• Title, Summary, Keyword: pentacyclic triterpenoids

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Role of Pentacyclic Triterpenoids in Chemoprevention and Anticancer Treatment: An Overview on Targets and Underling Mechanisms

  • Ghante, Mahavir H.;Jamkhande, Prasad G.
    • Journal of Pharmacopuncture
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    • v.22 no.2
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    • pp.55-67
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    • 2019
  • The incidences of cancer are continuously increasing worldwide, affecting life of millions of people. Several factors associated with the internal and external environment are responsible for this deadly disease. The key internal determinants like abnormal hormonal regulation, genetic mutations and external determinants such as lifestyle and occupational factors enhances onset of cancer. From the ancient time, plants were remained as the most trusted source of medicine for the treatment of diverse disease conditions. Extensive studies have been performed for the discovery of effective anticancer agent from the plant and still it is going on. Pentacyclic triterpenoids are biologically active phytochemicals having a different range of activities such as anti-inflammatory, hepatoprotective, anti-hypertensive, antiulcerogenic and anti-tumor. These compounds generally contain ursane, oleanane, lupane and friedelane as a chief skeleton of pentacyclic triterpenoids which are generally present in higher plants. Isoprene unit, phytochemical, with good antitumor/anticancer activity is required for the biosynthesis of pentacyclic triterpenoids. Mechanisms such as cytotoxicity, DNA polymerase inhibition, regulation of apoptosis, change in signal transductions, interfere with angiogenesis and dedifferentiation, antiproliferative activity and metastasis inhibition are might be responsible for their anticancer effect. Present review spotlights diverse targets, mechanisms and pathways of pentacyclic triterpenoids responsible for anticancer effect.

Isolation of Pentacyclic Triterpenoids from Semi-fermented Tea and Its Effects on Oxidative Stress

  • Chung, Ha-Sook
    • Preventive Nutrition and Food Science
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    • v.14 no.1
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    • pp.49-53
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    • 2009
  • Antioxidative activities of major pentacyclic terpenoids from the semi-fermented tea of Camellia sinensis L. were investigated. The free radical scavenging activities of triterpenoids $1{\sim}3$ were examined with of DPPH and superoxide anion radical scavenging activity. The $IC_{50}$ of compounds 1 and 2 for DPPH radical scavenging activities were 23.1 and $37.2{\mu}g/mL$ respectively, and for superoxide anion radical scavenging activities were 37.2 and $35.2{\mu}g/mL$, respectively. According to this result, compounds 1 or 2 in semi-fermented tea could be the candidates for bioactive material having antioxidant activity.

Anti-Platelet Pentacyclic Triterpenoids from Leaves of Campsis grandiflora

  • Jin Jing Ling;Lee Yong Yook;Heo Jung Eun;Lee Sanghyun;Kim Jeong Mi;Yun-Choi Hye Sook
    • Archives of Pharmacal Research
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    • v.27 no.4
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    • pp.376-380
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    • 2004
  • Five pentacyclic triterpenoids, oleanolic acid (1), hederagenin (2), ursolic acid (3), tormentic acid (4) and myrianthic acid (5), were isolated from the methanol extract of the leaves of Campsis grandiflora, and structures of the compounds were established by the spectroscopic methods. Compounds 2, 3, 4, and 5 were isolated for the first time from the genus Campsis. All of the compounds ($IC_{50}$: 45.3, 32.8, 82.6, 42.9 and $46.2{\mu}M$ respectively) were as equivalently inhibitive as acetylsalicylic acid ($IC_{50}:57.0{\mu}M$) on epinephrine induced platelet aggregation.

Pentacyclic Triterpenoids and Their Cytotoxicity from the Stem Bark of Styrax japonica S. et Z.

  • Kim, Mi-Ran;Lee, Hyang-Hee;Hahm, Kyung-Soo;Moon, Young-Hee;Woo, Eun-Rhan
    • Archives of Pharmacal Research
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    • v.27 no.3
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    • pp.283-286
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    • 2004
  • The methylene chloride soluble fraction of MeOH extract from the stem bark of Styrax japonica S. et Z. (Styracaceae) showed significant cytotoxicity by SRB method against five human tumor cell lines. Four known pentacyclic triterpenoids, oleanolic aldehyde acetate (1), erythrodiol-3-acetate (2), euphorginol (3), and anhydrosophoradiol -3-acetate (4) were isolated by activity-guided fractionation. Their structures were determined by chemical and spectral analysis. Compounds 1-4 were isolated from S. japonica for the first time.

Triterpenoid-Containing Liposome by Micelle-to-Vesicle Transition and Their Biological Activities

  • Kang, Hyung-Seok;Park, Ji-Eun;Nam, Gae-Won;Han, Sang-Hoon;Chang, Ih-Seop
    • Proceedings of the SCSK Conference
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    • pp.319-329
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    • 2003
  • Ursolic acid (UA) and oleanolic acid (OA) are pentacyclic triterpenoids which are widely distributed in plants, and their derivatives are aglycones of many naturally occurring saponins. It is known that pentacyclic acids may possibly enhance the mechanical barrier functions of cell membranes in plants. Recently, it has been reported that OA and UA have interesting biological activities on skin, such as anti-inflammatory and anti-wrinkle activities. Since triterpenoids are extremely insoluble and their solubility problem limits skin-care application, OA and UA were encapsulated in liposomes via micelle-to-vesicle transition to overcome poorly soluble property and enhance biological efficacy. Optimal molar ratio of OA to lecithin was found to exist for producing liposomes of small hydrodynamic size and liposomal suspensions without recrystallized precipitation of OA. From electron micrograph and dynamic light scattering studies, reconstituted OA-containing liposomes without severe mechanical treatment showed small hydrodynamic size about 150 nm. Wide-angle X-ray diffraction coupled with dynamic light scattering revealed that optimal amount of OA in liposome was 25.4 mole %. In biological evaluation, OA-containing liposome significantly increased filaggrin and transglutaminase as markers of keratinocyte differentiation in epidermal layer of hairless mouse, whereas ursolic acid-containing liposome did not show noticeable increase of filaggrin and transglutaminase compared to empty liposome. It is concluded that nano-scaled liposomes containing triterpenoids were spontaneously prepared by vesicular transition from mixed micelle and liposomal triterpenoids can enhance skin absorption of triterpenoid and biological efficacy.

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Design, Synthesis and Evaluation of Pentacyclic Triterpenoids Similar to Glycyrrhetinic Acid Via Combination of Chemical and Microbial Modification as Glycogen Phosphorylases Inhibitor

  • Zhu, Yuyao;Zhang, Jian;Huang, Xiaode;Chen, Bin;Qian, Hua;Zhao, Botao
    • Journal of Microbiology and Biotechnology
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    • v.28 no.11
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    • pp.1876-1882
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    • 2018
  • A series of pentacyclic triterpenoids similar to glycyrrhetinic acid were designed and synthesized via the combination of chemical modification and microbial catalysis. All products were screened for the glycogen phosphorylases inhibitory activities in vitro. Within this series of derivatives, compound 5 displayed good inhibitory activities with $IC_{50}$ value of $27.7{\mu}M$, which is better than that of the other derivatives and glycyrrhetinic acid. Structure-activity relationship (SAR) analysis of these inhibitors was also discussed.

Pentacyclic Triterpenoids from Mallotus apelta

  • Kiem, Phan-Van;Minh, Chau-Van;Huong, Hoang-Thanh;Nam, Nguyen-Hoai;Lee, Jung-Joon;Kim, Young-Ho
    • Archives of Pharmacal Research
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    • v.27 no.11
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    • pp.1109-1113
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    • 2004
  • A new triterpene (1) and six known pentacyclic terpenoids (2-7) were isolated from the methanol extract of the dried leaves from Mallotus apelta. Based on the spectral and chemical evidence, their structures were determined to be 3$\alpha$-hydroxyhop-22(29)-ene (1), hennadiol (2), friedelin (3), friedelanol (4), epifriedelanol (5), taraxerone (6), and epitaraxerol (7).

Pentacyclic Triterpenoids from Ilex macropoda

  • Kim, Dae-Keun;Nam, Il-Yong;Kim, Jin-Wook;Shin, Tae-Yong;Lim, Jong-Pil
    • Archives of Pharmacal Research
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    • v.25 no.5
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    • pp.617-620
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    • 2002
  • Six compounds were isolated from the twigs of Ilex macropoda. Their structures were elucidated as betulinic acid, lupeol, betulone, betulin, erythrodiol and 11-oxo-erythrodiol by physicochemical and spectroscopic analysis. Among them, lupeol, betulone, erythrodiol and 11-oxo-erythrodiol were isolated for the first time from this plant.