Isorhoifolin, a Flavonoid Glycoside from<i>Periploca nigrescens</i>Leaves

Ogundaini, A. O.; Okafor, E. O.

doi:10.1055/s-2006-962750

Cited by 5 publications

(7 citation statements)

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“…The aqueous leaf extract has been reported for anti-diabetic effect in alloxaninduced diabetic rats and it was also reported for its improvement in sexual activity in rats induced with sexual dysfunction [23,24]. Some of its isolated chemical constituents reported include strophanthidin, strophanthidin glycoside, cymarin and Isorhoifolin [15,25]. The chloroform soluble extract of the leaves was reported to ameliorate dichlorvos-induced cardio-and nephrotoxicity, neurotoxicity, oxidative stress and apoptosis in rats [26,27].…”

Section: Introductionmentioning

confidence: 99%

Anti-diabetic Activity of Convallatoxin Isolated from the Root Bark of Parquetina nigrescens (Afzel.) Bullock (Asclepiadaceae)

Faloye

Ayoola

Amos-Tautua

et al. 2018

EJMP

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This study investigated the anti-diabetic activity of the root bark extract of Parquetina nigrescens and the isolated compound, convallatoxin, from the root bark. A powdered sample of the plant was extracted with methanol, and the extract (A) was tested in glucose-loaded normal rats at 100, 200 and 400 mg/kg for the determination of the most active dose. The anti-diabetic activity of A at 200 mg/kg was carried out on streptozotocin-induced diabetic rats. A was further partitioned to obtain its n-hexane (B 1 ), dichloromethane (B 2 ), ethyl acetate (B 3 ) and mother liquor (B 4 ) fractions that were tested for blood glucose lowering activity using glucose-loaded normal rats model. The anti-

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Section: Introductionmentioning

confidence: 99%

Anti-diabetic Activity of Convallatoxin Isolated from the Root Bark of Parquetina nigrescens (Afzel.) Bullock (Asclepiadaceae)

Faloye

Ayoola

Amos-Tautua

et al. 2018

EJMP

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“…Eleven ursane-type triterpenes ( 186 – 196 ) were found in the species of genus Periploca . Ursolic acid ( 186 ) [94] was acquired in 1987 from P. nigrescens . Moreover, these triterpenes also illuminated a new triterpene ( 196 ), which also has a 13,28-lactone ring [94].…”

Section: Chemical Constituents From the Genus Periplocamentioning

confidence: 99%

“…Ursolic acid ( 186 ) [94] was acquired in 1987 from P. nigrescens . Moreover, these triterpenes also illuminated a new triterpene ( 196 ), which also has a 13,28-lactone ring [94]. Compounds 197 – 207 are triterpenes of the lupane type, and seven ( 197 – 203 ) of them were obtained from the latex of P. laevigata collected in Tunisia [87].…”

Section: Chemical Constituents From the Genus Periplocamentioning

confidence: 99%

Genus Periploca (Apocynaceae): A Review of Its Classification, Phytochemistry, Biological Activities and Toxicology

et al. 2019

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The genus Periploca belongs to the family Apocynaceae, which is composed of approximately ten species of plants according to incomplete statistics. Most of these plants serve as folk medicines with a long history, especially Periploca sepium and Periploca forrestii. The botanical classifications, chemical constituents, biological activities and toxicities of the genus Periploca were summarized in the literature from 1897 to early 2019. Though the botanical classification of this genus is controversial, these species are well-known to be rich sources of diverse and complex natural products—above all, cardiac steroids and C21 pregnane steroids with special structures and obvious pharmacological activities. The various crude extracts and 314 isolated metabolites from this genus have attracted much attention in intensive biological studies, indicating that they are equipped with cardiotonic, anti-inflammatory, immunosuppressive, antitumor, antimicrobial, antioxidant, insecticidal and other properties. It is noteworthy that some cardiac glycosides showed hepatotoxicity and cardiotoxicity at certain doses. Therefore, in view of the medical and agricultural value of the genus Periploca, in-depth investigations of the pharmacology in vivo, the mechanisms of biological actions, and the pharmacokinetics of the active ingredients should be carried out in the future. Moreover, in order to ensure the safety of clinical medication, the potential toxicities of cardiac glycosides or other compounds should also be paid attention. This systematic review provides an important reference base for applied research on pharmaceuticals and pesticides from this genus.

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“…Linarin, a glycosylated flavone, is identified in over 30 plant species from 13 families, and the majority of these species belong to the family Asteraceae ( Mottaghipisheh et al, 2021 ). Isorhoifolin was originally isolated from the leaves of Parquetina nigrescens ( Ogundaini and Okafor, 1987 ). Diosmin is a naturally occurring flavone glycoside that was isolated in 1925 from Scrophularia nodosa and introduced as a therapeutic agent in 1969 ( Bogucka-Kocka et al, 2013 ).…”

Section: Introductionmentioning

confidence: 99%

Rhamnosyltransferases involved in the biosynthesis of flavone rutinosides in Chrysanthemum species

Wei

Feng

et al. 2022

Plant Physiology

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Linarin (acacetin-7-O-rutinoside), isorhoifolin (apigenin-7-O-rutinoside), and diosmin (diosmetin-7-O-rutinoside) are chemically and structurally similar flavone rutinoside (FR) compounds found in Chrysanthemum L. (Anthemideae, Asteraceae) plants. However, their biosynthetic pathways remain largely unknown. In this study, we cloned and compared FRs and genes encoding rhamnosyltransferases (RhaTs) among eight accessions of Chrysanthemum polyploids. We also biochemically characterized RhaTs of Chrysanthemum plants and Citrus (Citrus sinensis and Citrus maxima). RhaTs from these two genera are substrate-promiscuous enzymes catalyzing the rhamnosylation of flavones, flavanones, and flavonols. Substrate specificity analysis revealed that Chrysanthemum 1,6RhaTs preferred flavone glucosides (e.g., acacetin-7-O-glucoside), whereas Cs1,6RhaT preferred flavanone glucosides. The nonsynonymous substitutions of RhaTs found in some cytotypes of diploids resulted in the loss of catalytic function. Phylogenetic analysis and specialized pathways responsible for the biosynthesis of major flavonoids in Chrysanthemum and Citrus revealed that rhamnosylation activity might share a common evolutionary origin. Overexpression of RhaT in hairy roots resulted in 13-, 2-, and 5-fold increases in linarin, isorhoifolin, and diosmin contents, respectively, indicating that RhaT is mainly involved in the biosynthesis of linarin. Our findings not only suggest that the substrate promiscuity of RhaTs contributes to the diversity of flavone rutinosides in Chrysanthemum species but also shed light on the evolution of flavone and flavanone rutinosides in distant taxa.

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Isorhoifolin, a Flavonoid Glycoside fromPeriploca nigrescensLeaves

Abstract: NMR data which distinguished a 1,2glycosidic linkage from a 1,6-attachment (9). Lastly, the structure of ursolic acid was confirmed by comparing its spectra, ('H-and 13C-NMR) and those of the 3

Cited by 5 publications

References 2 publications

Anti-diabetic Activity of Convallatoxin Isolated from the Root Bark of Parquetina nigrescens (Afzel.) Bullock (Asclepiadaceae)

Anti-diabetic Activity of Convallatoxin Isolated from the Root Bark of Parquetina nigrescens (Afzel.) Bullock (Asclepiadaceae)

Genus Periploca (Apocynaceae): A Review of Its Classification, Phytochemistry, Biological Activities and Toxicology

Rhamnosyltransferases involved in the biosynthesis of flavone rutinosides in Chrysanthemum species

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