n-Alkyl glycosides and p-hydroxybenzoyloxy glucose from fruits of Crescentia cujete

Kaneko, Tetsuo; Ohtani, Kazuhiro; Kasai, Ryoji; Yamasaki, Kazuo; Nguyen, Mai

doi:10.1016/s0031-9422(97)00409-3

Cited by 49 publications

(36 citation statements)

References 13 publications

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“…In the lowestenergy conformation of the (2'R,4'S)-1 isomer, on the other hand, Me(5') is quite distant from HÀC(1'') (4.5 ), and H b ÀC(3') is not anti-periplanar to either HÀC(2') or HÀC(4'). Therefore, 1 was identified as a (2'S,4'R)-isomer, a new natural product with the same configuration as 3 and in agreement with the configuration previously reported for the pentane-2,4-diol-derived glucoside on the basis of an empirical glycosylation shift rule [15]. We cannot exclude the possibility that 3 is formed by hydrolysis of its possible precursor 1.…”

supporting

confidence: 86%

“…An alkaline hydrolysis of 1 afforded a compound identical with 3. To verify whether the configuration of 1 and 3 is the same as that previously reported for the pentane-2,4-diol-derived glucoside isolated from Crescentia cujete fruits [15], we synthesized the mono-d-glucosides of (2R,4R)-and (2S,4S)-pentane-2,4-diols, i.e., 3a and 3b, respectively. A comparison of the NMR spectra of 3 with those of 3a and 3b (Tables 1 and 2) allowed us to exclude immediately configurations corresponding to the (2R,4R)-and (2S,4S)-isomers.…”

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confidence: 76%

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Unusual p‐Coumarates from the Stems of Vaccinium myrtillus

Hybelbauerová

Sejbal

Dračínský

et al. 2009

Helvetica Chimica Acta

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The two previously unreported esters 1 and 2 of pentane-2,4-diol and p-coumaric acid (¼ 3-(4-hydroxyphenyl)prop-2-enoic acid) along with 13 known compounds including 6 oleanane-and ursanetype triterpenoids were isolated from MeOH extracts of the stems of Vaccinium myrtillus. The structures of the new compounds were assigned as (2S,4R)-4-(b-d-glucopyranosyloxy)pentan-2-yl (2E)-pcoumarate (1) and its aglycone 2 on the basis of 1D-and 2D-NMR spectroscopic analyses of the isolated and synthesized compounds and molecular modelling experiments. This is the first report on the occurrence of a chiral pentane-2,4-diol linker between the phenol-derived acid and a glycoside part in natural products.Introduction. -Bilberry (Vaccinium myrtillus L., Ericaceae), also known as European blueberry, has a long history in European folk medicine of being widely used in the form of fruits, tinctures, teas, and other herbal formulas for the treatment of diarrhoea, circulatory diseases, eye conditions, inflammation, and diabetes [1]. The health-promoting properties of bilberry fruits have been largely associated with phenol-type antioxidants [2], among which delphinidin, cyanidin, and petunidin glycosides [3], p-coumaric acid, ferulic acid, and quercetin derivatives [4] [5] are the frequently found components. Recent reviews highlight the effects of berry (and other natural) phenols on some microbial infections [6] and different types of cancer [7].Unlike the berries, the other vegetative organs have attracted much less attention. Although some phenol compounds identified in Vaccinium berries have also been found in the leaves, roots, and stems of the plant [8] [9], most of the previous studies have been restricted to total-phenolic contents, as a result of which essential information on the authentic structure of the phytochemicals might have been lost [10]. Rather surprisingly, limited information is also available on the triterpenoid berry constituents [11] regardless of the well-documented ability of these compounds to influence various stages of tumor development [7] [12]. Considering the growing interest in hydroxycinnamic acid derivatives [13] and other berry phytochemicals [7] [14], we report here the isolation and identification of the two new pentane-2,4-diolderived p-coumarates 1 and 2 along with 13 known compounds including 6 triterpenoids (p-coumaric acid ¼ 3-(4-hydroxyphenyl)prop-2-enoic acid). The structure and configuration of the new compounds were determined by MS, 1D-and 2D-NMR, chemical, and molecular-modelling techniques.

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confidence: 86%

mentioning

confidence: 76%

Unusual p‐Coumarates from the Stems of Vaccinium myrtillus

Hybelbauerová

Sejbal

Dračínský

et al. 2009

Helvetica Chimica Acta

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“…The effectiveness of these two species as herbal remedies may be due to the presence of other types of secondary metabolites such as flavanoids, glycosides, phenols, sapogenins, saponins, and tannins (Heltzel et al, 1993a(Heltzel et al, , 1993bBinutu & Lajubutu, 1994;Kaneko et al, 1997Kaneko et al, , 1998Betancur-Galvis et al, 1999;Bystrom et al, 2008;Ogbuagu, 2008). For example, the fruit pulp of C. cujete contains flavanoids, saponins, cyanogenic glycosides (as HCN), phenols, and tannins (Ogbuagu, 2008).…”

Section: Discussionmentioning

confidence: 99%

The good and the bad: Alkaloid screening and brineshrimp bioassays of aqueous extracts of 31 medicinal plants of eastern Nicaragua

Coe

Parikh

Johnson

et al. 2011

Pharmaceutical Biology

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“…This biological activity lends support to its ethnomedical use to treat snakebite. Neurolaena lobata (leaves, ethanolic (Kaneko et al, 1998;Morton, 1968;Orso, 1970 (Filipoy, 1994;Duke, 1994;Guzman, 1947;Chou, 1960;Vitalyos, 1979;Darias et al, 1986;Okuyama et al, 1993) To expel worms LF: jc: 2 tblsp 3 (Krag, 1976;Heinrich et al, 1992;Aguilar Giron, 1966;Johnson and Croteau, 1984;Nakazawa, 1996) CONVOLVULACEAE -Salas, 1944;Hirschmann and Rojas de Arias, 1990;Weninger et al, 1982) Facilitate child birth WP: dec: 1 glass qid or bid 2 (Brenneker, 1961;Roig y Mesa, 1945) Fever WP: dec: 1/4-1/2 glass qid or bid 2 (Barrett, 1994;Coe and Anderson, 1996a;Gupta et al, 1979) Hypertension WP: dec: 1/4-1/2 glass qid or bid 2 (Hasrat et al, 1997;Mokkhasmit et al, 1971;Caballero-George et al, 2001) DILLENIACEAE (Comerford, 1996;Logan, 1973;Nuñez-Melendez, 1975) MYRTACEAE Psidium guajava L. (FLORPAN 1391; 10/10/93) NR Diarrhea AB: dec: 1 glass each 2-3 h 3 (Coe and Anderson, 1996b;Gill and Akinwumi, 1986;Ramírez et al, 1988;Gupta et al, 1979;Pittier, 1957) (Kamperdick et al, 1997;Freire et al, 1993;…”

Section: Discussionmentioning

confidence: 99%