Ardisiacrispin A and B, Two Utero-Contracting Saponins from<i>Ardisia crispa</i>

Jansakul, Chaweewan; Baumann, Herbert; Kenne, Lennart; Samuelsson, Gunnar

doi:10.1055/s-2006-962758

Cited by 66 publications

(46 citation statements)

References 5 publications

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“…It can be found in woodland garden, shady edges, hillsides or forests and is widely distributed in Asia stretching from Japan and the Himalayas to Java and the Philippines (Chen and Pipoly, 1996). The plant has been traditionally used to "wash out dirty blood" in women suffering from menstrual pain, to treat rheumatism, to serve as skin liniment, as well as to reduce pain and swellings (Perry and Metzger, 1980;Muhammad and Mustafa, 1994;Jansakul, 1995).…”

Section: Isolation Of a Quinone-rich Fraction From Ardisia Crispa Roomentioning

confidence: 99%

Isolation of a Quinone-rich Fraction from Ardisia crispa Roots and its Attenuating Effects on Murine Skin Tumorigenesis

Yeong

Hamid²,

Yazan³

et al. 2013

Asian Pacific Journal of Cancer Prevention

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Ardisia crispa (Family: Myrsinaceae) is an evergreen, fruiting shrub that has been traditionally used as folklore medicine. Despite a scarcity of research publications, we have succeeded in showing suppressive effects on murine skin papillomagenesis. In extension, the present research was aimed at determining the effect of a quinone-rich fraction (QRF) isolated from the same root hexane extract on both initiation and promotion stages of carcinogenesis, at the selected dose of 30 mg/kg. Mice (groups I-IV) were initiated with a single dose of 7,12-dimethylbenz(α)anthracene (DMBA, 100 µg/100 µl) followed by repeated promotion of croton oil (1%) twice weekly for 20 weeks. In addition, group I (anti-initiation) received QRF 7 days before and after DMBA; group II (anti-promotion) received QRF 30 minutes before each croton oil application; group III (anti-initiation/ promotion) was treated with QRF as a combination of group I and II. A further two groups served as vehicle control (group V) and treated control (group VI). As carcinogen control, group IV showed the highest tumor volume (8.79±5.44) and tumor burden (3.60±1.17). Comparatively, group III revealed only 20% of tumor incidence, tumor burden (3.00±1.00) and tumor volume (2.40±1.12), which were significantly different from group IV. Group II also showed significant reduction of tumor volume (3.11), tumor burden (3.00) and tumor incidence (11.11%), along with prominent increase of latency period of tumor formation (week 12). Group I, nonetheless, demonstrated marked increment of tumor incidence by 40% with prompted latency period of tumor formation (week 7). No tumor formation was observed in groups V and VI. This study provided clear evidence of inhibitory effects of QRF during promotion period which was in agreement with our previous findings. The mechanism(s) underlying such effects have yet to be elucidated.

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Section: Isolation Of a Quinone-rich Fraction From Ardisia Crispa Roomentioning

confidence: 99%

Isolation of a Quinone-rich Fraction from Ardisia crispa Roots and its Attenuating Effects on Murine Skin Tumorigenesis

Yeong

Hamid²,

Yazan³

et al. 2013

Asian Pacific Journal of Cancer Prevention

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“…Its roots have been traditionally used to treat respiratory tract infections and menstrual disorders.1) Other plants of this genus have also been used for this purpose, and are well documented in traditional medicine in Southeast Asia.2) Many saponins have been isolated from A. crenata, [3][4][5][6] A. crispa, 7) and A. japonica. 8) Recently, we have isolated six new triterpenoid saponins, ardisimamillosides A-F, from the roots of A. mamillata.…”

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confidence: 99%

“…2) Many saponins have been isolated from A. crenata, [3][4][5][6] A. crispa, 7) and A. japonica. 8) Recently, we have isolated six new triterpenoid saponins, ardisimamillosides A-F, from the roots of A. mamillata.…”

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confidence: 99%

Ardisimamillosides G and H, Two New Triterpenoid Saponins from Ardisia mamillata

Huang

Zhang

Shimizu

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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Ardisia mamillata HANCE (Myrsinaceae) is a widely occurring shrub in southern China. Its roots have been traditionally used to treat respiratory tract infections and menstrual disorders.1) Other plants of this genus have also been used for this purpose, and are well documented in traditional medicine in Southeast Asia.2) Many saponins have been isolated from A. crenata, [3][4][5][6] A. crispa, 7) and A. japonica. 8) Recently, we have isolated six new triterpenoid saponins, ardisimamillosides A-F, from the roots of A. mamillata. 9,10) In this paper, we report the isolation and structural elucidation of two additional new triterpenoid saponins (1, 2) from this species. Results and DiscussionThe roots of A. mamillata were extracted with 95% ethanol, and the ethanol extract was partitioned between water and hexane, ethyl acetate and 1-butanol, respectively. Chromatography of the n-butanol extract on silica gel, Lobar RP-18, and Sephadex LH-20, and then after repeated HPLC purification over octadecyl silica (ODS) gel, furnished two new saponins (1, 2).Saponin 1 . The 13 C-NMR spectral data of 1 revealed showed 53 carbon signals, 30 of which were assigned to the aglycone part, while 23 were assigned to the carbohydrate moiety. The six methyl carbon signals at d 16. 1, 16.4, 18.8, 21.7, 28.0, and 28.8 ppm, and a carbonyl carbon signal at d 212.9 ppm, indicated that the aglycone of 1 was similar to those of the aglycone of ardisimamilloside B.9,10) In saponin 1, there was a lack of the resonance due to the formyl group at C-30 of ardisimamilloside B, instead, a signal was observed at d 65.0 ppm [CH 2 by distortionless enhancement by polarization transfer (DEPT)]. This signal suggested that the -CHO group was reduced to a hydroxymethyl group. The long-range coupling between H-29 and C-30 in the heteronuclear multiple bond connectivity (HMBC) spectrum supports the same conclusion. As in ardisimamilloside B, the 13b,28-epoxy bridge could be explained by the 13 C-NMR resonances at d 86.3 (C-13) and d 75.2 ppm (C-28). These assignments could be confirmed through long-range coupling in the HMBC and through spatial interaction in rotating frame Overhauser enhancement spectroscopy (ROESY) experiment. The configuration of the hydroxyl at C-3 was determined using ROESY. The correlation of H ax -3 (d 3.17 ppm) with H-5 (d 0.69 ppm) indicated that the hydroxyl at C-3 should have a b-configuration. Based on these findings, the structure of the aglycone of 1 was established to be 13b,28-epoxy-16-oxo-oleanan-3b,30-diol.Acid hydrolysis of 1 gave three monosaccharides: arabinose, glucose and rhamnose in a ratio of 1 : 2 : 1, which were analyzed by the GC as their alditol acetate derivatives. The absolute configurations of the sugars were shown to be D-glucose, L-arabinose and L-rhamnose according to the method reported by Hara and co-workers. H shift correlation spectroscopy (COSY), 13 C-1 H heteronuclear correlated spectroscopy (HETCOR), HMBC, and ROESY, were used to determine the nature of the monosaccharides and sequences of the oli...

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“…For hundreds of years, this herbal plant has been used to treat edema, anthracnose and furuncle [1]. There are many chemical studies on Androsace genus, such as A. mamillata [2], A. crenata [3][4][5], A. crispa [6], A. japonica [7] and A. umbellata [8,9]. However, to our knowledge, there is no chemical report on the title plant so far.…”

Section: Introductionmentioning

confidence: 99%