Diterpenes from Sideritis infernalis and S. candicans

2008 ◽  
Vol 63 (5) ◽  
pp. 595-599 ◽  
Author(s):  
Braulio M. Fraga ◽  
Carlo Bressa ◽  
Concepción Fernández ◽  
Pedro González ◽  
Ricardo Guillermo ◽  
...  

A phytochemical study of Sideritis infernalis led to the isolation of the new nor-diterpene adejone (17-nor-7α,18-dihydroxy-ent-kaur-16-one). The biosynthesis of this compound implies the decarboxylation of an epoxy-acid as the last step. In addition, three diterpenes with an ent-kaurene skeleton, episideridiol, candicandiol 7α-monoacetate and candidiol 15α-monoacetate, have been isolated from S. candicans for the first time in nature.

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3256
Author(s):  
Luis C. Chitiva-Chitiva ◽  
Cristóbal Ladino-Vargas ◽  
Luis E. Cuca-Suárez ◽  
Juliet A. Prieto-Rodríguez ◽  
Oscar J. Patiño-Ladino

In this study, the antifungal potential of chemical constituents from Piper pesaresanum and some synthesized derivatives was determined against three phytopathogenic fungi associated with the cocoa crop. The methodology included the phytochemical study on the aerial part of P. pesaresanum, the synthesis of some derivatives and the evaluation of the antifungal activity against the fungi Moniliophthora roreri, Fusarium solani and Phytophthora sp. The chemical study allowed the isolation of three benzoic acid derivatives (1–3), one dihydrochalcone (4) and a mixture of sterols (5–7). Seven derivatives (8–14) were synthesized from the main constituents, of which compounds 9, 10, 12 and 14 are reported for the first time. Benzoic acid derivatives showed strong antifungal activity against M. roreri, of which 11 (3.0 ± 0.8 µM) was the most active compound with an IC50 lower compared with positive control Mancozeb® (4.9 ± 0.4 µM). Dihydrochalcones and acid derivatives were active against F. solani and Phytophthora sp., of which 3 (32.5 ± 3.3 µM) and 4 (26.7 ± 5.3 µM) were the most active compounds, respectively. The preliminary structure–activity relationship allowed us to establish that prenylated chains and the carboxyl group are important in the antifungal activity of benzoic acid derivatives. Likewise, a positive influence of the carbonyl group on the antifungal activity for dihydrochalcones was deduced.


Planta Medica ◽  
2018 ◽  
Vol 84 (12/13) ◽  
pp. 964-970 ◽  
Author(s):  
César Muñoz Camero ◽  
Antonio Vassallo ◽  
Marinella De Leo ◽  
Abeer Temraz ◽  
Nunziatina De Tommasi ◽  
...  

AbstractA phytochemical study of n-hexane, CHCl3, and CHCl3-MeOH extracts of Aphanamixis polystachya leaves led to the isolation of 10 compounds. Five of them turned out to be new natural compounds, including two mexicanolide-type (1, 2) and three polyoxyphragmalin-type (3–5) limonoids, together with two known andirobin-type limonoids (6, 7) and three phenolic derivatives. The structures of the new compounds were established on the basis of spectroscopic methods to be 8-hydro-14,15-en-cabralin (1), 3-deacetyl-8-hydro-cabralin-14,15-en-3-one (2), 20,22-dihydroxy-21,23-dimethoxytetrahydrofuran khayanolide A (3), 1-deacetyl-3-dehydroxy-3-oxokhaysenelide E (4), and meliaphanamixin A (5). All compounds were isolated for the first time from this species. The ability of the isolated limonoids to interact with the molecular chaperone Hsp90 was tested. Compounds 6 and 7 were the most active.


Molecules ◽  
2019 ◽  
Vol 24 (17) ◽  
pp. 3124 ◽  
Author(s):  
Wenwen Peng ◽  
Xiaoxiang Fu ◽  
Yuyan Li ◽  
Zhonghua Xiong ◽  
Xugen Shi ◽  
...  

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.


2013 ◽  
Vol 8 (5) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Daniil N. Olennikov ◽  
Larisa M. Tankhaeva ◽  
Vyacheslav V. Partilkhaev

Phytochemical study of flowering shoots of Caragana arborescens Lam. (Fabaceae family) collected in Buryatia Republic (Russian Federation) resulted in the isolation of twenty compounds identified as quercetin, isoquercitrin and rutin, previously identified in this species, and β-sitosterol, β-sitosterol-3- O-glucoside, umbelliferone, kaempferol, formononetin, isorhamnetin-3- O-glucoside, nicotiflorin, narcissin, myricetin-3- O-rutinoside, ononin, formononetin-7- O-rutinoside, caffeic, 3- O-caffeoylquinic, 5- O-caffeoylquinic, 3,5-di- O-caffeoylquinic acids and sucrose, isolated for the first time from C. arborescens.


2018 ◽  
Vol 2018 ◽  
pp. 1-10 ◽  
Author(s):  
Mohamed Shaaban ◽  
Mahmoud Ali ◽  
Michel Feussi Tala ◽  
Abdelaaty Hamed ◽  
Amal Zaki Hassan

This study deals with the ecology, phytochemistry, and biological activity investigation of Euphorbia retusa, belonging to Euphorbiaceae family, obtained from Egypt. Ecologically, Euphorbia retusa secretes white sap inhibiting the growth of the other species, so Euphorbia retusa is forming complete patches. Phytochemical study of the plant was visualized intensively based on its extraction with a protic organic solvent, working up and purifying its entire bioactive compounds using a series of different chromatographic techniques. A broad range of diverse compounds were isolated, namely, 1-hexacosanol (1), 3β-hydroxy-24-methylene-9,19-cyclolanostane; 24-methylenecycloartanol (2), 3β-hydroxy-9,19-cyclolanostane; cyclolaudanol (3), 3β,24S-Ergost-5-en-ol (4), and methyllinoleate. Additionally, GC-MS analysis of the unpolar fractions detected the existence of n-dodecane, methyllaurate, 6,10,14-trimethyl-pentadecan-2-one (5), 6,10-dimethyl-undecan-2-one (6), 2-methyl-hexadecanal (7), methylpalmitate, methyl-9,12,15-octadecatrienoate (8), and n-heneicosane (9). A full assignment for compounds 2 and 3 using 1 and 2 DNMR was carried out herein for the first time. The antimicrobial activity of the strain extract and obtained compounds was studied using a panel of pathogenic bacterial strains. The in vitro cytotoxicity of the compounds as well as the crude extract was studied against the human cervix carcinoma cell line (KB-3-1).


2010 ◽  
Vol 8 (3) ◽  
pp. 459-462 ◽  
Author(s):  
S. M. Mizanur Rahman ◽  
Serajum Munira ◽  
M. Amzad Hossain

Two new compounds were identified as 2-ethyl-cyclohex-2-ene-6-hydroxy-methylene-1-carboxylic acid and 3b-hydroxy-lup-20(29)-en-28-oic acid, respectively, from the petroleum ether extracts of Cleome rutidosperma plant. These two constituents is the first time occurrence in this plant. The structures of the two different type of compounds are elucidated with the help of UV, IR, 1H-NMR, 13C-NMR, COSY, DEPT 90, DEPT 135 and mass spectral data.   Keywords: Cleome rutidosperm DC; isolation; spectral analysis


2016 ◽  
Vol 11 (1) ◽  
pp. 1934578X1601100
Author(s):  
Noura S. Dosoky ◽  
Debra M. Moriarity ◽  
William N. Setzer

Conradina canescens (Lamiaceae) is an endemic evergreen shrub native to Florida, Mississippi and Alabama, with no phytochemical or biological studies registered in the literature. Thus, a phytochemical study and a toxicity analysis of the chloroform extract obtained from the leaves of C. canescens were performed for the first time. In our preliminary screening, the crude extract and its fractions were subjected to cytotoxicity, antimicrobial and antileishmanial bioassays. The crude extract showed substantial cytotoxic, antimicrobial and antileishmanial activities. A total of six compounds, namely ursolic acid (62.4%), betulin (8.4%), β-amyrin (4.6%), myrtenic acid (2.9%), n-tetracosane (1.4%), and oleanolic acid (1.1%), were isolated. The structures of the isolated compounds were established by spectroscopic studies using NMR and IR spectroscopy.


Molecules ◽  
2020 ◽  
Vol 25 (11) ◽  
pp. 2572
Author(s):  
Mi Jin Park ◽  
Young-Hwa Kang

Agrimonia pilosa L. (AP) showed potent α-glucosidase inhibitory (AGI) activity, but it is uncertain what phytochemicals play a key factor. The phytochemical study of AP based on AGI activity led to the isolation of four isocoumarins; agrimonolide (1), agrimonolide-6-O-β-d-glucopyranoside (2), desmethylagrimonolide (3), desmethylagrimonolide-6-O-β-d-glucopyranoside (4), and four flavonoids; luteolin (5), quercetin (6), vitexin (7), and isovitexin (8). The four isocoumarins were isolated as α-glucosidase inhibitors for the first time. Isocoumarins, compound 1 (agrimonolide) and 3 (desmethylagrimonolide) showed strong α-glucosidase inhibitory activities with IC50 values of 24.2 and 37.4 µM, respectively. Meanwhile, isocoumarin and flavonoid glycosides showed weak AGI activity. In the kinetic analysis, isocoumarins, compounds 1 and 3 showed non-competitive inhibition, whereas flavonoid, compound 6 showed competitive inhibition.


2014 ◽  
Vol 12 ◽  
pp. 117-122
Author(s):  
A Solongo ◽  
R Istatkova ◽  
S Philipov ◽  
S Javzan ◽  
D Selenge

From the aerial parts (700g) of berberis sibirica pall. 6 isoquinoline alkaloids of protoberberine, protopine, benzophenantridine and proaporphine type were isolated. The known alkaloids (-)-tetrahydropseudocoptisine, pseudoprotopine, (+)-chelidonine and (+)-glaziovine are new for the family berberidaceae. from the aerial part ii (3.9 kg) 14 isoquinoline alkaloids of aporphine, proaporphine, protoberberine, protopine, benzylisoquinoline, bisbenzylisoquinoline,proaporphine-benzylisoquinoline and simple isoquinolin type were isolated and identified. The aporphine alkaloid 1-o-methylisotebaidine and simple isoquinoline dehydrocorypalline have been found for the first time in the family of berberidaceae. From the roots of b. sibirica 10 isoquinoline alkaloids of protoberberine, benzylisoquinoline, bisbenzylisoquinoline, aporphine-benzylisoquinoline and proaporphine-benzylisoquinoline type were isolated. 1,10-di-omethylpakistanine has been reported for the first time as a natural alkaloid. The known alkaloids (-) -isothalidezine and (+)-armepavine have been found for the first time in the family berberidaceae. All structures were determined by physical and spectral data.DOI: http://dx.doi.org/10.5564/mjc.v12i0.185 Mongolian Journal of Chemistry Vol.12 2011: 117-122


Author(s):  
Dumaa M ◽  
Margit Gruner ◽  
Luebkim Tilo ◽  
Solongo T ◽  
Chunsriimyatav G ◽  
...  

There are hispidulin, quercetin-3-О-rutinoside, lupeol, taraxasterol, β-sitosterolwere isolated from the ethylacetate, n-buthanol and petroleum ether fractions of the aerial parts of Jurinea mongolica Maxim. grown in Mongolia. Molecular structures of these compounds were elucidated by using TLC, CC, IR, Mass spectrometer and 1H, 13C and 2D NMR (HSQC, HMBC, 1H-1H COSY, NOESY) methods. All of these compounds were isolated from the Mongolian J. mongolica for the first time. Монгол чоногоно (Jurinea mongolica Maxim.) ургамлын фитохимийн судалгаа Манай орны унаган ургамалд багтдаг Монгол чоногоно (Jurinea mongolica Maxim.) ургамлын газрын дээд хэсгийн этилацетат, н-бутанол, петролейний эфирийн фракцаас гиспидулин, кверцетин-3-О-рутинозид, тараксастерол, лупеол, β-ситостерол бодисыг химийн цэвэр төлөв байдлаар ялгав. Тэдгээр бодисын молекулын бүтэц байгууламжийг НУТ, масс спектрометр, хроматомасс спектроскоп, 1Н ПСР, 13С болон хоѐр хэмжээст ЦСР-ын спектроскопын аргаар таньж тодорхойлов. Судалгааны дүнд 2 фенолт нэгдэл, 2 тритерпен, 1 стеролын төрлийн бодисыг энэ зүйл ургамлаас анх удаа олсон нь шинжлэх ухааны шинэ мэдээлэл болов. Түлхүүр үгс: Монгол чоногоно, Нийлмэл цэцэгтэн, фенолт нэгдэл, тритерпен, стерол


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