Food consumption, utilization, and detoxification enzyme activity of the rice leaffolder larvae after treatment with <i>Dysoxylum</i> triterpenes

Senthil Nathan, S.,Choi, Man-Young,Paik, Chae-Hoon,Seo, Hong-Yul Elsevier 2007 Pesticide biochemistry and physiology Vol.88 No.3

<P><B>Abstract</B></P><P>The toxicity and physiological (enzyme and nutritional indices) effect of <I>Dysoxylum</I> triterpenes 3β,24,25-trihydroxycycloartane and beddomei lactone were evaluated on the rice leaffolder <I>Cnaphalocrocis medinalis</I> (Guenée). The LC<SUB>50</SUB> [6.66ppm (SD=0.31), 5.79ppm (SD=0.33) for 3β,24,25-DHCL and BL, respectively] and LC <SUB>90</SUB> [14.63ppm (SD=0.36), 13.49ppm (SD=0.27) for 3β,24,25-DHCL and BL, respectively] were identified by probit analysis. Fourth instars were exposed to various concentrations (1.5, 3, 6, and 12ppm) of <I>Dysoxylum</I> triterpenes. Results showed that treated larvae exhibited reduced food consumption and enzyme activity. Food consumption, digestion, relative consumption rate, efficiency of conversion of ingested food, efficiency of conversion of digested food, and relative growth rate values declined significantly but the approximate digestibility of treated larvae was significantly higher as a result of treatment (in particular 6 and 12ppm). Likewise, the gut enzymes acid phosphatases, alkaline phosphatases, and adenosine triphosphatases were significantly inhibited by the <I>Dysoxylum</I> triterpenes. The high biological activity of these triterpenes from <I>Dysoxylum</I> sp. could be used as an active principle during the preparation of botanical insecticides for insect pest like rice leaffolder.</P>

여러가지 조건하에서 재배한 바위솔에서 스테로이드와 테트라싸이클릭 트리테르펜의 가스 크로마토 그래피를 이용한 분석

이성중,강진호,배동원,진종성,신성철 한국약용작물학회 2008 한국약용작물학회지 Vol.16 No.1

The content of two steroids-campesterol (1) and β-sitosterol (2), and four triterpenes-taraxetrone (5), β-amyrin (6), (-)-friedelin (7), glutinol (8) in the Orostachys japonicus A. Berger cultivated under various conditions was estimated and compared with those in wild one. The present investigation disclosed that there are no significant difference in their contents between cultivated Orostachys japonicus A. Berger and wild one. from viewpoint of the content of the steroids 1 and 2, and the triterpenes 5-8, the quality of cultivated Orostachys japonicus A. Berger is not inferior to the wild one.

Biological Activities and Stability of a Standardized Pentacyclic Triterpene Enriched Centella asiatica Extract

Panupong Puttarak,Adelheid Brantner,Pharkphoom Panichayupakaranant 한국생약학회 2016 Natural Product Sciences Vol.22 No.1

Pentacyclic triterpenes, mainly, asiatic acid, madecassic acid, asiaticoside, and madecassoside are the active constituents of Centella asiatica. A pentacyclic triterpene enriched C. asiatica extract (PRE) was prepared and standardized to contain a total pentacyclic triterpenes not less than 65% w/w. This work was focused on determination of antiinflammatory, antioxidant, and tyrosinase inhibitory activities of PRE and its stability. The PRE exhibited a satisfactory nitric oxide inhibitory effect, with an IC50 value of 64.6 μg/mL. In addition, the PRE inhibited tyrosinase enzyme activity with an IC50 value of 104.8 μg/mL. In contrast, the PRE possessed only weak antioxidant activity. The PRE was stable over a period of four months when stored as a dried powder but only in a well-closed container protected from light at 4 oC. An aqueous alcoholic solution of the PRE was stable at pH values of 5.8 and 7.0, but was not stable at a pH of 8.2. Preparations of the PRE in an aqueous solution should be performed in acidic or neutral conditions.

Hypoglycemic triterpenes from <i>Gynostemma pentaphyllum</i>

Wang, Jun,Ha, Thi Kim Quy,Shi, Yan-Ping,Oh, Won Keun,Yang, Jun-Li Elsevier 2018 Phytochemistry Vol.155 No.-

<P><B>Abstract</B></P> <P>To search for bioactive gypenosides and their analogues, a saponin enriched fraction and its hydrolyzate from <I>Gynostemma pentaphyllum</I> were phytochemically investigated. Fractionation by diverse chromatographic methods, including HPLC, Sephadex LH-20, silica gel, and C18 reverse phase silica gel, led to the isolation and purification of twelve triterpenes, including five undescribed and seven known. The chemical structures of all compounds were determined as analyzed by nuclear magnetic resonance (NMR), high resolution mass spectrometry (HR-MS), infrared spectrum (IR), optical rotation, and chemical transformations. Among all isolates, nine compounds possessed a rare dammarane triterpenoid framework with A-ring modified. The relative configurations of three compounds were determined by 2D NMR for the first time. The absolute configurations of four compounds were determined by the modified Mosher's method. Two of all isolated compounds significantly enhanced 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose (2-NBDG) uptake and Glucose Transporter 4 (GLUT4) translocation via activating the AMP-activated protein kinase (AMPK) and acetyl-CoA carboxylase (ACC) signaling pathway. This study provided the potential candidates for the development of antidiabetic agents.</P> <P><B>Highlights</B></P> <P> <UL> <LI> <I>Gynostemma pentaphyllum</I> is a traditional medicinal and edible plant in China. </LI> <LI> Five undescribed triterpenes were isolated. </LI> <LI> The modified Mosher's method was used to determine the absolute configurations. </LI> <LI> Their hypoglycemic activity was evaluated in differentiated 3T3-L1 adipocytes. </LI> <LI> This study provided the potential candidates for antidiabetic agents. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>Five undescribed and nine known triterpenes were isolated from the hydrolyzate and extract of <I>Gynostemma pentaphyllum.</I> Their hypoglycemic activity was evaluated.</P> <P>[DISPLAY OMISSION]</P>

New Butyrylcholinesterase Inhibitory Triterpenes from Salvia santolinifolia

Sajid Mehmood,Naheed Riaz,Sarfraz Ahmed Nawaz,Nighat Afza,Abdul Malik,Muhammad Iqbal Choudhary 대한약학회 2006 Archives of Pharmacal Research Vol.29 No.3

Slavins A (1) and B (2), the new amyrin type triterpenes, have been isolated from the chloroform soluble fraction of Salvia santolinifolia and assigned structures on the basis of spectral studies including 2D NMR. Both the compounds displayed inhibitory potential against the enzyme butyrylcholinesterase.

New hydroperoxylated and 20,24-epoxylated dammarane triterpenes from the rot roots of Panax notoginseng

Shang, Jia-Huan,Sun, Wen-Jie,Zhu, Hong-Tao,Wang, Dong,Yang, Chong-Ren,Zhang, Ying-Jun The Korean Society of Ginseng 2020 Journal of Ginseng Research Vol.44 No.3

Background: Root rot is a serious destructive disease of Panax notoginseng, a famous cultivated araliaceous herb called Sanqi or Tianqi in Southwest China. Methods: The chemical substances of Sanqi rot roots were explored by chromatographic techniques. MS, 1D/2D-NMR, and single crystal X-ray diffraction were applied to determine the structures. Murine macrophage RAW264.7 and five human cancer cell lines were used separately for evaluating the antiinflammatory and cytotoxic activities. Results and Conclusion: Thirty dammarane-type triterpenes and saponins were isolated from the rot roots of P. notoginseng. Among them, seven triterpenes, namely, 20(S)-dammar-25-ene-24(S)-hydroperoxyl-3β,6α,12β,20-tetrol (1), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-6α,12β,20-triol (2), 20(S)-dammar-12-oxo-23-ene-25-hydroperoxyl-3β,6α,20-triol (3), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-12β,20-diol (4), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid (5), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid methyl ester (6), and 6α-hydroxy-22,23,24,25,26,27-hexanordammar-3,12,20-trione (7), are new compounds. In addition, 12 known ones (12-16 and 19-25) were reported in Sanqi for the first time. The new Compound 1 showed comparable antiinflammatory activity on inhibition of NO production to the positive control, whereas the known compounds 9, 12, 13, and 16 displayed moderate cytotoxicities against five human cancer cell lines. The results will provide scientific basis for understanding the chemical constituents of Sanqi rot roots and new candidates for searching antiinflammatory and antitumor agents.

New hydroperoxylated and 20,24-epoxylated dammarane triterpenes from the rot roots of Panax notoginseng

Jia-Huan Shang,Wen-Jie Sun,Hong-Tao Zhu,Dong Wang,Chong-Ren Yang,Ying-Jun Zhang 고려인삼학회 2020 Journal of Ginseng Research Vol.44 No.3

Background: Root rot is a serious destructive disease of Panax notoginseng, a famous cultivated araliaceousherb called Sanqi or Tianqi in Southwest China. Methods: The chemical substances of Sanqi rot roots were explored by chromatographic techniques. MS,1D/2D-NMR, and single crystal X-ray diffraction were applied to determine the structures. Murinemacrophage RAW264.7 and five human cancer cell lines were used separately for evaluating the antiinflammatoryand cytotoxic activities. Results and Conclusion: Thirty dammarane-type triterpenes and saponins were isolated from the rot rootsof P. notoginseng. Among them, seven triterpenes, namely, 20(S)-dammar-25-ene-24(S)-hydroperoxyl-3b,6a,12b,20-tetrol (1), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-6a,12b,20-triol (2), 20(S)-dammar-12-oxo-23-ene-25-hydroperoxyl-3b,6a,20-triol (3), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-12b,20-diol (4), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid (5), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid methyl ester (6), and 6a-hydroxy-22,23,24,25,26,27-hexanordammar-3,12,20-trione (7), are new compounds. In addition, 12 known ones (12e16 and 19e25)were reported in Sanqi for the first time. The new Compound 1 showed comparable antiinflammatoryactivity on inhibition of NO production to the positive control, whereas the known compounds 9, 12, 13,and 16 displayed moderate cytotoxicities against five human cancer cell lines. The results will providescientific basis for understanding the chemical constituents of Sanqi rot roots and new candidates forsearching antiinflammatory and antitumor agents.

Nuclear magnetic resonance assignment strategy for pentacyclic triterpenes, using lup‑20(29)‑ene from Pilotrichella flexilis as model system, combining spectrally filtered proton‑to‑carbon schemes and DFT–GIAO approach

Jose Enrique Herbert‑Pucheta,Cinthia Mejía‑Lara,Benito Reyes‑Trejo,Lino Reyes,Holber Zuleta‑Prada 한국응용생명화학회 2019 Applied Biological Chemistry (Appl Biol Chem) Vol.62 No.3

The present work comprises a method to obtain full proton-to-carbon nuclear magnetic resonance chemical shift assignment of a C30H50 lup-20(29)-ene, for the first time obtained from the Mexican native mosses Pilotrichella flexilis, wherein said method consists in a combination of the following NMR schemes: 1D-13C (DEPT-135), 2D-{1H–13C} HMBC with a spectral filter for promoting only weak-c.a. 2 Hz-long-range scalar couplings, 2D-{1H–1H} EXSY with long mixing times to favour only weak H–H dipolar correlations and ultra-high resolution one- and two-dimensional 1H instant homodecoupling Psyche pure shift. Full set of assigned resonances were compared against the theoretical isotropic chemical shifts computed with a gauge invariant atomic orbital–density functional theory with self consistent reaction field calculation, retrieving accurate agreements, despite the intrinsic severe signal overlap that these C30 hydrocarbon triterpenes experimentally present. Therefore, a 3D-structure supported by experimental NMR data of this type of important metabolite precursor in plants can be proposed.

A Cytotoxic Lupeol Fatty Acid Ester and Other Pentacyclic Triterpenes from Salvadora persica Seeds

Samy K. El-Desouky 한국생약학회 2023 Natural Product Sciences Vol.29 No.3

The phytochemical investigation of the ethyl acetate fraction of the methanol seed extract of Salvadora persica resulted in the isolation and identification of five pentacyclic triterpenes (1-5), oleanolic acid (1), ursolic acid (2), β-amyrin (3), β-amyrin acetate (4) and lupeol tricosanoate (5). The structures of these compounds were established by the analysis of their NMR spectroscopic and mass spectrometric data. In the bioactivity assay, compound 5 showed moderate cytotoxic activities against breast cancer cell lines (MCF-7), colon cancer cell lines (HT-29) and hepatocellular carcinoma cell lines (HepG2) with IC50 values of 9.4, 6.85 and 12.74 μg/mL. respectively. In all previous studies, lupeol tricosanoate (5) has been isolated as a mixture of triterpenoid long-chain fatty acid esters and this is the first report of its isolation and characterization as a pure molecule. Moreover, the occurrence of fatty acid ester of triterpene in this plant is of taxonomic importance.

In Vivo Anti-Nociceptive and Anti-Inflammatory Effect of the Two Triterpenes, Ursolic Acid and 23-Hydroxyursolic Acid, from Cussonia bancoensis

Tapondjou, L.A.,Lontsi, David,Sondengam, Beiban-Luc,Choi, Jong-Won,Lee, Kyung-Tae,Jung, Hyun-Ju,Park, Hee-Juhn The Pharmaceutical Society of Korea 2003 Archives of Pharmacal Research Vol.26 No.2

Triterpenoids, ursolic acid (1) and 23-hydroxyursolic acid (2) were obtained from the hydrolysis of BuOH fraction of Cussonia bancoensis extract to test anti nociceptive and anti-inflammatory effect of C. bancoensis (Araliaceae). Compound 1 and 2 exhibited anti-nociceptive effects, which were determined by acetic acid-induced writhing test and hot plate test. The effect of 2 was much more potent in acetic acid-induced writhing test than in hot plate test. Compound 1 and 2 significantly inhibited 1%-carrageenan-induced edema in the rat. These results suggest that the two triterpenes, ursolic acid and 23-hydroxyursolic acid, are responsible for the antinociceptive and anti-inflammatory effect of C. bancoesnsis.