Kauranoid dieterpenes in Espeletia grandiflora

Piozzi, Franco; Passannanti, Salvatore; Paternostro, Mariapia; Sprio, Vincenzo

doi:10.1016/s0031-9422(00)89958-6

Cited by 37 publications

(29 citation statements)

References 6 publications

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“…To a soln. As described for the preparation of 4, treatment of 16 (100 mg, 0.3 mmol) with LiAlH 4 (210 mg, 5.5 mmol) afforded 17 (80 mg, 88%), which was identified by spectral comparison with literature data [27]. To the mixture was added 1m HCl (5 ml) and H 2 O (5 ml), and stirred for a few min, then extracted with Et 2 O (2 Â 20 ml).…”

Section: Introduction -Steviosidementioning

confidence: 97%

Cytotoxic and Apoptosis‐Inducing Activities of Steviol and Isosteviol Derivatives against Human Cancer Cell Lines

Ukiya

Sawada²,

Kikuchi³

et al. 2013

Chemistry & Biodiversity

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Seventeen steviol derivatives, i.e., 2-18, and 19 isosteviol derivatives, i.e., 19-37, were prepared from a diterpenoid glycoside, stevioside (1). Upon evaluation of the cytotoxic activities of these compounds against leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK-BR-3) cancer cell lines, nine steviol derivatives, i.e., 5-9 and 11-14, and five isosteviol derivatives, i.e., 28-32, exhibited activities with single-digit micromolar IC(50) values against one or more cell lines. All of these active compounds possess C(19)-O-acyl group, and among which, ent-kaur-16-ene-13,19-diol 19-O-4',4',4'-trifluorocrotonate (14) exhibited potent cytotoxicities against four cell lines with IC(50) values in the range of 1.2-4.1 μM. Compound 14 induced typical apoptotic cell death in HL60 cells upon evaluation of the apoptosis-inducing activity by flow-cytometric analysis. These results suggested that acylation of the 19-OH group of kaurane- and beyerane-type diterpenoids might be useful for enhancement of their cytotoxicities with apoptosis-inducing activity.

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Section: Introduction -Steviosidementioning

confidence: 97%

Cytotoxic and Apoptosis‐Inducing Activities of Steviol and Isosteviol Derivatives against Human Cancer Cell Lines

Ukiya

Sawada²,

Kikuchi³

et al. 2013

Chemistry & Biodiversity

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“…The fractionation of the ether extract of J. kirkii resulted in the isolation of three ent-kaurenes, ent-16-kauren-19-oic acid (1), 8) ent-methyl-16-kauren-19-oate (2), 8) and ent-16-kauren-19-ol (3), 9) and two ent-isopimaranes, oblongifolic acid (4) 10) and ent-isopimara-7 (8), 15-dien-19-ol (5). 11) Their spectral data were identical to those of reference compounds.…”

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confidence: 99%

Diterpenoids and Aromatic Compounds from the Three New Zealand Liverworts Jamesoniella kirkii, Balantiopsis rosea, and Radula Species

Nagashima

Kuba

Asakawa

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Compound 1, obtained as white amorphous powder (CHCl 3 ), gave a molecular formula of C 20 (17)) and 4.79 (s, H b -C(17))). The 13 C-NMR spectrum ( Table 2) of 1 showed 20 C-atom resonances, which were classified by analysis of its chemical shift values and its HSQC spectrum as: three Me, eight sp 3 CH 2 , one sp 2 CH 2 (d(C) 103.1 (C(17))), three sp 3 CH, of which one was O-bearing (d(C) 68.7 (C(6))), four sp 3 quaternary C-atoms, of which one was 1 These two authors contributed equally to this work. O-bearing (d(C) 78.0 (C(9))), and one sp 2 quaternary C-atom (d(C) 154.8 (C(16))).…”

Section: Resultsmentioning

confidence: 94%

“…The molecular formula of compound 4 was deduced to be C 20 H 32 O 3 by 13 C‐NMR data and HR‐ESI‐MS, indicating one fewer index of hydrogen deficiency than kaur‐16‐en‐19‐al ( 7 ), which was isolated by Piozzi et al . from Espeletia grandiflora .…”

Section: Resultsmentioning

confidence: 99%

Four New Kaurane Diterpenoids from the Chinese Liverwort Jungermannia comata Nees

Wang

et al. 2016

Chemistry & Biodiversity

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In our continuing program to find new bioactive compounds from the Chinese liverworts, four new kaurane-type diterpenoids, (6β)-kaur-16-ene-6,9-diol (1), (6β,12β)-kaur-16-ene-6,9,12-triol (2), (6β)-kaur-16-ene-5,6,9-triol (3), and kaur-16-ene-9,19-diol (4), have been isolated from the Chinese liverwort Jungermannia comata Nees. Five known kaurane-type diterpenoids (5 - 9) and four known trachylobane-type diterpenoids (10 - 13) were also obtained. The structures of the new compounds were established unequivocally on the basis of spectroscopic data. The absolute configuration of compound 1 was established by comparing experimental and calculated electronic circular dichroism spectra.

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Kauranoid dieterpenes in Espeletia grandiflora

Cited by 37 publications

References 6 publications

Cytotoxic and Apoptosis‐Inducing Activities of Steviol and Isosteviol Derivatives against Human Cancer Cell Lines

Cytotoxic and Apoptosis‐Inducing Activities of Steviol and Isosteviol Derivatives against Human Cancer Cell Lines

Diterpenoids and Aromatic Compounds from the Three New Zealand Liverworts Jamesoniella kirkii, Balantiopsis rosea, and Radula Species

Four New Kaurane Diterpenoids from the Chinese Liverwort Jungermannia comata Nees

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