Chemical constituents from the calyces of Physalis alkekengi var. franchetii

One new monoterpenoid glycoside (1), together with seven known compounds, including two alkaloids (2–3), three phenylpropanoids (4–6), and two nucleosides (7–8) were isolated from the calyces of Physalis alkekengi var. franchetii. Their structures were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. These eight compounds were isolated for the first time from the genus Physalis. The chemotaxonomic significance of these compounds was summarized.     

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

Twenty-one compounds, including ten triterpenoids (1–10), two sterols (11 and 12), six flavonoids (13–18), and three cerebrosides (19–21) were isolated from the fruit of Zizyphus jujuba Mill. var. spinosa (Bunge) Hu ex. H. F. Chou. The structures were elucidated by spectroscopic methods and by comparison of their reported spectral data. These compounds have shown the relationship between this plant and other species from the Rhamnaceae family.     

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.     

Investigation of chemical compounds from Chlamydomonas sp. KSF108 (Chlamydomonadaceae)

Nine compounds (1–9) including one norisoprenoid (1), one polyol-glycoside (2), three sterols (3–5), three phenols (6, 8, and 9), and one fatty acid (7) were isolated from Chlamydomonas sp. KSF108. Their chemical structures were established using NMR spectroscopic techniques and compared with published data. None of the compounds have been previously reported from the genus Chlamydomonas and they may therefore serve as chemotaxonomic markers for Chlamydomonas sp. KSF108 within the genus.     

A new methoxylated flavone from Lonicera hypoglauca and its chemotaxonomic significance

Phytochemical investigation of the stems and leaves of Lonicera hypoglauca Miq. led to the isolation of one novel methoxylated flavone, acunminatin (7,2′,4′-trihydroxyl-5,5′- methoxyflavone) (1), and fourteen known compounds (2–15), including six flavonoids (mearnsetin 2, kaempferol 3, acacetin 4, 5,7,3′,4′-tetramethoxyflavone 5, tricin 6, and 5,7,3′,4′,5′-pentamethoxyflavone 7), two coumarins (umbelliferone 8 and scopoletin 9), two phenylpropanoids (trans-ferulic acid 10 and chlorogenic acid 11), two iridoid glycosides (loganin 12 and sweroside 13), and two triterpenoids (uvaol 14 and ursolic acid 15). The structures of the compounds were identified by spectroscopic analysis and by comparing their spectral data with those reported in the literature. Five of these compounds (1, 2, 4, 5, and 7) were isolated from the L. genus for the first time, and compounds 6–8 and 14–15 were isolated for the first time from L. hypoglauca. The chemotaxonomic significance of the isolated compounds in the L. genus and the Caprifoliaceae family are discussed herein.     

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 the leaves of Lyonia ovalifolia var. hebecarpa

A phytochemical investigation of the leaves of Lyonia ovalifolia var. hebecarpa (Franch. ex F.B. Forbes & Hemsl.) Chun (Ericaceae) led to the isolation of 22 compounds, including eight diterpenoids (1–8), two sesquiterpenoids (9 and 10), two monoterpenoids (11 and 12), two iridoids (13 and 14), four phenylpropanoids (15–18), and four lignans (19–22). Their structures were determined by spectroscopic data analysis and comparison with literature data. The absolute configuration of bisdeacetylkalmitoxin VI (1) was determined by single-crystal X-ray diffraction analysis for the first time. Notably, all the isolates 1–22 were reported from the genus of Lyonia for the first time, and compounds 9–12 and 15–22 were obtained from the Ericaceae family for the first time. The chemotaxonomic significance of compounds 1–22 was discussed.     

Phytochemical and chemotaxonomic study on Evodia rutaecarpa var. officinalis

Phytochemical investigations of the dried and nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth. var. of officinalis (Dode) Huang (family Rutaceae) led to the isolation of twenty compounds, including eight quinolone alkaloids (1–8), seven indole quinazoline alkaloids (9–15), two limonoids (16–17) and three sterols (18–20). The chemical structures of these compounds were elucidated by extensive spectroscopic analyses and by comparison with the literature data. Notably, seven compounds (1, 3, 7, 11 and 13–15) were reported from this species for the first time, and the chemotaxonomic significance of these compounds was discussed.     

Phytochemical and chemotaxonomic studies on Phyllodium pulchellum (Leguminosae)

A phytochemical investigation on the aerial part of Phyllodium pulchellum led to the isolation of 16 compounds including five flavonoids (1–5), three lignans (6–8), four indole alkaloids (9–12), and four other-type compounds (13–16). Their structures were elucidated by their spectroscopic data analysis. Among them, 12 compounds (1, 2, 4–9, and 11–14) are reported from the genus Phyllodium for the first time, while compound 14 was isolated from the Leguminosae family for the first time and compound 11 was firstly reported in the plant kingdom. The chemotaxonomic significance of these compounds was also summarized.     

Chemical constituents from the leaves of Cinnamomum parthenoxylon (Jack) Meisn. (Lauraceae)

Phytochemical investigation of the ethanolic extract from the leaves of Cinnamomum parthenoxylon (Jack) Meisn. led to the isolation of (3R, 4R, 3′R, 4′R)-6,6′-dimethoxy-3, 4, 3′, 4′-tetrahydro-2H, 2′H-[3, 3′]bichromenyl-4, 4′-diol (1), 4-hydroxybenzaldehyde (2), 1,2,4-trihydroxybenzene (3), kaempferol-3-O-α-l-rhamnoside (4), herbacetin (5), quercetin-3-O-α-l-rhamnoside (6), daucosterol (7), and β-sitosterol (8). The structures were established by extensive analysis of their MS and NMR spectroscopic data and comparison with literature data. In the present research, all of the isolated compounds 1–8 are reported for the first time in the species C. parthenoxylon. Compounds 1–6 were firstly isolated from genus Cinnamomum. Compounds 1, 3, 5 and 6 have not been reported from any species in Lauraceae family. The chemotaxonomic significance of the isolated compounds is discussed.     

Phytochemical constituents from the stem barks of Goniothalamus tapis Miq

Phytochemical investigation on the stem bark of Goniothalamus tapis Miq. led to the isolation of seven known styryl-lactones, 3-acetyl-isoaltholactone (1), goniothalamin (2), isoaltholactone (3), cheliensisin A (4), 7-epi-goniofufurone (5), goniopypyrone (6), garvensintriol (7), and two steroids, stigmasterol (8) and β-sitosterol (9). The structures of all the compounds were elucidated based on the analysis of spectroscopic data and comparison with reported literature. The chemotaxonomic significance of all these compounds were summarized. Among all the styryl-lactones, compound 1 was isolated naturally from plant for the first time while compounds 4, 5 and 7 have not been previously reported in Goniothalamus tapis Miq. Compound 2 was the first styryl-lactone isolated from many species of Goniothalamus including other families such as Cucurbitaceae, Lauraceae, Stemonaceae and Apocynaceae). Compounds 3 and 6 were found in ten species of Goniothalamus where the latter were also found in other genus (Polyalthia Blume).     

Phytochemical and chemotaxonomic study on the leaves of Rhododendron amesiae

The phytochemical study of the leaves of Rhododendron amesiae (Ericaceae) led to the isolation and identification of 19 compounds, including six diterpenoids (1–6), six triterpenoids (7–12) and seven flavonoids (13–19). The chemical structures of these compounds were identified by spectroscopic data, as well as by comparison with previously reported data in literature. This is the first systematic study on the chemical constituents of Rhododendron amesiae. All the compounds were isolated from this plant for the first time. Compounds 12, 14 and 15 were first isolated and reported from the genus Rhododendron and the family Ericaceae. Furthermore, the chemotaxonomic significance of these compounds was discussed.     

Chemical constituents with prenyl substitution from the stem and root of Daphne giraldii Nitsche. (Thymelaeaceae)

Phytochemical characterization of the stem and root bark of Daphne giraldii Nitsche. led to the isolation of eight flavones (1–8), six flavans (9–14) and six coumarins (15–20). The structures of these compounds were examined with spectroscopic methods, and also by comparing to previously reported spectroscopic data. Among them, ten compounds (1–3, 9 and 15–20) are reported for the first time for this species, and all compounds with prenyl substitutions have not been identified in other species of genus Daphne, or even in the family Thymelaeaceae. We also describe the chemotaxonomic significance of these compounds.     

Sterols,aromatic compounds,and cerebrosides from the Hericium erinaceus fruiting body

Chemical investigation of the methanolic extract from the fruiting bodies of Hericium erinaceus, led to the isolation of fifty-one compounds including thirty-five ergostane-type sterols (1–35), fourteen aromatic compounds (36–49), and two cerebrosides (50 and 51). Their structures were identified based on spectroscopic analyses and by comparison of their spectral data with those reported in literature. This is the first comprehensive low-polarity chemical investigation of H. erinaceus. Thirty-one of the compounds (6–8, 11–35, 39, 41, and 49) were isolated for the first time from the genus Hericium and the family Hericiaceae. The chemotaxonomic relationship between H. erinaceus and other Hericium species was also discussed.     

Chemical constituents from the roots of Fallopia multiflora var. Ciliinerve

Phytochemical investigations on the roots of Fallopia multiflora var. Ciliinerve led to the isolation of eighteen compounds, including six chromones [2-methyl-5- carboxymethyl-7-hydroxychromone (1), 2-methyl-5-methylcarboxymethyl-7- hydroxychromone (2), 2,5-dimethyl-7-hydroxychromone (3), 2-methyl-5-hydroxymeth-yl-7-hydroxychromone (4), 2-methyl-5-carboxylicacid-7-hydroxy-chromone (5), and 2,5-dimethyl-7-hydroxychromone-7-O-β-D-glucopyranoside (6)], three lignans [Isolariciresinol (8), 5-[4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,3-benzodioxole (9), and isolariciresinol-9-O-β-D-xylopyranoside (10)], four anthraquinones [physcion-8-O-β-D-glucopyranoside (11), emodin-8-O-β-D-glucopyranoside (12), Rhein (13), and Chrysophanol (14)], three isobenzofurans [5,7-dihydroxy-isobenzofuran (15), 5-methoxy-7-hydroxy-isobenzofuran (16), and 5-methoxy-isobenzofuran-7-O-β-D-glucoside (17)], one phenolic acid [2,5-diacethylhy-droquinone (7)], and one pyran [Zanthopyranone (18)]. Among them, compounds 1, 3, 6, 13 and 14 were reported from F. multiflora var. Ciliinerve for the first time, compounds 2, 8, 10 and 15–17 were isolated from the genus Fallopia for the first time, and compounds 4, 9 and 18 were isolated for the first time from Polygonaceae family. Furthermore, the isolation of compounds 5 and 7 were reported for the first time in plants. Their structures were identified by spectroscopic methods and compared with those previously published. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Chemical constituents isolated from the roots of Sanguisorba officinalis L. and their chemotaxonomic significance

Phytochemical investigation of the roots of Sanguisorba officinalis L. led to the isolation of thirty-eight compounds, including seventeen triterpenoids (1–17), six monoterpenoid glycosides (18–23), six flavonoids (24–29), six phenols (30–35), two glycosides (36–37), and one lignan (38). The chemical structures of these compounds were elucidated on the basis of spectral data and by comparisons of spectroscopic data with reported values in the literature. Compounds 18, 29, and 36–37 were the first to be reported in the family Rosaceae, compounds 10, 12, 15, 27–28, and 38 were firstly identified from the genus Sanguisorba, and compound 11 was obtained from S. officinalis for the first time. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Chemical constituents from the seeds of Raphanus sativus L. and their chemotaxonomic significance

The phytochemical investigations on the seeds of Raphanus sativus L. led to the isolation and identification of 15 compounds, including eleven sinapoyl derivatives (1–11), two terpenes (12–13), and two phenolic acids (14–15). All chemical structures were elucidated via ¹H NMR and ¹³C NMR spectroscopic methods, and further supported by comparison with literature data. Compound 11 was isolated from the genus Raphanus for the first time. Notably, Compounds 7, 9, and 12–14 were reported in the Brassicaceae family for the first time. The chemotaxonomic significance of these compounds is 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.     

Chemical constituents from Euphorbia hirta

Thirty-one compounds, including fourteen triterpenoids (1–14), seven coumarins (15–21), four lignans (22–25), and six diterpenes (26–31) were isolated from the aerial part of Euphorbia hirta. The structures were elucidated by spectroscopic methods and by comparison of their reported spectroscopic data. These compounds have shown the chemical relationships between this plant and other species from the genus Euphorbia.     

Chemical constituents from leaves of Cinnamomum subavenium

A new eudesmane sesquiterpene glycoside, 1α,6β-dihydroxy-5,10-bis-epi-eudesm-15-carboxaldehyde-6-O-β-d-Glucopyranoside (1), together with eleven known compounds (2–12) were isolated from the leaves of Cinnamomum subavenium Miq. Their structures were elucidated by a combination of spectroscopic data analysis and comparison with literature data. All compounds were isolated from C. subavenium for the first time. The chemotaxonomic significance of the isolated compounds was summarized.