The distribution of geraniin and mallotusinic acid in the order geraniales

Okuda, Takuo; Mori, Kazuko; Hatano, Tsutomu

doi:10.1016/0031-9422(80)87012-9

Cited by 68 publications

(54 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Geranium thunbergii is officially recognized as an herbal medicine in Japan ("Geranium Herb"), but herbs with a consistent content of geraniin and corilagin are necessary for cancer prevention. The following should also be noted: Geraniin is quickly hydrolysed during hot water extraction of the herb, while corilagin is relatively stable, 14) seasonal variations affect the content of geraniin and corilagin; and the leaves of A. nikoense are more efficacious than the bark now commercially sold. In summary, our screening for cancer preventive agents found that the main constituents of A. nikoense leaf extract are active compounds-geraniin and corilagin-that inhibited TNF-a release.…”

Section: Inhibition Of Tumor Promotion By Geraniinmentioning

confidence: 99%

“…14) In various biochemical and biological functions of tannins, 15) geraniin and corilagin function in a manner similar to (Ϫ)-epigallocatechin gallate (EGCG), the main constituent of green tea polyphenols, and this led us to study geraniin as a cancer preventive agent. We found that, like EGCG, repeated topical applications of geraniin inhibited tumor promotion of okadaic acid in a two-stage carcinogenesis experiment on mouse skin.…”

mentioning

confidence: 99%

See 1 more Smart Citation

New TNF-.ALPHA. Releasing Inhibitors, Geraniin and Corilagin, in Leaves of Acer nikoense, Megusurino-ki.

Okabe

Suganuma

Imayoshi

et al. 2001

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

We have recently reported that inhibition of tumor necrosis factor-a (TNF-a) release is a useful method for screening of cancer preventive agents, 1) because TNF-a and other inflammatory cytokines stimulate tumor promotion and progression of initiated cells as well as premalignant cells. 2,3) Since TNFa and interleukin-1 (IL-1), as endogenous tumor promoters, activate nuclear factor kB (NF-kB), 4,5) inhibitors of NF-kB activation are also assumed to be cancer preventive agents. 6) However, in a practical sense, it is quantitatively easier to measure inhibition of TNF-a release from cells treated with a tumor promoter such as okadaic acid than inhibition of NFkB activation using a gel mobility shift assay. 7) Based on the study of green tea as cancer preventive agent in the United States 8) and as cancer preventive beverage in Japan, 9) we decided to take a closer look at Japanese herbal medicine for other likely cancer preventives. One classical Japanese herb, Geranium thunbergii SIEB. et ZUCC. (Gennoshoko in Japanese), is used as an antidiarrhetic 10) ; it contains geraniin, which has been intensively studied as a representative tannin. 11) And the bark of Acer nikoense MAXIM (Megusurino-ki in Japanese), which contains diarylheptanoids, is sold as a folk medicine for eye and liver diseases in Japan. 12) The Forestry Experiment Station of Saitama Prefecture succeeded in culturing young plants of A. nikoense collaborated with us on the scientific utilization of the plant. We received four water extracts-leaves, bark, small branches, and timber-from the Station and subjected them to inhibition of TNF-a release assay using BALB/3T3 cells treated with okadaic acid 13) : The leaves showed the strongest activity among the four extracts. Each extract was subjected to highperformance liquid chromatography (HPLC) with CAP-CELL PAK C18, and geraniin and corilagin were identified in the active leaf extract (Fig. 1).In The success of green tea as a cancer preventive is based on evidence that green tea contains tannins and antioxidants, does not show toxicity in humans and has long traditional use in Asia. In the light of this, herbal medicines are now also attracting attention as potential sources of cancer preventive agents. Using the inhibition of TNF-a a release assay, we studied Acer nikoense (Megusurino-ki in Japanese), one of the herbal medicines. The inhibitory activity of TNF-a a release was found in the leaf extract rather than the bark extract, and the main active constituents were identified as geraniin and corilagin, which are present in another Japanese traditional herb, Geranium thunbergii (Genno-shoko). The IC 50 values of TNF-a a release inhibition were 43 m mM for geraniin and 76 m mM for corilagin, whereas that for (؊)-epigallocatechin gallate (EGCG) was 26 m mM. Treatment with geraniin prior to application of okadaic acid, a tumor promoter on mouse skin initiated with 7,12-dimethylbenz(a)anthracene, reduced the percentage of tumor-bearing mice from 80.0 to 40.0% and the average numbers of tumor per mouse ...

show abstract

Section: Inhibition Of Tumor Promotion By Geraniinmentioning

confidence: 99%

mentioning

confidence: 99%

New TNF-.ALPHA. Releasing Inhibitors, Geraniin and Corilagin, in Leaves of Acer nikoense, Megusurino-ki.

Okabe

Suganuma

Imayoshi

et al. 2001

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

show abstract

“…In each of the fractions FA4, FA5 and FA8 compound 14, an isomer of geraniin, was the second most abundant compound present (9.3, 26.6 and 15.1 mg/g, respectively, Table 3). Geraniin has been described as the main phenolic compound in various Geranium species (Harborne and Williams, 2002;Okuda et al, 1980Okuda et al, , 1979Okuda et al, , 2000Piwowarski et al, 2014;Tuominen, 2013;Tuominen et al, 2013;Wu et al, 2011) and is endowed with several beneficial biological activities (Cheng et al, 2017). Apart from the identified ellagitannins, FA8 showed to contain also some phenolic acids and flavonoids.…”

Section: Vc Graça Et Al Industrial Crops and Products 108 (2017) 543mentioning

confidence: 99%

Bio-guided fractionation of extracts of Geranium robertianum L.: Relationship between phenolic profile and biological activity

Graça

Barros

Calhelha

et al. 2017

Industrial Crops and Products

View full text Add to dashboard Cite

A B S T R A C TGeranium robertianum L. is used in folk medicine and herbalism practice for the treatment of a variety of ailments. Recently, we studied the bioactivity of several aqueous and organic extracts of this plant. In this work, the more active extracts were fractionated and the fractions evaluated for their antioxidant activity and cytotoxicity against several human tumor cell lines and non-tumor porcine liver primary cells. Some of the fractions from the acetone extract consistently displayed low EC 50 and GI 50 values and presented the higher contents of total phenolic compounds in comparison to other fractions. The phenolic compounds profile of the fractions was determined. The bio-guided fractionation of the extracts resulted in several fractions with improved bioactivity relative to the corresponding extracts. Their lower compositional complexity allowed the identification of more than two dozen compounds, to the best of our knowledge, so far not reported in G. robertianum.

show abstract

“…Although the structures of the tannins in most Geranium species are largely unknown (Okuda et al, 1980), the presence of ellagitannins, a class of hydrolysable tannins containing hexahydroxydiphenic (HHDP) acid (1) units esterified to a core polyol, has been reported based on the detection and quantification of ellagic acid (2) (Ascacio-Valdés et al, 2011). In leaves and other tissues there seems to be little if any free ellagic acid (Bate-Smith, 1973a) but this is readily produced by the spontaneous lactonization of the HHDP esters upon acid hydrolysis in aqueous solution and, therefore, it is considered mostly as product of the hydrolysis of ellagitannins in plants (Scheme 1).…”

Section: Phytochemical Characterizationmentioning

confidence: 99%

Phytochemical composition and biological activities of Geranium robertianum L.: A review

Graça

Ferreira

Santos

2016

Industrial Crops and Products

View full text Add to dashboard Cite

After a period of a certain indifference, in which synthetic compounds were favored, the interest in the study of the biological properties of plants and the active principles responsible for their therapeutic properties has been growing remarkably. Geranium robertianum L., commonly known as Herb Robert or Red Robin, is a spontaneous, herbaceous plant that has been used for a long time in folk medicine of several countries and in herbalism's practice for the treatment of a variety of ailments. Herein, we present a comprehensive review on the phytochemical characterization and the biological activities of this species, which, accompanying the remarkable increase of its use in herbal medicine, has been disclosed in the literature mainly in the last decade.The phytochemical characterization of G. robertianum has been focused mostly on the investigation of solid-liquid extracts of the plant, with special emphasis on phenolic compounds, particularly flavonoids. Studies concerning the essential oils of this species are still scarce but the number of identified compounds is high. The chemistry of G. robertianum is clearly dominated by phenolic constituents, the most studied classes of compounds being tannins, flavonoids and phenolic acids.The confirmation of the antioxidant, antimicrobial, anti-inflammatory, anti-hyperglycaemic and 2 cytotoxic activities of G. robertianum, closely related to the high content of phenolic compounds, has come to corroborate in some extent the recognized beneficial proprieties of this medicinal plant.

show abstract

The distribution of geraniin and mallotusinic acid in the order geraniales

Cited by 68 publications

References 15 publications

New TNF-.ALPHA. Releasing Inhibitors, Geraniin and Corilagin, in Leaves of Acer nikoense, Megusurino-ki.

New TNF-.ALPHA. Releasing Inhibitors, Geraniin and Corilagin, in Leaves of Acer nikoense, Megusurino-ki.

Bio-guided fractionation of extracts of Geranium robertianum L.: Relationship between phenolic profile and biological activity

Phytochemical composition and biological activities of Geranium robertianum L.: A review

Contact Info

Product

Resources

About