Partially-acetylated dodecanyl tri- and tetra-rhamnoside derivatives from (annonaceae)

Tané, Pierre; Ayafor, J. Foyere; Sondengam, B.L.; Lavaud, Catherine; Massiot, Georges; Connolly, Joseph D.; Rycroft, David S.; Woods, Neill

doi:10.1016/s0040-4039(00)82058-4

Cited by 20 publications

(28 citation statements)

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“…These are lipid glycosides whose lipid portion is derived from fatty alcohol linked carbohydrate through glycosidic bond. This type of glycosides have been previously reported from the genus Cleistopholis (Annonaceae) [6][7][8] and were found to possess significant antibacterial 9) activity. The specimens of the soft coral were cut into thin slices and extracted with methanol.…”

supporting

confidence: 61%

“…The methanol soluble materials were concentrated under reduced pressure below 50°C and the dark brown residue was fractionated with ethyl acetate and n-butanol successively. The ethyl acetate soluble fraction led to the isolation of six pure compounds (3)(4)(5)(6)(7)(8) 11) spectra revealed the presence of three pentose rings. All three rings were assigned as a-D-arabinopyranoside on the basis of small vicinal coupling constant (Jϭ3.0 Hz) of C-5a protons.…”

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confidence: 99%

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Two New Glycosides from the Soft Coral Sinularia firma

Kumar

Lakshmi

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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confidence: 61%

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confidence: 99%

Two New Glycosides from the Soft Coral Sinularia firma

Kumar

Lakshmi

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Investigation of the non-polar fractions led to the isolation of cleistetroside peracetate (5) [12]. Cleistrioside-2 and -3 (2, 3) and cleistetroside-6 (4) [13,14] were obtained as gummy solids from the polar fractions.…”

Section: Resultsmentioning

confidence: 99%

“…As part of our study of the family Annonaceae, we report here the isolation and the structural elucidation of a new monoterpene derivative together with four known partially and total acetylated tri-and tetrarhamnoside dodecanyl ether derivatives [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

4,5-Epoxide-1,6-dimethyl-1-vinylhexyl p-coumarate: A novel monoterpene derivative from Cleistopholis patens

Ngnokam

Tsopmo

Ayafor

et al. 2004

Bull. Chem. Soc. Eth.

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“…1,2 From the stem bark of Cleistopholis glauca and the leaves of Cleistopholis patens (Annonaceae), a number of partially acetylated oligorhamnoside derivatives were isolated. [1][2][3][4] Among these compounds, cleistetroside-2…”

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confidence: 99%

Facile synthesis of cleistetroside-2, a partially acetylated oligorhamnoside from Cleistopholis glauca and patens

Cheng

Chen

2007

Carbohydrate Research

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(cleistetroside-2), was synthesized via '2+2' convergent strategy. Annonaceae is a family of large trees that grow in the rain forests of Africa. Extracts from the stem bark of this species are used to treat stomach pain, bronchial diseases and hepatitis. The root is believed to be a vermifuge, and the leaves are commonly employed for the treatment of fever.1,2 From the stem bark of Cleistopholis glauca and the leaves of Cleistopholis patens (Annonaceae), a number of partially acetylated oligorhamnoside derivatives were isolated.1-4 Among these -rhamnopyranoside] was found to show significant in vitro antibacterial activity against Gram-positive bacteria. 4 For investigation of the oligosaccharide's structure-bioactivity relationships in respect to antibacterial activities, 5 we have prepared a series of L L-rhamnose oligosaccharides. 6 Here we would like to report a facile synthesis of cleistetroside-2, a partially acetylated oligorhamnoside isolated from the stem bark of Cleistopholis glauca and the leaves of Cleistopholis patens (Annonaceae).As outlined in Scheme 1, fully acetylated L L-rhamopyranose 1 was converted into dodecanyl 2,3-O-isopropylidene-a-L L-rhamnopyranoside (2) by a method similar to that of reported. 7 Similarly, compound 1 was transformed into isopropyl 2,3,4-tri-O-acetyl-1-thio-a-L Lrhamnopyranoside (3) under modified Helferich reaction conditions. 8 Deacetylation of 3 with NaOMe in methanol gave the acceptor, isopropyl 1-thio-a-L Lrhamnopyranoside (4). 2,3-O-Isopropylidenation of 4 with Me 2 C(OMe) 2 in the presence of TsOH in acetone, and acetylation with Ac 2 O in pyridine, afforded isopropyl 2,3-O-isopropylidene-1-thio-a-L L-rhamnopyranoside (5) in 85.5% yield over three steps. Cleavage of the isopropylidene group from 5 using aq 80% AcOH at 55°C gave isopropyl 4-O-acetyl-1-thio-a-L L-rhamnopyranoside (6), which was then silylated with TBSCl and imidazol in DMF at 50°C to give the building block, isopropyl 4-O-acetyl-2,3-di-O-tert-butyldimethylsilyl-1-thio-a-L L-rhamnopyranoside (7) in 89% yield. Glycosyl donor 4-O-acetyl-2,3-O-isopropylidene-a-L L-rhamnopyranosyl trichloroacetimidate (8) was obtained from 5 0008-6215/$ -see front matter Ó

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Partially-acetylated dodecanyl tri- and tetra-rhamnoside derivatives from (annonaceae)

Cited by 20 publications

References 2 publications

Two New Glycosides from the Soft Coral Sinularia firma

Two New Glycosides from the Soft Coral Sinularia firma

<b>4,5-Epoxide-1,6-dimethyl-1-vinylhexyl <i>p</i>-coumarate: A novel monoterpene derivative from <i>Cleistopholis patens</i></b>

Facile synthesis of cleistetroside-2, a partially acetylated oligorhamnoside from Cleistopholis glauca and patens

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