Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots

The ethanolic root extract of Scrophularia lepidota, an endemic plant of the Turkish flora, has been investigated for its anti-protozoal and inhibitory effect towards plasmodial enoyl-ACP reductase (FabI), a key enzyme of fatty acid biosynthesis in Plasmodium falciparum. Chromatographic separation of the extract yielded 10 iridoids (1-10), two of which are new, and a known phenylethanoid glycoside (11). The structures of the new compounds were determined as 3,4-dihydro-methylcatalpol (8) and 6-O-[4'-O-trans-(3,4-dimethoxycinnamoyl)-alpha-L-rhamnopyranosyl]aucubin (scrolepidoside, 9) by spectroscopic means. The remaining metabolites were characterized as catalpol (1), 6-O-methylcatalpol (2), aucubin (3), 6-O-alpha-L-rhamnopyranosyl-aucubin (sinuatol, 4), 6-O-beta-D-xylopyranosylaucubin (5), ajugol (6), ajugoside (7), an iridoid-related aglycone (10) and angoroside C (11). Nine isolates were active against Leishmania donovani, with the new compound 9 being most potent (IC50 6.1 microg/ml). Except for 4, all pure compounds revealed some trypanocidal potential against Trypanosoma brucei rhodesiense (IC50 values 29.3-73.0 microg/ml). Only compound 10 showed moderate anti-plasmodial (IC50 40.6 microg/ml) and FabI enzyme inhibitory activity (IC50 100 microg/ml). 10 is the second natural product inhibiting the fatty acid biosynthesis of Plasmodium falciparum.     

Benzoxazinoids and iridoid glucosides from four Lamium species

A new class of compounds for the plant family Lamiaceae, benzoxazinoids, was found in Lamium galeobdolon. From the aerial parts of the species were isolated the new 2-O-beta-D-glucopyranosyl-6-hydroxy-2H-1,4-benzoxazin-3(4H)-one (6-hydroxy blepharin) together with four known benzoxazinoids, DHBOA-Glc, blepharin, DIBOA, DIBOA-Glc, as well as harpagide, 8-O-acetyl-harpagide and salidroside. Eight known iridoid glucosides, 24-epi-pterosterone and verbascoside were isolated from Lamium amplexicaule, L. purpureum and L. garganicum. The iridoids, 5-deoxylamiol and sesamoside, as well as the phytoecdysone, 24-epi-pterosterone, were found for the first time for the genus Lamium. The phytochemical data are discussed from a systematic and evolutionary point of view.     

Iridoids from Globularia dumulosa

Two new iridoids, 10-O-benzoylglobularigenin (1) and dumuloside (2) were isolated from the aerial parts of Globularia dumulosa together with seven known iridoid glucosides, davisioside (3), aucubin (4), melampyroside (5), catalpol (6), 10-O-benzoylcatalpol (7), alpinoside (8) and deacetylalpinoside (9). Three phenylethanoid glycosides, verbascoside, decaffeoyl-verbascoside, leucosceptoside A and three flavone glucosides, pectolinarigenin 7-O-beta-D-glucopyranoside, nepetin 7-O-B-D-glucopyranoside, demethoxycentaureidin 7-O-beta-D-glucopyranoside were also isolated and characterized. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, HR-MALDIMS, 1D- and 2D NMR) methods.     

Studies on the Chemical Constituents of the Leaves of WTBX]Pseudotaxus chienii (Cheng) Cheng

Fourteen compounds were isolated from the leaves of Pseudotaxus chienii (Cheng) Cheng which is uniquely indigenous to China, and their structures were identified mainly by spectrum analyses. Among them, 13 known compounds were determined as: 2-guaiacylpropane-1, 3-diol (1), vanillic acid (2), 3-methoxy-4-hydroxy cinnamic acid (3). 3. 5-dimethoxy-phenol (4), taxicatin (5), 5-oxymaltol (6), quercetin-3-rhamnoside (7), (±)-catechin (8), ecdysterone (9), β-sitosterol (10), D-glucose (11), (±)-10-nonacosanol (12) and octacosanoic acid (13). All these compounds butβ-sitosterol were isolated from this plant for the first time. Compounds 1 and 6 have never been reported in plant kingdom. Another compound was tentatively established as a new compound, named pseudotaxlactone (14).     

Non-glycosidic iridoids from Cymbaria mongolica

Six non-glycosidic iridoids, i.e. (1R,4S,4aS,7S,7aS)-7-hydroxyl-4-hydroxy- methyl-7-methyl-1-methoxyl-1,4,4a,7a-tetrahydrocyclopenta[e]pyran-3-one (1), (1S,4R,4aS,7S,7aS)-7-hydroxyl-4-hydroxymethyl-7-methyl-1-methoxyl-1,4,4a,7a-tetrahydrocyclopenta[e]pyran-3-one (2), (1R,4R,4aS,7S,7aS)-7-hydroxyl-4-hydroxy-methyl-7-methyl-1-methoxyl-1,4,4a,7a-tetrahydrocyclopenta[e]pyran-3-one (3), (1R, 4R, 4aS, 7aS)-4,7-dihydroxymethyl-1-methoxyl-1,4,4a,7a-tetrahydrocyclopenta-6-ene[e]pyran-3-one (4), (1R, 4R, 4aS, 7aS)-4,7-dihydroxymethyl-1-hydroxyl-1,4,4a, 7a-tetrahydrocyclopenta-6-ene[e]pyran-3-one (5), (1R, 4S, 4aS, 7aS)-4,7-dihydroxy-methyl-1-methoxyl-1,4,4a,7a-tetrahydrocyclopenta-6-ene[e]pyran-3-one (6), as well as five known non-glycosidic iridoids mussaenin A (7), gardendiol (8), isoboonein (9), 4-epi-alyxialactone (10) and rehmaglutin D (11) have been isolated from the Chinese medicinal plant Cymbaria mongolica. Their structures were elucidated by spectroscopic methods. These compounds exhibit significant antitumor and antibacterial activity.     

Iridoid glucosides with insecticidal activity from Galium melanantherum

The insecticidal activity of the endemic species Galium melanantherum was evaluated against Crematogaster scutellaris ants and Kalotermes flavicollis termites. Iridoid glucosides 1-7 were isolated for the first time as metabolites of the investigated plant, along with the coumarin scopolin. The main components of the extract were found to be the non-acetylated iridoids: geniposidic acid (1), 10-hydroxyloganin (2), deacetyldaphylloside (3), monotropein (4), deacetylasperulosidic acid (5) and scandoside (6), while asperulosidic acid (7) was present only in minute quantities. All isolated metabolites were identified on the basis of their spectral data. Laboratory bioassays revealed significant levels of toxicity for 1-4 against Kalotermes flavicollis termites and Crematogaster scutellaris ants.     

Five new iridoids from Patrinia rupestris

Five new iridoids, namely rupesin A-E (1-5, resp.), together with six known iridoids, 6-11, were isolated from the roots of Patrinia rupestris. Their structures were elucidated by spectroscopic methods including IR, UV, MS, and 1D- and 2D-NMR experiments, and comparison with data of known analogues. Compounds 4 and 11, compounds 1, 2, 5, 6, 8, 9, and 10, and compounds 3, 4, and 8 showed significant antibacterial activities against Bacillus subtilis, Escherichia coli, and Staphylococcus aureus, respectively.     

Antifungal amides from Piper arboreum and Piper tuberculatum

In continuation of our study of the Piperaceae we have isolated several amides, mainly those bearing isobutyl, pyrrolidine, dihydropyridone and piperidine moieties. Bioactivity-guided fractionation of extracts from leaves of Piper arboreum yielded two new amides, N-[10-(13,14-methylenedioxyphenyl)-7(E),9(Z)-pentadienoyl]-pyrrolidine (1), arboreumine (2) together with the known compounds N-[10-(13,14-methylenedioxyphenyl)-7(E)-pentaenoyl]-pyrrolidine (3) and N-[10-(13,14-methylenedioxyphenyl)-7(E),9(E)-pentadienoyl]-pyrrolidine (4). Catalytic hydrogenation of 3 yielded the amide N-[10-(13,14-methylenedioxyphenyl)-pentanoyl]-pyrrolidine (5). We also have isolated six amides (6-11) and two antifungal cinnamoyl derivatives (12, 13) from seeds and leaves of Piper tuberculatum. Compounds 1-11 showed antifungal activity as determined by direct bioautography against Cladosporium sphaerospermum while compounds 3-4 and 6-13 also showed antifungal activity against C. cladosporioides.     

C(15) Acetogenins from the red alga Laurencia obtusa.

Four C(15) acetogenins, 13-epilaurencienyne (3Z) (1), 13-epipinnatifidenyne (3E) (2), (3E, 6S(*), 7R(*), 9S(*), 10S(*), 12R(*))-9-chloro-13-bromo-6:12-epoxy-7, 10-diacetoxypentadec-3-en-1-yne (3), (3Z, 6S(*), 7R(*), 9S(*), 10S(*), 12R(*))-9-chloro-13-bromo-6:12-epoxy-7, 10-diacetoxypentadec-3-en-1-yne (4), along with the known 13-epilaurencienyne (3E) (5), have been isolated from the organic extract of the red alga Laurencia obtusa, collected in the Aegean Sea, Greece. The structures of the new natural products, as well as their relative stereochemistry, were established by means of spectral data analysis, including 2D NMR spectroscopic experiments. Some of the new metabolites exhibited significant insecticidal activity.     

花生茎叶酚性成分研究

运用大孔树脂对花生茎叶提取液进行富集,不同浓度乙醇洗脱,硅胶、RP-18、Sephadex LH-20等多种材料进一步分离纯化,研究花生茎叶化学成分,并通过理化方法和光谱分析对化合物进行结构鉴定。结果表明:从花生茎叶大孔树脂10%乙醇洗脱部位中分离并鉴定了10个化合物,分别为邻苯二甲酸二异丁酯(1)、水杨酸(2)、儿茶酚(3)、对羟基苯甲酸(4)、(反)-3,4-二羟基苯丙烯酸(5)、对羟基苯酚(6)、邻苯二甲酸二丁酯(7)、3,4-二羟基苯乙醇(8)、对羟基苯乙醇(9)、3,4-二羟基苯甲酸(10)。除化合物1、2和4外,其余均为首次从该植物中分离得到。     

分布于日本和中国的鹅观草及其杂种的形态学和细胞学研究

本文对分布于日本的Agropyron tsukushiense(Honda)Ohwi var. transiense(Hack.)Ohwi(2n＝6X＝42）和分布于中国的Roegneria kamoji Ohwi(2n＝6X＝42）及其杂种F1(2n＝6x＝42）进行了形态学及细胞学的研究,并同时探讨了亲本种的亲缘关系。总体来看,亲本材料之间在形态上虽有差异但并不十分显著。杂种F1的形态特征介于其父、母本之间。在减数分裂过程中,亲本种和杂种F1的染色体配对行为均十分正常。但在检查了大量的成熟花粉和穗状花序之后,发现杂种F1有部份不育现象。上述研究结果表明A.tsuku-shiense var.transiens的三个染色体组与R.kamoji的三个染色体组同源。结合形态学和育性等方面的研究资料,作者认为上述两个材料仍应属于同一分类等级。但必须指出,由于长期的地理隔离,他们之间产生了一定的形态变异和生殖障碍。按照国际植物命名法规（ICBN）上述两个材料应组合:Roegneria tsukushiensis(Honda)B．R．Lu,Yen et J.L.Yang 及其变种var.transiens(Hack.)B．R．Lu,Yen et J.L.Yang comb.nov．     

黄瓜藤的化学成分研究

从丽江产黄瓜藤甲醇提取物的氯仿部位分离得到9个化合物,经理化和波谱分析鉴定为α-菠甾醇(1)、α-菠甾醇-3-O-β-D-葡萄糖苷(2)、β-谷甾醇(β-sitosterol,3)、豆甾-7-烯-3-O-β-D-葡萄糖苷(4)、22-亚甲基-9,19-环羊毛甾烷-3β-醇(5)、(2S,3S,4R,10E)-2-(2′,3′-二羟基二十四烷酰氨基)-10-十八烯-1,3,4-三醇(6)、(2S,3S,4R,10E)-2-[(2′R)-2-羟基二十四烷酰氨基]-10-十八烯-1,3,4-三醇(7)、(2S,3S,4R,10E)-1-(β-D-葡萄糖苷)-2-[(2′R)-2-羟基二十四烷酰氨基]-10-十八烯-1,3,4-三醇(8)、大豆脑苷(9),除化合物3外,其它化合物均为首次从该植物中分离得到.     

Constituents of Pterocarpus marsupium: an ayurvedic crude drug

Five new flavonoid C-glucosides, 6-hydroxy-2-(4-hydroxybenzyl)-benzofuran-7-C-beta-d-glucopyranoside (1), 3-(alpha-methoxy-4-hydroxybenzylidene)-6-hydroxybenzo-2(3H)-furanone-7-C-beta-d-glucopyranoside (2), 2-hydroxy-2-p-hydroxybenzyl-3(2H)-6-hydroxybenzofuranone-7-C-beta-d-glucopyranoside (4), 8-(C-beta-d-glucopyranosyl)-7,3',4'-trihydroxyflavone (5) and 1,2-bis(2,4-dihydroxy,3-C-glucopyranosyl)-ethanedione (6) and two known compounds C-beta-d-glucopyranosyl-2,6-dihydroxyl benzene (7) and sesquiterpene (8), were isolated from an aqueous extract of the heartwood of Pterocarpus marsupium. The structure has been established using spectroscopic data.     

直立百部的非生物碱化学成分研究(英文)

从直立百部(Stemona sessilifolia)根中首次分离到十四个非生物碱成分.依据波谱数据,它们鉴定为豆甾醇(1)、4-甲氧基苯甲酸(2)、苯甲酸(3)、3,4-二甲氧基苯酚 (4)、4-甲氧基苯甲酸(5)、4-羟基苯甲酸(6)、4-羟基-3-甲氧基苯甲酸(7)、4-羟基-3,5-二甲氧基苯甲酸(8)、3,3′-bis(3,4-dihydro-4-hydroxy-6-methoxy)-2H-1-benzopyran(9)、4-羟基-3-甲氧基苯甲醛(10)、羽扇豆烷-3-酮 (11)、绿原酸(12)、胡萝卜苷(13),3-feruoyl-chinasueure (14).化合物5～14为首次从百部属植物中分离得到.     

Benzofurans and another constituent from seeds of Styrax officinalis

The benzofuran constituents of the seeds of Styrax officinalis were investigated. From the hexane extract, two new constituents named 5-(3"benzoyloxypropyl)-7-methoxy-2-(3',4'-methylenedioxyphenyl)-benzofuran (5) and 4-[3"-(1c-methylbutanoyloxy)propyl]-2-methoxy-(3',4'-methylenedioxyphenyl)-1a, 5b-dihydrobenzo-[3,4]-cyclobutaoxirene (6) were isolated together with four known compounds, 5-[3"-(1c-methylbutanoyloxy)propyl]-7-methoxy-2-(3',4'-dimethoxyphenyl)-benzofuran (4), 5-[3"-(1c-methylbutanoyloxy)propyl]-7- methoxy-2-(3',4'-methylenedioxyphenyl)-benzofuran (3), 5-(3"-acetoxypropyl)-7-methoxy2-(3',4'-methylenedioxphenyl)-benzofuran (2) and 5-(3"-hydroxypropyl)-7-methoxy-2-(3',4'-met hylenedioxyphenyl)-benzofuran (1). Although the compounds 1, 2, and 3 have been isolated previously from the seeds of Styrax obassia, this is the first record of their isolation from seeds of Styrax officinalis. The structures of the isolated compounds were established by 1D- and 2D-NMR (HMBC, HMQC, COSY), FABMS and high-resolution ESI FTMS.     

Pensteminoside, an unusual catalpol-type iridoid from Penstemon gentianoides HBK (Plantaginaceae)

From the MeOH and ethyl acetate extracts of aerial parts of Penstemon gentianoides HBK (Plantaginaceae) an unusual iridoid of the catalpol-type, was isolated and characterized as pensteminoside: (8-O-trans-cinnamoyl, 6-hydroxy, 1-[beta-D-glucopyranoside-6'-O-((4'-hydroxy)-cinnamoyl)]-catalpol) was isolated, along with the known iridoids: plantarelanoside and globularisicin, the flavone: luteolin and diosmetin, as well the phenylpropanoids, verbascoside and martynoside. Their structures were established by 1D and 2D NMR spectroscopic analyses.     

Iridoids from Gentiana loureirii

Iridoid glycosides, 2′,3′,6′-tri-O-acetyl-4′-O-trans-p-(O-β-d-glucopyranosyl)coumaroyl-7-ketologanin (1), 2′-O-caffeoylloganic acid (2), 2′-O-p-hydroxybenzoylloganic acid (3), 2′-O-trans-p-coumaroylloganic acid (4), and 2′-O-cis-p-coumaroylloganic acid (5), were isolated from whole plants of Gentiana loureirii along with six known iridoids, 7-ketologanin (6), loganin (7), loganic acid (8), sweroside, boonein, and isoboonein, and three other known compounds. Their structures were elucidated by spectroscopic means and chemical correlations. The isolated iridoids were evaluated for antibacterial and antioxidant activities, but were either inactive or very weakly active.     

Marine polyprenylated hydroquinones, quinones, and chromenols with inhibitory effects on leukotriene formation

A series of polyprenylated hydroquinones, quinones, and chromenols were isolated from the extracts of the marine sponge Ircinia spinosula and the brown alga Taonia atomaria, which gave rise to the constituents 1-4 and 5-8, respectively. Compounds 1, 2, 6, and 7 are new natural products, which were fully characterized. Their anti-inflammatory activities in terms of leukotriene formation were evaluated in an in vitro assay with pork leukocytes. The new hydroxylated compound, 2'-[28-hydroxy]heptaprenyl-1',4'-hydroquinone (= 2-[(2E,6E,10E,14E,18Z,22E)-19-(hydroxymethyl)-3,7,11,15,23,27-hexamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl]benzene-1,4-diol; 1), the known tetraprenyl benzoquinone sargaquinone (5), and the known polyprenyl chromenols 3 and 4 exhibited the highest anti-inflammatory activities, with IC50 values of 1.9-9.4 microM (Table 3). Potential structure-activity relationships (SAR) are discussed.     

Phenolic and other constituents of fresh water fern Salvinia molesta

Two glycosides, 6'-O-(3,4-dihydroxy benzoyl)-beta-D-glucopyranosyl ester (1), and 4-O-beta-d-glucopyranoside-3-hydroxy methyl benzoate (2), along with five known compounds methyl benzoate (3), hypogallic acid (4), caffeic acid (5), paeoniflorin (6) and pikuroside (7) were isolated for the first time from a fresh water fern Salvinia molesta D.S. Mitch. These compounds showed a potent antioxidant radical scavenging activity in a non-physiological assay. Their structures were determined by NMR spectroscopic and CID mass spectrometry techniques.     

Homoisoflavonoids from Ophiopogon japonicus Ker-Gawler

From the ethyl acetate extract of the tuberous roots of Ophiopogon japonicus (Liliaceae) eight known and five new homoisoflavonoidal compounds were isolated. The new compounds are 5,7-dihydroxy-8-methoxy-6-methyl-3-(2'-hydroxy-4'-methoxybenzyl)chroman-4-one (1), 7-hydroxy-5,8-dimethoxy-6-methyl-3-(2'-hydroxy-4'-methoxybenzyl)chroman-4-one (2), 5,7-dihydroxy-6,8-dimethyl-3-(4'-hydroxy-3'-methoxybenzyl)chroman-4-one (3), 2,5,7-trihydroxy-6,8-dimethyl-3-(3',4'-methylenedioxybenzyl)chroman-4-one (4) and 2,5,7-trihydroxy-6,8-dimethyl-3-(4'-methoxybenzyl)chroman-4-one (5). Their structures have been elucidated by mass and NMR spectroscopy. Compounds 4 and 5 are the first isolated homoisoflavonoids with a hemiacetal function at position 2.