• Archives of Pharmacal Research
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• v.7 no.2
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• pp.121-126
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• 1984

From the roots of Patrinia scabiosaefolia Valerianaceae), scopoletin (1), esculetin (2), oleanonic acid (3), 3-O-.alpha.-L-rhamnopyranosyl (1.rarw.2)-.alpha.-l-arabinopyranosyl oleanolic acid (4) and 3-O-.alpha.-L- rhamnopyranosyl (1 .rarw. 2)-.alpha.-L-arabinopyranosyl header agenin (5) were isolated and characterized by spectral data.

• Journal of Applied Biological Chemistry
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• v.66
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• pp.67-72
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• 2023

A simple and accurate method was developed for the quantitative analysis of oleanonic acid (OA) from mastic gum. The analysis was carried out using reverse-phase high-performance liquid chromatography combined with a photodiode array detector (HPLC/PDA). Our optimized method was validated by measuring various parameters, using an INNO C18 column fitted with a gradient elution system. The results revealed limits of detection and quantification of 0.34 and 1.042 ㎍/mL, respectively. The OA calibration curve exhibited excellent linearity over the concentration range of 0.0625 to 2.0 mg/mL, with r² =0.9996. Accuracy tests revealed a high recovery rate of 99.44-103.66%, with precision values below 0.15%. These results suggest that the present analytical method can identify and quantify OA in mastic gum with high precision. The HPLC approach developed in this study might be applied to routine analyses and large-scale extraction procedures for OA content quantification.

• Natural Product Sciences
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• v.10 no.3
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• pp.93-95
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• 2004

Eleven triterpenoids, colubrinic acid (1), alphitolic acid (2), 3-O-cis-p-coumaroyl alphitolic acid (3), 3-O-trans-p-coumaroyl alphitolic acid (4), 3-O-cis-p-coumaroyl maslinic acid (5), 3-O-trans-p-coumaroyl maslinic acid (6), betulinic acid (7), oleanolic acid (8), betulonic acid (9), oleanonic acid (10), and zizyberenalic acid (11), were isolated from the fruits of Zizyphus jujuba Mill. A simple and rapid HPLC method, using a $C_{18}$ column, has been developed for the quantitative analysis of these compounds 1 (0.74%),2 (0.09%), 3 (0.19%), 4 (0.19%), 5 (0.08%),6 (0.08%), 7 (0.41%), 8 (0.05%), 9 (0.50%),10 (0.59%), and 11 (0.19%).

• Natural Product Sciences
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• v.14 no.4
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• pp.249-253
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• 2008

Two oleanane-type triterpenes (1, 2) and their glycosides (4-6), and one ursane-type triterpene (3) have been isolated from a methanolic extract of Patrinia saniculaefolia Hemsley (Valerianaceae) through repeated silica gel and reversed-phase C-18 column chromatography. Their chemical structures were determined as oleanolic acid (1), oleanonic acid (2), 23-hydroxyursolic acid (3), 3-O-${\alpha}$-L-arabinopyranosyl-oleanolic acid (4), 3-O-${\beta}$-D-glucopyranosyl-oleanolic acid (5), and oleanolic acid 3-O-[${\alpha}$-D-xylopyranosyl-($1{\rightarrow}3$)-${\beta}$-D-glucuronopyranoside-6-O-butyl-ester] (6) on the basis of their MS, $^1H$-, and $^{13}C$-NMR spectral data. All compounds were isolated from the whole plant of the P. saniculaefolia for the first time. These compounds were examined for their anti-complement activity against the classical pathway of the complement system. Among them, compounds 1 - 3 exhibited anti-complement activity with $IC_{50}$ values of 470.1, 212.2, and 121.0 ${\mu}M$, respectively, whereas compounds 4 - 6 were inactive. These results suggest that the carbonyl or hydroxy group at C-3 in the oleananeand/or ursane-triterpenes are important for the anti-complement activity against the classical pathway.

• Natural Product Sciences
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• v.17 no.2
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• pp.90-94
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• 2011

An in vitro bioassay-guide revealed that the methanol (MeOH) extract of the whole plant of Patrinia saniculaefolia (Valerianaceae) showed cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin $D_2$ ($PGD_2$) and leukotriene $C_4$ ($LTC_4$) in mouse bone marrow-derived mast cells (BMMCs). Phytochemical study of the MeOH extract of this plant led to the isolation of twelve compounds; ${\beta}$-farnesene (1), squalene (2), nardostachin (3), patridoid I (4), patridoid II (5), patridoid II-A (6), oleanolic acid (7), oleanonic acid (8), 23-hydroxyursolic acid (9), oleanolic acid 3-O-${\alpha}$-L-arabinopyranoside (10), oleanolic acid 3-O-${\beta}$-D-glucopyranoside (11), oleanolic acid 3-O-[${\beta}$-D-xylopyranosyl-(1${\rightarrow}$3)-${\beta}$-D-(6-O-butyl)glucuronopyranoside] (12). Among the compounds, 4 and 5 strongly inhibited both the COX-2-dependent $PGD_2$ generation with $IC_{50}$ values of 8.7 and 13.6 ${\mu}M$, respectively, and the generation of $LTC_4$ in the 5-LOX dependent phase with $IC_{50}$ values of 41.7 and 46.9 ${\mu}M$, respectively, which suggest that the anti-inflammatory activity of P. saniculaefolia might occur in part via the inhibition of both $PGD_2$ and $LTC_4$ generation by 4 and 5.