scholarly journals Biologically Active Secondary Metabolites from Asphodelus Microcarpus

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Mohammed M. Ghoneim ◽  
Guoyi Ma ◽  
Atef A. El-Hela ◽  
Abd-Elsalam I. Mohammad ◽  
Saeid Kottob ◽  
...  
Keyword(s):  
Mammalian Cells ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Biologically Active ◽  
Naphthoic Acid ◽  
Bioassay Guided Fractionation ◽  
Resistant Strains ◽  
Asphodelus Microcarpus ◽  
First Time

Bioassay guided fractionation of the ethanolic extract of Asphodelus microcarpus Salzm.et Vivi (Asphodelaceae) resulted in the isolation of one new metabolite, 1,6-dimethoxy-3-methyl-2-naphthoic acid (1) as well as nine known compounds: asphodelin (2), chrysophanol (3), 8-methoxychrysophanol (4), emodin (5), 2-acetyl-1,8-dimethoxy-3-methylnaphthalene (6), 10-(chrysophanol-7’-yl)-10-hydroxychrysophanol-9-anthrone (7), aloesaponol-III-8-methyl ether (8), ramosin (9) and aestivin (10). The compounds were identified by 1D and 2D NMR and HRESIMS. Compounds 3, 6 and 10 were isolated for the first time from this species. Compounds 3 and 4 showed moderate to weak antileishmanial activity with IC50 values of 14.3 and 35.1 μg/mL, respectively. Compound 4 exhibited moderate antifungal activity against Cryptococcus neoformans with an IC50 value of 15.0 μg/mL, while compounds 5, 7 and 10 showed good to potent activity against methicillin resistant Staphylococcus aureus (MRSA) with IC50 values of 6.6, 9.4 μg/mL and 1.4 μg/mL respectively. Compounds 5, 8 and 9 displayed good activity against S. aureus with IC50 values of 3.2, 7.3 and 8.5 μg/mL, respectively. Compounds 7 and 9 exhibited a potent cytotoxic activity against leukemia LH60 and K562 cell lines. Compound 10 showed potent antimalarial activities against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum with IC50 values in the range of 0.8-0.7 μg/mL without showing any cytotoxicity to mammalian cells.

scholarly journals A Synthetic Butenolide Diterpene is now a Natural Product Isolated from Metaporana sericosepala, a Plant from the Madagascar Dry Forest [1a]

2015 ◽  
Vol 10 (9) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Christopher C. Presley ◽  
L. Harinantenaina Rakotondraibe ◽  
Peggy J. Brodie ◽  
Martin W. Callmander ◽  
Richard Randrianaivo ◽  
...  
Keyword(s):  
Natural Product ◽  
Ovarian Cancer Cell Line ◽  
Cancer Cell Line ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Dry Forest ◽  
Synthetic Compound ◽  
Nmr Data ◽  
Bioassay Guided Fractionation ◽  
Product Compound

Antiproliferative bioassay-guided fractionation of the ethanolic extract of the endemic Madagascan plant Metaporana sericosepala led to the first natural product isolation of a butenolide diterpene, which was synthesized during an anti-inflammatory study in 1988. The structure of the compound was elucidated as 3-homofarnesyl-4-hydroxybutenolide (1) by analysis of its spectroscopic data, including 1D- and 2D-NMR data and chemical evidence. The once synthetic compound can now also be considered as a natural product. Compound 1 had modest antiproliferative activity towards the A2780 ovarian cancer cell line with an IC50 value of 8 μM.

scholarly journals Compounds from the Fruits of the Popular European Medicinal PlantVitex agnus-castusin Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Shenghong Li ◽  
Shengxiang Qiu ◽  
Ping Yao ◽  
Handong Sun ◽  
Harry H. S. Fong ◽  
...  
Keyword(s):  
Biological Effects ◽  
Cancer Chemoprevention ◽  
2D Nmr ◽  
Biologically Active ◽  
Hydroxybenzoic Acid ◽  
Induction Effect ◽  
Quinone Oxidoreductase ◽  
Labdane Diterpene ◽  
First Time

As part of our continuing efforts in the search for potential biologically active compounds from medicinal plants, we have isolated 18 compounds including two novel nitrogen containing diterpenes from extracts of the fruits ofVitex agnus-castus. These isolates, along with our previously obtained novel compound vitexlactam A (1), were evaluated for potential biological effects, including cancer chemoprevention. Chemically, the nitrogenous isolates were found to be two labdane diterpene alkaloids, each containing anα,β-unsaturatedγ-lactam moiety. Structurally, they were elucidated to be 9α-hydroxy-13(14)-labden-16,15-amide (2) and 6β-acetoxy-9α-hydroxy-13(14)-labden-15,16-amide (3), which were named vitexlactams B and C, respectively. The 15 known isolates were identified as vitexilactone (4), rotundifuran (5), 8-epi-manoyl oxide (6), vitetrifolin D (7), spathulenol (8),cis-dihydro-dehydro-diconiferylalcohol-9-O-β-D-glucoside (9), luteolin-7-O-glucoside (10), 5-hydroxy-3,6,7,4′-tetramethoxyflavone (11), casticin (12), artemetin (13), aucubin (14), agnuside (15),β-sitosterol (16),p-hydroxybenzoic acid (17), andp-hydroxybenzoic acid glucose ester (18). All compound structures were determined/identified on the basis of 1D and/or 2D NMR and mass spectrometry techniques. Compounds6,8,9, and18were reported from aVitexspieces for the first time. The cancer chemopreventive potentials of these isolates were evaluated for NADP(H):quinone oxidoreductase type 1 (QR1) induction activity. Compound7demonstrated promising QR1 induction effect, while the new compound vitexlactam (3) was only slightly active.

scholarly journals Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro

Molecules ◽  
2020 ◽  
Vol 26 (1) ◽  
pp. 42
Author(s):  
Katrin Kuck ◽  
Guido Jürgenliemk ◽  
Bartosz Lipowicz ◽  
Jörg Heilmann
Keyword(s):  
Ethanolic Extract ◽  
2D Nmr ◽  
Preparative Hplc ◽  
Reference Compound ◽  
2D Nmr Spectroscopy ◽  
Vitro Assay ◽  
Chemical Structures ◽  
Inflammatory Processes ◽  
First Time

By using various chromatographic steps (silica flash, CPC, preparative HPLC), 16 sesquiterpenes could be isolated from an ethanolic extract of myrrh resin. Their chemical structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS. Among them, six previously unknown compounds (1–6) and another four metabolites previously not described for the genus Commiphora (7, 10, 12, 13) could be identified. Sesquiterpenes 1 and 2 are novel 9,10-seco-eudesmanes and exhibited an unprecedented sesquiterpene carbon skeleton, which is described here for the first time. New compound 3 is an 9,10 seco-guaian and the only peroxide isolated from myrrh so far. Compounds 1, 2, 4, 7–9, 11, 13–16 were tested in an ICAM-1 in vitro assay. Compound 7, as well as the reference compound furanoeudesma-1,3-diene, acted as moderate inhibitors of this adhesion molecule ICAM-1 (IC50: 44.8 and 46.3 μM, respectively). These results give new hints on the activity of sesquiterpenes with regard to ICAM-1 inhibition and possible modes of action of myrrh in anti-inflammatory processes.

scholarly journals Antiparasitic Indole Alkaloids from Aspidosperma desmanthum and A. spruceanum from the Peruvian Amazonia

2014 ◽  
Vol 9 (8) ◽  
pp. 1934578X1400900
Author(s):  
Matías Reina ◽  
Lastenia Ruiz-Mesia ◽  
Wilfredo Ruiz-Mesia ◽  
Frida Enriqueta Sosa-Amay ◽  
Leonor Arevalo-Encinas ◽  
...  
Keyword(s):  
Mammalian Cells ◽  
Indole Alkaloids ◽  
2D Nmr ◽  
Stem Bark ◽  
Spectroscopic Techniques ◽  
Root Bark ◽  
Antiparasitic Activity ◽  
Specific Cytotoxicity ◽  
First Time ◽  
Selective Activity

Twenty-three indole alkaloids were isolated from Aspidosperma desmanthum and A. spruceanum. Alkaloids 1-4 were isolated from the leaves, 5-8 from the stem bark and 9-15 from the root bark of A. desmanthum. Alkaloids 5, 11, 16, 17 and 19 were isolated from the stem bark, 18 and 20-22 from the root bark and 23 from the flowers of A. spruceanum. Compounds 4, 14, and 15 have not been previously reported as natural products while 16 and 20 have been isolated for the first time from the genus Aspidosperma. Their structures were determined by spectroscopic techniques including 1D and 2D NMR experiments (COSY, NOESY, HSQC, HMBC). The antiparasitic activity of these compounds was tested against Trypanosoma cruzi and Leishmania infantum and their non-specific cytotoxicity on mammalian cells. The most active compounds were 10, 12, 13, and 14 from A. desmanthum, and 19, 21 and 22 from A. spruceanum. Aspidolimine (10) aspidocarpine (12) and tubotaiwine (21) showed selective activity against L. infantum.

scholarly journals Chemical constituents of ethanol extract of leaves and molluscicidal activity of crude extracts from vitex trifolia linn.

2013 ◽  
Vol 59 (4) ◽  
pp. 19-32 ◽  
Author(s):  
Jeet S. Jangwan ◽  
Rita P. Aquino ◽  
Teresa Mencherini ◽  
Patrizia Picerno ◽  
Raghubir Singh
Keyword(s):  
Ursolic Acid ◽  
Chemical Constituents ◽  
Ethanolic Extract ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Chloroform Extract ◽  
Biomphalaria Alexandrina ◽  
The Family ◽  
Hexane Extracts ◽  
First Time

Abstract β-sitosterol and two triterpenoids: ursolic acid acetate and platanic acid have been isolated from ethanolic extract of Vitex trifola leaves. β-sitosterol was previously isolated from the leaves, stem and seeds of Vitex trifolia. Ursolic acid acetate has been isolated for the first time in this plant species. Platanic acid has been reported for the first time in Vitex trifolia and even in the family of this plant: Verbenaceae. These compounds were characterized using spectroscopic methods including 1D-1HNMR, 13CNMR, ESIMS and 2D-NMR (HSQC, HMBC, COSY) experiments and confirmed by comparison of their NMR data with those from the literature. A preliminary molluscicidal test for ethanol, chloroform and n-hexane extracts of leaves of Vitex trifolia against Biomphalaria alexandrina adult snails showed that ethanol extract of leaves with LC50 value 26.42 mg/l (27.92 mg/l - 24.99 mg/l) was more effective than n-hexane extract with LC50 value 35.48 mg/l (43.81 mg/l - 28.72mg/l) and chloroform extract with LC50 value 46.77 mg/l (53.59 mg/l - 43.81 mg/l) after 24 h exposure.

scholarly journals Flavonoid Glycosides from Endemic Bulgarian Astragalus aitosensis (Ivanisch.)

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1419 ◽  
Author(s):  
Hristo Vasilev ◽  
Samir Ross ◽  
Karel Šmejkal ◽  
Petr Maršík ◽  
Dagmar Jankovská ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
Structural Analysis ◽  
Secondary Metabolites ◽  
Chromatographic Separation ◽  
2D Nmr ◽  
Biologically Active ◽  
Spectral Studies ◽  
Flavonoid Glycosides ◽  
Phenolic Components ◽  
First Time

Astragalus is a very interesting plant genus, well-known for its content of flavonoids, triterpenes and polysaccharides. Its secondary metabolites are described as biologically active compounds showing several activities, e.g., immunomodulating, antibacterial, antiviral and hepatoprotective. This inspired us to analyze the Bulgarian endemic A. aitosensis (Ivanisch.) to obtain deeper information about its phenolic components. We used extensive chromatographic separation of A. aitosensis extract to obtain seven phenolic compounds (1–7), which were identified using combined LC-MS and NMR spectral studies. The 1D and 2D NMR analyses and HR-MS allowed us to resolve the structures of known compounds 5–7 as isorhamnetin-3-O-robinobioside, isorhamnetin-3-O-(2,6-di-O-α-rhamno-pyranosyl-β-galactopyranoside), and alangiflavoside, respectively, and further comparison of these spectral data with available literature helped us with structural analysis of newly described flavonoid glycosides 1–4. These were described in plant source for the first time.

scholarly journals Chemical constituents of the whole plant of PHLOGACANTHUS TURGIDUS (FUA EX HOOK.F.) LINDAU

2021 ◽  
Vol 5 (3) ◽  
pp. first
Author(s):  
Nguyen Tan Phat ◽  
Mai Thanh Chi ◽  
Phan Nhat Minh ◽  
Dang Chi Hien ◽  
Mai Dinh Tri
Keyword(s):  
Biological Activities ◽  
Chemical Constituents ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Published Data ◽  
Cytotoxic Activities ◽  
Phenylethanoid Glycosides ◽  
Whole Plant ◽  
The Family ◽  
First Time

The genus Phlogacanthus belongs to the family Acanthaceae and consists of more than 49 species, These species are widespread in tropical and subtropical zones such as Bangladesh, Bhutan, China, Indonesia, India, Myanmar and Vietnam. In Vietnam, the genus contains about 06 species. The extracts from some species in this genus have been evaluated for biological activities as analgesic, antiinflammatory, antimicrobial, antioxidant, antihyperglycemic and cytotoxic activities. In this study, the whole plant of Phlogacanthus turgidus was collected, dried, cut into small species, and extracted with ethanol to yield the ethanolic extract. Isolation of chemical constituents was performed using column chromatography on silica gel; their structures were elucidated by HRESI-MS, 1D & 2D-NMR and compared with published data. Six compounds, including two nor-isoprenoids: (+)-dehydrovomifoliol (1), (3S,5R,6R,7E,9S)-megastiman-7-ene-3,5,6,9-tetrol (2), two steroids b - sitosterol (3), daucosterol (4), one lignan (+)-syringaresinol (5), a derivative of phenylethanoid glycosides: martynoside (6) were isolated from the ethyl acetate extract of the whole plant of P. turgidus. Among them, 1, 2 were reported for the first time from the genus Phlogacanthus, while 3, 4, 5, 6, were found for the first time from this species.

scholarly journals A Novel 3,4-Secocycloartane Triterpene, Bearing a Tetrahydropyran Moiety, from Pasania formosana Leaf

2016 ◽  
Vol 11 (8) ◽  
pp. 1934578X1601100
Author(s):  
Shoei-Sheng Lee ◽  
Yue Xi ◽  
Chien-Kuang Chen ◽  
Ching-Chia Chang ◽  
Sheng-Fa Tsai
Keyword(s):  
Nmr Spectra ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Poor Solubility ◽  
Chromatographic Methods ◽  
Bioassay Guided Fractionation ◽  
2D Nmr Spectra ◽  
Weak Activity

Bioassay guided fractionation against α-glucosidase and separation of the ethanolic extract of Pasania formosana leaf by chromatographic methods led to the isolation of a novel secocycloartane triterpene. This compound, named pasasecocycloartenoic acid, was elucidated as 21,24( R)-epoxy-25-hydroxy-3,4-secocycloart-4(28)-en-3-oic acid through analysis of 1D and 2D NMR spectra and on the basis of HRESIMS data. The compound showed weak activity against α-glucosidase, but its poor solubility hampered the bioassay.

scholarly journals Gastroprotective Activity of Parastrephia quadrangularis (Meyen), Cabrera from the Atacama Desert

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2361 ◽  
Author(s):  
Alejandro Ardiles ◽  
Ruth Barrientos ◽  
Mario Simirgiotis ◽  
Jorge Bórquez ◽  
Beatriz Sepúlveda ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Mouse Model ◽  
Atacama Desert ◽  
Ethanolic Extract ◽  
Biologically Active ◽  
Gastroprotective Activity ◽  
Control Drug ◽  
Orbitrap Mass Spectrometry ◽  
Clerodane Diterpenes ◽  
First Time

Forty-three metabolites including several methoxylated flavonoids, tremetones, and ent-clerodane diterpenes were accurately identified for the first time in the ethanolic extract of P. quadrangularis by means of hyphenated UHPLC-quadrupole Orbitrap mass spectrometry, and seven isolated compounds were tested regarding gastroprotective activity using the HCl/EtOH-induced lesion model in mice. A new tremetone (compound 6) is reported based on spectroscopic evidence. The isolated clerodanes and tremetones showed gastroprotective activity in a mouse model, evidenced by compound 7 (p-coumaroyloxytremetone), which showed the highest gastroprotective activity (76%), which was higher than the control drug lansoprazole (72%). Our findings revealed that several constituents of this plant have gastroprotective activity, and particularly, p-coumaroyloxytremetone could be considered as a lead molecule to explore new gastroprotective agents. This plant is a rich source of biologically active tremetones and terpenoids which can support the ethnobotanical use of the plant.

scholarly journals Biofilm Inhibitory Abscisic Acid Derivatives from the Plant-Associated Dothideomycete Fungus, Roussoella sp.

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2190 ◽  
Author(s):  
Chayanard Phukhamsakda ◽  
Allan Macabeo ◽  
Kamila Yuyama ◽  
Kevin Hyde ◽  
Marc Stadler
Keyword(s):  
Abscisic Acid ◽  
Biofilm Formation ◽  
2D Nmr ◽  
Biologically Active ◽  
Undescribed Species ◽  
Addition Compound ◽  
2D Nmr Spectroscopy ◽  
Cytotoxic Effects ◽  
Murine Fibroblasts ◽  
Bioassay Guided Fractionation

Roussoella species are well recorded from both monocotyledons and dicotyledons. As part of a research program to discover biologically active compounds from plant-associated Dothideomycetes in Thailand, the strain Roussoella sp. (MFLUCC 17-2059), which represents an undescribed species, was isolated from Clematis subumbellata Kurz, fermented in yeast-malt medium and explored for its secondary metabolite production. Bioassay-guided fractionation of the crude extract yielded the new abscisic acid derivative, roussoellenic acid (1), along with pestabacillin B (2), a related congener, and the cyclodipeptide, cyclo(S-Pro-S-Ile) (3). The structure of 1 was determined by 2D NMR spectroscopy and HR-ESIMS data analysis. Compounds 1 and 2 showed inhibitory activity on biofilm formation by Staphylococcus aureus. The biofilm formation of S. aureus was reduced to 34% at 16 µg/mL by roussoellenic acid (1), while pestabacillin B (2) only showed 36% inhibition at 256 µg/mL. In addition, compound 1 also had weak cytotoxic effects on L929 murine fibroblasts and human KB3-1 cancer cells.

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