Cycloartane Glycosides from <i>Sutherlandia frutescens</i>

Xiang, Fu; Li, Xing-Cong; Smillie, Troy J.; Carvalho, Paulo; Mabusela, Wilfred T.; Syce, James; Johnson, Quinton; Folk, William R.; Avery, Mitchell A.; Khan, Ikhlas A.

doi:10.1021/np800328r

Cited by 56 publications

(51 citation statements)

References 21 publications

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“…[25][26][27][28][29][30] Although the chemical semi-synthesis of compoundsw ith aC 6 -C 7 -C 6 -C 5 core has been reported, only biocatalysis couldr ealize this reactionu nder mild conditions. [31][32][33] More interestingly,t he biocatalysis of CA by S. racemosum could form 3,10-epoxy (23-26)o r6 ,19-epoxy (27)s tructures, which are reported for the first timef or 9,10-seco-cycloartanes.…”

Section: C-3 or C-6 Acetylation Products 9-12mentioning

confidence: 93%

Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti‐Aging Derivatives

Feng

Qiao

et al. 2015

Adv Synth Catal

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Cycloastragenol is ac ycloartane-type triterpenoid with significant telomerase-activating activities.Inthis paper, the biocatalysisofc ycloastragenol by two strains of filamentous fungi, namely Syncephalastrum racemosum AS 3.264 and Alternaria alternata AS 3.4578, was investigated. Scaled-up biotransformation reactions yielded 27 metabolites. Their structures were established on the basis of extensiveN MR and HR-ESI-MS data analyses,a nd 18 of them are new compounds.T he twof ungal strains exhibited distinct biocatalytic features. S. racemosum could catalyzer ing expansion ande poxidation reactions to form 3b,10b-epoxy-o r6 a ,19a-epoxy-9,10-seco-cycloartane structures,w hereas A. alternata preferredt oc atalyzea cetylation reactions,e specially at 3-OH, 6-OH and1 9-OH. These regio-ands tereoselective reactions are difficult to achieve by chemical means,b ut could be realized under mild conditions by biocatalysis.F urthermore,w ef ound that some acetylated derivatives at 50 mMc ould significantly extend the lifespan of Caenorhabditise legans from 16.93 AE 0.70 do ft he control group to 20.01 AE 0.75 d (P < 0.01), versus 18.54 AE 0.67 df or cycloastragenol. These biotransformed derivatives of cycloastragenol could be potential anti-aginga gents.

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Section: C-3 or C-6 Acetylation Products 9-12mentioning

confidence: 93%

Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti‐Aging Derivatives

Feng

Qiao

et al. 2015

Adv Synth Catal

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“…Extracts are also reported to inhibit the action of HIV target enzymes (Hartnett et al 2005). Furthermore, aqueous extracts of field leaves have been shown to contain L-canavanine, gamma amino butyric acid (GABA), D-pinitol, flavonoids and saponins (Fu et al 2008;van Wyk and Albrecht 2008), but reports on their yields in seeds and in vitro cultures are lacking. The objective of this study was therefore to quantify the content of L-canavanine, arginine, GABA and D-pinitol, in seeds, field leaves and in vitro leaves of L. frutescens using modern analytical techniques such as gas and liquid chromatography (Cheng et al 2007;Dias et al 2009).…”

Section: Introductionmentioning

confidence: 99%

HPLC and GC analyses of in vitro-grown leaves of the cancer bush Lessertia (Sutherlandia) frutescens L. reveal higher yields of bioactive compounds

Shaik

Singh

Nicholas

2010

Plant Cell Tiss Organ Cult

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Lessertia frutescens L., commonly known as cancer-bush, is a medicinally reputed plant species indigenous to southern Africa. Field leaf extracts of this species are known to exhibit many curative properties. However, little is known about the bioactive compounds that are present in in vitro leaf extracts and seed extracts. The objective of this study was to verify the presence of and quantify L-canavanine, gamma amino butyric acid (GABA), arginine and D-pinitol in the seeds, field leaves and in vitro leaves of L. frutescens using gas and liquid chromatography. Methanolic extracts of in vitro leaves, field leaves and seeds were used. MRM chromatograms were recorded for L-canavanine and arginine using tandem mass spectrometry. GC chromatograms were recorded for GABA and D-pinitol using gas chromatography. D-Pinitol was found to be most abundant and was 14.75 and 18.17 mg/g in in vitro and field leaf extracts respectively, followed by GABA (7.29 and 3.48 mg/g), arginine (7.08 and 0.35 mg/g) and L-canavanine (0.55 and 0.08 mg/g). In the seed extracts, GABA content was found to be the highest (1.69 mg/g) followed by L-canavanine (0.37 mg/g), then D-pinitol (0.25 mg/g), and arginine (0.02 mg/g). In vitro leaves had higher quantities of all compounds, except for D-pinitol. This study therefore highlights the potential of bulking in vitro leaves for the extraction of the medicinal compounds, L-canavanine and GABA.

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“…The above information implied that compound 1 might possess a 9,10-seco-cycloartane triterpenoid skeleton. [11][12][13] Acid hydrolysis of 1 produced a triterpenoid aglycone (1a), and D-glucose, D-xylose, L-arabinose and D-glucuronic acid as sugar residues which were identified by comparison with the respective authentic samples by GC analysis. The 1 Hand 13 C-NMR spectra of 1a confirmed that the structure of the aglycone moiety (1a) was the same as secomacrogenin B 13) (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Cyprotuoside C and Cyprotuoside D, Two New Cycloartane Glycosides from the Rhizomes of <i>Cyperus rotundus</i>

Lin

Zhou

2018

Chem. Pharm. Bull.

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Cyprotuoside C (1) and cyprotuoside D (2), two new cycloartane glycosides were isolated from the ethanol extract of the rhizomes of Cyperus rotundus. Their structures were identified as 24R-9,10-seco-cycloartan-1(10),9(11)-dien-3β,7β,24,25-tetraol (1) and 9,10-seco-cycloartan-1(10),9(11),23(24)-trien-3β,7β,25-triol 3-O-β- 3-O-β-D-xylopyranosyl-(1→4)-[α-L-arabinopyranosyl-(1→6)]-β-Dglucopyranosyl-25-O-β-D-glucuronide D-xylopyranosyl-(1→4)-{α-L-arabinopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→2)]}-β-D-glucopyranosyl-25-O-β-D-glucuronide (2) by spectroscopic methods.

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Cycloartane Glycosides from Sutherlandia frutescens

Cited by 56 publications

References 21 publications

Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti‐Aging Derivatives

Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti‐Aging Derivatives

HPLC and GC analyses of in vitro-grown leaves of the cancer bush Lessertia (Sutherlandia) frutescens L. reveal higher yields of bioactive compounds

Cyprotuoside C and Cyprotuoside D, Two New Cycloartane Glycosides from the Rhizomes of <i>Cyperus rotundus</i>

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