Flavonoids and Isoflavonoids of Millettia dura and Millettia ferruginea: Phytochemical review and chemotaxonomic values

The phytochemical information on Millettia dura Dunn, M. ferruginea (Hochst.) Baker and M. ferruginea subsp. darassana (Cufod.) J.B. Gillett was reviewed. All the three taxa elaborate mainly isoflavones (33 reported), occurring in the flowers, seeds/seed pods, stem bark and root bark. Out of the 33 isoflavones reported, some 19 (ca. 58%) contain prenyl at C-8 or its modification as 2,2-dimethylchromene ring at C-7/C-8, occurring in all the three taxa. Except for three isoflavones isolated from M. ferruginea subsp. darassana, all the isoflavones of these taxa are 5-deoxygenated. In these taxa, oxygenation at C-6 is a common feature, while isoflavones with C-8 oxygenation are rare, only three reported, and all of these from M. dura. There are 7 rotenoids reported from these taxa, and occur almost entirely in the seeds/seedpods of these plants. The major rotenoid with methylenedioxy group at C-2/C-3, millettone and its 12a-hydroxy derivative, millettosine, occur only in M. dura, this appears to distinguish M. dura from M. ferruginea.     

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.     

Phytochemical and chemotaxonomic study on Dictamnus angustifolius G. Don ex Sweet (Rutaceae)

A phytochemical investigation of Dictamnus angustifolius led to the isolation of 14 compounds, including six furoquinoline alkaloids (1–6), two sesquiterpenoids (7, 8) and six flavonoids (9–14). The structures of these compounds were identified by spectroscopic methods and a comparison of their data with those reported in the literature. This is the first report of three furoquinoline alkaloids 1–3 and six flavonoids 9–14 from the genus Dictamnus and the first isolation of compounds 4–8 from D. angustifolius. The chemotaxonomic significance of furoquinoline alkaloids and sesquiterpenoids has also been summarized.     

Phytochemical and chemotaxonomic study on Dianella ensifolia (L.) DC

Phytochemical investigation of the roots of Dianella ensifolia led to the isolation of eleven known compounds, including two aromatics (1, 2), two chromones (3, 4), and seven flavonoids (5–11). The structures of these compounds were elucidated on the basis of spectral analysis and comparison with data reported in literature. In the present research, all of the isolated compounds 1–11 were reported for the first time in the species D. ensifolia. Compounds 1–4 and 7–11 were firstly isolated from the genus Dianella. Compounds 1, 2, 8, and 9 have not been reported from any species in Liliaceae family. The chemotaxonomic significance of the isolated compounds was summarized.     

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.     

Phytochemical investigation of Boscia angustifolia A. Rich. (Capparaceae)

Boscia angustifolia A. Rich. leaves were collected and subjected to a phytochemical investigation. Ten compounds; six flavonols, two coumarins, one methyl benzoate and one phthalate compound were isolated and identified for the first time from the studied taxa. Tamarixetin-3-O-β-sophoroside-7-O-methylether and rhamnocitrin-3-O-β-sophoroside are reported here as new natural compounds. The chemosystematic relationship between Boscia species is also discussed.     

Phytochemical investigation of Eremostachys moluccelloides Bunge (Lamiaceae)

Phytochemical investigation of the aerial parts of Eremostachys moluccelloides Bunge led to the identification of a new diterpene, 2β,14-dihydroxy −11-formyl- 12-carboxy-13-des-isopropyl-13-hydroxymethyl-abieta-8,11,13- triene- 16(17)- lactone (1), along with the known compounds 12, 18-dicarboxy-14-hydroxy-13-des -isopropyl-13-hydroxymethyl- abieta-8,11,13-triene-16(17)-lactone (2), 5-hydroxy-3′,4′,7-trimethoxyflavone (3), 5-hydroxy-4’,7-dimethoxyflavone (4), luteolin-7-O-β-glucoside (5), verbascoside (6), luteolin 7-O-(6″-O-β-D-apiofuranosyl) -β-D-glucopyranoside (7), chlorogenic acid (8), echinacoside (9), apigenin-7-O-β-D-glucoside (10), p-coumaric acid (11), vanillic acid (12), apigenin-7-O-(6″-E-p-coumaroyl)-β-D-glucopyranoside (13), apigenin-7-O-(3″,6″-E-p-dicoumaroyl)-β-glucoside (14), lamalbide (15), 6β-hydroxy-7-epi-loganin (16), phloyoside II (17) The structures were elucidated on the basis of 1D and 2D NMR spectroscopy, UV, MS and by comparison with compounds previously reported in the literature. Compounds 1–4, 8, 9, 11, 12, 14 have not been reported previously from any species within the genus Eremostachys. Compounds 1–14, 17 were obtained from this species for the first time. The chemotaxonomic significance of the isolated compounds is discussed.     

Phytochemical and chemotaxonomic investigation from the roots of Anemone vitifolia Buch.-Ham. (Ranunculaceae)

Phytochemical investigation from the roots of Anemone vitifolia Buch.-Ham. led to the isolation of eight compounds, including one triterpenoid saponin, two sugars, one coumarin, one amide, one saturated alkane, one olefin and one fatty acid. The structures of these metabolites were elucidated by spectroscopic data and comparisons with the data available in the literature. Among them, compound 7 ((6Z,9Z,12Z)-6,9,12-Eicosatriene) was isolated for the first time as a natural product. Furthermore, compounds 2 (D-(+)-raffinose), 3 (mixture of β-D-fructopyranose and β-D-fructofuranose) and 5 (bonaroside) were obtained from the Ranunculaceae family for the first time. Compounds 4 (siderin) and 6 (n-hexadecane) were isolated from A. vitifolia for the first time. The chemotaxonomic significance of the isolated compounds was discussed.     

Phytochemical investigation on the fruits of Camptotheca acuminata and their chemotaxonomic significance

A phytochemical investigation on the fruits of Camptotheca acuminata led to the isolation of 13 compounds, including five coumarins (1–5), two alkaloids (6 and 7), two triterpenoids (8 and 9), three lactones (10–12) and a sesquiterpene (13). The structures of these compounds were elucidated by extensive spectroscopic methods and comparion with literature data. All compounds were isolated from the Nyssaceae family for the first time. Additionally, it should be noted that this is the first report of coumarins in the C. acuminata. The chemotaxonomic significance of the isolated compounds was summarised.     

Phytochemical and biological investigation of Hymenocallis littoralis SALISB

A phytochemical investigation of the bulbs and flowers of Hymenocallis littoralis SALISB., cultivated in Egypt, was carried out, which resulted in the isolation of four alkaloids, lycorine (1), hippeastrine (2), 11-hydroxyvittatine (3), and (+)-8-O-demethylmaritidine (4), and of two flavonoids, quercetin 3'-O-glucoside (5), and rutin (6). The volatile constituents of the plant flowers were analyzed for the first time by GC/MS, which led to the identification of 26 known compounds (Table 1). Finally, the antimicrobial activity of the petroleum ether extract of the flowers of H. littoralis was investigated.     

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.     

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.     

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.     

Triterpenoids from Rosa odorata Sweet var. gigantea (Coll.et Hemsl.) Rehd.et Wils and their chemotaxonomic significance

Thirty-three reported compounds were obtained for the first time from Rosa odorata Sweet var. gigantea (Coll.et Hemsl.) Rehd. et Wils and were all identified as triterpenoids. The structure of these compounds was determined by physicochemical constants and spectral analyses (NMR, MS). This is the first report on four compounds (7, 9, 10 and 22) from the family Rosaceae and thirteen compounds (2, 3, 4, 11, 17, 19, 20, 23, 24, 26, 29, 31 and 33) from the genus Rosa. Finally, the chemotaxonomic significance of these compounds is discussed.     

Sesquiterpenoids and flavonoids from Pteris multifida Poir.

Phytochemical research of Pteris multifida Poir. led to the isolation of fifteen compounds, including six flavonoids (1–6) and nine sesquiterpenoids (7–15). Their structures were characterized by NMR, MS, ORD and CD data. Compounds kaempferol 3-O-α-L-rhamnoside-7-O-β-D-glucoside (1), myricetin 3-O-β-D-glucoside (2), kaempferol 3-O-β-D-glucoside (4), luteolin-7-O-β-D-rutinoside (5), quercetin-3-O-α-L-rhamnopyranoside (6), (2S,3S)-12-hydroxypterosin Q (7), (2S,3S)-pterosin Q (8), 2-hydroxypterosin C (9) and (2S)-12-hydroxypterosin A (10) were first isolated from P. multifida, and compounds 1–2 and 10 were first isolated from the family Pteridaceae. Furthermore, the chemotaxonomic significance of the isolates was discussed.     

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.     

Phytochemical and chemotaxonomic study on Saussurea medusa Maxim. (Compositae)

A phytochemical investigation of Saussurea medusa Maxim. led to the isolation of eleven compounds, including neoechinulin A (1), 8-hydroxypinoresinol (2), caruilignan D (3), 7(S)-hydroxyarctigenin (4), pinoresinol (5), arctigenin (6), arctii (7), epipinoresinol (8), loliolide (9), apigenin (10), and luteolin (11). Their structures were elucidated by spectroscopic methods and comparison with previously reported spectral data. Among them, compounds 1 and 2 were firstly obtained from this species, compounds 3 and 4 were isolated from the genus Saussurea for the first time. Furthermore, the chemotaxonomic significance of these compounds was discussed in details.     

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.