化合物,其中一个是新化合物,通过波谱学方法确定其结构为2-甲氧基-4-（2,3-二羟基-丙酰基）-苯基-1—O-（6′-O-没食子酰基）-β-D-吡喃葡萄糖苷（1）。     

女贞小蜡树的酚性配糖体成分研究

从女贞小蜡树 (LigustrumsinenseLour.)茎叶甲醇提取物的水溶性部分得到 1个新的和 6个已知酚性配糖体成分。它们是两个已知的裂环环烯醚萜类化合物 :1 0 hydroxyoleuropein( 1 )和specneuzhenide( 2 ) ,五个苯乙醇类化合物 :3 ,4 二羟基苯乙醇 ( 3 ) ,3 ,4 二羟基苯乙醇 2′ O β D 吡喃葡萄糖甙 ( 4 ) ,3 甲氧基 苯乙醇 4 O β D 吡喃葡萄糖甙 ( 5 ) ,4 羟基苯乙醇 ( 6) ,4 羟基苯乙醇 2′ O β D 吡喃葡萄糖甙 ( 7) ,化合物 5为新化合物 ,命名为小蜡甙A(sinenosideA) ,经理化和波谱分析鉴定了论文中的所有化合物的结构