Chemical constituents from the fruits of Rhus typhina L. and their chemotaxonomic significance

This work describes the isolation and characterization of twenty-nine compounds from the fruits of Rhus typhina L., including eleven flavonoids (1–11), eleven phenols (12–22), two pentacyclic triterpenes (23–24), two organic acids (25–26), one lumichrome (27), one courmarin (28) and one pyrimidine (29) on the basis of their spectroscopic data. Compounds apigenin (1), daidzein (4), orobol (5), 3′, 5, 5′, 7-tetrahydroxyflavanone (6), naringenin (7), butein (8), (-)-catechin (9), quercetin-3-O-α-L-(3″-O-galloyl)-rhamnoside (11), 2-hydroxybenzoic acid (13), 4-hydroxybenzaldehyde (14), vanillin (15), methyl 3,4-dihydroxybenzoate (16), 3,5-dihydroxybenzamide (18), tyrosol (19), caffeic acid (20), 3-(2,4,6-trihydroxyphenyl)-1-(4-hydroxyphenyl)-propan-1-one (21), phlorizin (22), friedelin (23), oleanolic acid (24), 4,4-dimethyl-heptanedioic acid (25), anthranilic acid (26), lumichrome (27), scoparone (28) and uracil (29) have not been recorded before in this plant. This is the first report on the occurrence of compounds 4–7, 9, 11, 13–14, 16, 18–21, 25–29 from the genus Rhus. Moreover, the chemotaxonomic significance of these isolated compounds was also summarized.     

Alkaloids and monoterpenes from the leaves of Isatis tinctoria Linnaeus and their chemotaxonomic significance

Phytochemical investigation of the leaves of Isatis tinctoria Linnaeus led to the isolation of thirty compounds, including thirteen indole alkaloids (1–13), seven quinazolinone alkaloids (14–20), two quinoline alkaloids (21–22), one quindoline alkaloid (23), one simple amide alkaloid (24) and six monoterpenes (25–30). According to spectroscopic data analysis and comparison with the previously reported literature, their structures were elucidated. Among them, six compounds (12, 13, 17, and 22–24) have not been reported from the family Brassicaceae and eight compounds (3, 7, and 25–30) were isolated from the genus Isatis for the first time. Furthermore, the chemotaxonomic significance of isolated compounds has also been elaborated.     

Chemical constituents of Leucas zeylanica and their chemotaxonomic significance

Chemical study of the whole plant of Leucas zeylanica (L.) B. Br. has led to isolation of a new norditerpenoid isomer (1), along with 29 known compounds, including one norditerpenoid (2), three flavonoid glycosides (3–5), six flavonoids (6–11), two phytosterols (12–13), two phenylpropanoids (14, 19), two phthalate esters (15, 16), two phenolic compounds (17, 18), five terpenoids (20–24), one aliphatic glycoside (25), one nucleobase (26), one amino acid (27), two alkaloids (28–29), and one cytochalasin (30). The structures of these compounds were identified using NMR spectroscopic methods and comparing them with those previously reported. Twelve compounds (6, 15, 17–20, 22, 23, 26–29) were isolated for the first time from Leucas zeylanica and ten others (2, 4, 5, 7, 14, 16, 21, 24, 25, 30) from the Leucas genus. This study also discusses the chemotaxonomic relationships between Leucas zeylanica and other species of Leucas.     

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 Polygonum capitatum Buch-Ham. ex D. Don

This work describes the isolation and characterization of thirty-one compounds from Polygonum capitatum Buch-Ham. ex D. Don, including two triterpenes (1–2), ten flavonoids (7–16), nine lignans (17–25), nine phenolic compounds (4–7, 26–31) and one anthraquinones (3). Their structures were elucidated on the basis of various spectroscopic methods (UV, IV and NMR, including 2D experiments). It was the first report of compounds 13, 15, 17, 24, 25, 28, 29, 30, 31 from the genus Ploygonum, and the first report of compounds 13, 15, 17, 24, 25 from the family Polygonaceae.     

Phytochemical and chemotaxonomic study on Ficus tsiangii Merr. ex Corner

Thirty-four compounds, including ten coumarins (1–10), thirteen flavonoids (11–23), three triterpenoid, one lignanoid (24), seven triterpenes (25–31) and three other compounds (32–34), were isolated from the stems of Ficus tsiangii Merr. ex Corner (F. tsiangii). Their structures were identified as xanthyletin (1), coumarin (2), umbelliferone (3), isoangenomalin (4), dihydroxanthyletin (5), scopoletin (6), nodakenetin (7), 6,7-dihydroxy-coumarin (8), 4'-O-β- glucopyranosyl-3'-hydroxy-nodakenetin (9), 6-carboxy-umbelliferone (10), 5,7,4'-trimethoxy- 3'-hydroxy-aurone (11), apigenin (12), naringenin (13), genistein (14), luteolin (15), prunetin (16), chrysoeriol (17), 5,6,7,-trihydroxy-4'-methoxy-flavone (18), eriodictyol (19), isocarthamidin (20), 5,7,2',4'-tetrahydroxyflavone (21), taxifolin (22), dihydro-kaempferol (23), syringeresinol (24), taraxerol (25), taraxerone (26), lupeolacetate (27), 3-acetoxy-12- oleanene-11-ketone (28), 3-acetoxy-lup-12,20(29)-diene (29), oleanic acid (30), ursolic acid (31), 3,4,5-trimethoxy phenyl-1-O-glucopyranoside (32), 8'-hydroxyabscisic acid glucoside (33) and adenosine (34). Among them, all compounds except 3, 14, 17, 25, 26, 30, 33 were isolated from the plant for the first time, and compounds 1, 4, 5, 8–11, 16, 18, 20, 23, 24, 32, 34 were firstly reported from the genus Ficus. The chemotaxonomic significance of these compounds was summarized as follows.     

Chemical constituents of the Piper crocatum leaves and their chemotaxonomic significance

Chemical study of Piper crocatum leaves has led to isolation of a new megastigmane glucoside isomer (18), along with 23 known compounds including fifteen phenolic compounds (1–15), two monoterpenes (16 and 17), three sesquiterpenes (19–21), a phenolic amide glycoside (22), a neolignan (23), and a flavonoid C-glycoside (24). Structures of these compounds were identified via spectroscopic methods and compared with those reported in the literature. Seven compounds (7, 11, 13, 14, 17, 20, and 24) from the P. crocatum species and 17 others (1–6, 8–10, 12, 15–16, 18–19, and 21–23) from the Piper genus and Piperaceae family were isolated and reported for the first time. Furthermore, this study discusses chemotaxonomic relations between P. crocatum and other Piper species.     

Chemical constituents from the flower buds of Daphne genkwa (Thymelaeaceae)

Phytochemical investigation on the flower buds of Daphne genkwa led to the isolation of 22 compounds, including 17 daphne diterpenes (1–17), three tigliane types (18–20), and two diphenylpentanes (21–22). Compounds 19–21 were isolated from D. genkwa for the first time. These compounds were elucidated using spectroscopic methods and by comparing their data to those reported in the literature. On the basis of chemical research, the chemotaxonomic significance of the isolated compounds were 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 of the roots of Scorzonera divaricata and their chemotaxonomic significance

The phytochemical study of the roots of Scorzonera divaricata Turcz led to the isolation of 27 compounds, including eight sterols (1–8), one lignan (9), two cumarins (10, 11), five phenylpropanoids (12–16), six benzene derivatives (17–22), methyl-β-D-fructofuranoside (23), monolinolein (24), and three aliphatic acids (25–27). The structures of isolated compounds were identified using NMR and ESI-MS spectroscopic methods and comparing them with those previously reported. Except for β-daucosterol (8), scopoletin (10) and caffeic acid (16) from S. divaricata, this is the first report of the other 24 compounds from S. divaricata. Among them, eleven compounds (2–6, 11, 17, 19, 20, 23, 25) were reported from genus Scorzonera for first time, suggesting that they could be used to distinguish S. divaricata from the other species of Scorzonera. Furthermore, the chemotaxonomic significance of isolated compounds from S. divaricata 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.     

Chemical constituents from Dendropanax morbiferus H. Lév. Stems and leaves and their chemotaxonomic significance

The phytochemical investigation of Dendropanax morbiferus H. Lév. Led to the isolation of 28 known compounds: 4 alkaloids (1–4), 1 pyranoglucoside (5), 1 benzoic acid and 5 benzoic acid derivatives (6–11), 10 phenylpropanoids (12–21), 4 flavone glucoside derivatives (22–25), 1 neolignan (26) and 2 sesquiterpenes (27–28). The structures of these compounds were identified using spectroscopic methods; their nuclear magnetic resonance spectra were compared with those previously reported. This is the first report on compounds 2–4, 10, and 12 isolated from D. morbiferus. Compounds 5 and 26 from the genus Dendropanax and 1, 6–9, 11, 13, 14–25, 27 and 28 from the family Araliaceae were isolated for the first time. Additionally, to the best of our knowledge, this is the first comprehensive chemical investigation of D. morbiferus stems and leaf compounds. Chemotaxonomic relationship between D. morbiferus and other Dendropanax species is also discussed.     

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.     

Chemical constituents from the heartwood of Toxicodendron vernicifluum (Stokes) F.A. Barkley

A phytochemical investigation of the heartwood of Toxicodendron vernicifluum (Stokes) F.A. Barkley led to the isolation of twenty-five compounds, including sixteen flavonoids (1–15), one flavonolignan (16), one chromone (17), four benzoic acid derivatives (18–21), two triterpenes (22–23) and two sterols (24–25). The structures of these compounds were elucidated on the basis of spectroscopic analysis and comparison with previous literature data. Among them, 8 and 21were isolated from the genus Toxicodendron and 5, 9, 13, 17–20, 22 from the family Anacardiaceae for the first time. Furthermore, 21 had been identified only by LC/MS before. 20 was a synthetic product used as anthelmintics, newly identified as a natural product. Furthermore, the chemotaxonomic value of these isolates was also discussed in detail.     

Two new quinic acid derivatives from the fruits of Chaenomeles speciosa

Two new quinic acid derivatives (1, 2), together containing eighteen (3–20) known compounds, were isolated from the fruits of Chaenomeles speciosa. Spectroscopic methods and previous data retrieved from the literature were used to determine the chemical structures of the compounds. Among the compounds, quinic acid derivatives (3, 4, 6, 7), phenolic acid compounds (8, 10, 11) and catechin derivatives (18, 19, 20) were isolated for the first time from the family Chaenomeles. The chemotaxonomic significance of the compounds was also discussed.     

Phytochemical investigation on the roots of Juglans mandshurica and their chemotaxonomic significance

Phytochemical research of the roots of Juglans mandshurica Maxim. (Juglandaceae) verified 37 secondary metabolites, including thirteen diarylheptanoids (1–13), five naphthoquinones (14–18), five tetralones (19–23), three lignans (24–26), three phenols (27–29), two anthraquinones (30–31), two triterpenoids (32–33), two secoiridoids (34–35), one naphthalenyl glycoside (36), and one flavonoid (37). The chemical structures of these constituents were elucidated by NMR spectroscopy and compared with data from the literature. This is the first confirmation of the presence of ten compounds (6, 12, 16, 18, 24–26, 30, 32–33) isolated from the family Juglandaceae, two compounds (1 and 8) from the genus Juglans, and four compounds (27, 31, 34–35) from J. mandshurica. The isolation and chemotaxonomic significance of the metabolites from the roots of J. mandshurica were described in this study.     

Chemical constituents of Chimaphila japonica Miq

A phytochemical study of the whole plants of Chimaphila japonica Miq. led to the isolation of 23 compounds, including ten triterpenoids (1–10), six flavonoids (11–16), two sterols (17 and 18), two quinonoids (19 and 20), one saccharide derivative (21), one phenolic glycoside (22), and one megastigmane glycoside (23). The structures of these isolated compounds were identified using NMR spectroscopy (¹H and ¹³C) by comparison with previously reported data. All compounds, except 19 and 22, were reported from C. japonica for the first time. Among them, 16 compounds (1–4, 6–9, 12, 13, 15, 16, 18, 20, 21, and 23) were reported from genus Chimaphila for the first time, while compounds 12, 16, and 23 were isolated from the Ericaceae family for the first time. The chemotaxonomic significance of the isolates was also discussed.     

Chemical constituents from the fruits of Vitex trifolia L. (Verbenaceae) and their chemotaxonomic significance

One new labdane-type diterpenoid (1) named viterotulin D, along with twenty-three known compounds, including fourteen diterpenoids (2–15), one monoterpenoid (16), three steroids (17–19), one flavonoid (20), and four phenols (21–24) were isolated from the fruits of Vitex trifolia L. The structures of these compounds were identified based on spectroscopic data interpretation and comparison with previously reported values in the literature. This is the first report on the isolation of compounds (1, 6, 14, 15, 17, and 22) and (2, 9, and 10) from the family Verbenaceae and Vitex trifolia, respectively. The chemotaxonomic significant of the isolates was also discussed.     

Chemical constituents isolated from Clusia criuva subsp. Criuva and their chemophenetics significance

Clusia criuva belongs to the Clusiaceae family and it is endemic to the rupestrian fields in Chapada Diamantina National Park (Brazil). Phytochemical investigation of C. criuva trunks led to the isolation of five triterpenoids [winchic acid (1), betulinic acid (2), lupeol (3), friedelin (4), and friedelinol (5)], four steroids [lanosterol (6), stigmasterol (7), β-sitosterol (8), and sitostenone (9)], seven polyprenylated benzophenone derivatives [propolone A (10), propolone B (11), propolone C (12), propolone D (13), sampsonione B (14), hyperisampsin E (15), and hyperisampsin F (16)], four xanthones [neriifolone C (17), 6-deoxyisojacareubin (18), osajaxanthone F (19), and brasilixanthone B (20)], two biphenyls [aucuparina (21) and 2,2-dimethyl-5-hydroxy-7-phenylchromene (22)], and two tocotrienol derivatives [2Z- and 2E-δ-tocotrienoloic acids (23 and 24)]. Compounds 1, 11, 12, 15, and 16 were isolated for the first time in the Clusiaceae family, compounds 17, 19 and 21 were isolated for the first time in the genus Clusia, whereas 2–10, 13, 14, 18, 20, 22–24 were isolated for the first time in Clusia criuva. Compounds 1, 2, 11, 12, 13 and 15 showed potent in vitro cytotoxic activity against GL-15 glioblastoma-derived human cell line. Chemophenetics significance of these compounds is described herein.     

Chemical constituents from Ilex urceolatus

Twenty-four compounds were obtained from the extract of the leaves of I. urceolatus, which were divided into saturated fatty alcohols (1 and 2), triterpenoids (3–8 and 14–16), lignanoids (9, 20 and 22), coumarins (10 and 19), flavonoids (11–13, 21, 23 and 24) and others (17 and 18). Among them, compounds 1, 2, 17 and 18 were firstly obtained from the genus Ilex, others were isolated from this species for the first time. The chemotaxonomic relationships between I. urceolatus and other species of genus Ilex were also discussed. As a result, the isolated compounds closely matched the ones obtained in other species of the genus.