Chemical constituents from Ailanthus altissima (Mill.) Swingle and chemotaxonomic significance

Sixteen compounds were isolated from the root barks of Ailanthus altissima (Mill.) Swingle, including thirteen lignans (1–13), two coumarins (14–15), and one chalcone (16). This is the first report on the occurrence of compounds 1–16 in the genus Ailanthus. Their structures were elucidated on the basis of NMR spectroscopic data. The plant distribution network of all isolated compounds was described to illustrate the significance of taxonomy. The presence of these congenetic lignans (1–13) and their biosynthetic relationships may be used for identification of Ailanthus genus.     

Sesquiterpenoids and lignans from the fruits of Illicium simonsii Maxim

Twenty-two known compounds were isolated from the 95% alcohol extract of the fruits of Illicium simonsii Maxim, including seven sesquiterpenoids (16–22) and fifteen lignans (1–15). In the present research, compounds 3 ((7S,8R,8′S)-3,3′-dimethoxy-4,4′,9-trihydroxy-7,9′-epoxylignan-7′-one), 4 ((−)-(7′S,8S,8′R)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one), 5 ((+)-8-hydroxypinoresinol), 6 ((+)-8-hydroxymedioresinol), 8 ((2R,3R)-2β-(4″-hydroxy-3″-methoxybenzyl)-3α-(4′-hydroxy-3′-methoxybenzyl)-γ-butyrolactone 2-O-(β-D-glucopyranoside), 12 ((+)-8-methoxyisolariciresinol), 13 (α-conidendrin), 14 (boehmenan) and 15 (7R,8R,7′E-7′,8′-didehydro-4,7,9,9′- tetrahydroxy-3-methoxy-8-O-4′-neolignan) were reported from the Illicium genus for the first time, and compounds 1 (simulanol), 7 ((+)-secoisolariciresinol monoglucoside), 10 ((+)-9-O-β-D-glucopyranosyl lyoniresinol), 11 ((+)-isolariciresinol), 18 (neoanisatin), 19 (veranisatin A), 20 (4,5-d₂-8′-oxo-dihydrophaseic acid) and 22 (Oligandrumin A) were firstly isolated from the plant. Their structures were elucidated on the basis of NMR spectroscopic and mass spectrometric data. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.     

Chemical constituents from Picrasma quassioides (D.Don) Benn. and their network analysis of chemotaxonomic significance

A phytochemical investigation of Picrasma quassioides (D.Don) Benn led to the isolation of seventeen compounds including five coumarins (1–5), six lignans (6–11), two alkaloids (12–13), two phenolic compounds (14–15), one megastigman glycoside (16) and one phenylpropanoid (17). The structures of those compounds were determined by spectroscopy data of NMR spectra. All of the compounds were isolated from P. quassioides for the first time. In this study, in order to discuss the chemotaxonomic significance of those compounds from P. quassioides, network analysis was carried out to determine the chemotaxonomic relationships among the Simaroubaceae family and the other families. The result showed that the Simaroubaceae family and the Rutaceae family, together with the Asteraceae family have some chemotaxonomic relationships.     

Chemotaxonomic significance of lindenane sesquiterpenoid dimers and eudesmane sesquiterpenoids from Chloranthus henryi Hemsl. var. hupehensis (Pamp.) K. F. Wu

Seventeen known compounds were isolated from the 95% alcohol extract of the aerial parts of Chloranthus henryi Hemsl. var. hupehensis (Pamp.) K. F. Wu, including five lindenane sesquiterpenoid dimers (1–5) and twelve eudesmane sesquiterpenoids (6–17). In the present research, compounds 3 sarcaglabrin C, 6 neolitacumone C, 7 ent-Atractylenolide III and 8 dehydrocarissone were reported from the Chloranthus genus for the first time, and compounds 1 spicachlorantin B, 2 chloramultilide C, 4 shizukaol B, 5 japonicone C, 9 6α-hydroxyeudesma-4(15),7(11),8(9)-triene-12,8-olide, 10 ent-(3R)-3-hydroxyatractylenolide III, 11 8βH-hydroxyeudesma-4(14),7(11)-dien-12,8-olide, 12 lasianthuslactone A, 13 (5S,6R,8S,10R)-6-hydroxyeudesma-4(15),7(11)-diene-12,8-olide, 14 4β-hydroxy5α,8β(H)-eudesm-7(11)-en-8,12-olide, 15 4β,8β-dihydroxy-5α(H)-eudesm-7(11)-en-8,12-olide, 16 curcolonol and 17 1β, 8β-dihydroxyeudesm - 3,7(11)-dien-8α,12-olide were firstly isolated from the plant. Their structures were elucidated on the basis of extensive spectroscopic and chemical analyses. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.     

Phytochemical and network-based chemotaxonomic study of Lonicera japonica Thunb

Phytochemical research on the flower buds of Lonicera japonica Thunb. led to the isolation of 15 compounds, including nine terpenoids (1–9), three phenylpropanoid glycosides (10–12), two alkyl glycosides (13–14) and an alkaloid (15). The structures of these compounds were determined by NMR spectroscopy and comparison with data from previous literatures. Among them, eleven compounds (2–5, 8, 10 and 11–15) were reported from the genus Lonicera for the first time and compounds 3, 4, 5, 10 and 11–15 were firstly reported from the family Caprifoliaceae. Network analysis was carried out to explore the chemotaxonomic significance of these compounds for L. japonica in this study.     

Chemical constituents from the roots of Zizyphus jujuba Mill. var. spinosa

One new flavonoid, named (R)-2-hydroxynaringenin (1), along with fifteen known compounds, including six flavonoids (2–7), six lignans (8–13), two phenolic glycosides (14–15) and one alkaloid (16) were isolated from the roots of Zizyphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chou. Their structures were established on the basis of spectroscopic evidence, including 1D and 2D NMR, circular dichroism (CD) curve analysis, and by comparison with literature data. Compounds 2, 3 and 8–16 were found in Z. jujuba Mill. var. spinosa for the first time, while compounds 8, 10 and 13–15 were new to the Rhamnaceae family. In addition, the chemotaxonomic significance of the isolates was discussed in this paper.     

Natural neuroprotective alkaloids from Stephania japonica (Thunb.) Miers

Modulating inflammatory responses after stroke can prevent brain injury and, therefore, improve neurological outcome. Stephania japonica (Thunb.) Miers is a Chinese folk medicine with the function of dispelling the “wind and blockage” in the human body according to the Chinese medicine theory, in which the symptoms of stroke are caused by the “wind and blockage” in the body. In this paper, we for the first time linked S. japonica to stroke by clarifying fifteen alkaloidal constituents including five undescribed (1–5) ones and screening out six hasubanan type alkaloids (1–4, 7, 15) that elicited stronger anti-neuroinflammatory activities than the positive drug. Moreover, the total alkaloid fraction (ASJ) with previously undescribed 3 as the main component was subject to the in vivo evaluation of the protective effect in the MCAO-induced brain injury. The results showed that ASJ exhibited potent protective effect against brain injury in the MCAO rat model. The results reported in this paper suggested that the hasubanan alkaloids from S. japonica would be an important molecular source for discovering novel therapeutic agents for neuroinflammation-related diseases, such as stroke diseases.     

Triterpenes and lignans from the leaves of Styrax tonkinensis

Two triterpenes (1 and 2) and eight lignans (3–10) were isolated from the ethyl acetate-soluble fraction of the leaves of Styrax tonkinensis (Pierre) Craib ex Hartw (Styracaceae). Their structures were established as ursolic acid (1), pomolic acid (2), 3,3′-bis(3,4-dihydro-6-methoxy-2H-1-benzopyran) (3), rac-(8α,8′β)-4,4′-dihydroxy-3,3′-dimethoxylignan-9,9′-diyldiacetate (4), (-)-secoisolariciresinol (5), (+)-pinoresinol (6), 4,4′-dihydroxy-3,3′-dimethoxy-9-ethoxy-9,9′-epoxylignan (7), (2S,3R, 4R)-4-[1-ethoxy-1-(4-hydroxy-3-methoxy)phenyl]methyl-2-(4-hydroxy-3-methoxy)phenyl-3-hydroxymethyl-tetrahydrofuran (8), (-)-neo-olivil-(9-O-9″)-seco-isolariciresinol (9) and isolariciresinol (10) based on MS, ¹H-and ¹³C-NMR spectral data. All these compounds (1–10) were firstly isolated from this plant, and compounds 2–5 and 7–9 were reported from the Styrax genus for the first time. Furthermore, the chemotaxonomic significance of the isolated compounds was discussed.     

Chemical constituents from Melodinus cochinchinensis (Lour.) Merr. and their chemotaxonomic significance

A phytochemical investigation on the twigs and leaves of Melodinus cochinchinensis (Lour.) Merr. resulted in the isolation and identification of 22 compounds, including seven sesamin-type lignans (1–7), three pentacyclic triterpenes (8–10), one anthraquinone (11), one flavanone (12), two phenolic compounds (13 and 14), five aspidosperma-type indole alkaloids (15–19), and three eburnan-type indole alkaloids (20–22). The structures of these compounds were elucidated by means of spectroscopic analysis, including HREIMS together with 1D and 2D NMR experiments, and comparison with reported data. Among them, compounds 1/4, 2/5, and 3/6 are three pairs epimers at C-7''. Compounds 1–6, 8 and 11 were firstly isolated from the family Apocynaceae, whereas 17 was isolated from Melodinus species for the first time. Compound 8 was only found in Juglans hopeiensis, while 11 was only found in roots of Rubia cordifolia. Compounds 1–6, 8, 11 and 15–22 could be considered as chemotaxonomic markers for M. cochinchinensis. Furthermore, the chemotaxonomic significance and distribution of these isolates in Melodinus genus are discussed in detail.     

Monoterpene indole alkaloids in Uncaria rhynchophlly (Miq.) Jacks chinensis and their chemotaxonomic significance

From the Uncaria rhynchophlly (Miq.) Jacks, twelve monoterpene indole alkaloids, such as harman (1), strictosamide (2), vincosidelactam (3), cadambine (4), 3α-dihydrocadambine (5), 7-epi-javaniside (6), rhynchophylline (7), isorhynchophylline (8), hirsutine (9), vincosamide-6′-O-β-D-glucopyranoside (10), vincosamide-11-O-β-D-glucopyranoside (11) and 2′-O-[β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-11-hydroxyvincosamide (12) were isolated and identified. Structure elucidation of these compounds was performed on the basis of NMR spectroscopic data. Compounds 2, 5, 6, 10, 11 and 12 were obtained from this species for the first time. Chemotaxonomic significance of these compounds is described herein.     

Development of microsatellite markers from loquat, Eriobotrya japonica (Thunb.) Lindl

Loquat (Eriobotrya japonica) is a minor fruit which has become an interesting alternative into the European fruit industry. This interest resulted in a loquat germplasm collection established at the Instituto Valenciano de Investigaciones Agrarias, Valencia, Spain. Currently, it is the main reservoir of this species outside Asia. We developed and characterized the first 21 polymorphic microsatellite loci from a CT/AG-enriched loquat genomic library. The observed heterozygosity ranged between 0.20 and 1.00, expected heterozygosity ranged between 0.17 and 0.81, three markers were multilocus and eight loci departed significantly from Hardy-Weinberg equilibrium. These markers will facilitate diversity and genetic studies into the species.     

A serine endopeptidase from the fruits of Melothria japonica (Thunb.) maxim

An endopeptidase from the fruits of Melothria japonica (Thunb.) Maxim. has been purified by DEAE-Sepharose chromatography and gel-filtration by a Sephacryl S-300. The enzyme has Mr of 61 kDa. The optimum pH of the enzyme was 8. The enzyme activity was inhibited by diisopropyl fluorophosphate and phenylmethanesulfonylfluoride, but not by EDTA. Casein was a poor substrate, but angiotensin I was cleaved by the enzyme within 30 min at four different sites. These results indicated that the enzyme was a serine oligopeptidase of broad substrate specificity.     

茶藨子叶孔菌子实体(忍冬)的化学成分研究(英文)

从茶藨子叶孔菌(忍冬)中分离了8个化合物,通过波谱法和理化性质分别鉴定为豆甾醇(1),二十八酸(2),β-谷甾醇(3),麦角甾醇(4),麦角甾醇过氧化物(5),壬二酸(6),烟酸(7),原儿茶酸(8)。化合物1,3,6均为首次从该属真菌中分到。     

青荚叶〔Helwingia japonica(Thunb.)Dietr.〕种下新组合

青荚叶〔Ｈｅｌｗｉｎｇｉａｊａｐｏｎｉｃａ (Ｔｈｕｎｂ .)Ｄｉｅｔｒ.〕为山茱萸科(Ｃｏｒｎａｃｅａｅ)青荚叶属 (ＨｅｌｗｉｎｇｉａＷｉｌｌｄ .)植物 ,我国民间常将其髓部、叶及果实作为药用。该种主要特征为叶片纸质 ,卵形、卵圆形、长卵形或卵状披针形 ,背面粉白或淡绿色等[1 ] 。作者在对馆藏的青荚叶标本进行整理时 ,发现《中国植物志》中的个别变种描述与该变种原始文献的描述有出入 ,而且该种种内的一些分类依据不明确。为此作者查阅了有关标本及文献 ,对该种的这些问题进行了分析和讨论。青荚叶Ｈｅｌｗｉｎｇｉａｊａｐｏｎ…     

Lignans from the Twigs of Euonymus alatus (Thunb.) Siebold and Their Biological Evaluation

A new sesquilignan, euonymolin A ( 1 ), and six known lignans, (?)‐de‐O‐methylmagnolin ( 2 ), (+)‐de‐O‐methylepimagnolin A ( 3 ), (+)‐syringaresinol ( 4 ), (+)‐pinoresinol ( 5 ), (+)‐medioresinol ( 6 ), and (+)‐lariciresinol 4′‐O‐β‐d ‐glucopyranoside ( 7 ), were isolated from the twigs of Euonymus alatus (Thunb .) Siebold (Celastraceae). The structures of the isolated compounds were elucidated based on spectroscopic analyses, including extensive 1D‐ and 2D‐NMR techniques, HR‐MS analysis and circular dichroism (CD) data, and the literature data. All of the isolated compounds were evaluated for antiproliferative activity against A549, SK‐OV‐3, SK‐MEL‐2, and HCT‐15 cell lines and inhibition of nitric oxide (NO) production in a lipopolysaccharide (LPS)‐activated BV2 cell line. All compounds showed cytotoxicity against the SK‐MEL‐2 cell line with IC₅₀ values of 23.24 – 48.14 μm and inhibited NO production in LPS‐activated BV‐2 cells with IC₅₀ values of 6.75 – 23.53 μm .     

Phenological growth stages of loquat tree (Eriobotrya japonica (Thunb.) Lindl.)

Conservation, characterisation and utilisation of minor fruit tree species is an important objective for diversification of agro-food production. One such fruit tree is the loquat, a tree that originated in China but is well adapted to the Mediterranean area. The conservation and utilisation of suitable germplasm requires an accurate characterisation and evaluation of the material. A first step in characterisation is to use phenotypic traits. This paper describes the phenological growth stages of loquat tree using the extended BBCH scale. Seven principal growth stages (PGS) for bud, leaf and shoot development, inflorescence emergence, flowering, fruit development and fruit maturity and 31 secondary growth stages are described and compared with a previous scale based on Fleckinger classical methodology. An example of application of the extended BBCH scale for characterisation of loquat cultivars from IVIA germplasm collection is reported.     

Bioactive lignans from the stems of Mappianthus iodoides

Two new lignans, mappianthines A (1) and B (2), along with ten known analogues (3-12), were isolated from the stems of Mappianthus iodoides. The structures with the absolute configurations of 1 and 2 were elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons their data with those reported in the literatures. All new compounds were evaluated for their anti-inflammatory activities via examining the inhibitory activity on nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro. Compounds 1 and 2 exhibited inhibitory effects with IC₅₀ values comparable to that of hydrocortisone.     

Bioactive lignans from Zanthoxylum planispinum with cytotoxic potential

Zanthoxylum planispinum Sieb. et Zucc is used in traditional oriental medicinal for preventing toothache, treating colds and expelling roundworms. Its fruit is widely used as a spice in cuisines in East Asian countries. Two previously unreported dilignans with a rare α,β-unsaturated ketone group, bizanthplanispine A and B (1–2), together with two known dilignans, zanthpodocarpins A and B (3–4), and four known lignans, fargesin (5), planispine A (6), pinoresinol-di-3,3-dimethylallyl (7), and eudesmin (8), were isolated from the roots of Z. planispinum. The structures of these compounds were elucidated by extensive NMR and MS analysis. The cytotoxic activity of the isolated compounds was evaluated on three human cancer cell lines. Compounds 1–4 significantly reduced the proliferation of Hela with IC₅₀ values ranging from 15.00 to 26.44 μg/mL. Furthermore, compound 6 showed the strongest inhibitory effect on the growth of HL-60 and PC-3 with IC₅₀ values of 4.90 and 23.45 μg/mL, respectively. These data suggested that compounds 1–4, and 6 from Z. planispinum have potential as anticancer substances.     

Antioxidant lignans from Larrea tridentata

Three lignans, (7S,8S,7'S,8'S)-3,3',4'-trihydroxy-4-methoxy-7,7'-epoxylignan, meso-(rel 7S,8S,7'R,8'R)-3,4,3',4'-tetrahydroxy-7,7'-epoxylignan, and (E)-4,4'-dihydroxy-7,7'-dioxolign-8(8')-ene, together with 10 known compounds, were isolated from the leaves of Larrea tridentata. The structures of the new compounds were determined primarily from 1D and 2D NMR spectroscopic analysis. Their antioxidant activities against intracellular reactive oxygen species were evaluated in HL-60 cells.     

The Constituents of the Essential Oil from Litsea japonica (Thunb.) Juss., FRUIT

Tetragenococcus halophila D10 decarboxylates aspartate to alanine, but T. halophila D10 derivatives generated by a curing treatment could not (Asd^- derivatives). We observed by electrophoresis three plasmid bands in T. halophila D10; all Asd^- derivatives lost the largest of these bands. This plasmid, pD1, has two SalI sites. We cloned and sequenced the 10 kb SalI fragment. The DNA sequence suggests that this fragment contains the aspartate decarboxylating trait.