Chemotaxonomic Significance Research Articles

Chemical constituents from the whole plant of Odontites vulgaris Moench and their chemotaxonomic significance

A phytochemical investigation of the whole plant of Odontites vulgaris Moench led to the isolation and characterization of 40 compounds, including ten terpenoids (1–10), seven sterols (11–17), seven flavonoids (18–24), five phenols (25–29), five lipids (30–34), four lignans (35–38), one alkaloid (39), and one benzensulfonic acid (40). The structures of isolated compounds were elucidated by interpretation of their NMR spectroscopic data and comparison with reported ones in the literature. This is the first confirmation of the presence of twenty-one compounds (2, 5, 6, 9–14, 17, 24, 27, 30–35, 38–40) isolated from the family Orobanchaceae, nine compounds (7, 8, 16, 22, 23, 25, 29, 36, 37) from the genus Odontites, and three compounds (3, 4, 15) from O. vulgaris. Furthermore, the chemotaxonomic significance of these constituents from the whole plant of O. vulgaris were also summarized.

Xanthone derivatives from Cratoxylum formosum (Jack) Dyer subsp. pruniflorum (Kurz) Gogelin and their chemotaxonomic significance

The phytochemical investigation of the stems of Cratoxylum formosum (Jack) Dyer subsp. pruniflorum (Kurz) Gogelin led to the isolation of a new xanthone derivative cratoxanthone (1), together with seven known biogenetically related xanthone derivatives (2–8). The structures of these compounds were elucidated using comprehensive spectroscopic methods. All compounds were isolated from C. formosum for the first time. The chemotaxonomic significance of the isolates was also discussed.

Chemical constituents with chemotaxonomic value from Asparagus lycopodineus (Baker) Wang et Tang

Asparagus lycopodineus (Baker) Wang et Tang (Asparagusate) is a perennial herbaceous plant that is used medically in China. In the current study, A. lycopodineus was phytochemically studied for the first time, which led to the isolation of fourteen compounds, including nine steroids (1-9), four lignans (10-13), and one flavone (14). Among them, five compounds (1, 3, 4, 13, and 14) have never been found in the Asparagus genus before. The chemotaxonomic significance of the isolated compounds was discussed based on the results combined with literature analysis. Some of the isolates, such as aspafilioside A (8), 3′-hydroxy-4′-methoxy-4-dehydroxynyasol (11), and (+)-syringaresinol (12), showed a narrow distribution in the Asparagus genus, which might serve as unique chemotaxonomic metabolites for the identification of A. lycopodineus. In addition, the results also highlight the close evolutionary relationship among A. lycopodineus, A. cochinchinensis and A. filicinus.

Chemical constituents of the leaves of Coriaria nepalensis and their chemotaxonomic significance

Phytochemical investigation of the leaves of Coriaria nepalensis led to the isolation of fourteen compounds, including five sesquiterpenoids (1–5), two oleanane-type triterpenoids (6, 7), one cycloartane triterpenoid (8), one phytosterol (9), one diterpenoid (10), two α-tocopheroids (11, 12), and two vitamins (13, 14). These structures were elucidated on the basis of 1D and 2D NMR spectra (COSY, HSQC, HMBC, and NOESY) and HRESIMS data. To the best of our knowledge, compounds 2, 3, 5, 7, 8, 11, 12, and 14 are reported from the Coriariaceae family for the first time, and compound 4 was isolated only from the Coriariaceae family. Importantly, compound 1 was identified as a new sesquiterpenoid. Furthermore, chemotaxonomic significance of these isolates was also discussed.

A new diterpenoid and other chemical constituents from the stem bark of Sapium ellipticum and their chemophenetic significance

A chemical study of the stem bark extract of Sapium ellipticum (Hochst.) Pax led to the isolation of a total of fourteen compounds including one new diterpenoid, sapiumic acid (1) together with thirteen known derivatives (2–14). Their structures were determined by spectroscopic analysis and, by comparison of their spectral data with those of related compounds in the literature. Extracts and fractions were assessed in vitro against some resistant bacterial strains. Fraction C of the ethyl acetate was the most active one among all of the tested samples against Pseudomonas agarici DSMZ 11810 with a MIC value of 58.6 μg mL−1. The chemotaxonomic significance of the obtained compounds was also discussed.

Chemical constituents from Mytilaria laosensis Lec. leaves and branches

Phytochemical investigations on the leaves and branches of Mytilaria laosensis Lec. led to the isolation of eight compounds, including four ecdysteroids (1-4), three flavonoids (5–7), and one phenylpropanoid (8). The identification of isolated compounds was achieved on the basis of NMR data, mass spectral data, and comparison with previous literature data. These eight compounds were isolated from M. laosensis for the first time. In addition, compounds 1–4 and 8 were found for the first time in the Hamamelidaceae family. Furthermore, the metabolite profiling of ethyl acetate and n-butanol fractions of M. laosensis were also measured by using liquid chromatography coupled with ion trap and time of flight mass spectrometry (LCMS-IT-TOF). The results of LCMS-IT-TOF analysis showed that this plant has other ecdysteroids and glycosides besides the eight isolated constituents. The chemotaxonomic significance of these compounds was discussed.

Chemical constituents from Mallotus tetracoccus (Roxb.) Kurz (Euphorbiaceae) and their chemotaxonomic significance

The phytochemical investigation of the leaves and twigs of Mallotus tetracoccus (Roxb.) Kurz led to the isolation of nineteen compounds, including four lignans (1–3, 18), three flavonoids (4–6), four kaurane diterpenes (7–10), two sesquiterpenes (11–12), four phenols (13–16), one fatty acid (17), and one triterpene (19). Their structures were elucidated by spectroscopic analyses and published data to determine the chemical constituents of the Mallotus tetracoccus (Roxb.) Kurz, which are reported here for the first time. The compounds 3, 7–9, 11–14, 16–18 were reported from the family Euphorbiaceae, and the compounds 3, 4, 5, 7–9, 11–14, 16–18 were the reported from the genus Mallotus for the first time. Meanwhile, the chemotaxonomic significance of these compounds was discussed.

Phytochemical and chemotaxonomic study on Atractylodes lancea

Based on previous studies on Atractylodes lancea (Thunb.) DC., this paper focuses on the chemical composition of fresh rhizome of Atractylodes lancea. And fifteen compounds were isolated, including six guaiane-type sesquiterpenoids (1–5), one eudesmane-type sesquiterpenoid (6), one monoterpene glycoside (7), one polyacetylene glycoside (8), one phenylpropanoid glycoside (9), two nucleosides (10–11), one alkaloid (12), one amino acid (13), one purine (14) and one fatty acid (15). The structures of the isolated compounds (1–15) were elucidated by 1H and 13C NMR spectroscopic analyses and comparisons with previously reported data. Compounds 7 and 12 were isolated from the Compositae family for the first time. Compound 11 was isolated from genus Atractylodes for the first time. Compound 14 was isolated from this plant for the first time. Furthermore, the chemotaxonomic significance of these isolates was discussed.

Phytochemical investigation on the roots of Piper nigrum Linn. and the chemotaxonomic significance

Phytochemical investigation into the roots of Piper nigrum Linn. led to the isolation of ten compounds, including six lignans (1–6), two aromatic compounds (7–8), one lactone (9), and one sesquiterpenoid (10). Compounds 1, 2, 4, 7, 8, 9, and 10 were isolated from Piperaceae for the first time. The structures of these compounds were elucidated by comprehensive spectral methods, including UV, NMR, CD, optical rotation and other spectroscopy methods. The chemotaxonomic significance of isolated compounds was also elucidated.

Chemical constituents from Potentilla kleiniana and their chemotaxonomic significance

Phytochemical study of Potentilla kleiniana gave one C21 steroidal glycoside (1), seven ellagic acid derivatives (2–8), five flavonoids (9–13), one alkaloid (14), one nucleoside (15), one aromatic aldehyde (16), one aromatic ketone (17), one phenylacetic acid derivative (18), one phenolic acid (19), one phenolic acid derivative (20), and one dehydrodiconiferyl alcohol derivative (21). The chemical structures of these compounds were elucidated based on spectroscopic methods and comparison with reported data. Among them, compound 1 was a new compound, and compounds 3–4, 7–18, 20–21 were first reported from this plant. Moreover, the chemotaxonomic significance of the isolated compounds from the whole plants of P. kleiniana has been discussed in detail.

Metabolic Characterization of Four Members of the Genus Stachys L. (Lamiaceae)

Several members of Stachys L. (among the largest Lamiaceae genera) have been traditionally used as medicinal plants. With 54 Stachys taxa (species and subspecies) occurring in mainland and/or insular Greece, the present study aimed to investigate the metabolic profiling of four range-restricted local Stachys members: Stachys candida and S. chrysantha (protected and endangered local Greek endemics), S. leucoglossa subsp. leucoglossa (local Balkan endemic), and S. spinulosa (local Balkan subendemic). In this investigation, the infusions of their above-ground parts were characterized using NMR and HPLC-PDA-MS techniques. Thus, 1D- and 2D-NMR spectra were obtained to compare the chemical fingerprints of these plants. Furthermore, previously isolated compounds from Stachys spp. were used to identify specific constituents. NMR screening revealed the presence of: (i) phenylethanoid glycosides, mainly acteoside in S. candida and S. chrysantha (section Candida, Swainsoniana phyloclade), and (ii) flavone 7-O-allosylglucoside (isoscutellarein 7-O-[6‴-O-acetyl-β-D-allopyranosyl]-(1→2)-β-D-glucopyranoside) and iridoids (monomelittoside or/and melittoside) in S. leucoglossa subsp. leucoglossa (section Olisia, Swainsoniana/Olisia phyloclade, Swainsoniana phyloclade) and caffeoylquinic acid (chlorogenic acid) in S. spinulosa (section Campanistrum, Stachys phyloclade). In total, 26 compounds were detected by HPLC-PDA-MS belonging to flavonoids, phenylethanoid glycosides, and phenolic acids. Among them, chlorogenic acid was identified in all samples as one of their main metabolites. The present study complements previous studies with first reports of constituents detected in the studied taxa, reports for the first time on the metabolic characterization of S. spinulosa, and discusses the chemotaxonomic significance of such findings.

Distinctive Arbutin-Containing Markers: Chemotaxonomic Significance and Insights into the Evolution of Proteaceae Phytochemistry.

Natural products isolation studies of eight endemic Tasmanian Proteaceae species - Agastachys odorata, Persoonia juniperina, Hakea megadenia, Hakea epiglottis, Orites diversifolius, Orites acicularis, Orites revolutus, and Telopea truncata - and three endemic Australian Proteaceae species Banksia serrata, Banksia praemorsa, and Banksia marginata were undertaken. Two previously unreported glycoside-derived natural products were identified, in addition to four other tremendously rare arbutin esters. The results of this study provide further evidence consistent with the proposal that these distinctive arbutin esters represent markers that can provide valuable insights into the chemical evolution of plant species within the family Proteaceae.

Chemical Characterization and Chemotaxonomic Significance of Essential Oil Constituents of Matricaria aurea Grown in Two Different Agro-Climatic Conditions.

A comprehensive study on chemical characterization of essential oil (EO) constituents of a rarely explored plant species (Matricaria aurea) of the Asteraceae family grown in Saudi Arabia and Jordan was carried out. Analyses were conducted employing gas chromatographic approaches such as GC-MS, GC-FID, and Co-GC, as well as RT, LRI determination, and database and literature comparisons, on two diverse stationary phase columns, which led to the identification of a total of 135 constituents from both EOs. Oxygenated sesquiterpenes were found to be the most predominant chemical class of Saudi M. aurea EOs, in which α-bisabolol (27.8%), γ-gurjunenepoxide (21.7%), (E, E)-α-farnesene (16.3%), and cis-spiroether (7.5%) were present as major components. In contrast, the most dominant chemical class of Jordanian M. aurea oil was found to be sesquiterpene hydrocarbons, where (E, E)-α-farnesene (50.2%), γ-gurjunenepoxide (8.5%), (E)-β-farnesene (8.1%), and (Z, E)-α-farnesene (4.4%) were detected as chief constituents. It is interesting to mention here that Saudi and Jordanian M. aurea EOs showed quite interesting chemical compositions and were found to have different chemotypes when compared to previously reported M. aurea EO compositions.

Phytochemical investigation on the roots of Bupleurum chinense DC. and their chemotaxonomic significance

Twenty-two compounds were isolated from Bupleurum chinense DC. They included five phenylpropanoids (1–5), one phenylpropanol glucoside (6), six coumarins (7–12, compound 12 is a coumarin glycoside), six flavonoids (13–18), one triterpene saponin (19), one fatty acid ester (20), one fatty acid (21), and one sterol (22). Their structures were determined using 1D and 2D NMR spectroscopy and compared with previously published structures. The results showed that compounds 2, 4, 16, and 18, were first isolated from Umbelliferae; compounds 1, 7, 9, 10, and 12 were first isolated from the genus Bupleurum; and compounds 11, 15, and 17 were first isolated from B. chinense DC. Their chemotaxonomic significance has also been discussed.

Chemical constituents from Vitex negundo var. cannabifolia (Sieb. et Zucc.) Hand.-Mazz. (Lamiaceae) and their chemotaxonomic significance

Vitex negundo var. Cannabifolia (Sieb. et Zucc.) Hand.-Mazz. leaves and twigs were used to isolate a new phenyldihydronaphthalene-type lignan (1) along with twenty known compounds. Comprehensive spectroscopic techniques such as UV, IR, NMR, HR-ESI-MS, ORD and ECD were used to identify their structures. Quantum chemical computations were used to assign the absolute configurations (AC) of (1). Using DP4+ analysis, the computed chemical shifts were used to pinpoint relative configuration. Compounds (1–6) were tested for biological activities. Compound (5) significantly decreased the release of lactate dehydrogenase (LDH) by 38% at a concentration of 10 μM, demonstrating that compound (5) had significant anti-inflammatory effects on the activation of the NLRP3 inflammasome, while no compound was found potent at a concentration of 200 μM against tyrosinase. Additionally, the chemotaxonomic significance of the isolated compounds was studied.

Phytochemical and chemotaxonomic studies on Pteris plumbea Christ

A phytochemical investigation on Pteris plumbea Christ led to the isolation of 19 compounds, including four diterpenoids (1–4), five sesquiterpenoids (5–9), eight flavonoids (10–17), and two lignans (18–19). The chemical structures of these compounds were elucidated by ORD, CD, MS, and NMR data. All of them were found from P. plumbea for the first time. Noticeably, compounds diosmetin (10), genkwanin (11), luteolin-7-O-rhamnoside (16), genistein 7-O-gentiobioside (17), and (+)-medioresinol (19) have not been reported from the family Pteridaceae. Meanwhile, the chemotaxonomic significance of the isolated compounds was summarized.

Chemical constituents of Pteris ensiformis from Guizhou

The phytochemical investigation of Pteris ensiformis from Guizhou has resulted in the isolation of 15 phenolic compounds (1–15), including kaempferol-3-O-glucoside (1), kaempferol-3-O-rhamnoside (2), kaempferol-4′,7-dimethyl ether-3-O-glucoside (3), apigenin-7-O-glucopyranoside (4), diosmetin-7-O-glucoside (5), esculetin (6), 4-methoxycinnamic acid (7), (+)-pinoresinol (8), bockioside B (9), 7-O-caffeoyl-hydroxymaltol-3-O-glucopyranoside (10), cylindol B (11), salicylic acid (12), vanillin (13), vanillic acid (14) and catechol (15). The structures of these compounds were determined based on the analysis of spectroscopic data and comparison with the data reported in literatures. Compounds 1–9, 11–15 were isolated from P. ensiformis for the first time. In addition, the chemotaxonomic significance of the isolated compounds was discussed.

Secondary metabolites with chemotaxonomic value from Paecilomyces marquandii

A systematic investigation on the secondary metabolites of Delphinium-associated fungus Paecilomyces marquandii afforded eight compounds, including six sorbicillinoid polyketides (1–6) and two ergosterol sterols (7–8). Among them, six compounds (1–5, 8) were identified for the first time from the genus Paecilomyces, and seven compounds (1–5, 7–8) have not previously been found in the fungus P. marquandii. The chemotaxonomic significance of these compounds was discussed. Some of the isolates (2, 5, and 6) showed limited distribution and could serve as chemotaxonomic markers to facilitate strain identification of P. marquandii.

Phytochemical and chemotaxonomic investigations on the aerial parts of Artemisia halodendron Turcz. ex Bess

Phytochemical research on the aerial parts of Artemisia halodendron Turcz. ex Bess. (Asteraceae) resulted in the isolation of 57 compounds, which could be subdivided into 26 flavonoids (1–26), 8 phenylpropanoids (27–34), 7 phenols (35–41), 5 polyacetylenes (42–46), 5 terpenoids (47–51), 4 benzofurans (52–55), and 2 sterols (56 and 57). The chemical structures of these metabolites were elucidated by NMR spectroscopy and compared with previously reported literature data. This is the first confirmation of the isolation of 7 compounds (25–26, 29, 34, 50–51, and 57) from the family Asteraceae, 6 compounds (17, 19, 21, 24, 30, and 56) from the genus Artemisia, and 18 compounds (1, 3, 5, 7, 12, 15–16, 22–23, 31–33, 40, 42, 46, 48–49, and 52) from A. halodendron. The chemotaxonomic significance of these compounds is discussed in detail.

Chemical constituents from the leaves of Callicarpa arborea Roxb. and their chemotaxonomic significance

A new diterpene (3R,5S,8S,9R,10R)-3-hydroxycleroda-4(18),13(14)-dien-15,16-olide (1), as well as ten known compounds (2–11), were isolated from Callicarpa arborea Roxb. The structure of Compound 1 was determined based on spectroscopic (mainly 1H-NMR, 13C-NMR, HSQC, and HMBC) and spectrometric methods (HR-ESI-MS). With the exception of compounds 3–7, all compounds were isolated from Callicarpa arborea Roxb. for the first time, and their chemotaxonomic significance was discussed. At concentrations greater than 100 μM, compound 1 exhibited significant toxicity towards RA-FLSs.