Novel acetylated flavonoid glycosides from the leaves of Allium ursinum

Wu, Haipeng; Dushenkov, Slavik; Ho, Chi‐Tang; Sang, Shengmin

doi:10.1016/j.foodchem.2008.12.058

Cited by 59 publications

(48 citation statements)

References 13 publications

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“…Connectivity of the latter to the C-4Ј was confirmed from the HMBC correlations of the methylene protons at d H 4.95 (H 2 -4Ј) and the aromatic proton at d H 7.98 (H-2/H-6) with the carbonyl group at d H 167.6 (C-7). By combination of the above evidence and 1 Hand 13 C-NMR spectroscopic analysis, it was concluded that the structure of cucullamide is 1. Several putrescine bisamides such as aglaiduline, leptagline, gigantamide A, grandiamide D were isolated from different Aglaia plants.…”

Section: Resultsmentioning

confidence: 95%

“…The ethyl acetate fraction was then subjected to repeated column chromatography on Sephadex LH20, silica gel 60N, octadecylsilyl (ODS) gel, and preparative thin layer chromatography (PTLC) to obtain dasyclamide (2), 9) ent-2b-hydroxymanool (3), 10) chrysin (4), 11) apigenin (5), 12) and kaempferol-3-O-b-D-glucopyranoside (6). 13) All of the known compounds were identified by spectroscopic data including 1D and 2D NMR and by comparison with those published in the literature. All these five known compounds are isolated and reported for the first time from this plant.…”

Section: Resultsmentioning

confidence: 99%

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Cucullamide, a New Putrescine Bisamide from Amoora cucullata

et al. 2010

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Amoora cucullata (Meliaceae) is a tall tree, grown in the coastal areas of Southeast Asia and the Indian Ocean. This plant has been used as a folk medicine for treatment of inflammation, marrow and diarrhea.1) Additionally, juice of the leaves has antibacterial activity and extensively used for the treatment of dysentery, skin and cardiac diseases.2) The crude methanolic extracts of leaves were reported to show antiinflammatory, antinociceptive, diuretic, and central nervous system (CNS) depressant activities.3,4) Phytochemical analysis of the stem bark of Amoora cucullata led to the isolation of fridelin, stigmasterol, b-sitosterol, betulinic acid and caffeic acid.5) Furthermore, analysis of the leaves showed the presence of several polyphenols and tannins, whether from its fruits, several rocagloic acid derivatives were isolated.6) In continuation of our phytochemical screening of A. cucullata leaves, we report the isolation and structure elucidation of one new putrescine bisamide, cucullamide (1), along with five known natural compounds (2-6) ( Fig. 1). The new putrescine bisamide derivative (1) and dasyclamide (2) were evaluated for their Wnt signal inhibitory activities, since we are recently interested in screening studies targeting signaling molecules related to cancer diseases. 7) Results and DiscussionThe fresh leaves of Amoora cucullata were collected from the Sundarbans Mangrove Forests, Bangladesh.8) The methanolic extract of A. cucullata was partitioned successively with ethyl acetate, nBuOH, and water. The ethyl acetate fraction was then subjected to repeated column chromatography on Sephadex LH20, silica gel 60N, octadecylsilyl (ODS) gel, and preparative thin layer chromatography (PTLC) to obtain dasyclamide (2), 9) ent-2b-hydroxymanool (3), 10) chrysin (4), 11) apigenin (5), 12) and kaempferol-3-O-b-D-glucopyranoside (6). 13) All of the known compounds were identified by spectroscopic data including 1D and 2D NMR and by comparison with those published in the literature. All these five known compounds are isolated and reported for the first time from this plant.Compound 1 was isolated as a white solid. On the TLC plate after developing compound 1, it gave a positive color reaction after spraying with Dragendorff reagent and dark fluorescence under UV light at 254 nm. The electrospray ion- Sciences, Chiba University; 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan: b Pharmacy Discipline, Life Science School, Khulna University; Khulua-9208, Bangladesh: and c Chemistry Department, Faculty of Science, Helwan University; Cairo 11795, Egypt. Received April 30, 2010; accepted May 21, 2010; published online May 21, 2010 A new putrescine bisamide derivative named cucullamide (1) was isolated from the leaves of Amoora cucullata, together with five known natural products, dasyclamide (2), ent-2b-hydroxymanool (3), chrysin (4), apigenin (5), and kaempferol-3-O-b-D-glucopyranoside (6). The structure of the new isolated compound was elucidated on the basis of 1D and 2D NMR as well as high resolution-ele...

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

Cucullamide, a New Putrescine Bisamide from Amoora cucullata

et al. 2010

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“…Many kaempferol glycosides have been reported so far from many kinds of plants, and recent studies have revealed various diglycosides, 21) branched triglycosides, 22) and remarkable tetra- 23) or pentaglycosides. 24) With regard to peach leaf investigated here, it is known to be a rich source of kaempferol 3-O-glucoside.…”

Section: Fig 2 Separation Scheme For An Inhibitor Of Glucose Absorpmentioning

confidence: 99%

Peach Leaf Contains Multiflorin A as a Potent Inhibitor of Glucose Absorption in the Small Intestine in Mice

Shirosaki

Gotö²,

Hirooka³

et al. 2012

Biological & Pharmaceutical Bulletin

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Peach leaf extract has anti-hyperglycemic effects on the postprandial blood glucose level in glucoseloaded mice. In our previous study, the mechanism of action was considered to be the inhibition of glucose absorption in the small intestine. To elucidate the active principle in peach leaf, purification of the active compound and a structure determination were performed. With the use of bioassay-guided fractionation using glucose-loaded mice, the acetylated kaempferol glycoside multiflorin A (MFA), a potent inhibitor of glucose absorption from the intestine, was isolated from the MeOH extract of leaf of the edible peach Prunus persica. The structure was identified by HPLC using thiazolizine derivatives and by an analysis of its spectral data. The inhibitory effect of MFA against glucose absorption was demonstrated in the dose dependent manner in mice. However, as the deacetylated analog of MFA, multiflorin B did not show the activity at the in vivo, the activity of MFA was suggested to depend on the acetyl group on the sugar moiety. This is the first report of anti-hyperglycemic activity of MFA in peach leaf extract. MFA may be useful in functional foods or medicines for preventing the postprandial absorption of glucose in hyperglycemia.

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“…The leaves of wild garlic are edible and can be used boiled as a vegetable, as a salad, or as an ingredient for pesto. The stems and bulbs are also edible and highly palatable [2,3].…”

Section: Introductionmentioning

confidence: 99%

Determination of triterpenoids, carotenoids, chlorophylls, and antioxidant capacity in Allium ursinum L. at different times of harvesting and anatomical parts

Lachowicz

Oszmiański

Wiśniewski

2018

Eur Food Res Technol

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Triterpenoids, carotenoids, chlorophylls, and antioxidant capacity of individual parts of wild garlic at different times of harvesting were studied. Leaves, flowers, bulbs, and stems of Allium ursinum were used in this study. The contents of triterpenoids, carotenoids, and chlorophylls were determined by UPLC-PDA-Q/TOF-MS, and the antioxidant capacity was determined by ABTS and FRAP assay. A total of 21 compounds including 3 triterpenoids, 11 carotenoids, and 7 chlorophylls were identified in anatomical parts of A. ursinum in March and June 2016. These compounds present in individual anatomical parts of wild garlic were determination in this study for the first time ever. The average content of total triterpenoids ranged from 750.7 to 4159.5 mg/kg dry matter (dm) and that of carotenoids and chlorophylls ranged from 14.4 to 14,424.5 mg/kg dm for bulbs and leaves. The average level of the antioxidant capacity ranged from 37.1 to 91.7 µmol Trolox/g dm in bulbs and leaves, respectively. The leaves, flowers, and stems of wild garlic are a good source of health-promoting compounds. They can be used as functional food ingredients, dietary supplements, and additives.

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Novel acetylated flavonoid glycosides from the leaves of Allium ursinum

Cited by 59 publications

References 13 publications

Cucullamide, a New Putrescine Bisamide from Amoora cucullata

Cucullamide, a New Putrescine Bisamide from Amoora cucullata

Peach Leaf Contains Multiflorin A as a Potent Inhibitor of Glucose Absorption in the Small Intestine in Mice

Determination of triterpenoids, carotenoids, chlorophylls, and antioxidant capacity in Allium ursinum L. at different times of harvesting and anatomical parts

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