Eight &lt;i&gt;ent&lt;/i&gt;-Kaurane Diterpenoid Glycosides Named Diosmariosides A–H from the Leaves of &lt;i&gt;Diospyros maritima&lt;/i&gt; and Their Cytotoxic Activity

Kawakami, Susumu; Nishida, Shoko; Nobe, Ayaka; Inagaki, Michio; Nishimura, Motohiro; Matsunami, Katsuyoshi; Otsuka, Hideaki; Aramoto, Mitsunori; Hyodo, Tadashi; Yamaguchi, Kentaro

doi:10.1248/cpb.c18-00529

Cited by 7 publications

(8 citation statements)

References 11 publications

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“…The leaves of D. maritima extracted with MeOH and the MeOH extracts were separated by solvent partition according to the polarity of the constituents. The relatively polar 1-BuOH-soluble fraction was separated by various kinds of chromatography to afford four new triterpene saponins (1)(2)(3)(4) and two new megastigmanes (5,6), together with two known flavonol glycosides (7,8). The structures of new triterpene derivatives were elucidated using one-and two-dimensional spectroscopies.…”

Section: Resultsmentioning

confidence: 99%

“…It is known that the fruits contain a toxic naphthoquinone derivative, plumbagin, and their constituents have been extensively investigated by Higa et al [2][3][4] Recently, from the leaves and branches of a related Thai medicinal plant, D. mollis, the isolation of naphthoquinone glycosides was reported. 5) In our continuing work on Okinawan resource plants, the constituents of the leaves of D. maritima were investigated to give eight ent-kaurane-type diterpenoid glycosides, called diosmariosides A-H. 6) Further extensive work resulted in the isolation of four new triterpene saponins, named ebenamariosides A-D (1-4) and two megastigmanes (5,6), along with two known flavonol glycosides, kaempferol 3-O-β-D-(2″,6″-di-O-α-L-rhamonopyranosyl) glucopyranoside (7) 7) and 3-O-β-D-(2″,6″-di-α-L-rhamonopyranosyl) galactopyranoside (8) 8) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

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Ebenamariosides A–D: Triterpene Glucosides and Megastigmanes from the Leaves of <i>Diospyros maritima</i>

Kawakami

Miura

Nobe

et al. 2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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The 1-BuOH-soluble fraction of the methanol (MeOH) extract of Diospyros maritima was separated by chromatographic techniques to give three new oleanane-type and one new ursane-type triterpene glucoside, named ebenamariosides A-D (1-4); two megastigmanes were also isolated. The structures of triterpene glucosides was elucidated with extensive investigation by one and two dimensional NMR spectroscopy and the structures were confirmed by partial enzymatic hydrolyses to give the corresponding mono-glucosides and aglycones. The structures of the megastigmanes, including their absolute stereochemistries, were elucidated by spectroscopic evidence and by the modified Mosher's method. Two megastigmanes were chemically correlated and their absolute structures were unambiguously determined. The cytotoxicity of the triterpene glucosides and their degradation products were assayed. They did not show any significant activity.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ebenamariosides A–D: Triterpene Glucosides and Megastigmanes from the Leaves of <i>Diospyros maritima</i>

Kawakami

Miura

Nobe

et al. 2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Naphthoquinones, plumbagin (2) , isodiospyrin (3) , and 8′‐hydroxyisodiospyrin (13) , isolated from D. maritima revealed cytotoxic activity against different cell lines such as hepatoma (HEPA‐3B, ED 50 = 1.72, 0.87, and 0.25 μg/mL), nasopharynx carcinoma (KB, ED 50 = 1.85, 3.27, 1.81 μg/mL), colon carcinoma (COLO‐205, ED 50 = 2.24, 0.56, 0.13 μg/mL), and cervical carcinoma (HELA, ED 50 = 1.92, 0.35, 0.27 μg/mL), respectively (Kuo et al, 1997). Moreover, diosmarioside D (138) , a diterpenoid isolated from the methanol extracts of the leaves of D. maritima , showed strong cytotoxic activity against lung adenocarcinoma (A549) cell line (Kawakami et al, 2018). Diosquinone (5) isolated from the root bark of D. mespiliformis and D. tricolor was assessed for cytotoxicity against ten cancer cell lines by standard NIH method.…”

Section: Pharmacological Actions Of Dsmentioning

confidence: 99%

“…Moreover, diosmarioside D (138), a diterpenoid isolated from the methanol extracts of the leaves of D. maritima, showed strong cytotoxic activity against lung adenocarcinoma (A549) cell line (Kawakami et al, 2018). Diosquinone (5) isolated from the root bark of D. mespiliformis and D. tricolor was assessed for cytotoxicity against ten cancer cell lines by standard NIH method.…”

Section: Antitumor Activitymentioning

confidence: 99%

Unveiling major ethnopharmacological aspects of genus Diospyros in context to its chemical diversity: A comprehensive overview

Fareed

El‐Kersh

Youssef

et al. 2022

Journal of Food Biochemistry

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Diospyros species (DS), “Ebenaceae,” were known for their therapeutic uses in folk medicine since days of yore. Thereafter, scientific evidence related their health benefits to a myriad of chemical classes, for instance, naphthoquinones, flavonoids, tannins, coumarins, norbergenin derivatives, sterols, secoiridoids, sesquiterpenes, diterpenoids, triterpenoids, volatile organic compounds (VOCs), and carotenoids. The available literature showed that more than 200 compounds were isolated and identified via spectroscopic techniques. Many pharmacological activities of DS have been previously described, such as antioxidant, neuroprotective, antibacterial, antiviral, antiprotozoal, antifungal, antiinflammatory, analgesic, antipyretic and cosmeceutical, investigated, and confirmed through versatile in vitro and in vivo assays. Previous studies proved that genus Diospyros is a rich reservoir of valuable bioactive compounds. However, further comparative studies among its different species are recommended for more precise natural source‐based drug discovery and clinical application. Accordingly, this review is to recall the chemical abundance and diversity among different members of genus Diospyros and their ethnopharmacological and pharmacological uses. Practical Applications Practically, providing sufficient background on both secondary metabolites divergence and pharmacological properties of genus Diospyros has many fruitful aspects. As demonstrated below, extracts and many isolated compounds have significant curative properties, which can lead to the discovery of pharmaceutically relevant alternative substitutes to conventional medicine. Consequently, molecular docking on various receptors can be applied. On the grounds, Naoxinqing tablets, a standardized herbal product containing D. kaki leaves extract, have been patented and recorded in Chinese Pharmacopeia as an approved Traditional Chinese Medicine (TCM) for the treatment of cerebro‐ and cardiovascular diseases, although the underlying mechanism remains under advisement. Moreover, the antimicrobial applications of DS are of considerable concern; since the widespread use of antibiotics resulted in different forms of bacterial resistance, hence, limiting and compromising effective treatment. In addition, as a result of contemporary rampant memory disorders, neuroprotective activities of different extracts of DS became of great emphasis.

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“…Diosmarioside D 222, a new glycoside based on ent-kaurane-type diterpenoid, was isolated from the leaves of Diospyros maritima (Ebenaceae) (Figure 87). Diosmarioside D 222 showed strong activity, with an IC 50 value of 5.11 µM against the A549 cell line, using etoposide as a positive control [136]. [136] and scopariusol L 223 [137].…”

Section: Figure 84 Structures Of Isoresbin a 212mentioning

confidence: 99%

New Diterpenes with Potential Antitumoral Activity Isolated from Plants in the Years 2017–2022

Forzato

Nitti

2022

Plants

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Diterpenes represent a wider class of isoprenoids, with more than 18,000 isolated compounds, and are present in plants, fungi, bacteria, and animals in both terrestrial and marine environments. Here, we report on the fully characterised structures of 251 new diterpenes, isolated from higher plants and published from 2017, which are shown to have antitumoral activity. An overview on the most active compounds, showing IC50 < 20 μM, is provided for diterpenes of different classes. The most active compounds were extracted from 29 different plant families; particularly, Euphorbiaceae (69 compounds) and Lamiaceae (54 compounds) were the richest sources of active compounds. A better activity than the positive control was obtained with 33 compounds against the A549 cell line, 28 compounds against the MCF-7 cell line, 9 compounds against the HepG2 cell line, 8 compounds against the Hep3B cell line, 19 compounds against the SMMC-7721 cell line, 9 compounds against the HL-60 cell line, 24 compounds against the SW480 cell line, and 19 compounds against HeLa.

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Eight <i>ent</i>-Kaurane Diterpenoid Glycosides Named Diosmariosides A–H from the Leaves of <i>Diospyros maritima</i> and Their Cytotoxic Activity

Cited by 7 publications

References 11 publications

Ebenamariosides A–D: Triterpene Glucosides and Megastigmanes from the Leaves of <i>Diospyros maritima</i>

Ebenamariosides A–D: Triterpene Glucosides and Megastigmanes from the Leaves of <i>Diospyros maritima</i>

Unveiling major ethnopharmacological aspects of genus Diospyros in context to its chemical diversity: A comprehensive overview

New Diterpenes with Potential Antitumoral Activity Isolated from Plants in the Years 2017–2022

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