Triterpenoids from leaves of Ilex guayusa / 中国中药杂志

The chemical constituents from the leaves of Ilex guayusa were investigated. Sixteen triterpenoids were isolated from the 95% ethanol extract of dried leaves of I. guayusa by silica gel, Sephadex LH-20, and ODS column chromatographies and semi-prepa-rative HPLC. Those triterpenoids were identified by NMR, HR-MS, and literature analysis: 3β-hydroxy-11α,12α-epoxy-24-nor-urs-4(23)-ene-28,13β-olide(1), 3β-hydroxy-24-nor-4(23),12-oleanadien-28-methyl ester(2), oleanolic acid(3), 3β,28-dihydroxy-12-oleanene(4), 2α,3β-dihydroxy-11α,12α-epoxy-24-'nor-olean-4(23)-ene-28,13β-olide(5), ursolic acid(6), 3β,23-dihydroxy ursolic acid(7), 3β,28-dihydroxy-12-ursene(8), 3β-28-nor-urs-12-ene-3,17-diol(9), 3β-hydroxyurs-11-ene-28,13β-olide(10), 13β,28-epoxy-3β-hydroxy-11-ursene(11), 3β-hydroxy-28,28-dimethoxy-12-ursene(12), 3β-hydroxy-24-nor-urs-4(23),12-dien-28-oic acid(13), 3β-hydroxy-24-nor-urs-4(23),12-dien-28-methyl ester(14), 2α,3β-dihydroxy-11α,12α-epoxy-24-nor-urs-4(23)-ene-28,13β-olide(15) and 2α,3β-dihydroxy-11α,12α-epoxy-24-nor-urs-4(23),20(30)-dien-28,13β-olide(16). Compounds 1-2 were new compounds, and compounds 4-5, 7 and 9-16 were isolated from I. guayusa for the first time.

Phenolic constituents from stems of Ilex asprella / 中国中药杂志

Phytochemical investigation on Ilex asprella stems by using various chromatographic techniques led to the isolation of 18 phenolic constituents. Based on spectroscopic data analyses and/or comparison of the spectroscopic data with those in literature, these constituents were identified, including two lignans (1, 2), five phenylpropanes (3-7), six chlorogenic analogues (8-13), and five benzoic analogues (14-18). Among them, compounds 3-7, 9, 11, 13, 14, 17, and 18 were isolated from genus Ilex for the first time, and 2, 8, 10, 15, and 16 were isolated from this species for the first time. The in vitro anti-inflammatory assay results showed that compounds 8, 9, 11, 13, and 15 possessed moderate inhibition on the NO production in RAW264.7 cells with IC₅₀ values of 51.1-85.8 μmol·L⁻¹. The present study brought preliminary reference for the clarification of therapeutic ingredients of I. asprella with anti-inflammatory efficacy and its quality evaluation.

Three new triterpenoids isolated from the aerial parts of Ilex cornuta and protective effects against HO-induced myocardial cell injury / 中国天然药物

In the present study, three new triterpenoids, 23-hydroxyurs-12, 18-dien-28-oic acid 3β-O-α-L-arabinopyranoside (1), 23-hydroxyurs-12, 18-dien-28-oic acid 3β-O-β-D-glucuronopyranoside-6-O-methyl ester (2), and urs-12, 18-dien-28-oic acid 3β-O-β-D-glucuronopyranoside-6-O-methyl ester (3), and a known triterpenoid, 3β-hydroxy-urs-2, 18-dien-28-oic acid (4, randialic acid B), were isolated from the aerial parts of Ilex cornuta. Their structures were identified by the spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, and 1D and 2D NMR) and chemical reactions. Compound 4 showed significant cell-protective effects against HO-induced H9c2 cardiomyocyte injury. Compounds 1-4 did not show any significant DPPH radical scavenging activity.

Chemical constituents from stems of Ilex asprella / 中国中药杂志

Phytochemical investigation on the stems of Ilex asprella by using various chromatographic techniques led to the isolation of 13 compounds. By spectroscopic analyses and comparisons the spectral data with those in literatures, these compounds were identified as salicifoneoliganol(1), rel-(7R,8S)-3,3',5-trimethoxy-4',7-epoxy-8,5'-neolignan-4,9,9'-triol 9-β-D-glucopyranoside(2),(+)-cycloolivil(3),(+)-syringaresinol-4'-O-β-D-monoglucoside(4), liriodendrin(5), caffeic acid (6), 3,4-dihydroxy-5-methoxybenzaldehyde(7), benzene-1,2,4-triol(8), 3,4,5-trimethoxyphenyl-1-O-β-D-apiofuranosyl(1″→6')-glucopyranoside(9), aeculetin(10), cryptochlorogenic acid ethyl ester(11), chlorogenic acid ethyl ester(12), and rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo [3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid(13). Among them, compounds 7, 8, 11, and 13 were isolated from genus Ilex for the first time, and 1-3, 9, 10, and 12 were isolated from this speciesfor the first time. The anti-inflammatory assay results of these compounds showed that compounds 1 and 9 showed moderate inhibitory effect against NO production in RAW 267. 4 cells with IC₅₀ values of 35.7 and 50.6 μmol•L⁻¹, in vitro respectively, whereas compound 10 showed weak inhibition(IC₅₀ value 98.7 μmol•L⁻¹).

A new oleanane-type triterpenoid glycoside from roots of Ilex asprella / 中国中药杂志

A new δ-oleanane-type triterpenoid glycoside, 3-O-(3-O-sulfo)-β-D-glucopyranosiduronic acid 3β-hydroxy-13(18)-oleanen- 28-oic acid 28-β-D-glucopyranosyl ester (1), along with ten known triterpenoid glycosides, rotundinoside A (2), oblonganoside M (3), 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl 3β,19α-dihydroxy-20α- urs-12-en-28-oic acid 28-O-β-D- glucopyranosyl ester (4), ilexsaponin B2 (5), ilexside Ⅱ (6), rotundinoside B (7), ilekudinoside B (8), ilexpublesnin E (9), ilekudinoside D (10) and ilexpernoside D (11), was isolated from the 75% ethanol extract of the roots of Ilex asprella by various chromatographic separation. Their structures were identified on the basis of MS, NMR spectroscopic analysis and chemical methods. In addition, 2-11 were isolated from I. asprella for the first time.

Genus llex L.: Phytochemistry, Ethnopharmacology, and Pharmacology / 中草药·英文版

The genus llex L. has been used as remedies in traditional Chinese medicine in Aquifoliaceae and beverages for thousands of years due to abundant pharmaceutical bioactivities. There are 600 species in genus Ilex L. containing various compounds such as terpenoids, saponins, glycosides, etc. Three species, I. cornuta, I. chinensis, and I. rotunda have been admitted in Chinese Pharmacopoeia 2015 to treat dyspepsia, stomatitis, and hyperactivity cough and protect the liver and kidney. Recent studies showed that several species have been daily drunk to promote human health and prevent cardiovascular diseases in the folk. Here we reviewed the genus Ilex L. in phytochemistry, ethnopharmacology, and pharmacology.

Two new triterpenoid glycosides from leaves of Ilex latifolia / 中国中药杂志

Two new triterpenoid glycosides, latifolosides R and S (1 and 2), were isolated from the leaves of Ilex latifolia by various column chromatographic methods. Their structures were elucidated based on NMR spectroscopic data and chemical evidence.

Chemical constituents in roots of Ilex kudingcha / 中草药

Objective: To investigate the chemical constituents in the roots of Ilex kudingcha. Methods: Column chromatography such as silica gel, Sephadex LH-20, and preparative HPLC were used to isolate and purify the compounds. Spectroscopic methods like MS, 1H-NMR, and 13C-NMR, and physical constants were used to elucidate their structures. Results: Nineteen compounds were isolated from 95% ethanol extracts of I. kudingcha, including α-aromadendrol-3β-palmitate (1), β-sitosterol (2), α-amyrin (3), 3-acetoxyolean-12-en-28-ol (4), 3-acetoxyurs-12-en-28-ol (5), 3β-acetoxyurs-12-en-28-al (6), oleanolic acid (7), ursolic acid (8), quercetin (9), daucosterol (10), ficuscarpanoside B (11), 3β-hydroxy-28-norurs-12, 17-dien (12), siaresinolic acid (13), pomolic acid (14), α-D-glucose (15), 2, 6-dimethoxy-benzoquinone (16), syringaldehyde (17), dibutyl phthalate (18), and ilexoside D (19). Conclusion: Compounds 6, 12, 16-18 are isolated from the plant for the first time. Compound 11 is isolated from Ilex L. for the first time.

Evaluation of foam properties of saponin from Ilex paraguariensis A. St. Hil. (Aquifoliaceae) fruits

Saponins are natural compounds able to form abundant foam, a desirable quality required in some chemical, foods, cosmetic and pharmaceutical processes. Ilex paraguariensis A. St. Hil. (Aquifoliaceae) known as mate, is a South American widely cultivated specie due to the preparation of a tea-like beverage from its leaves. Moreover, its green fruits are a rich source of non-toxic and very low haemolytic saponins. In this study, mate saponin fraction (MSF) was evaluated as a foam former, focusing on its foamability, foam lifetime, and film drainage in the presence of different electrolytes (ionic strength I = 0.024 M). Sodium dodecyl sulphate (SDS) and polysorbate 80 (Poly-80) were used as reference surfactants. The critical micelle concentration (CMC), the minimum attainable surface tension (γCMC), surface excess concentration (Γ) and cross-section molecular surface (A) values of MSF were comparable to those of Poly-80. The foamability of MSF and both reference surfactants was equivalent. The addition of MgCl2 resulted in a negative effect on MSF foamability. The salts NaCl, KBr, and KNO3 exhibited a negative influence on MSF foam lifetime. Similar behavior was observed for MSF film drainage (order of activity: Na2HPO4 > MgCl2 ≈ NaCl ≈ KNO3 > KBr), where a primary fast film drainage rate was followed by film thinning stabilization after around 5 min. The behavior described above seems to be uncorrelated to the solutions' zeta potential.

As saponinas são compostos naturais capazes de formar espuma abundante, qualidade desejável exigida em alguns processos químicos, alimentícios, cosméticos e farmacêuticos. Ilex paraguariensis A. St. Hil. (Aquifoliaceae), mais conhecida como mate, é uma espécie largamente cultivada devido ao consumo do chimarrão. Além disso, seus frutos verdes representam uma fonte rica de saponinas pouco tóxicas e pouco hemolíticas. Nesse trabalho avaliou-se a fração de saponinas de mate (MSF) como formadora de espuma, com ênfase na espumabilidade, permanência da espuma e drenagem do filme na presença de diferentes eletrólitos (I = 0,024 M). Dodecil sulfato de sódio (SDS) e polissorbato 80 (Poly-80) foram utilizados como tensoativos-referência. Os valores de concentração micelar crítica (CMC), tensão superficial na CMC (γCMC), concentração de excesso de superfície (Γ) e área do grupamento polar na interface (A) referente à MSF foram comparáveis ao Poly-80. A espumabilidade da MSF e de ambos os tensoativos-referência foram equivalentes. A adição de MgCl2 resultou em um efeito negativo sobre a espumabilidade de MSF. Os sais NaCl, KBr e KNO3 tiveram influência negativa sobre a estabilidade da espuma. Em relação à drenagem do filme de MSF, após 60 min. seguiu-se a ordem Na2HPO4 > MgCl2 ≈ NaCl ≈ KNO3 > KBr, caracterizando uma drenagem inicial acelerada seguida pelo equilíbrio hidrodinâmico do filme após 5 min. O comportamento observado parece não estar relacionado com o potencial zeta das soluções.

Atividade antimicrobiana dos extratos de folhas e ramos da Ilex paraguariensis A. St.-Hil., Aquifoliaceae / Antimicrobial activity of extracts of the leaves and branches of Ilex paraguariensis (erva-mate)

Para avaliação da atividade antimicrobiana de Ilex paraguariensis foram utilizados seis microrganismos: Candida albicans, Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus aureus e Staphylococcus epidermidis. O método utilizado foi de difusão do disco. Foram adicionados em discos de papel filtro 10 µl de extratos hidro-alcoólicos das folhas e ramos coletados de dois ambientes distintos, com e sem exposição ao sol. As placas foram incubadas a 35- 37 ºC por 24 h. Os extratos inibiram levedura, bacilos gram-negativos e cocos gram-positivos, não mostrando atividade frente à Escherichia coli.

For the evaluation of the antimicrobial activity of Ilex paraguariensis six microorganisms were used: Candida albicans, Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus aureus and Staphylococcus epidermidis. In disks of filter paper 10 µl of hydro-alcoholic extracts of the leaves and branches from two distinct environments were added, with and without sun exposure. The extracts have inhibited levedura, gram-negative bacillus and gram-positive cocos, with no activity to Escherichia coli.

Aquifoliaceae endémicas del Perú

Esta es una de las familias más conspicuas en los bosques pluviales montanos y húmedos de la vertiente oriental. La familia Aquifoliaceae es reconocida en el Perú por 34 especies en el género Ilex (Brako & Zarucchi, 1993; Ulloa Ulloa et al., 2004), básicamente árboles. En este trabajo reconocemos nueve especies endémicas, casi la mitad de ellas son conocidas solamente en una localidad, y de éstas sólo una ha sido recolectada en el siglo XX. Estos taxones endémicos habitan principalmente las regiones Bosques Muy Húmedos Montanos y Bosques Muy Húmedos Premontanos, entre los 1100 y 3500 m de altitud. Cuatro especies endémicas de Ilex han sido reportadas en el Sistema Nacional de Áreas Naturales Protegidas por el Estado.

This is one of the most conspicuous families in the pluvial and humid forests of the eastern Andean slopes. The Aquifoliaceae are represented in Peru by 34 species in the genus Ilex (Brako & Zarucchi, 1993; Ulloa Ulloa et al., 2004), mostly trees. Here we recognize nine endemic species, nearly half of which are known from a single locality. Of these, only one species has been collected in the 20th century. These endemic taxa are found mainly in Very Humid Montane and Premontane Forests regions, between 1100 and 3500 m elevation. Four endemic species of Ilex have been reported within Peru's protected areas system.