Chemical constituents isolated from Valeriana officinalis L

Phytochemical investigations on the leaves of Valeriana officinalis L. led to the isolation of 18 compounds, including eight lignans (1–8), three sesquiterpenoids (9–11), five iridoids (12–16), and two aldehydes (17–18) The structure elucidation of isolated compounds was achieved on the basis of NMR and mass spectral data. Among them, three compounds (9–16, 18) are reported from V. officinalis for the first time and one compound (5) was isolated from the genus Valeriana for the first time. In addition, six compounds (2, 4, 6–8, 17) are isolated for the first time from Valerianaceae family. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Chemical constituents from Valeriana officinalis L. var. Iatifolia Miq. and their chemotaxonomic significance

Twenty-one compounds, including four monoterpenoids (1–4) (two new natural products, 1 and 2), four sesquiterpenes (5–8), two iridoids (9 and 10), four steroids (11–14), five phenolic compounds (15–19), and two alkaloids (20 and 21), were isolated from the roots of Valeriana officinalis L. var. Iatifolia Miq. Their chemical structures were established by spectroscopic methods and further confirmed by comparison with published data in the literature. Among them, eight compounds (1, 2, 6–8, 13, 18, and 21) are being reported from the family Valerianaceae for the first time, and compounds 9–12 were obtained from V. officinalis for the first time. The chemotaxonomic significance of the isolated compounds is discussed.     

Flavonoids,megastigmanes and other constituents from Ardisia incarnata

Phytochemical investigation of the leaves and twigs of Ardisia incarnata Pit. (syn. Ardisia hanceana Mez, Primulaceae) led to the isolation of one bicyclic monoterpene (1), five phenolic compounds (2–5, 8), two megastigmanes (6–7) and one glyceroglycolipid (9). Their structures were established based on analysis of their spectroscopic data and comparison with literature. The compounds 1 and 6–9, isolated for the first time from Ardisia genus, may constitute chemomarkers of A. incarnata within Primulaceae family. Moreover, the flavonoid fingerprint may also be of chemotaxonomic significance.     

Chemical constituents from Orobanche cernua Loefling

Phytochemical study of Orobanche cernua Loefling afforded 17 compounds, including eleven phenylpropanoid glycosides (1–11), two flavonoids (12, 13), one lignan (14), and three phenolic acids (15–17) were isolated from the fresh whole plant of O. cernua. Their structures were identified by spectroscopic analyses and by comparison of their spectral data with those reported in the literature. This is the first report of isolation of compounds (6, 8, 9, 11, 14–16) from O. cernua and compounds (14, 15) from the family Orobanchaceae, respectively. Compound 14 was obtained from natural source for the first time, the chemotaxonomic significance of these compounds was summarized.     

A new bicyclic sesquiterpenoid from Merremia yunnanensis

A new sesquiterpenoid, 1α,4β,8β,9β-eudesmane-tetrol-1-O-β-D-glucopyranoside (1), together with nine known compounds (2–10), were isolated from Merremia yunnanensis. The structures of these compounds were elucidated by spectroscopic methods and compared to data in the literature. All these compounds (1–10) were firstly isolated from this plant, and compounds 3, 5, 7, and 10 were reported from the Merremia genus for the first time. The significance of the chemotaxonomy for these compounds is described herein.     

Chemical constituents from the roots of Caragana grandiflora (M. B.) DC. and their chemotaxonomic importance

A comprehensive phytochemical research on roots of Caragana grandiflora, a native plant to Iran, resulted in isolation of ten compounds including four phenolic compounds (2, 4, 5, 8), two fatty alcohols (1, 6), one fatty acid (9), one triterpene (3), one glyceride derivatives (7) and one fatty acid methyl ester (10), from which eight compounds (1, 2, 4–6 and 8–10) were isolated from the genus Caragana and two compounds (5 and 10) from the family Fabaceae, for the first time. All compounds (1–10) were described from Caragana grandiflora for the first time. Chemical structures of the purified compounds were identified through FT-IR, NMR and MSS, and spectral data comparison with literature reported evidences.Our findings provide valuable information in reporting the rare existence of natural fatty acid methyl ester (10) in the Fabaceae family. Moreover, the chemotaxonomic significance of these compounds was discussed.     

Chemical constituents from Cistanche sinensis (Orobanchaceae)

Phytochemical investigation of 70% aqueous EtOH extract of Cistanche sinensis led to the isolation of fifteen compounds (1–15), including nine phenylethanoid glycosides (PhGs, 1–9), five iridoid glycosides (10–14), and one lignan glycoside (15). Their structures were determined on the basis of 1D- and 2D-NMR experiments and by comparison with physical data of known compounds. Among the isolated compounds, 1 was identified as a new compound, three compounds (9, 14, and 15) were firstly reported from the genus Cistanche, and seven compounds (2–6, 11, and 12) were isolated from C. sinensis for the first time. PhGs with a 6′-O-rhamnosyl moiety such as cistansinenside B (1), poliumoside (7), and 2′-O-acetylpoliumoside (9) could serve as chemotaxonomic markers to differentiate C. sinensis from other species of Cistanche.     

Chemical constituents from the roots of Asarum sieboldii Miq. var. Seoulense Nakai

Fourteen compounds were isolated from the 95% ethanol reflux extract of Asarum sieboldii Miq. var. Seoulense Nakai, including five phenanthrene derivatives (1–5), three isobutyl amides (6–8), three phenylpropanoids (9–11) and three lignins (12–14). The structures of these compounds were identified by spectroscopic methods and by comparison with the reported spectroscopic data. Among them, compounds 6 and 11 were firstly reported from the family Aristolochiaceae, and compounds 3 and 4 were reported for the first time from the genus Asarum. Additionally, compounds 1, 2 and 8 were isolated from A. sieboldii Miq. var. Seoulense Nakai for the first time. These compounds have shown chemical relationships between A. sieboldii Miq. var. Seoulense Nakai and other species of Asarum as well as those found in the genus Aristolochia in the family Aristolochiaceae.     

Chemical constituents from Euphorbia stracheyi Boiss

The chemical investigation of whole plants Euphorbia stracheyi Boiss. led to the isolation of 14 compounds, including eight diterpenes (1–8), one monoterpene (9), three coumarins (10–12), and two phenols (13–14). Their structures were elucidated by extensive spectroscopic analyses and by comparison with the literature. Compounds 1–6, and 8–12 were firstly isolated from E. stracheyi, while compounds 6, and 9 were isolated from Euphorbia genus for the first time. The chemotaxonomic significance of these isolated compounds is discussed.     

Chemical constituents from the Jasminum lanceolarium Roxb.

Twelve compounds (1–12) are isolated from Jasminum lanceolarium Roxb. Among them, compounds 5, 7, 8, 11 and 12 are reported here for the first time from J. lanceolarium, and compounds 6, 9, 10 are firstly isolated from Jasminum genus. The existence of iridoids and lignanoids might be regarded as valuable chemotaxonomic markers for further classification and subdivision of the genus of Jasminum.     

Chemical constituents from the pericarps of Zanthoxylum bungeanum and their chemotaxonomic significance

The phytochemical study of the pericarps of Zanthoxylum bungeanum Maxim under the guidance of bioactivity led to the isolation of 18 compounds, including a new isobutylhydroxyamide (1) and 17 known compounds, i.e. six alkylamides (2–7), five coumarins (8–12), one benzene derivative (13), three flavonoids (14–16), and two sterols (17–18). Their structures were elucidated based on extensive spectroscopic methods (HRESIMS, 1D and 2D NMR experiments) and by comparison with literature data. New compound (1) and known compound (2) are cis-trans isomeric isobutylhydroxyamides. Among them, compounds 9, 10, and 12 were isolated for the first time from Z. bungeanum, compound 11 was firstly recovered from the genus Zanthoxylum, and compound 14 was reported for the first time from the Rutaceae family. The chemotaxonomic significance of isolated compounds from Z. bungeanum is discussed.     

Chemotaxonomic significance of limonoids and triterpenoids from Dictamnus angustifolius G. Don ex Sweet

Phytochemical investigation of the root bark of Dictamnus angustifolius G. Don ex Sweet (Rutaceae) resulted in the isolation and characterization of three degraded limonoids (1–3), five limonoids (4–8) and four triterpenoids (9–12). All structures were elucidated on the basis of spectral analysis. Among them, compounds 4, 6, 8, 9 and 12 were isolated from the genus Dictamnus for the first time. Compounds 10 and 11 were obtained from D. angustifolius for the first time. Moreover, the chemotaxonomic significance of these compounds was summarized.     

Chemical constituents with ɑ,β-unsaturated carbonyl group from the whole plants of Erigeron breviscapus (Vant.) Hand.-Mazz. (Asteraceae)

Phytochemical characterization of the whole plants of Erigeron breviscapus (Vant.) Hand.-Mazz. Led to the isolation of two indole derivatives (1–2), seven monoterpenoids (3–9), two sesquiterpenoids (10–11), and four pyrone derivatives (12–15). The structures of these compounds were examined with spectroscopic methods, and also by comparing with previously reported spectroscopic data. Among them, ten compounds (1–2, 6–11, 14–15) are reported from Erigeron breviscapus for the first time. In addition, three compounds (2, 8–9) are isolated for the first time from Asteraceae family. On the basis of chemical research, we also described the chemotaxonomic significance of these compounds.     

A new C21 steroidal compound from the whole herb of Pachysandra terminalis Sieb. et Zucc

A new C21 steroidal compound (1), along with 12 known compounds (2–13) were isolated from the whole herb of Pachysandra terminalis Sieb. et Zucc. Their structures were determined by extensive analysis using various spectroscopic techniques. Notably, compound 6 was reported for the first time from P. terminalis, and compounds 3–5, 7 and 9 were isolated from the family Buxaceae for the first time.     

Chemical constituents from Lomatogonium carinthiacum (Gentianaceae)

Lomatogonium carinthiacum (Wulfen) Rchb. (Gentianaceae) is an annual plant which used in the Mongolian system of medicine against liver and bile diseases. In the present study, three flavones (1–3), four xanthones (4–7), and two iridoids (8, 9) were isolated and identified. Among them, compounds 3–5, 7, 8 were firstly isolated from the species L. carinthiucum, compounds 3-5 were isolated from the genus Lomatogonium for the first time. The Chemotaxonomic significance of these compounds was discussed in the article.     

Chemotaxonomic significance of lignans from Serissa japonica (Thunb.) Thunb

Sixteen known lignans were isolated from the 95% alcohol extract of the whole plant of Serissa japonica (Thunb.) Thunb., including nine furofurans (1–9), three tetrahydrofurans (10–12) and four arylnaphthalenes (13–16). In the present report, compounds (+)-epipinoresinol (1), (+)-1-hydroxy-6-epipinoresinol 4,4″-di-O-methyl ether (3), (−)-pinoresinol (4), (+)-8-hydroxypinoresinol (6), pseuderesinol (7), (+)-1-hydroxysyringaresinol (8), (−)-(7′S,8S,8′R)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one (10), wikstrone (11), 7'-(+)-oxomatairesinol (12), (+)-cycloolivil (13), (+)-isolariciresinol (14), 5-methoxy-(+)-isolariciresinol (15) and cyclolignans (16) were reported from the Serissa genus for the first time, and compounds (+)-lirioresinol A (2) and (−)-lirioresinol B (5) 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.     

Chemical constituents from the fruiting bodies of Xylaria euglossa Fr. and its chemotaxonomic study

Three anthracenones (1–3), two lactams (4–5), three sterols (6–8), one ceramides (9), one long-strain fatty acid (10) were isolated from the fruiting bodies of Xylaria euglossa Fr. All the compounds were isolated from this fungus for the first time. Compound 1, 4 and 5 were isolated from the family Xylariaceae for the first time. Compound 1 and 4–5 were considered chemotaxonomically significant for the species Xylaria euglossa.     

Chemical constituents from Schefflera leucantha R.Vig. (Araliaceae)

Processive phytochemistry and pharmacological investigation of Schefflera leucantha R.Vig. (Araliaceae) led to the isolation of fifteen known compounds: a nucleobase (1), six small aromatic molecules (2–7), three phenylpropanoids (8–10), four lignans (11–14) and a fatty acid derivative (15). Spectroscopic methods were used to establish the structure and configuration of isolates, followed by their unambiguous confirmation with literature data. We report for the first time (to the best of our knowledge), the isolation of β-amino-3-methoxy-4-hydroxybenzene-ethanol (4) from a natural source. Furthermore, compounds 1, 5, 9–15 are being reported from Araliaceae family for the first time, whereas compounds 2, 3, 6–8 from the genus Schefflera for the first time. The biological screening results show that compounds 9 and 10 induce a moderate inhibitory effect on aldose reductase, while compounds 3, 5, and 8 display significantly high neuroprotective activities.     

Chemical constituents from bulbs of Fritillaria pallidiflora Schrenk

A new steroidal alkaloid, 5α, 14α, 17β-cevanin-6-oxo-3β, 20β, 24β-triol(1), together with ten known compounds (2–11) were isolated from the bulbs of Fritillaria pallidiflora Schrenk. Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. Compounds 8, 9, 10 were obtained from the genus Fritillaria for the first time; Compounds 2, 3, 4 and 11 are isolated from this plant for the first time.     

Phytochemical constituents from Neolamarckia cadamba (Roxb.) Bosser

Phytochemical study on Neolamarckia cadamba (Roxb.) Bosser has yielded ten indole alkaloids, neolarmarckine A-E (1–5), cadamine (6), 3β-isodihydrocadambine (7), angustine (8) and naulafine (9) and harmane (10). The structural elucidation of all the compounds were conducted based on the thorough analysis of spectroscopic data and comparison with reported data. The chemotaxonomic significance of all these compounds were summarized. Among all the indole alkaloids, compound 3–5 were new compounds and isolated from Neolamarckia cadamba (Roxb.) Bosser for the first time. Compounds 1 and 2 were only found in Neolamarckia species while compounds 6 and 7 were only isolated from the family of Rubiaceace. Besides, compound 8 has been found in six genera of Rubiaceae and two genera of Apocynaceae while compound 9 was isolated from Neolamarkia species for the first time. Compound 10 can be found in many genera of Rubiaceae and also more than ten families such as Zygophyllaceae, Cyperaceae, Passifloraceae, Bignoniaceae, Sapotaceae, Elaeagnaceae, Leguminosae, Loganiaceae, Apocynaceae, Combretaceae, Chenopodiaceae, Commelinaceae and Polygalaceae.