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.     

The triterpenes and steroids from the fruiting body Ganoderma duripora

Two new triterpenes (1–2) and seven steroids (3–9) were isolated from the fruiting bodies of Ganoderma duripora. Structure elucidation of these compounds was generated by a combination of spectroscopic means (HRTOFMS, ¹H and ¹³C NMR). There are significant differences between the compounds isolated from Ganoderma duripora and from the other Ganoderma species, suggesting that we need to reconsider the classification of G. duripora according to the taxonomy of chemistry.     

Chemical constituents from Cremanthodium brunneo-pilosum S. W. Liu

Fourteen compounds were isolated from Cremanthodium brunneo-pilosum, including two steroids (1 and 14), five sesquiterpenoids (2–6), six flavonoids (7–12) and one isoflavone (13). Graveolide (2) was obtained from a plant for the first time. 5,7-Dihydroxy-3,6,3′,4′-tetramethoxy-flavone (9), centaureidin (10) and tectoridin (13) have not been isolated from the family Compositae. The chemotaxonomic data support the relationship between this species and others in the family Compositae.     

Flavonoids and anthraquinones from Murraya tetramera C. C. Huang (Rutaceae)

Phytochemical investigation of Murraya tetramera C. C. Huang led to the isolation of ten flavonoids (1−10) and three anthraquinones (11−13). Their structures were determined on the basis of MS, NMR, specific optical rotation, and CD spectroscopic data analysis, and by comparison of the obtained data with those reported in the literature. This is the first report for the occurrence of compounds 2, 4–7, and 11–13 in the Murraya species, and all the compounds were isolated from M. tetramera for the first time with the exception of compound 3. The chemotaxonomic significance of these compounds was also discussed.     

Flavonoids and xanthones from the leaves of Amorphophallus titanum (Araceae)

The flavonoids and xanthones in the leaves of Amorphophallus titanum, which has the largest inflorescence among all Araceous species, were surveyed. Eight C-glycosylflavones, five flavonols, one flavone O-glycoside and two xanthones were isolated and characterized as vitexin, isovitexin, orientin, isoorientin, schaftoside, isoschaftoside, vicenin-2 and lucenin-2 (C-glycosylflavones), kaempferol 3-O-robinobioside, 3-O-rutinoside and 3-O-rhamnosylarabinoside, and quercetin 3-O-robinobioside and 3-O-rutinoside (flavonols), luteolin 7-O-glucoside (flavone), and mangiferin and isomangiferin (xanthones). Although the inflorescence of this species has been surveyed for flavonoids, those of the leaves were reported for the first time.     

Phytochemical study of Joannesia princeps Vell. (Euphorbiaceae) leaves

A phytochemical study of chloroform-methanol and methanol extracts of Joannesia princeps Vell. Leaves led to the isolation of twenty eight compounds, including two α-ionones (2, 5), three glycosylated monoterpenes (1, 3, 4), eight phenolic compounds (6, 8, 9, 12, 14, 17, 18, 24), two gallotannins (10, 11), twelve flavonoids (7, 15, 16, 19, 20–23, 25–28), and one lignan (13). The structural characterization of the isolated compounds was performed by spectroscopic data and comparison with the literature. All compounds were isolated from this species and from the genus Joannesia for the first time. The chemotaxonomic importance of these metabolites is therefore summarized.     

药用植物天门冬染色体核型分析

对天门冬根尖细胞进行染色体常规制片,并进行核型分析。结果表明,天门冬染色体数为2n=20,核型公式为K(2n)=2x=20=8 sm+128m,其中中部着丝粒染色体(m)为4对,近中部着丝粒染色体(sm)为5对。核型类型为2B。     

Chemical constituents from Cyclocarya paliurus (Batal.) Iljinsk

A novel triterpenoid, cyclocarioside K, together with fifteen known compounds, including seven triterpenoids (2–8), five flavonoids (9–13), three phenolic derivatives (14–16), was obtained from the leaves of Cyclocarya paliurus (Batal.) Iljinsk (Juglandaceae). Their structures were elucidated by spectroscopic methods, including two-dimensional NMR experiments (HSQC DEPT and HMBC). The chemotaxonomic relationships were also discussed. As a result, 3, 4-secodammarane triterpenoids and kaempferol glycosides may represent phytochemical fingerprints for C. paliurus, and C. paliurus has close relationships with other species of Juglandaceae.     

Phenolics from Tanacetum sinaicum (Fresen.) Delile ex Bremer & Humphries (Asteraceae)

The phytochemical investigation on Tanacetum sinaicum (Fresen.) Delile ex Bremer & Humphries led to the isolation of eight flavonoid aglycones (apigenin 1, acacetin 2, luteolin 3, chrysoeriol 4, cirsilineol 5, jaceidin 6, chrysosplenetin 7 and vitexicarpin; casticin 8), four flavonoid glycosides (apigenin 7-O-β-glucopyranoside 9, apigenin 7-O-β-glucuronide 10, luteolin 7-O-β-glucopyranoside 11 and luteolin 7-O-β-glucuronide 12) and three phenolics (4-hydroxy-3-methoxy benzoic acid 13, 3,4-dimethoxy benzoic acid 14 and 4-hydroxy acetophenone 15). Their structures were determined by chemical and spectroscopic analysis. Among them, compounds 1–3, 9, 11, 13 and 14 were reported for the first time from T. sinaicum. The chemotaxonomic significance of the isolated flavonoids was also summarized.     

Terpenoids and a coumarin from aerial parts of Psychotria vellosiana Benth. (Rubiaceae)

The phytochemical investigation of Psychotria vellosiana aerial parts yielded five compounds, including two triterpenes (squalene and lupeol), two steroids (stigmasterol and sitosterol), and one coumarin (scopoletin). The structures of the isolates were established based on analysis of their spectroscopic data and comparison with literature. All metabolites isolated were previously detected in Psychotria, excepting squalene that is being described for the first time from this genus. This study adds a new species to a number of reports showing the absence of alkaloid in Psychotria.     

Chemical constituents from the leaves of Crataegus pinnatifida Bge

The phytochemical investigations on the leaves of Crataegus pinnatifida led to the isolation of 20 compounds, including seven triterpenoids (1-7), three hydroxycinnamic acids (8-10), three lignans (11-13) and seven flavonoids (14-20). All chemical structures were established on the basis of NMR (1H NMR, 13C NMR) spectroscopic data. Meanwhile, compounds 3-12 are reported for the first time from Crataegus genus. In addition, compounds 10-11 are isolated from the family Rosaceae for the first time. On the basis of chemical research, the chemotaxonomic significance of the isolated compounds has been discussed.     

Chemotaxonomic significance of sesquiterpenes and amide derivatives from Chloranthus angustifolius Oliv.

Phytochemical investigation of the aerial parts of Chloranthus angustifolius Oliv. (Chloranthaceae) resulted in the isolation and characterization of seven sesquiterpenes (1–7) and six amide derivatives (8–13). All structures were established based on analysis of their spectroscopic data. This is the first report of compounds 2 and 8–13 from the family Chloranthaceae, and the first report of compounds 3–5 from C. angustifolius. Moreover, the chemotaxonomic significance of these compounds was summarized.     

Chemotaxonomic implications of the absence of sesquiterpene lactones in Grazielia multifida (DC.) R.M.King & H.Rob. (Asteraceae)

The phytochemical investigation of Grazielia multifida aerial parts yielded eight compounds, including four ent-kaurenic acid diterpenes derivatives, 15-tiglinoyloxy-ent-kaur-16-en-19-oic acid (1), 15-hydroxy-ent-kaur-16-en-19-oic acid (2), 17-hydroxy-ent-kaur-15-en-19-oic acid (3) and 15-isovaleroyloxy-ent-kaur-16-en-19-oic acid (4), one amino acid, tryptophan (5), and three flavonoids, eupafolin (6), guaijaverin (7) and quercitrin (8). The structures of the isolated compounds were established based on analysis of their spectroscopic data and comparison with literature. All the compounds were isolated from this species for the first time. The chemotaxonomic significance of the absence of sesquiterpene lactones in G. multifida has also been summarized.     

New amides from the roots of Anisodus tanguticus

Two new amides (1 and 2) and four known analogues (3–6) were isolated from the roots of Anisodus tanguticus (Maxim.) Pascher. Their structures were determined by extensive spectroscopic analyses. The absolute configuration of compound 1 was determined by comparison of the calculated optical rotation (OR) value with the experimental OR value. All known amides were isolated from the genus Anisodus for the first time, of which compounds 3, 5, and 6 were first reported from the family Solanaceae. Furthermore, the chemotaxonomic significance of these secondary metabolites is discussed.     

Chemical constituents from Piper boehmeriifolium (Miq.) Wall. ex C. DC

The chemical investigation of whole plants Piper boehmeriifolium (Miq.) Wall. ex C. DC. led to the isolation of 22 compounds, including two lignans (1–2), sixteen amide alkaloids (3–18), one diterpene (19), two monoterpenes (20–21), and one phenylpropanoid (22). Their structures were elucidated by extensive spectroscopic analyses including NMR, MS, and by comparison with the literature. Compounds 1–2, 6–7, 11–12, 14, and 17–22 were firstly isolated from P. boehmeriifolium, while compounds 2, and 19–20 were isolated from Piper genus for the first time. The chemotaxonomic significance of these isolated compounds is discussed.     

Chemical constituents from Cymbaria dahurica L. (Scrophulariaceae)

Phytochemical study of Cymbaria dahurica L. afforded 16 compounds, including 12 flavonoids (1–12) and 4 iridoids (13–16). Structure elucidation of these compounds was generated by a combination of spectroscopic means (ESI-MS, ¹H and ¹³C NMR) and comparisons with the published data. This is the first report of isolation of compounds (1–6, 10–16) from C. dahurica and compounds (5, 10, 12) from the family Scrophulariaceae, respectively. The chemotaxonomic data can support the genus Cymbaria being accepted as a member of transitional taxa between the family Scrophulariaceae and Orobanchaceae.     

Chemical constituents from the aerial parts of Impatiens hypophylla Makino var. hypophylla

Seven flavonoids such as luteolin (1), luteolin 7-O-β-glucopyranoside (2), luteolin 3'-O-β-glucopyranoside (3), chryseriol (4), apigenin (5), apigenin 7-O-β-glucopyranoside (6) and astragalin (7) and one coumarin, scopoletin (8) were isolated from the aerial parts of Impatiens hypophylla Makino var. hypophylla (Family: Balsaminaceae). Structures of these compounds were elucidated on the basis of spectroscopic methods. All these compounds were isolated for the first time from I. hypophylla var. hypophylla.     

A new flavonoid from the bark of Ulmus pumila L

A new flavonoid (6), together with eight (1–5 and 7–9) known flavonoids, were isolated from the n-butyl alcohol soluble portion of the EtOH extract of Ulmus pumila L. The chemical structures of the compounds were determined by using spectroscopic methods and further supported by comparison with previously literature values. Among them, flavonoids 4, 6 and 9 were isolated for the first time from the family Ulmaceae. Furthermore, the chemotaxonomic significance of the isolates was also discussed.