Chemotaxonomic Significance Research Articles

Fortunefuroic Acid J from Keteleeria Hainanensis and its Dual Inhibitory Effects on ATP-Citrate Lyase and Acetyl-CoA Carboxylase.

A previously undescribed triterpenoid (fortunefuroic acid J, 1) was isolated from the endangered conifer Keteleeria hainanensis, along with 20 other known terpenoids. Compound 1 is characterized by an unusual 3,4-seco-9βH-lanost-3-oic acid motif, featuring a rare furoic acid moiety in its lateral chain. The structure elucidation of this compound was achieved through a combination of spectroscopic and computational methods. The C-15 epimers of 15-methoxypinusolidic acid (15R-8 and 15S-9) were successfully separated and identified for the first time. Compound 1 demonstrated dual inhibitory effects against ATP-citrate lyase (ACL, IC50: 0.92 μM) and acetyl-CoA carboxylase 1 (ACC1, IC50: 10.76 μM). Compounds 2 and 11 exclusively inhibited ACL, exhibiting IC50 values of 2.64 and 6.35 μM, respectively. Compound 1 is classified among the fortunefuroic acid-type compounds, previously isolated from K. fortunei, distinguished by the presence of a rare furoic acid moiety in their lateral chain. The chemotaxonomic significance of the 9βH-lanost-26-oic acids in Keteleeria was briefly discussed. These findings highlight the importance of conserving plant species diversity, thereby enhancing the exploration of structurally diverse compounds and potential avenues for developing new therapeutics targeting ACL/ACC1-associated diseases.

Chemical constituents from noni (Morinda citrifolia L.) fruit juice and their chemotaxonomic significance

Extensive phytochemical investigation on the noni juice, a globally renowned health beverage derived from the fermentation of noni (Morinda citrifolia L.) fruit in tropical regions, led to the discovery of a new coumarin glycoside, esculetin-7-O-β-d-glycopyranosyl-(1 → 6)-β-d-glucopyranoside (1), along with a new natural product (8), and eighteen known compounds: six coumarin derivatives (2–7), two alkaloids (9 and 16), six diketopiperazines (10–15), a furan derivative (17), and three lignans (18–20). The structures of these compounds were elucidated through extensive NMR and HRESIMS analysis. The NMR data of compounds 2 and 8 are reported comprehensively for the first time. The chemotaxonomic significance of the isolated compounds was also examined, highlighting their significance. Notably, compounds 1–4, 8–16, and 18 were being reported from the genus Morinda for the first time. These findings contribute to the growing understanding of the chemical diversity of noni juice.

Antimicrobial and anti-acetylcholinesterase activities of secondary metabolites isolated from Aspergillus fumigatus MNY-14

A systematic investigation of the secondary metabolites of Aspergillus fumigatus MNY-14, which was isolated from the ripe leaves of Achyranthes longifolia, led to the isolation of eighteen compounds, including twelve indole diketopiperazine alkaloids (1–12), an α-pyrone meroterpenoid (13), a nortriterpenoid (14), two benzophenones (15–16), and two quinoline alkaloids (17–18). Among them, compounds 8, 17 and 18 were isolated for the first time from A. fumigatus. The chemotaxonomic significance of the secondary metabolites was discussed. Some of the isolates (6, 10, 11, 10, 15 and 16) could be used as chemical markers for strain identification of this fungus. In addition, some of the isolates showed certain antimicrobial and acetylcholinesterase inhibitory activities.

Natural products and chemotaxonomic studies from the twigs of Neobalanocarpus heimii (King) P.S. Ashton (Dipterocarpaceae, Malvales)

Neobalanocarpus heimii is one of the toughest timbers in the world and resistant to termites and fungi. Phytochemical investigation from the twigs of N. heimii led to the isolation of eight resveratrol oligomers namely trans-resveratrol (1), (−)-ε-viniferin (2), balanocarpol (3), ampelopsin A (4), (+)-α-viniferin (5), vaticanol A (6), vaticanol B (7) and hopeaphenol (8). The structures of the isolated compounds were successfully elucidated using various spectroscopic techniques as well as comparison with the literature data. The chemotaxonomic significance of the isolated compounds was summarized, along with a compound-genus network analysis.

A novel normonoterpene glycoside and a new benzophenone derivative from Hypericum cerastioides and their in vitro cytotoxic activities

Phytochemical investigations on the aerial parts of Hypericum cerastioides led to the isolation and identification of a novel normonoterpene (1) and a previously undescribed benzophenone glycoside (3) along with eleven known secondary metabolites (2, 4–13). Their structures were deduced based on extensive 1D and 2D NMR analyses as well as HRESIMS. Compound 1 is a rare type of normonoterpene derivative with eight carbon atoms. The chemotaxonomic significance of the isolates was also discussed. Compounds were evaluated for their in vitro cytotoxic activities against SW480, A375, DU145 and MCF7 cancer cell lines using doxorubicin as a reference drug. Compounds 1 and 7 demonstrated weak cytotoxicity.

Chemical composition and neuroprotective activity of hemp seed aqueous extract and their chemotaxonomic significance

Fructus Cannabis (hemp seed) is important in food and traditional Chinese medicinal applications. Several studies have shown it has antioxidant, antiaging, anti-inflammatory, and neuroprotective properties. Studies have reported its anti-Alzheimer's disease effects. However, its active substances have not been defined, and little is known about the chemical constituents of the aqueous extract. The chemical profile of the aqueous extract of Fructus Cannabis (EFC) was obtained via isolation, structural identification, and qualitative and quantitative analyses. Twenty-seven compounds were identified, including seven nucleosides (1–7), five phenylpropanamides (8–11, and 24), three alkaloids (15, 16, and 26), two cyclic dipeptides (17 and 25), and one pyrimidine (19). Compounds 1, 3–7, 12, 14–19, and 21–27 were not reported previously in the Cannabis genus. Therefore, their chemotaxonomic significance is discussed. Neuroprotective activity screening revealed that EFC and the isolated compounds, particularly 9, 11, and 17, showed significant neuroprotective effects in PC12 ​cells (rat pheochromocytoma cells). The novel object recognition experiment and Nissl staining showed that EFC improved cognitive impairment in APP/PS1 mice and that EFC intervention reduced the number of senile plaques. These findings will contribute to the utility of Fructus Cannabis.

Chemical constituents from Croton lauioides Radcl.-Sm. & Govaerts and their chemotaxonomic significance

The phytochemical study of Croton lauioides Radcl.-Sm. & Govaerts led to the isolation of twenty-one compounds (1–21), including three diterpenoids (1–3), two triterpenoids (4–5), eight flavonoids (6–13), three lignans (14–16), four aromatic compounds (17–20), and one glycolipid (21). Their structures were determined by NMR spectroscopic analysis as well as comparison with previously reported data. All compounds (1–21) were isolated from C. lauioides for the first time, while twelve compounds 3, 5, 9–10, 12–18, and 21 were firstly isolated from the family Euphorbiaceae, and two compounds 2, and 20 were isolated from the genus Croton for the first time. Meanwhile, the chemotaxonomic significance of these isolated compounds from the whole plant of C. lauioides was also discussed.

Chemical constituents from the leaves of Scutellaria baicalensis Georgi and their chemotaxonomic significance

The phytochemical investigation of the Scutellaria baicalensis Georgi (S. baicalensis) leaves separation obtained two phenols (1, 2), one coumarin (3), thirteen flavones (4–16). Compounds 7–16 are valuable chemical classification markers in S. baicalensis leaves. Their structures were further determined by spectroscopic method in which compounds 1, 2, 5, and 6 have not yet been reported to be isolated from S. baicalensis, serving as chemical classification markers for S. baicalensis. Furthermore, compounds 1–3, 5, 6, 8 and 10 were successfully isolated from S. baicalensis leaves for the first time. The most important is that the significance of chemical taxonomy was discussed, which can provide theoretical principle on the separation of S. baicalensis leaves for subsequent research.

Chemical constituents of Acer tegmentosum Maxim and their chemotaxonomic significance

A phytochemical study of Acer tegmentosum Maxim (the dried stem bark of Acer tegmentosum Maxim) led to the isolation of 28 compounds, including thirteen phenols, five coumarins, four benzoate esters, three tetracyclic triterpenoids, one carbohydrate, one hydrocarbon and one lignan. The structures of these isolated compounds were identified using NMR spectroscopy (1H and 13C) by comparison with previously reported data. To the best of our knowledge, salidroside, 2-(4-Hydroxyphenyl)ethyl β-d-galactopyranoside, 2-(4-hydroxyphenyl)ethyl 3,4,5-trihydroxybenzoate, 3,3´,4,4´-tetrahydroxybiphenyl, (4-methoxyphenyl)acetic acid, daphnetin, 5,6,7-trimethoxycoumarin, 1,2-bis(2-methylheptyl) 1,2-benzenedicarboxylate, 1,4-benzenedicarboxylic acid, periplocoside N and 3,4-dimethoxycinnamyl alcohol were reported from this plant for the first time. Chemotaxonomic significance was discussed.

Alkaloids from the seeds of Peganum harmala and their chemotaxonomic significance

A phytochemical study on the seeds of Peganum harmala led to the separation of 22 alkaloids, including quinazoline alkaloids (1–10), β-carboline alkaloids (11–18), and others alkaloids (19–22). Their structures were identified by comprehensive spectroscopic analysis and comparison with literature data. Compounds 14 and 20–22 were first isolated from Zygophyllaceae family. Compounds 8 and 15 were firstly discovered as natural products. Moreover, the chemotaxonomic significance of the isolated alkaloids is discussed.

New terpenoids from Callicarpa nudiflora and their chemotaxonomic significance

The comprehensive phytochemical investigation of the Callicarpa nudiflora resulted in the isolation of a new labdane diterpenoid 16(R/S)-3,4-seco-11E,13E-labdien-15,16-olide-3-al (2), together with sixteen known compounds: two sesquiterpenoids (1R,3S,4R,5S,9S)-3,4-epoxy-5-hydroxy-8(13)-caryophyllen (1), and 4β,10α-aromadendranediol (3), eight labdane analogues (4–11), a pimarane-type diterpenoid (12), three flavonoids (13–15), and two lignans (16, and 17). The structures were elucidated by extensive NMR and HRESIMS analysis. This marks the first comprehensive report of the NMR data of compound 1, as well as the absolute configurations of compounds 1 and 3. The chemotaxonomic significance of the isolated compounds was also discussed. Compounds 1, 3, 14, 16, and 17 were being reported from the genus Callicarpa for the first time, while 3,4-seco-labdane diterpenoids 4–11 were previously obtained only from C. nudiflora.

Cytotoxicity and Chemotaxonomic Significance of Saponins from Wild and Cultured Asparagus Shoots.

The shoots of Asparagus L. are consumed worldwide, although most species belonging to this genus have a restricted range, and several taxa remain unstudied. In this work, a total of four taxa from different locations were scrutinized and compared with cultivated A. officinalis. All shoots were screened for saponins via LC-MS, and in vitro antiproliferative activities against the HT-29 colorectal cancer cell line were assessed via the MTT assay. The total saponins (TS) contained in the crude extracts ranged from 710.0 (A. officinalis) to 1258.6 mg/100 g dw (A. acutifolius). The richness of the compounds detected in this work stands out; a total of 47 saponins have been detected and quantified in the edible parts (shoots) of five taxa of Asparagus. The structure of all the saponins found present skeletons of the furostane and spirostane type. In turn, the structures with a furostane skeleton are divided into unsaturated and dioxygenated types, both in the 20-22 position. The sum of dioscin and derivatives varied largely among the studied taxa, reaching the following percentages of TS: 27.11 (A. officinalis), 18.96 (A. aphyllus), 5.37 (A. acutifolius), and 0.59 (A. albus); while in A. horridus, this compound remains undetected. Aspachiosde A, D, and M varied largely among samples, while a total of seven aspaspirostanosides were characterized in the analyzed species. The hierarchical cluster analysis of the saponin profiles clearly separated the various taxa and demonstrated that the taxonomic position is more important than the place from which the samples were acquired. Thus, saponin profiles have chemotaxonomic significance in Asparagus taxa. The MTT assay showed dose- and time-dependent inhibitory effects of all saponins extracts on HT-29 cancer cells, and the strongest cell growth inhibition was exercised by A. albus and A. acutifolius (GI50 of 125 and 175 µg/mL). This work constitutes a whole approach to evaluating the saponins from the shoots of different Asparagus taxa and provides arguments for using them as functional foods.

Phytochemical study of the leaves of Coelocaryon klainei Pierre ex Heckel (Myristicaceae)

The present study deals with the phytochemical study of the leaf extract of C. klainei, a plant used in folk medicine to treat diabetes, venereal diseases, hypertension, malaria, cough and hemorrhoids. The liquid-liquid extraction and chromatographic separation of the dichloromethane/methanol (1:1) extract of this plant led to the isolation of eleven (11) known compounds identified from the analysis of their spectroscopic and physical data, and in comparison, with data from the literature. These compounds were identified to hentriancontane (1), β-sitosterol (2), stigmasterol (3), β-amyrin (4), betulinic acid (5), sitosterol-3-O-β-D-glucopyranoside (6), diosmetin (7), iristectorigenin A (8), gallic acid (9), bergenin (10) and scyllitol (11) respectively. Furthermore, the chemotaxonomic significance of these compounds was discussed.

Monoterpenoid indole alkaloids from the stem barks of Voacanga africana and their chemotaxonomic significance

The phytochemical investigation of the stem barks of Voacanga africana resulted in the isolation of fifteen known monoterpenoid indole alkaloids (1–15). The structures of the alkaloids were determined by comparison of their physical and spectroscopic data with those reported in literature. Twelve of these metabolites (4–15) were previously unreported within the genus Voacanga, thus they can serve as chemotaxonomic markers for V. africana to differentiate between V. africana from other species of the genus Voacanga. The alkaloids 3-oxoconopharyngine (6), ervahainanmine (10), crassanine (14) and conolobine A (15) hold the potential to serve as chemical markers for distinguishing V. africana from other family species. Furthermore, compounds 3, 6, 10, 12 showed potential antimicrobial activities against Candida albicans and Bacillus subtilis with MIC values of 6.25–12.50 μg/mL.

Structurally diverse diterpenoids from the seeds of Caesalpinia minax Hance and their bioactivities

Eight previously undescribed diterpenoids, caesamins A–H (1–8), were separated and identified from the seeds of Caesalpinia minax Hance. Their structures were characterized by extensive spectroscopic data and X-ray crystallographic analysis. Structurally, caesamin A (1) is the first cassane-type diterpenoid with a C23 carbon skeleton containing an unusual isopropyl. Caesamin F (6) represents the first example of cleistanthane diterpenoid from the genus Caesalpinia. Caesamins B (2) and F (6) exhibited inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages with IC50 values of 45.67 ± 0.92 and 42.99 ± 0.24 μM, comparable to positive control 43.69 ± 2.62 μM of NG-Monomethyl-L-arginine. Furthermore, the chemotaxonomic significance of the isolates was discussed.

Flavonoids from Mimosa tenuiflora Green Propolis: Chemotaxonomy, Antioxidant, Anti‐Inflammation, Anti‐Bacteria, Mosquito Larvicidal Activity, and In Silico Approach

AbstractPhytochemical study of green propolis alcohol extract of Brazilian Caatinga Mimosa tenuiflora (Willd.) Poir resulted in the separation of six flavonoids, including quercetin 3‐methyl ether (1) and 3,3′‐O‐dimethylquercetin (2), and four flavanones eriodictyol 5‐O‐methyl ether (3), 5,4′‐dihydroxy‐6,7‐dimethoxyflavanone (4), licoflavanone (5), and macarangaflavanone B (6). All these metabolites were first isolated from green propolis and the genus Mimosa. Metabolites 3–4 also established chemotaxonomic significance since they had never been observed in the bean family Fabaceae. Flavones 1–2 showed strong antioxidative activity against DPPH (1,1‐diphenyl‐2‐picryl hydrazyl) radicals with IC50 values of 12.40 and 16.23 μg/mL, respectively. All six isolates showed anti‐inflammatory effects against NO (nitric oxide) production in LPS (lipopolysaccharide)‐stimulated Raw 264.7 cells, in which the activity of flavone 1 was better than the standard dexamethasone (IC50 13.35 μg/mL). Flavonoids 1–3 also strongly controlled the growth of the Gram‐positive bacteria Bacillus subtilis ATCC 6051, and Staphylococcus aureus ATCC 29213 with MIC values of 32–64 μg/mL. Six isolated flavonoids exhibited strong or moderate mosquito larvicidal activity against Aedes aegypti and Ae. albopictus fourth instar larvae with the 24 h LC50 values of 29.62–55.89 μg/mL. By in silico approach, compound 1 was a non‐toxic agent with an LD50 value of 5000 mg/kg.

A pair of cadinane-type sesquiterpene enantiomers and other chemical constituents from the whole plants of Chloranthus henryi

Continual phytochemical investigation on the whole plants of Chloranthus henryi Hemsl afforded fourteen compounds (1–14), including eight sesquiterpene monomers (1–8), four sesquiterpene dimers (9–12), a diterpene (13), and a simple coumarin (14). The structures of these compounds were assigned by means of spectroscopic techniques and ECD calculations. Compounds 1a and 1b are a pair of cadinane-type sesquiterpene enantiomers, while compounds 3–7 and 11–14 are isolated from C. henryi for the first time. Moreover, the chemotaxonomic significance corresponding to the aforementioned compounds was investigated.

Chemotaxonomic significance of catechin 7-O-beta-D-apiofuranoside in Ulmus species native to Asia

Ulmus davidiana has been used as food or medicine in oriental due to its safety, including its roots, bark, and fruits. The roots and bark of Ulmus were used as a diuretic and for treatment due to their anti-cancer, antioxidant, and anti-inflammatory effects. Ulmus species are known to contain flavan-3-ols as their main component. In previous research the presence of (+)-catechin 5-O-β-D-apiofuranoside was isolated from the roots of Ulmus davidiana, and (+)-catechin 7-O-β-D-xylopyranoside was confirmed in the bark Ulmus Americana, and the presence of catechin 7-O-β-D apiofuranoside in the stems and bark of Ulmus davidiana var. japonica. The catechin-glycosides of flavan-3-ols have various effects, including antiulcer properties, and have also been used as analgesics. Additionally, chemotaxonomy studies of the Ulmus species have been reported. However, the chemotaxonomy of Ulmus species native to Asia has not been reported. In this study, we report the screening of catechin 7-O-beta-D apiofuranoside from various Ulmus species native to Asia. We confirmed the presence of catechin 7-O-β-D-apiofuranoside in a total of 22 Ulmus samples, including 18 Ulmus species native to China, and 1 sample each from Mongolian, Nicaragua, Vietnam, and Korea through HPLC and LC-MS/MS analysis. We also confirmed the content of the indicator materials. Therefore, the potential of using native Ulmus species from Korea as a natural material has been confirmed.

Secondary metabolites from Penicillium chrysogenum WX6 and their chemotaxonomic significance

A strain of Penicillium chrysogenum, isolated from a volcanic area, was subjected to chemical analysis, leading to the isolation of fifteen compounds. Six compounds were isolated for the first time from this species, including the benzophenone derivative 1, pencillixanthone A (5), a pair of trichodimerol derivatives (7, 8), 4-epipenicillone (9), and the small pyrone 14. Several of the compounds were tested for antimicrobial properties; among them, the secalonic acid derivative (5) had significant antibacterial activity against five test strains, while the trichodimerol derivatives (8 and 9) and the anthranilate derivative 15 were reported to be active against four strains (S. aureus, S. mutans, P. fluorescens, M. catarrhalis) for the first time. In addition, this is the first time that haenamindole's antibacterial activity has been reported. The chemotaxonomic significance of the isolated compounds is discussed.

Pentacyclic triterpenoids as potential ACL inhibitors from the rare medicinal plant Semiliquidambar cathayensis

An extensive phytochemical investigation on the rare medicinal plant Semiliquidambar cathayensis (family: Hamamelidaceae) led to the isolation of four new (1–4, named semiliquidacids A–D, respectively) and 25 related known pentacyclic triterpenoids. The new structures with absolute configurations were elucidated by spectroscopic methods, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. Compound 1 represents the first naturally occurring ursane-type triterpenoid featuring an uncommon C-25 formyl group. Compound 4 and oleanolic acid (13) exhibited remarkable inhibitory effects against the ATP-citrate lyase (ACL, an emerging drug target for hyperlipidemia and related metabolic disorders) with IC50 values of 6.5 and 11.9 μM, respectively. The molecular interaction and binding mode between the bioactive triterpenoids and ACL were elaborated by conducting a molecular docking study. Meanwhile, the chemotaxonomic significance of the isolated triterpenoids has been briefly discussed.