First examples of dammarane triterpenes isolated from Celastraceae

Chávez, Haydee; Estévez‐Braun, Ana; Ravelo, Ángel G.; González, Antonio G.

doi:10.1016/s0040-4020(97)00303-7

Cited by 27 publications

(20 citation statements)

References 7 publications

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“…Moreover, the 13 C NMR spectrum displayed signals attributed to an oxymethine carbon (δ 81.1), an ester carbonyl group C NMR spectra of 1 were in close agreement with those of 24(E/Z)-3-oxodammara-20,24-dien-26-al, except for the side-chain moiety. 9 The presence of an α,β-unsaturated-δ-lactone moiety was established by observation of the HMBC spectrum data (Fig. 2), which showed long-range correlations from 10 The δ-lactone moiety was confirmed the 22S configuration on the basis of a negative Cotton effect at 257 nm (Δε −16.9) in the CD spectrum.…”

Section: Resultsmentioning

confidence: 86%

A New Dammarane-type Triterpene with PTP1B Inhibitory Activity from Gynostemma pentaphyllum

Li¹,

Tuo²,

Shen³

et al. 2014

Bulletin of the Korean Chemical Society

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Gynostemma pentaphyllum (Thunb.) Makino (Cucurbitaceae), a perennial liana herb, is widely cultivated in China, Japan and Korea. It has been traditionally used as medicinal herbs for treatment of cardiovascular disease, hyperlipidaemia, hypertension, hepatitis, diabetes and cancer, 1 and the biologically active components are believed to be Saponins. (Fig. 1). Herein we reported the isolation, structural elucidation of a new dammaranetype triterpene and evaluation of PTP1B inhibitory activity about these isolates. Results and DiscussionCompound 1 was obtained as white solid. Its molecular formula was determined as C 30 H 45 O 3 by HRESIMS. The 1 H NMR spectrum of 1 showed the presence of six methyl singlets at δ 0.91, 0.92, 0.97, 1.02, 1.06, 1.91, an oxymethine signal as a doublet of doublets at d 4.75 (J = 12.4, 3.6 Hz), a exomethyene singlets at δ 5.22 and 5.25, and another olefinic signal at δ 6.59 as a broad triplet (J = 6.4 Hz) ( Table 1). These data indicated that the structure of 1 might contain terminal olefinic and tri-substituted olefinic groups, which also supported by the presence of four sp 2 signals (δ 149.4, 139.4, 128.6 and 113.7) in 13 C NMR spectrum of 1 (Table 1). Moreover, the 13 C NMR spectrum displayed signals attributed to an oxymethine carbon (δ 81.1), an ester carbonyl group

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Section: Resultsmentioning

confidence: 86%

A New Dammarane-type Triterpene with PTP1B Inhibitory Activity from Gynostemma pentaphyllum

Li¹,

Tuo²,

Shen³

et al. 2014

Bulletin of the Korean Chemical Society

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“…Don leaves ( family Rubiaceae) afforded a new dammarane triterpenoid obtained as white needle crystals; (74.7 mg) gave positive Liebermann-Burchard test, pink color after spraying with EtOH/H 2 SO 4 reagent indicating terpenoid nature. [13] ; whereas the terminal methylene showed vibration at 915 cm -1 in CDCl 3 [16] . 13 C NMR Table ( [17] .…”

Section: Resultsmentioning

confidence: 99%

A New Dammarane Triterpenoid Compound Isolated From Ixora Finlaysoniana

Ibrahim¹,

Meselhy²,

Ali³

et al. 2017

IOSRJPBS

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Abstract:The air-dried leaves of Ixora finlaysoniana Wall. ex. Don ( family Rubiaceae) afforded a new dammarane triterpenoid named: 17β-dammara-1-one -20 ene-3β-3', 8'-dimethyloctanoate (1) together with two known saturated fatty acids capric (2) and palmitic (3) from the chloroform extract as well as three phenolic acids: gallic (4), caffeic (5), chlorogenic (6), six flavonols: )(4''-trans-p-coumaroyl)-D-glucopyranoside-7-O--L-rhamnopyranoside (10), Kaempferol-3-O--L-rhamnopyranosyl(1'''→2'')(4''-trans-p-coumaroyl)-D-arabinopyranosid-7-O--Lrhamnopyranoside (11) and kaempferol (12) in addition to two isoflavones: Biochanin A (13), Biochanin A-7-O--D-rutinoside (14)were isolated from methanol extract . All these structures were isolated for the first time from Ixora finlaysoniana leaves and were elucidated by different chromatographic and UV, extensive 1D and 2D NMR spectroscopy and MS.

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“…Fraction A provided friedelin, 25) 29-hydroxyfriedelane-3-one, 26) and olean-12-ene-3b, 6b-diol. 27) Fraction B yielded tingenone, 28) pristimerin, 28) glut-5-ene-3b,29-diol, 29) celastrol, 30) 24-(Z)-3-oxodammara-20(21),24-dien-26-al, 7) and 24-(E)-3-oxodammara-20(21),24-dien-26-al. 7) Fraction C afforded 24-(E)-6b, 26-dihydroxydammara-20(21),24-dien-3-one, 7) 28-hydroxyfriedelane-1,3-dione 8) and 25-oxo-friedelane-3-one, 32) netzahualcoyene, 33) glut-5-ene-3b, 29-diol, 27) 24(E)-26-hydroxydammara-20(21),24-dien-3-one, 7) 24(E)-23a-hydroxy-26-oxodammara-20(21),24-dien-3-one, 7) 24(E)-23b-hydroxy-26-oxodammara-20(21),24-dien-3-one, 7) 24(E)-6b-hydroxy-26-oxodammara-20(21),24-dien-3-one, 7) 24(E)-6b,26-dihydroxydammara-20(21),24-dien-3-one, 7) 24(E)-26-hydroxydammara-20(21),24-dien-3-one, 7) and 23(Z)-25-nordammara-20(21),24-dien-3,25-dione.…”

Section: Methodsmentioning

confidence: 99%

“…7) Fraction C afforded 24-(E)-6b, 26-dihydroxydammara-20(21),24-dien-3-one, 7) 28-hydroxyfriedelane-1,3-dione 8) and 25-oxo-friedelane-3-one, 32) netzahualcoyene, 33) glut-5-ene-3b, 29-diol, 27) 24(E)-26-hydroxydammara-20(21),24-dien-3-one, 7) 24(E)-23a-hydroxy-26-oxodammara-20(21),24-dien-3-one, 7) 24(E)-23b-hydroxy-26-oxodammara-20(21),24-dien-3-one, 7) 24(E)-6b-hydroxy-26-oxodammara-20(21),24-dien-3-one, 7) 24(E)-6b,26-dihydroxydammara-20(21),24-dien-3-one, 7) 24(E)-26-hydroxydammara-20(21),24-dien-3-one, 7) and 23(Z)-25-nordammara-20(21),24-dien-3,25-dione. 7) From the last fraction E, we isolated 1 (11.2 mg), 2 (10.6 mg), and ilicifoline. 31) 3H, s, H 3 -26), 4.72 (1H, s, H-21a), 4.78 (1H, s, H-21b), 6.10 (1H, t, Jϭ 3 (CH 3 , C-19), 15.8 (CH 3 , C-30 Octa-nor-13-hydroxydammara- C-7 Biological Assays.…”

Section: Methodsmentioning

confidence: 99%