Ent-beyerene and ent-atisene diterpenes from viguiera insignis

Delgado, Guillermo; Vivar, Alfonso Romo de; Cárdenas, Jorge; Pereda‐Miranda, Rogelio; Huerta, E. M.

doi:10.1016/s0031-9422(00)80536-1

Cited by 14 publications

(16 citation statements)

References 10 publications

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“…The active n-hexane extract was fractionated by vacuum liquid chromatography [6] over silica gel (300 g) using n-hexane-ethyl acetate mixtures to yield an active fraction (F-1, 15.0 g) eluted with n-hexane-ethyl acetate (97: 3 v/v, 6900 ml) which was composed of a diterpenic acid mixture. This mixture (500 mg) was further purified by column chromatography on silica gel (30.0 g) impregnated with 50 % silver nitrate solution [7], using mixtures of n-hexane-CH 2 Cl 2 resulting in the isolation of 40 mg of 1 (4 : Letter parison of mass, 1 H-, 13 C-, and DEPT-NMR data with literature values [8], [9]. Copies of the original spectra are available from the author of correspondence.…”

Section: Methodsmentioning

confidence: 99%

Antispasmodic and Antimicrobial Diterpenic Acids from Viguiera hypargyrea Roots

Zamilpa¹,

Tortoriello²,

Navarro³

et al. 2002

Planta med

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Section: Methodsmentioning

confidence: 99%

Antispasmodic and Antimicrobial Diterpenic Acids from Viguiera hypargyrea Roots

Zamilpa¹,

Tortoriello²,

Navarro³

et al. 2002

Planta med

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“…The EtOAc fraction (110 g) was chromatographied on a silica gel column with a gradient CHCl 3 -MeOH solvent system to afford ten fractions (Fr. [1][2][3][4][5][6][7][8][9][10]. Purification of some parts of the fractions was reported in our previous report.…”

Section: Methodsmentioning

confidence: 99%

Beyerane Derivatives and a Sesquiterpene Dimer from Japanese Cypress (Chamaecyparis obtusa)

Gao

Muto

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Social problems resulting from aging and degeneration of brain function have drawn attention around the world and especially in Japan. Biologically active constituents from plant resources are expected to suppress the development of these problems. We have studied various biologically active constituents from woody plants collected in the Chugoku area of Japan.1-3) In our previous work, the ethyl acetate (EtOAc) soluble fraction of Japanese Cypress (Chamaecyparis obtusa) showed neurite outgrowth-promoting activity on neuronal PC12 cells, and we isolated two novel compounds, 9-O-acetoxydihydrosesamin and a lignan-sesquiterpene conjugate, together with eleven known compounds, and some of the compounds showed potent neurite outgrowth activity. 4) In order to find more new constituents from this fraction, further chemical investigations of the residual fraction were carried out and four new beyerene type derivatives 1-4 (named obtsurins A-D) and a new sesquiterpene dimer ent-cryptomeridiol-4-yl-hinokiate (5), were obtained. Their structures were determined by means of spectral analysis including 2D-NMR and high-resolution (HR)-MS. This paper deals with the isolation and structural elucidation of the new compounds from C. obtusa.

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“…The main classes of secondary metabolites known from the genus so far are terpenoids, i.e., sesquiterpene lactones (STLs), represented mainly by germacranolides, heliangolides and furanoheliangolides [3,4,5,6,7], as well as diterpenes, whose presence has been largely described in the genus. Among the diterpenes, ent -kauranes are the most common types [3,6,8,9,10,11], although ent -beyerane, ent -atisane [12,13] and trachylobane [14] have also been described. Pimarane diterpenes have been found only in A. pinnatilobata [15] and A. arenaria [16,17].…”

Section: Introductionmentioning

confidence: 99%

ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity

Nogueira

Costa²,

Brun

et al. 2016

Molecules

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Aldama discolor (syn.Viguiera discolor) is an endemic Asteraceae from the Brazilian "Cerrado", which has not previously been investigated for its chemical constituents and biological activity. Diterpenes are common secondary metabolites found in Aldama species, some of which have been reported to present potential antiprotozoal and antimicrobial activities. In this study, the known ent-3-α-hydroxy-kaur-16-en-18-ol (1), as well as three new diterpenes, namely, ent-7-oxo-pimara-8,15-diene-18-ol (2), ent-2S,4S-2-19-epoxy-pimara-8(3),15-diene-7β-ol (3) and ent-7-oxo-pimara-8,15-diene-3β-ol (4), were isolated from the dichloromethane extract of A. discolor leaves and identified by means of MS and NMR. The compounds were assayed in vitro against Trypanosoma brucei rhodesiense, T. cruzi and Leishmania donovani, Plasmodium falciparum and also tested for cytotoxicity against mammalian cells (L6 cell line). The ent-kaurane 1 showed significant in vitro activity against both P. falciparum (IC 50 = 3.5 µM) and L. donovani (IC 50 = 2.5 µM) and ent-pimarane 2 against P. falciparum (IC 50 = 3.8 µM). Both compounds returned high selectivity indices (SI >10) in comparison with L6 cells, which makes them interesting candidates for in vivo tests. In addition to the diterpenes, the sesquiterpene lactone budlein A (5), which has been reported to possess a strong anti-T. b. rhodesiense activity, was identified as major compound in the A. discolor extract and explains its high activity against this parasite (100% growth inhibition at 2 µg/mL).

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Ent-beyerene and ent-atisene diterpenes from viguiera insignis

Cited by 14 publications

References 10 publications

Antispasmodic and Antimicrobial Diterpenic Acids from Viguiera hypargyrea Roots

Antispasmodic and Antimicrobial Diterpenic Acids from Viguiera hypargyrea Roots

Beyerane Derivatives and a Sesquiterpene Dimer from Japanese Cypress (Chamaecyparis obtusa)

ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity

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