Pentacyclic triterpenoid and saponins from Gambeya boukokoensis

Wandji, Jean; Tillequin, François; Mulholland, Dulcie A.; Shirri, Jovita Chi; Tsabang, Nolé; Seguin, Elisabeth; Vérité, Philippe; Libot, Francine; Fomum, Z. Tanee

doi:10.1016/s0031-9422(03)00495-3

Cited by 35 publications

(17 citation statements)

References 11 publications

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“…Our continuing efforts of the phytochemical study of this plant have led to the isolation of two new nor-ursane type triterpenoids with a five-membered A ring and a novel 2,3-seco-ursane triterpene, which were named davinvolunic acids A-C (compounds 1-3). Moreover, two known ursane triterpenoids, euscaphic acid (4) [7] and myrianthic acid (5) [8], as well as four lupane triterpenes, including lupeol (6) [9], betulin (7) [10], betulinic acid (8) [11] and platanic acid (9) [12] were also obtained in the current study ( Figure 1). This paper deals with the isolation and structure elucidation of the new compounds on the basis of spectroscopic methods, including 1D NMR, 2D NMR analyses, and MALDI-TOF-MS.…”

Section: Introductionsupporting

confidence: 70%

“…In addition, three oxygenated carbons including a methyl (δ C 51.9), a quaternary (δ C 72.9) and a tertiary (δ C 74.7) carbon were recognized in the 13 C-NMR as well as a characteristic double of triplet signal at δ H 2.42 (dt, J = 13.5, 5.0 Hz, 1 H) assignable to H-16α, which is caused downfield shift by the anisotropic effect due to a 19α-hydroxyl group, suggested that compound 1 is an urs-12-ene derivative possessing an α-hydroxyl group at C-19 [13,14]. The characteristic NMR data of compound 1 were comparable to those of euscaphic acid (4) [7] and myrianthic acid (5) [8], two known 19α-hydroxy-urs-12-en triterpenes that were also identified in the present investigation. ).…”

Section: Resultsmentioning

confidence: 78%

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Three New Ring-A Modified Ursane Triterpenes from Davidia involucrata

2014

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Three new ursane triterpenes, 3α,19α-dihydroxy-2-nor-urs-12-en-23,28-dioic acid-23-methyl ester (1), 19α3-dihydroxy-3-oxo-2-nor-urs-12-en-28-oic acid (2), and 2,3-seco-3-methoxy-3,19α3-trihydroxy-urs-12-en-2-al-28-oic acid (3), were isolated from the MeOH extract of the branch barks of Davidia involucrata, together with six known compounds. Their structures were elucidated by means of various spectroscopic analyses. The isolated triterpenes provide important evolutionary and chemotaxonomic knowledge about the monotypic genus Davidia. Five of the identified compounds showed moderate cytotoxicities against the cell proliferation of SGC-7901, MCF-7, and BEL-7404 with IC 50 range from 7.26 to 47.41 μM.

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Section: Introductionsupporting

confidence: 70%

Section: Resultsmentioning

confidence: 78%

Three New Ring-A Modified Ursane Triterpenes from Davidia involucrata

2014

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“…O espectro de absorção na região IV, obtido em KBr, revelou bandas de absorção indicativas da presença de grupos hidroxilas de álcool (3432 e 1042 cm -1 ) e de ácido carboxílico (3100-2500 e 1706 cm A análise dos dados obtidos dos espectros de Tabela 1. Dados de RMN 13 C dos compostos 2, 4 e 5 e comparação com dados da literatura do ácido miriântico (Wandji et al, 2003) e dos modelos 6 (Taketa et al, 2004) C e DEPT 135 da mistura permitiu reconhecer a natureza de um total de 43 sinais de átomos de carbonos (10 não hidrogenados, 08 monoidrogenados, 16 diidrogenados e 09 triidrogenados). Dentre os quais, atenção especial foi dada aos sinais cujos valores de deslocamentos químicos [4+5: δ 127,9 (CH, C-12) e δ 139,9 (C, C-13)], sugeriram esqueletos do tipo ursano (Olea;Roque, 1990;Mahato;Kundu, 1994).…”

Section: Resultsunclassified

“…A ausência de sinais com deslocamentos químicos característicos de carbonos anoméricos eliminou a possibilidade de existência de triterpenos glicosilados, permitindo sugerir estruturas de triterpenos pentacíclicos oxigenados. O sinal no espectro de RMN 1 H em δ 3,07 (sl, H-18) sugeriu para ambos a presença de um grupo hidroxila em C-19 (Taketa et al, 2004) (Wandji et al, 2003). O valor do deslocamento químico atribuído ao C-24 (δ 17,0) no composto 5, sugeriu a confi guração alfa para o grupo hidroxila em C-3.…”

Section: Resultsunclassified

Terpenóides e avaliação do potencial antimalárico, larvicida, anti-radicalar e anticolinesterásico de Pouteria venosa (Sapotaceae)

Montenegro¹,

Oliveira²,

Conserva³

et al. 2006

Rev. bras. farmacogn.

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RESUMO:O presente trabalho descreve o isolamento de quatro triterpenos (taraxerol, ácido ursólico, ácido 3β,19α,23-triidroxiurs-12-en-28-óico e ácido 2α,3α,19α,23-tetraidroxiurs-12-en-28-óico) e um fi toesteróide (espinasterol), bem como a avaliação do potencial antimalárico (cepa NK-65 do Plasmodium berghei), larvicida (larvas do 4º instar do Aedes aegypti), anti-radicalar (2,2-difenil-1-picril-hidrazila, DPPH) e anticolinesterásico de extratos das folhas, cascas do caule e caule de Pouteria venosa (Mart.) Baehni. Todos os compostos isolados estão sendo descritos pela primeira vez nesta espécie e foram identifi cados com base na análise de dados espectrais (IV e RMN, incluindo APT e DEPT), bem como pela comparação com dados descritos na literatura.Unitermos: Pouteria venosa, terpenóides, anticolinesterase, anti-radicalar, malária, larvicida.ABSTRACT: "Terpenoids and evaluation of the antimalarial, larvicidal, anti-radicalar and anticholinesterase potential of Pouteria venosa (Sapotaceae)". This work describes the isolation of four triterpenes (taraxerol, ursolic acid, 3β,19α,23-trihydroxyurs-12-en-28-oic acid and 2α,3α,19α,23-tetrahydroxyurs-12-en-28-oic acid) and a phytosteroid (spinasterol), as well as a preliminary evaluation of antimalarial (NK-65 strains of Plasmodium berghei), larvicidal (4 th instar of Aedes aegypti), anti-radicalar (2,2-diphenyl-1-pycryl-hydrazyl, DPPH) and anticholinesterase activities of Pouteria venosa (Mart.) Baehni extracts from leaves, stem barks and stems. All isolated compounds are being described for the fi rst time in this species and were identifi ed on basis of the spectral data (IR and NMR, including APT, DEPT), as well as by comparison with literature data

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“…Os dados obtidos dos respectivos espectros de RMN 1 H, registrados em CD 3 OD, permitiram identificar C-24, o C-23 absorve em torno de δ C 23,5 (Wandji et al, 2003) e o C-24 é mais protegido (δ C 13,1-15,5) (Mahato & Kundu, 1994).…”

Section: Resultsunclassified

Triterpenos de Guettarda grazielae M: R.V. Barbosa (Rubiaceae)

Lima¹,

Moura²,

Lemos³

et al. 2009

Rev. bras. farmacogn.

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RESUMO:O presente trabalho descreve o isolamento e a identificação estrutural de seis triterpenos (acetato de a-amirina, cicloartenona, 3b,19a,23-triidroxi-urs-12-eno e os ácidos ursólico, 6b,19a,23-tetraidroxi-urs-12-en-28-óico), além de um fitoesteróide (sitostenona) de extratos das folhas, cascas do caule e caule de Guettarda grazielae M.R.V. Barbosa (Rubiaceae). Os compostos isolados, exceto o ácido 3-b-O-b-D-glicopiranosilquinóvico, estão sendo descritos pela primeira vez no gênero Guettarda e foram identificados com base na análise de dados espectrais de RMN, incluindo APT e DEPT, bem como pela comparação com dados da literatura.Unitermos: Guettarda grazielae, Rubiaceae, triterpenos.ABSTRACT: "Triterpenes from Guettarda grazielae M.R.V. Barbosa (Rubiaceae)". This work describes the isolation and structural identification of six triterpenes (a-amyrin acetate, cycloartenone, 3b,19a,23-trihydroxyurs-12-ene, and ursolic, 3-b-O-b-D-glucopyranosylquinovic, 3b,6b,19a,23-tetrahydroxyurs-12-en-28-oic acids), beside a phytosteroid (sitostenone) from leaves, stem barks and stems of Guettarda grazielae (Rubiaceae). All isolated compounds, except 3-b-O-b-D-glucopyranosylquinovic acid, are being described for the first time in the genus Guettarda and were identified on basis of the spectral NMR data, including APT and DEPT, as well as by comparison with data of the literature.

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Pentacyclic triterpenoid and saponins from Gambeya boukokoensis

Cited by 35 publications

References 11 publications

Three New Ring-A Modified Ursane Triterpenes from Davidia involucrata

Three New Ring-A Modified Ursane Triterpenes from Davidia involucrata

Terpenóides e avaliação do potencial antimalárico, larvicida, anti-radicalar e anticolinesterásico de Pouteria venosa (Sapotaceae)

Triterpenos de Guettarda grazielae M: R.V. Barbosa (Rubiaceae)

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