A phenolic glucoside isolated fromPrunus serrulata var.spontanea and its peroxynitrite scavenging activity

A new phenolic glucoside (1), pursargentoside, was isolated from the leaves of Prunus serrulata var. spontanea, along with three other known compounds, orobol 7-omicron-glucoside (2), 1beta, 2alpha, 3alpha, 24-tetrahydroxy-urs-12-en-28-oic acid (3), and chlorogenic acid (4). The structure of pursargentoside (1) was identified by spectroscopic data analysis including 1D and 2D NMR spectroscopy, as 2-omicron-beta-(6'-benzoyl)-glucopyranosyl omicron-(Z)-coumaric acid. Compounds 1, 2, and 4 exhibited ONOO scavenging activity, whereas compound 3 was determined to be virtually inactive.     

北沙参中的新8-O-4′型异木脂素

为了研究北沙参的化学成分，通过大孔树脂吸附柱色谱、 Sephadex LH-20及反相ODS柱色谱进行化合物的分离， 利用多种波谱技术鉴定化合物结构。从醇提物的乙酸乙酯溶部分， 分离得到1个新化合物， 命名为可来灵素D(glehlinoside D，1)， 以及5个已知化合物： 裂异落叶松脂醇(2)、 阿魏酸(3)、 咖啡酸(4)、 香草酸(5)和丁香苷(6)。化合物1为一新的8-O-4′型异木脂素类化合物。     

A new pancreatic lipase inhibitor isolated from the roots of <Emphasis Type="Italic">Actinidia arguta</Emphasis>

A new coumaroyl triterpene, 3-O-trans-p-coumaroyl actinidic acid (1), as well as five known triterpenes, ursolic acid (2), 23-hydroxyursolic acid (3), corosolic acid (4), asiatic acid (5) and betulinic acid (6) were isolated from an EtOAc-soluble extract of the roots of Actinidia arguta. The structure of compound 1 was elucidated from interpretation of the spectroscopic data, particularly by extensive 1D and 2D NMR studies. All the isolates (1-6) were evaluated in vitro for their inhibitory activities on pancreatic lipase (PL). Of the isolates, the new compound 1 possessed the highest inhibitory activity on PL, with an IC(50) of 14.95 microM, followed by ursolic acid (2, IC(50) = 15.83 microM). The other four triterpenes (3-6) also showed significant PL inhibitory activity, with IC(50) values ranging from 20.42 to 76.45 microM.     

Ophiopojaponin D, a new phenylpropanoid glycoside fromOphiopogon Japonicus Ker-Gawl

A new phenolic glycoside, ophiopojaponin D (1), together with two known compounds, was isolated from the tubers of a famous traditional Chinese herb-Ophiopogon japonicus Ker-Gawl. The spectroscopic and chemical data revealed their structures to be 3-tetradecyloxy-4-hydroxy-allylbenzene-4-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside (1), 3, 4-dihydroxy-allylbenzene-4-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside (2) and L-pyroglutamic acid (3).     

山慈菇的化学成分

为研究山慈菇药材——杜鹃兰(Cremastra appendiculata (D.Don) Makino)干燥假鳞茎的化学成分,采用硅胶、葡聚糖凝胶和反相硅胶柱色谱法分离纯化,运用现代波谱技术进行结构鉴定。本文分离得到7个化合物,分别鉴定为5-甲氧基联苄-3,3′-二-O-β-D-吡喃葡糖苷(1)、 militarine (2)、 loroglossin (3)、 原儿茶酸(4)、 丁二酸(5)、 天麻苷(6)和胡萝卜苷(7)。化合物1为新化合物,化合物2～6均为首次从杜鹃兰中分得。     

A new cytotoxic prenylated dihydrobenzofuran derivative and other chemical constituents from the rhizomes of <Emphasis Type="Italic">Atractylodes lancea</Emphasis> DC

A new prenylated dihydrobenzofuran derivative (1), was isolated from the rhizomes of Atractylodes lancea DC (Asteraceae), along with ten known compounds, including atractylenolide II (2), phi-taraxasteryl acetate (3), taraxerol acetate (4), beta-sitosterol (5), stigmasterol (6), beta-eudesmol (7), atractylenolide III (8), atractylenolide IV (9), daucosterol (10), and stigmasterol 3-O-beta-D-glucopyranoside (11). The structure of the new compound (1) was elucidated as trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid by the combination of 1D, 2D NMR analysis and mass spectrometry, and it was the first reported 2,3-dihydrobenzofuran derivative having a carboxyl residue at C-5 and an isopentene moiety at C-7 contemporaneously. In addition, compound 1 exhibited significant cytotoxicity against cancer cell lines HCT-116 and MKN-45.     

北沙参中一个新香豆素苷

为了研究北沙参的化学成分，本文通过大孔树脂吸附柱色谱、Sephadex LH-20及开放反相ODS柱色谱进行化合物的分离，利用多种波谱技术鉴定化合物结构。分离得到9个化合物，鉴定为：bergaptol 5-O-β-D-gentiobioside (1)、(7R，8S)-dehydrodiconiferylalcohol-4，9-di-O-β-D-glucoside (2)、橙皮素A(3)、(-)-seco-isolariciresinol 4-O-β-D-glucopyranoside (4)、白花前胡苷(5)、花椒毒酚8-O-β-D-吡喃葡糖苷(6)、5′-硫甲基腺苷(7)、腺苷(8)、色氨酸(9)。化合物1为新化合物；化合物2和7为首次从该属植物中分离得到。     

Constituents of the flowers of Erigeron annuus with inhibitory activity on the formation of advanced glycation end products (AGEs) and aldose reductase

Seven phenolic compounds, caffeic acid (1), 4-hydroxybenzoic acid (2), 4-methoxybenzoic acid (3), protocatechuic acid (4), eugenol O-beta-D: -glucopyranoside (5), 3,6-di-O-feruloylsucrose (6), and 3,5-di-O-caffeoylquinic acid methyl ester (7), were isolated from an EtOAc-soluble partition of the flowers of Erigeron annuus. The structures of 1-7 were determined by spectroscopic data interpretation, particularly 1D and 2D NMR studies, and by comparison of their data with those published in the literature. All the isolates were subjected to in vitro bioassays to evaluate their inhibitory activities against the formation of advanced glycation end products (AGEs) and rat lens aldose reductase (RLAR). Of the compounds, 1, 6, and 7 exhibited potent inhibitory activities against the formation of AGEs. In the RLAR assay, compound 7 showed the most potent inhibitory activity.     

中药地枫皮中三萜酸类成分研究

中药地枫皮中三萜酸类成分研究黄平西正敏郑学忠赖茂祥中西勤（广西中医药研究所,南宁５３００２２;日本摄南大学药学部,枚方５７３０１）前文报道从广西特产中药材地枫皮（ＩｌｉｃｉｕｍｄｉｆｅｎｇｉＫ．Ｉ．Ｂ．ｅｔＫ．Ｉ．Ｍ．）的树皮中分离得到地枫皮...     

Structure-activity relationship of triterpenoids isolated from Mitragyna stipulosa on cytotoxicity

Chromatographic separation of the stem bark extract of Mitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid 3-O-beta-D-glucopyranoside (3, quinovin glycoside C), quinovic acid 3-O-[(2-O-sulfo)-beta-D-quinovopyranoside] (4, zygophyloside D) and quinovic acid 3-O-beta-D-quinovopyranosyl-27-O-beta-D-glucopyranosyl ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound 1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to 2 decreased the cytotoxicity. Compound 4 more potent than 3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.     

卷柏中化学成分的分离与结构鉴定

目的研究中药卷柏(Selaginella tamariscina (Beauv.) Spring)水提物中的化学成分。方法用Sephadex LH-20及硅胶等色谱技术进行分离纯化,根据理化性质、光谱数据进行结构鉴定。结果得到9个化合物,分别鉴定为(2r,3s)-二氢-2-(3′,5′-二甲氧基-4′-羟基苯基)-3-羟甲基-7-甲氧基-5-乙酰基苯骈呋喃(1),3-羟基-苯丙酸-(2′-甲氧基-4′-羧基苯酚)酯(卷柏酯A,2),丁香脂素(3),1-(4′-羟基-3′-甲氧基苯基)丙三醇(4),阿魏酸(5),咖啡酸(6),香荚兰酸(7),丁香酸(8),7-羟基香豆素(9)。结论化合物1,2为新化合物,其余化合物均为首次从卷柏属植物中分离得到。     

Di- and sesqui-terpenoids isolated from the pods of<Emphasis Type="Italic">Sindora sumatrana</Emphasis> and their potential to inhibit lipopolysaccharide-induced nitric oxide production

Activity-guided fractionation of the n-hexane and CHCl3-soluble fractions of Sindora sumatrana using a bioassay based on the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production by inducible nitric oxide synthase (iNOS) in murine macrophage RAW 264.7 cells led to the isolation of the known compound, (+)-7beta-acetoxy-15,16-epoxy-3,13(16),14-clerodatriene-18-oic acid (2) as an active constituent. In addition, a new trans-clerodane diterpenoid, (+)-2-oxokolavenic acid (1), together with six known compounds, (+)-3,13-clerodadiene-16,15-olide-18-oic acid (3), (+)-7beta-acetoxy-3,13-clerodadiene-16,15-olide-18-oic acid (4), (+)-7beta-acetoxy-16-hydroxy-3,13-clerodadiene-16,15-olide-18-oic acid (5), beta-caryophyllene oxide (6), clovane-2beta,9beta-diol (7), and caryolane-1,9beta-diol (8) were isolated and found to be inactive. The structure of compound 1 was determined using physical and spectroscopic methods such as 1D and 2D-NMR experiments. The known compounds 2-8 were identified by the spectroscopic data and by comparison with the published values. Of eight isolates (1-8), only compound 2 exhibited an iNOS inhibitory activity with IC50 value of 51.6 microM.     

Spinoside,new coumaroyl flavone glycoside from<Emphasis Type="Italic">Amaranthus spinosus</Emphasis>

Spinoside, new coumaroyl flavone glycoside was isolated from the n-butanol fraction of the mathanolic extract of the whole plant of Amaranthus spinosus and assigned the structure 7-p-coumaroyl apigenin 4-O-beta-D-glucopyranoside (1) on the basis of spectroscopic techniques including 1D and 2D NMR spectroscopy. In addition alpha- xylofuranosyl uracil (2), beta-D-ribofuranosyl adenine (3) and beta-sitosterol glucoside (4) have also been isolated for the first time from this species.     

Chemical constituents from the roots of Ranunculus ternatus

Two new glycosides named as ternatoside A (1) and ternatoside B (2), with four known constituents sternbin (3), methylparaben (4), 4-O-D-glucopyranosyl-p-coumaric acid (5) and linocaffein (6) were isolated from the roots of Ranunculus ternatus, The structures of new compounds were determined by 1D and 2D NMR, MS techniques, and chemical methods.     

Kaurane-type diterpene glycoside from the stem bark of Acanthopanax trifoliatus

A new diterpene glycoside, acantrifoside D ( 1), as well as three known diterpenes (2 - 4) were isolated from the stem bark of Acanthopanax trifoliatus from Vietnam. Based on 1D and 2D NMR spectroscopic data, their chemical structures were determined to be 16alpha,17-dihydroxy- ent-kauran-19-oic acid 16- O-beta- D-glucopyranoside 19- O-beta- D-glucopyranosyl ester (1), 16alpha H,17-isovalerate- ent-kauran-19-oic acid (2), ent-kaur-16-en-19-oic acid ( 3), and ent-pimara-8(14),15-dien-19-oic acid (4). Compounds 2 - 4 had strong inhibitory effects against COX-1 in an in vitro assay, with IC50 values of 0.21, 0.15 and 0.19 mM, respectively.     

Water-soluble constituents from the leaves of Ilex oblonga

Four new water-soluble constituents, oblongaroside A (1), oblongar ester A (2), oblongaroside B (3), and oblongaroside C (4), were isolated along with four known compounds: 4-O-beta-D-glucopyranosyl-3-hydroxybenzalcohol (5), 7-methoxyl-4-O-beta-D-glucopyranosyl-3-hydroxybenzalcohol (6), 4-O-beta-D-glucopyranosyl-3-hydroxybenzoic acid (7), and 3,4-dihydroxybenzoic acid (8) from the leaves of Ilex oblonga. Identification of their structures was achieved by 1D and 2D NMR experiments, including (1)H-(1)H COSY, NOESY, HMQC, and HMBC methods and FAB mass spectral data.     

New cytotoxic oleanane saponins from the infructescences of Polyscias amplifolia from the Madagascar rainforest

Bioassay-guided fractionation of an ethanolic extract of the infructescences of Polyscias amplifolia resulted in the isolation of two new oleanolic acid saponins, polyfoliolides A (1) and B (2), in addition to the two known saponins 3-O-beta-D-galactopyranosyloleanolic acid (3) and 3-O-beta-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyloleanolic acid (4). The structures of the two new compounds were established as 3-O-beta- D-galactopyranosyl-(1-->4)-beta-D-xylopyranosyloleanolic acid (1) and 3-O-beta-D-galactopyranosyl-(1-->4)-alpha-L-arabinopyranosyloleanolic acid (2) on the basis of extensive 1D and 2D NMR spectroscopic data interpretation and chemical conversions. All the isolated compounds showed weak cytotoxicity against A2780 human ovarian cancer cell line, with IC50 values in the range 6.7 to 10.8 microg/mL.     

楤木根皮中皂甙化学成分的研究

楤木根皮中的主要成分是皂甙。将总皂甙以柱层析分离,得到三个化合物(Ⅰ～Ⅲ),经光谱分析和化学方法证明,Ⅰ为楤木皂甙A(araloside A);Ⅱ为银莲花甙(narcissiflorine);Ⅲ是3-O-[β-D-吡喃葡萄糖-(1→2)-β-D-吡喃木糖-(1→)2)-α-L-阿拉伯糖]-齐墩果酸。Ⅲ为一新皂甙,命名为楤木皂甙D(araloside D)。     

Jacaranone and related compounds from the fresh fruits ofTernstroemia japonica and their antioxidative activity

Jacaranone and related compounds (1-3) were isolated, along with three triterpenes (4-6), from the fresh fruits of Ternstroemia japonica. The compounds were identified as jacaranone (1), 3-hydroxy-2,3-dihydrojacaranone (2), 3-methoxy-2,3-dihydrojacaranone (3), 3-O-acetyloleanolic acid (4), 3-O-acetylursolic acid (5), and ursolic acid (6). Jacaranone and its derivatives were isolated for the first time from Theaceae. Of the isolated compounds, compound 3 is a new compound. Jacaranone (1) exhibited weak antioxidative effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical.     

Four new lignans from the stems of Kadsura heteroclita

Two new C(18) dibenzocyclooctadiene lignans named heteroclitalignans A and B (1 and 3), one new C(19) homolignan named heteroclitalignan C(4) and one new natural product named heteroclitalignan D(2), together with the four known lignans kadsurarin (5), kadsulignan E (6), d-epigalbacin, and meso-dihydroguaiaretic acid were isolated from the stems of Kadsura heteroclita. The structures of these compounds were characterized by extensive 1D and 2D NMR spectral data analysis.