Monoterpenoid and phenylethanoid glycosides from Ligustrum pedunculare

He, Zheng-Dan; Ueda, Shinichi; Akaji, Masako; Fujita, Tetsuro; Inoue, Ken‐ichiro; Yang, Chong‐Ren

doi:10.1016/s0031-9422(00)89802-7

Cited by 64 publications

(47 citation statements)

References 8 publications

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“…Glycosylated secondary metabolites include flavonols (Wollenweber and Jay, 1988), anthocyanins (Harborne and Grayer, 1988), monoterpenes (He et al, 1994), and plant hormones (Bandurski et al, 1995). Glycosylation of secondary products invariably results in enhanced water solubility and lower chemical reactivity.…”

Section: Discussionmentioning

confidence: 99%

Meristem-Localized Inducible Expression of a UDP-Glycosyltransferase Gene Is Essential for Growth and Development in Pea and Alfalfa

et al. 1999

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PsUGT1 , which encodes a microsomal UDP-glucuronosyltransferase, was cloned from root tips of Pisum sativum . PsUGT1 expression is correlated with mitosis and strongly induced in dividing cells. A region at the C terminus of the encoded protein is closely related to the UDP-glucuronic acid binding site consensus sequence, and the protein encoded by PsUGT1 catalyzes conjugation of UDP-glucuronic acid to an unknown compound. Overexpression of PsUGT1 sense mRNA has no detectable effect on transgenic pea hairy root cultures or regenerated alfalfa. However, inhibiting PsUGT1 expression by the constitutive expression of antisense mRNA (under the control of the cauliflower mosaic virus 35S promoter) markedly retards growth and development of transgenic alfalfa. Cell structure and organization in the antisense plants are similar to those of controls, but plant growth is reduced and development is delayed. This inhibition in growth is correlated with a twofold delay in the time required for completion of a cell cycle and with a Ͼ 99% inhibition of border cell production. Inhibition of PsUGT1 expression by meristem-localized inducible expression of PsUGT1 antisense mRNA (under the control of its own promoter) is lethal both in pea hairy roots and in transgenic alfalfa plants. These results indicate that PsUGT1 expression is required for normal plant growth and development, and they are consistent with the hypothesis that this UDP-glycosyltransferase regulates activity of a ligand(s) needed for cell division.

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Section: Discussionmentioning

confidence: 99%

Meristem-Localized Inducible Expression of a UDP-Glycosyltransferase Gene Is Essential for Growth and Development in Pea and Alfalfa

et al. 1999

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“…Chemical studies have found volatile components, triterpenes, flavonoids, secoiridoid glucosides, and phenolic compounds from this plant, and constituents such as phenylethanoids, monoterpenes, and secoiridoid glucosides from other Ligustrum species. 11,[14][15][16][17][18][19] In our screening program, ethanol extract of the fruits of L. lucidum showed antioxidative effect. Through bioassayguided analysis, ten secoiridoid glucosides were isolated from the active fractions.…”

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confidence: 99%

Antioxidative Glucosides from the Fruits of Ligustrum lucidum.

But

Chan

et al. 2001

Chem. Pharm. Bull.

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The metabolic processes in the human body, inevitably, often produce harmful free radicals. These free radicals have been shown to possibly contribute to aging and various diseases, such as atherosclerosis and cancer.1-2) Therefore, it is important to identify effective radical scavengers to help relieve the damaging effects of free radicals. Our screening program for potent antioxidants from natural products have confirmed that polyphenolic compounds present in foods of plant origin do have strong radical scavenging and oxidationinhibiting effects. For example, the phenylethanoid glycosides from Brandisia hancei were found to have potent antioxidative properties. 3)Recently, our attention focused on the fruit of Ligustrum lucidum AIT. (Oleaceae), which is known as "Nuzhenzi" in China. It is commonly used in Chinese medicine to supplement "kidneys", nourish "yin", strengthen liver and clear vision.4) Previous studies reported that the fruit of L. lucidum has immunomodulatory, 5) hypolipemic, 6) antiinflammatory, 7) hepatoprotective, 8) antitumor 9) and antiaging effects. 10) Related species of the same genus showed inhibitory effect on acyl CoA cholesteryl acyltransferase, 11) and immunomodulatory 12) and anticomplementary activities. 13) These biological effects appear to support some of the ethnomedical claims. Chemical studies have found volatile components, triterpenes, flavonoids, secoiridoid glucosides, and phenolic compounds from this plant, and constituents such as phenylethanoids, monoterpenes, and secoiridoid glucosides from other Ligustrum species. 11,[14][15][16][17][18][19] In our screening program, ethanol extract of the fruits of L. lucidum showed antioxidative effect. Through bioassayguided analysis, ten secoiridoid glucosides were isolated from the active fractions. Two of the secoiridoid glucosides, lucidumosides C (9) and D (10), were new. Here we report the antioxidative activity of these constituents of Nuzhenzi against hemolysis of red blood cells (RBC) induced by free radicals, and also the structure elucidation of compounds 9 and 10.The fruits of L. lucidum were extracted with ethanol and the ethanol extract showed significant inhibitory effects (IC 50 ϭ125 mg/ml) on the hemolysis of RBC induced by free radicals (Fig. 1). The ethanol extract was partitioned with water into an aqueous fraction (A) and an insoluble fraction (B). The bioactivity of the ethanol extract against hemolysis of RBC test system was found concentrated in fraction A (IC 50 ϭ40 mg/ml). This fraction A was chromatographed on a porous polymer gel D-101 column with water, 60% aqueous ethanol and ethanol, to give fractions A1, A2 and A3 (Fig. 2). The biological activity was found concentrated in fraction A2, IC 50 being 31 mg/ml. From the active fraction A2, two new secoiridoid glucosides, lucidumosides C (9) and D (10), were isolated together with eight known secoiridoid glucosides, oleoside dimethyl ester (1), ligustroside (2), oleuropein (3), nuezhenide (4), isonuezhenid (5), neonuezhenide (6), lucidumoside A (7) and ...

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“…Previous studies have found volatile components, including triterpenes, flavonoids, secoiridoid glucosides, and phenolic compounds, in this plant and constituents such as phenylethanoids, monoterpenes, and secoiridoid glucosides in other species of the genus Ligustrum [12][13][14][15].…”

Section: )mentioning

confidence: 99%

Excellent Anti-aging Effects of Ursolic acid and Oleanolic acid Present in Ligustrum lucidum

Hong¹,

Yoo²,

Nam³

et al. 2012

Journal of the Society of Cosmetic Scientists of Korea

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Ligustrum lucidum (L. lucidum) contains large quantities of ursolic acid and oleanolic acid. In this study, we evaluated anti-wrinkle effects of three parts of L. lucidum extracts. We found that L. lucidum extracts were not only innocuous to human skin fibroblasts but also significantly decreased the expression of both MMP-1 and MMP-2 and increased the expression of COL1A1. Among the three parts of L. lucidum extracts (i.e., fruit, cane, and leaf extracts), the fruit extract was found to contain the greatest amounts of ursolic acid and oleanolic acid. These three parts of L. lucidum extracts increased the expression of COL1A1 and decreased the expression of MMP-1 and MMP-2 in a dose-dependent manner. Especially, the fruit extract of L. lucidum had the greatest upregulating effect on COL1A1 and the greatest downregulating effect on MMP-1 and MMP-2 in a non-toxic and dose-dependent manner. These results suggest that L. lucidum, especially the fruit, could be used as active ingredients for functional cosmetics.

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Monoterpenoid and phenylethanoid glycosides from Ligustrum pedunculare

Cited by 64 publications

References 8 publications

Meristem-Localized Inducible Expression of a UDP-Glycosyltransferase Gene Is Essential for Growth and Development in Pea and Alfalfa

Meristem-Localized Inducible Expression of a UDP-Glycosyltransferase Gene Is Essential for Growth and Development in Pea and Alfalfa

Antioxidative Glucosides from the Fruits of Ligustrum lucidum.

Excellent Anti-aging Effects of Ursolic acid and Oleanolic acid Present in Ligustrum lucidum

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