Chemical Constituents of the Leaves of Diospyros kaki (Persimmon)

Abstract

Diospyros kaki (persimmon) leaves have long been utilized as traditional medicine for the treatment of ischemic stroke, angina, and hypertension and as a healthy beverage and cosmetic for anti-aging. This study aimed to isolate as many compounds as possible from an ethanol extract of the persimmon leaves to identify the biologically active compounds. The antioxidative effect of the ethyl acetate layer from the ethanol extract of the persimmon leaves was demonstrated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and online high-performance liquid chromatography-2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (HPLC-ABTS) analysis. A new flavonoid, kaempferol-3-O-β-d-2″-coumaroylgalactoside (1), and a new natural compound, kaempferol-3-O-β-d-2″-feruloylglucoside (3) were isolated from the ethyl acetate layer, along with 25 previously known compounds, including fourteen flavonoids, one ionone, two coumarins, seven triterpenoids, and one acetophenone. Their structures were determined by the interpretation of spectrometric and spectroscopic data. All isolated compounds were rapidly evaluated using an online HPLC-ABTS assay, and of these, compounds 4–8, 11, 13, 15, and 16 clearly showed antioxidative effects. The amount of these compounds was 0.3–0.65% of the extract.

Persimmon Leaves: Nutritional, Pharmaceutical, and Industrial Potential—A Review

“…For instance, Fan and He [ 46 ] developed an HPLC method to identify triterpene acids from PL, and the compounds were rotungenic acid, 24-hydroxyursolic acid, and barbinervic acid and its epimer. Similar to this study, seven triterpenoids were isolated from the Korean PL, namely barbinervic acid, diospyric acid B, pomolic acid, rotungenic acid, oleanolic acid, siaresinolic acid, and ursolic acid [ 16 ]. Moreover, Chen et al [ 47 ] reported five triterpenoids such as ursolic acid, α-amyrin, uvaol, 19 α,24-dihydroxyursolic acid, and 19α-hydroxy ursolic acid in PL.…”

“…The major compounds of PL are flavonoids, tannins, vitamins, and terpenoids. PL have long been considered a traditional medicine to treat ischemic angina, stroke, internal hemorrhage, hypertension, atherosclerosis, and infectious diseases, as well as paralysis, frostbite, burns, and constipation, which have been mentioned in ancient Chinese medical books [ 10 , 16 ]. In particular, NXQ is a protected drug of Traditional Chinese Medicine and is used in managing cardio- and cerebrovascular diseases [ 5 ].…”

“…So far, this is the highest number of phenolic compounds identified from PL. Meanwhile, a new flavonoid (kaempferol-3- O -β-D-2″-coumaroylgalactoside) along with kaempferol-3- O -β-D-2″-feruloylglucoside were identified from the Korean PL [ 16 ]. The overall identified chemical compounds were 14 flavonoids, 7 triterpenoids, 2 coumarins, 1 ionone, and 1 acetophenone.…”

“…It was found that flavonoids, mainly quercetin and kaempferol, showed strong DPPH radical scavenging activity and inhibited the H 2 O 2 -induced human vascular endothelial (EA.hy926) cell injury and intracellular ROS generation. Likewise, flavonoids and terpenoids were identified from the Korean PL and it was found that kaempferol and quercetin derivatives, mainly those with galloyl moieties, exhibited strong antioxidant activities using DPPH and HPLC-ABTS assays [ 16 ]. Furthermore, water-soluble PL extracts showed strong antioxidant activities using DPPH, ABTS, nitric oxide (NO), and reducing power assays [ 68 ], whereas methanolic extracts were able to decrease the production of malondialdehyde (MDA) [ 84 ].…”

In-vitro antioxidant, lipoxygenase inhibitory, and in-vivo muscle relaxant potential of the extract and constituent isolated from Diospyros kaki (Japanese Persimmon)

“…The extract of Japanese persimmon has been shown to have antioxidant properties [ 15 , 16 ]. Various Phytochemicals such as flavonoids, diospyric acid, scopoletin, quercetin, kaempferol, oleanolic acids tannins, catechin, anthocyanidin, etc have been reported from different parts of D. Kaki [ 17 ]. These isolated phytochemicals have been reported for excellent antioxidant potential [ 7 , 18 ].…”