A New C-methyl Isoflavone and Other Compounds from the Roots of Amphiblemma monticola(Melastomataceae)

The phytochemical study of the EtOH extract of the roots of Amphiblemma monticola Jacq.-Fél. led to the isolation of a new C-methyl isoflavone, amphiblemmone A (1), along with ten known compounds, including 3,4’-di- O-methylellagic acid (2), dimethyl 4,4’,5,5’,6,6’- hexahydroxybiphenyl-2,2’-dicarboxylate (3), lupeol (4), ellagic acid (5), β-sitosterol (6), sitosterol 3- O-β-D-glucopyranoside (7), 3-hydroxy-4,5-dimethoxybenzoic acid (8), 3- O-methylellagic acid 4′- O-β-D-xylopyranoside (9), and a mixture of oleanolic acid (10) and ursolic acid (11). The structures were elucidated using spectroscopic analyses (IR, UV, NMR and MS) and comparison with literature data. Compounds 2-11 were isolated for the first time from the genus Amphiblemma. This is the first report of compounds 2-4, 8 and 9 from the Melastomataceae family.

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Establishment and triterpenoid production of Ocimum basilicum cambial meristematic cells

Plant Cell Tissue and Organ Culture (PCTOC) ◽

10.1007/s11240-020-01942-y ◽

2020 ◽

Vol 143 (3) ◽

pp. 573-581

Author(s):

Alexander Mehring ◽

Janik Haffelder ◽

Jonas Chodorski ◽

Judith Stiefelmaier ◽

Dorina Strieth ◽

...

Keyword(s):

Ursolic Acid ◽

Oleanolic Acid ◽

Biomass Accumulation ◽

Ocimum Basilicum ◽

Meristematic Cells ◽

Cultivation Period ◽

Shake Flasks ◽

Valuable Compounds ◽

Whole Plants ◽

First Time

AbstractThe application of plant suspension culture to produce valuable compounds, such as the triterpenoids oleanolic acid and ursolic acid, is a well-established alternative to the cultivation of whole plants. Cambial meristematic cells (CMCs) are a growing field of research, often showing superior cultivation properties compared to their dedifferentiated cell (DDC) counterparts. In this work, the first-time establishment of O. basilicum CMCs is demonstrated. DDCs and CMCs were cultivated in shake flasks and wave-mixed disposable bioreactors (wDBRs) and evaluated regarding triterpenoid productivity and biomass accumulation. CMCs showed characteristic small vacuoles and were found to be significantly smaller than DDCs. Productivities of oleanolic and ursolic acid of CMCs were determined at 3.02 ± 0.76 mg/(l*d) and 4.79 ± 0.48 mg/(l*d) after 19 days wDBR cultivation, respectively. These values were consistently higher than any productivities determined for DDCs over the observed cultivation period of 37 days. Elicitation with methyl jasmonate of DDCs and CMCs in shake flasks resulted in increased product contents up to 48 h after elicitor addition, with the highest increase found in CMCs at 232.30 ± 19.33% (oleanolic acid) and 192.44 ± 18.23% (ursolic acid) after 48 h.

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LC-MS- and NMR-Guided Isolation of Monoterpene Dimers from Cultivated Thymus vulgaris Varico 3 Hybrid and Their Antityrosinase Activity

Planta Medica ◽

10.1055/a-0927-7041 ◽

2019 ◽

Vol 85 (11/12) ◽

pp. 941-946 ◽

Cited By ~ 1

Author(s):

Ilias Stefanis ◽

Dimitra Hadjipavlou-Litina ◽

Anna-Rita Bilia ◽

Anastasia Karioti

Keyword(s):

Ursolic Acid ◽

Oleanolic Acid ◽

Inhibitory Activity ◽

Kojic Acid ◽

2D Nmr ◽

Thymus Vulgaris ◽

Reference Compound ◽

Aerial Parts ◽

Spectroscopic Analyses ◽

Antityrosinase Activity

AbstractTargeted isolation based on a combination of NMR and HPLC-PDA-MS of a dichloromethane extract of Thymus vulgaris Varico 3 aerial parts afforded one new p-cymene dimer, 6,3′,4′-trihydroxy-5,5′-diisopropyl-2,2′-dimethylbiphenyl (1), together with two known p-cymene derivatives (2 and 3), as well as five known compounds, namely, thymol (4), oleanolic acid (5), ursolic acid (6), cirsimaritin (7), and xanthomicrol (8). The structural elucidation of all compounds was performed by spectroscopic analyses, including 1D and 2D NMR, and HRESIMS experiments. The biphenyls were assayed for their inhibitory activity on tyrosinase. Compounds 2 and 3 showed negligible activity on tyrosinase, while compound 1 effectively inhibited the enzyme with 35% (± 0.3) inhibitory activity, higher than the inhibition of the reference compound kojic acid (18.6 ± 0.02).

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Phytochemical Study of Stem and Leaf of Clausena lansium

Molecules ◽

10.3390/molecules24173124 ◽

2019 ◽

Vol 24 (17) ◽

pp. 3124 ◽

Cited By ~ 6

Author(s):

Wenwen Peng ◽

Xiaoxiang Fu ◽

Yuyan Li ◽

Zhonghua Xiong ◽

Xugen Shi ◽

...

Keyword(s):

Biological Activities ◽

Healthcare Systems ◽

Water Soluble ◽

Phytochemical Analysis ◽

Phytochemical Study ◽

Spectroscopic Analyses ◽

First Time ◽

Local Healthcare ◽

Carbazole Alkaloids ◽

Aromatic Glycoside

Clausena lansium Lour. Skeels (Rutaceae) is widely distributed in South China and has historically been used as a traditional medicine in local healthcare systems. Although the characteristic components (carbazole alkaloids and coumarins) of C. lansium have been found to possess a wide variety of biological activities, little attention has been paid toward the other components of this plant. In the current study, phytochemical analysis of isolates from a water-soluble stem and leaf extract of C. lansium led to the identification of 12 compounds, including five aromatic glycosides, four sesquiterpene glycosides, two dihydrofuranocoumarin glycosides, and one adenosine. All compounds were isolated for the first time from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), and two new sesquiterpene glycosides (8 and 9). The phytochemical structures of the isolates were elucidated using spectroscopic analyses including NMR and MS. The existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to some extent.

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A New Cardenolide and Other Compounds from Salsola tetragona

Natural Product Communications ◽

10.1177/1934578x1701200102 ◽

2017 ◽

Vol 12 (1) ◽

pp. 1934578X1701200

Author(s):

Hamida Ghorab ◽

Abdelkrim Khettaf ◽

Meriem Lehbili ◽

Ahmed Kabouche ◽

Abdulmagid Alabdul Magid ◽

...

Keyword(s):

Fatty Acids ◽

Phenolic Compounds ◽

Spectral Data ◽

First Report ◽

Aerial Parts ◽

Spectroscopic Analyses ◽

First Time

One new cardenolide, 3- O-β-D-allopyranosylcoroglaucigenin (salsotetragonin) (1), was isolated from the aerial parts of Salsola tetragona Delile with four known cardenolides (2–5), two known flavonoids (6–7), three known phenolic compounds (8–10) and two known fatty acids (11–12). Their structures were identified by spectroscopic analyses and by comparison of their spectral data with those reported in the literature. Compounds 1–5, 7, 10 and 12 were isolated from the genus Salsola for the first time. This is the first report on cardenolides identified in the Amaranthaceae family.

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Extractives of Australian timbers. XVI. The constituents of the wood of Eugenia crebrinervis (syn. Syzigium crebrinerve) and Eugenia gustavioides (syn. Cleistocalyx gustavioides)

Australian Journal of Chemistry ◽

10.1071/ch9761135 ◽

1976 ◽

Vol 29 (5) ◽

pp. 1135

Author(s):

CD Bannon ◽

RA Eade ◽

JJH Simes

Keyword(s):

Ursolic Acid ◽

Oleanolic Acid ◽

Ellagic Acid ◽

Dry Weight ◽

Acid Extraction ◽

Asiatic Acid ◽

Arjunolic Acid

Extraction of the wood of Eugenia crebrinervis has yielded ellagic acid and a triterpenoid fraction composed of a 1 : 1 mixture of asiatic acid and arjunolic acid. Extraction of the wood of Eugenia gustavioides has given a mixture of triterpenoid acids (2.7 % of the dry weight of the wood) of which crategolic acid (c.1%) is the principal constituent; other major constituents are asiatic acid and arjunolic acid, while oleanolic acid, ursolic acid and 2α-hydroxyursolic acid are minor constituents.In both Eugenia species the α-amyrin component occurs with the corresponding β-amyrin analogue giving a mixture separable only with difficulty; use has been made of the previously described chlorination procedure1 to enable comparatively easy isolation of the α-amyrin component.

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Chemical Constituents of Nepeta Distans

Natural Product Communications ◽

10.1177/1934578x1000501117 ◽

2010 ◽

Vol 5 (11) ◽

pp. 1934578X1000501 ◽

Cited By ~ 3

Author(s):

Javid Hussain ◽

Nausheen Bukhari ◽

Hidayat Hussain ◽

Najeeb U Rehman ◽

Syed Murtaza Hussain

Keyword(s):

Spectral Data ◽

Phenolic Compound ◽

Ursolic Acid ◽

Oleanolic Acid ◽

Chemical Constituents ◽

2D Nmr ◽

Phytochemical Investigation ◽

Reported Data ◽

First Time

Phytochemical investigation of Nepeta distans Raul resulted in the isolation of a new phenolic compound, nepatanol (1), and eight known compounds, markhamioside F, netidiol, nepedinol, thymoquinone, eugenol, oleanolic acid, ursolic acid, and β-sitosterol, which have been isolated for the first time from this source. Structures of all the isolates were established on the basis of MS, and 1D and 2D NMR spectral data and by comparison with reported data.

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Two New Triterpenes and Other Compounds from Mentha aquatica (Lamiaceae)

Natural Product Communications ◽

10.1177/1934578x1701200404 ◽

2017 ◽

Vol 12 (4) ◽

pp. 1934578X1701200 ◽

Cited By ~ 1

Author(s):

Maria Ferhat ◽

Zahia Kabouche ◽

Yoshinori Fujimoto ◽

Hiroshi Araya

Keyword(s):

Ursolic Acid ◽

Oleanolic Acid ◽

Maslinic Acid ◽

Mentha Aquatica ◽

Pomolic Acid ◽

First Time ◽

Tormentic Acid ◽

Plant Compounds

Two new triterpenoids, maquatic acid (1), a 2,3- seco-triterpene having an acetal in its A-ring, and 3- O-benzoyltormentic acid (2), were isolated from underground parts of Mentha aquatica, in addition to twelve known compounds, tormentic acid (3), 1- O-benzoylhyptadienic acid (4), 3- epi-ursolic acid (5), hyptadienic acid (6), 3- epi-maslinic acid (7), 3- epi-tormentic acid (8), ursolic acid (9), β-sitosterol (10), oleanolic acid (11), pomolic acid (12), micromeric acid (13) and 21α-hydroxyursolic acid (14) from aerial and underground parts of the plant. Compounds 4-6, 8, 13 and 14 have been isolated from the genus Mentha for the first time.

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Chemical Constituents from Fadogia homblei De Wild (Rubiaceae)

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.14.116 ◽

2013 ◽

Vol 14 ◽

pp. 116-124 ◽

Cited By ~ 4

Author(s):

Abdelhafeez M.A. Mohammed ◽

Philip H. Coombes ◽

Neil R. Crouch ◽

Dulcie A. Mulholland

Keyword(s):

Ursolic Acid ◽

Oleanolic Acid ◽

Betulinic Acid ◽

Chemical Constituents ◽

First Report ◽

Plant Source ◽

Lupane Triterpenoids ◽

Coumarin 7

The total of fourteen known compounds was isolated from the fruits, leaf and stem of Fadogia homblei De Wild. (Rubiaceae) and identified as: a coumarin, 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one (scopoletin) 1, two flavones; 3′,4′,5,7-tetrahydroxyflavone (luteolin) 2 and quercetin-3-O-β-D-galactoside 3, four lupane triterpenoids; lupeol 4, betulinic acid 5, 3β-dodecanoyllup-20(29)-en-28-al 6, lup-20(29)-en-3β-ylhexadecanoate 7, and two steroids; sitosterol 8, stigmasterol 9, a lignan 4,4′-dihydroxy-3,3′-dimethoxy-7,9′:7′,9-diepoxylignan ((-)-pinoresinol) 10, a phaeophytin A 11, an uracil 12, an oleanolic acid 13, and an ursolic acid 14. To our best knowledge, this is the first report for isolation of these compounds from this species. This finding is nevertheless significant as it is the first report of uracil from a plant source other than from various species of ferns.

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Antimicrobial Activity of the Extract and Isolated Compounds from Baccharis dracunculifolia D. C. (Asteraceae)

Zeitschrift für Naturforschung C ◽

10.1515/znc-2008-1-208 ◽

2008 ◽

Vol 63 (1-2) ◽

pp. 40-46 ◽

Cited By ~ 34

Author(s):

Ademar A. da Silva Filho ◽

João P. B. de Sousa ◽

Sandra Soares ◽

Niege A. J. C. Furtado ◽

Márcio L. Andrade e Silva ◽

...

Keyword(s):

Antimicrobial Activity ◽

Ursolic Acid ◽

Methicillin Resistant Staphylococcus Aureus ◽

Antibacterial Activities ◽

Antimicrobial Activities ◽

Phytochemical Study ◽

Propolis Extract ◽

Acid Lactone ◽

First Time ◽

Mic Value

Baccharis dracunculifolia D.C. (Asteraceae) is the most important plant source of the Brazilian green propolis. Since propolis is known for its antimicrobial activity, the aim of this work was to evaluate the antimicrobial activities of B. dracunculifolia and some of its isolated compounds. The results showed that the leaves extract of B. dracunculifolia (BdE) presents antifungal and antibacterial activities, especially against Candida krusei and Cryptococcus neoformans, for which the BdE showed IC50 values of 65 μg mL −1 and 40 μg mL−1, respectively. In comparison to the BdE, it was observed that the green propolis extract (GPE) showed better antimicrobial activity, displaying an IC50 value of 9 μg mL−1 against C. krusei. Also, a phytochemical study of the BdE was carried out, affording the isolation of ursolic acid (1), 2α-hydroxy-ursolic acid (2), isosakuranetin (3), aromadendrin-4′-methylether (4), baccharin (5), viscidone (6), hautriwaic acid lactone (7), and the clerodane diterpene 8. This is the first time that the presence of compounds 1, 2, and 8 in B. dracunculifolia has been reported. Among the isolated compounds, 1 and 2 showed antibacterial activity against methicillin- resistant Staphylococcus aureus, displaying IC50 values of 5 μg mL−1 and 3 μg mL−1, respectively. 3 was active against C. neoformans, showing an IC50 value of 15 μg mL−1 and a MIC value of 40 μg mL−1, while compounds 4→8 were inactive against all tested microorganisms. The results showed that the BdE, similar to the GPE, displays antimicrobial activity, which may be related to the effect of several compounds present in the crude extract.

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TRITERPENE AND STEROL COMPOUNDS ISOLATED FROM ANODENDRON PANICULATUM (ROXB.) A.DC.

HUE UNIVERSITY JOURNAL OF SCIENCE NATURAL SCIENCE ◽

10.26459/hueuni-jns.v126i1b.4447 ◽

2017 ◽

Vol 126 (1B) ◽

pp. 155

Author(s):

Nguyen Thi Hoai

Keyword(s):

Cell Lines ◽

Ursolic Acid ◽

Human Cancer ◽

Hep G2 ◽

Cytotoxic Effects ◽

Phytochemical Study ◽

Human Cancer Cell Lines ◽

Chemical Structures ◽

Aerial Parts ◽

Spectroscopic Analyses

Phytochemical study on the aerial parts of Anodendron paniculatum led to the isolation of three triterpenes, including ursolic acid (1), esculentic acid (2), cycloartenol (3), and one sterol, desmosterol (4). Their chemical structures were elucidated on the basis of spectroscopic analyses. The cytotoxicity of the isolated compounds against the growth of human cancer cell lines were evaluated using a sulforhodamin B bioassay. Compounds 1 exhibited moderate cytotoxicity against the LU-1 and MKN-7 cell lines with IC50 values of 44.37 ± 5.40, 30.89 ± 3.60 μg/mL, respectively. Meanwhile, compound 4 possessed moderate cytotoxic effects toward the LU-1, KB, Hep-G2, MKN-7 and SW-480 cell lines with IC50 values ranging from 28.11 ± 1.95 to 41.41 ± 2.31 μg/mL.Key words: Anodendron paniculatum, ursolic acid, esculentic acid, cycloartenol, desmosterol, cytotoxicity.

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