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 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.     

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 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.     

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.     

Phytochemical and chemotaxonomic study on Piper pleiocarpum Chang ex Tseng

The phytochemical study of Piper pleiocarpum Chang ex Tseng led to the isolation of eighteen compounds (1–18), including ten lignanoids, galbelgin (1), (+) sesamin (2), denudatin A (3), hancinone (4), (7S,8S, 3′R)-Δ^8'-3,3′,4-trimethoxy-3′,6′-dihydro-6′-oxo-7.0.4′,8.3′-lignan[(2S,3S,3aR)-2-(3,4-dimethoxyphenyl)-3,3a-dihydro-3a-methoxy-3-methyl-5-(2-propenyl)-6(2H))-benzofuranone] (5), (−)-(7R,8R)-machilin D (6), (1R,2R)-2-[2-methoxy-4-((E)-prop-1-enyl)phenoxy]-1-(3,4-dimethoxyphenyl)propyl acetate (7), piperbonin A (8), machilin D (9), 4-methoxymachilin D (10), one amide alkaloid, Δ^α,β-dihydropiperine (11), six polyoxygenated cyclohexenes, ent-curcuminol F (12), uvaribonol E (13), ellipeiopsol A (14), 1S,2R,3R,4S-1-ethoxy-2-[(benzoyloxy)methyl]cyclohex-5-ene-2,3,4-triol, 3-acetate (15), (+)-crotepoxide (16), (+)-senediol (17), and one benzoate derivative, 2-acetoxybenzyl benzoate (18). Their structures were established by spectroscopic data and by comparison with the literature. All the compounds were firstly isolated from P. pleiocarpum, while ten compounds 6–7, 9–10, 12–15, 17–18 were isolated from the genus Piper and the family Piperaceae for the first time. The chemotaxonomic significance of these compounds was also discussed. The isolation of compounds 6–7, 9–10 may be used as chemotaxonomic markers for the genus of Piper.     

Phytochemical and chemotaxonomic studies on Dioscorea collettii

A chemical investigation of Dioscorea collettii led to the isolation of twenty-nine compounds, including six steroid saponins (1–6), thirteen monocyclic phenols (7–19), two flavonoids (20–21), three sterols (22–24), and five cyclodipeptides (25–29). The chemical structures of these compounds were elucidated using spectroscopic methods and by comparing their data to that reported in the literature. This study is the first report of compounds 2–4, 7, 14–17, 21, and 23–24 in D. collettii, while compounds 8–13, 18–20, and 25–29 were first isolated from the genus Dioscorea and the family Dioscoreaceae. The chemotaxonomic significance of the isolated compounds is 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 from the whole plants of Sedum sarmentosum Bunge and their chemotaxonomic significance

Phytochemical study of the whole plants of Sedum sarmentosum Bunge (Crassulaceae) led to the isolation of thirty-six constituents, including sixteen megastigmanes (1–16), seven sterols (17–23), five lignans (24–28), three triterpenoids (29–31), three phenols (32–34), one flavonoid (35), and one glycoside (36). The chemical structures of these metabolites were elucidated by NMR spectroscopy and compared with literature data previously reported. This is the first confirmation of the presence of eleven compounds (4, 15, 16, 18, 19, 22, 24–26, 28, 32) isolated from the family Crassulaceae, one compound (3) from the genus Sedum, and two compounds (17 and 33) from S. sarmentosum. Furthermore, the chemotaxonomic significance of these ingredients from the whole plants of S. sarmentosum were discussed in detail.     

Phytochemical and chemotaxonomic study on the Lichen Lethariella cladonioides

The comprehensive phytochemical research of Lethariella cladonioides (Nyl.) Krog, (Parmeliaceae), a lichen in southwest China, resulted in isolation of eighteen compounds (1–18), including a new phenolic acid 3,5-dihydroxy-4-methylbenzaldehyde (1) and seventeen known compounds, nine phenolic acids (2–10), one dibenzofuran (11), two depsides (12 and 13), one alkane (14), one glucoside (15), two polyols (16 and 17), and one fatty acid (18). The structures of these compounds were assigned by detailed interpretations of spectroscopic data (1D and 2D NMR, HR-ESI-MS) and comparisons with the published data. Among them, 3,5-dihydroxy-4-methylbenzaldehyde (1) is a new one. (−)-hydroxypropan-2′,3′-diol-orsellinate (10) have not been reported from any species in the lichens. Compounds 6, 7, 9, 12, 14, 16 and 18 were firstly isolated from the genus Lethariella (Motyka) Krog. Compounds 2, 6, 7, 9, 10, 12, 14, 16 and 18 were reported from L. cladonioides firstly. The chemotaxonomic significance of these compounds was also discussed.     

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.     

Sesquiterpenoids from Saussurea laniceps and their chemotaxonomic significance

Twenty-five sesquiterpenoids including seventeen guaiane-type sesquiterpenoids and glucose glycosides (1–17), six eudesmane-type sesquiterpenoids (18–23), and two germacrane-type sesquiterpenoids (24 and 25) were isolated from the aerial parts of Saussurea laniceps Hand.-Mazz. Their structures were elucidated by spectroscopic methods and comparison with previously reported spectral data. Among them, compounds (6 and 8) are new, and seven compounds (2, 9, 12, 18–19, 22–23) are reported for the first time from the genus Saussurea. This paper deals with the isolation, structural elucidation and chemotaxonomic significance of these sesquiterpenoids from S. laniceps.     

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.     

Phytochemical and chemotaxonomic studies on Pteris wallichiana J. Agardh

A systematic phytochemical investigation of Pteris wallichiana J. Agardh resulted in the isolation of twenty compounds, including five sesquiterpenes (1–5), six flavonoids (6–11), seven phenolic acids (12–18) and two fatty acids (19 and 20). Their structures were deduced from MS, NMR and ORD data. This is the first report of compounds dehydropterosin B (2), (2R,3S)-pterosin C (4), (2R,3R)-pterosin L (5), apigenin (6), luteolin (7), luteolin-7-O-glucoside (10), caffeic acid (13), vanillin (14), 3,4-dihydroxybenzaldehyde (15), chlorogenic acid (17), 3,5-dicaffeoylquinic acid (18), suberic acid (19) and azelaic acid (20) from P. wallichiana and of compounds 15, 19 and 20 from the family Pteridaceae. Furthermore, a chemotaxonomic study of the isolates was performed.     

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.     

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 Chonemorpha griffithii

Chemical investigation of the aerial part of Chonemorpha griffithii has led to the isolation of 20 compounds, comprising six lignans (1–6), six triterpenoids (7–12), four phenolic acids (13–16), two flavonoids (17 and 18), one cyclitol (19) and one aliphatic acid (20). Among them, 5′-methoxy-7′-oxomatairesinol (1) was identified to be a new lignan. It is the first report of the presence of those compounds in this genus. Two 24-methyl-29-norcycloartane triterpenoids (10 and 11) were considered as the chemotaxonomic markers for the species C. griffithii.     

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.     

Chemical constituents of Bulbophyllum wendlandianum (Kraenzl.) Dammer and their chemotaxonomic significance

Phytochemical investigation of Bulbophyllum wendlandianum (Kraenzl.) Dammer led to the isolation of twenty-three compounds 1–23 (flavanthrinin 1, coelonin 2, lusianthridin 3, densiflorol B 4, plicatol B 5, batatasin-lll 6, gigantol 7, 5-hydroxy-3,3′-dimethoxy-2-(p-hydroxybenzyl) bibenzyl 8, 2,2-dimethyl-5-hydroxy-6-carboxy-7-(2-phenylethyl) 9, tristin 10, p-hydroxybenzyl ethyl ether 11, p-hydroxybenzaldehyde 12, hydroquinone 13, coniferaldehyde 14, p-hydroxybenzyl alcohol 15, 3,4-dihydroxy benzaldehyde 16, stigmasterol 17, β-sitosterol 18, ergosterol peroxide 19, (+)pinoresinol 20, n-butyl sulfoxide 21, tridec-4E-en-l-yl acetate 22, ethyl linolate 23) including five phenanthrenes 1–5, five bibenzyls 6–10, six phenols 11–16, three sterols 17–19, one lignan 20, one n-butyl sulfoxide 21 and two fatty acids 22–23. The structures of these compounds were elucidated by spectroscopic analyses. This is the first report of isolation of compounds 1–23 from Bulbophyllum wendlandianum and compounds 8–9, 11, 13, 15–16 and 19–23 within genus Bulbophyllum. Compound 21 is a new natural product, isolated from a natural source for the first time. Furthermore, the chemotaxonomic significance of the isolates was also discussed.