Matrix metalloproteinase-1 inhibitor from the aerial parts of Viola ibukiana MAKINO

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Title
Matrix metalloproteinase-1 inhibitor from the aerial parts of Viola ibukiana MAKINO
Author(s)
H I Moon; J E Kim; Joongku Lee; O P Zee; J H Chung
Bibliographic Citation
Bulletin of Korean Chemical Society, vol. 26, no. 3, pp. 451-453
Publication Year
2005
Abstract
Viola ibukiana (Violaceae) distributed in southern part of Korea. In traditional medicine, the herb has been used as an expectorant, a diuretic, and an antiinflammatory for bron-chitis, rheumatism, skin eruptions, and eczema. 1,2 Previous phytochemical studies on Viola species have revealed them to be a rich source of cyclotides, 3,4 and several flavone glycosides. 5,6 Although some common triterpene saponin has been reported, this plant has not been investigated in detail. 7 The matrix metalloproteinases (MMPs) are a family of >20 zinc-dependent endoproteinases that are capable of degrading almost all of the components of the extracellular matrix. 8 MMPs can be divided into four categories based on substrate preference: collagenases, gelatinases, stromelysins, and membrane-associated matrix metalloproteinases. 9 MMPs are necessary for tissue remodeling and the healing cascade under normal physiological condition. The aging process of skin can be divided into intrinsic aging and photoaging. Clinically, naturally aged skin is smooth, pale, and finely wrinkled. In contrast, photoaged skin is coarsely wrinkled. 10 Alterations in collagen, the major structural component of skin, have been suggested as a cause of the changes, such as skin wrinkling and loss of elasticity, which are observed in naturally aged and photoaged skin. 11 With increasing age, collagen synthesis becomes lower and MMP-1 levels become higher in sun-protected human skin in vivo. UV irradiation induces the synthesis of MMPs in fibroblast cell in vitro and MMP-mediated collagen destruction accounts, in large part, for the connective tissue damage that occurs in photoaging. 10 In an ongoing investigation into MMP-1 inhibitory compound from Viola ibukiana, a new active compound was isolated from the EtOAc soluble fraction. In this notes, we report on the constituent of Viola ibukiana, which inhibits UV-induced MMP-1 expression in human skin fibroblasts Experimental Section General Procedure. IR spectra were obtained with a Perkin Elmer 1710 spectrophotometer. The NMR spectra was taken on a Bruker AMX 500 (1 H, 500 MHz; 13 C, 125 MHz) spectrometer. FAB-MS spectra were obtained on a JMS AX505WA spectrometer. TLC was carried out on silica gel 60 F 254 and RP-18 F 254 plates (Merck, Germany). Column chromatography was performed over silica gel 60 (Merck, particle size 230-400 mesh) and Sephadex LH-20 (Pharmacia, Sweden). Plant Material. The whole plants of Viola ibukiana (Violaceae) were collected in April 2004 at Ullung Island, Korea. The botanical identification was made by one of the authors, Dr. JoongKu Lee. A voucher specimen of this raw material has been deposited at the herbarium of the Seoul National University (SNU-04-04-15). Extraction and Purification of Active Compound. The dried whole plants (562 g) of Viola ibukiana were extracted five times with 80% MeOH in an ultrasonic apparatus for 3 hrs. This residue was evaporated in vacuo to yield the total extract (48.7 g). This extract was then suspended in distilled water and partitioned with n-hexane, CHCl 3 , EtOAc, and n-BuOH. The EtOAc fraction (7.8 g) was subjected to silica gel column chromatography using CHCl 3 -EtOAc gradient system (9 : 1 → 1 : 1) to provide 11 fractions (fractions 1-11). From fraction 8, compound 2 (16.3 mg) was isolated using a silica gel column chromatography (CHCl 3 -EtOAc, 20 : 1), and then purified by semipreparative RP-HPLC (YMC J'sphere-H80, 4 μm, 250 × 10 mm, MeOH-H 2 O = 6 : 4). Compounds 1 (28.5 mg) was separated from fraction 9 by the same procedure as those of the fraction 8. Figure 1. Structures of isolated compound from Viola ibukiana.
Keyword
Matrix metalloproteinase-1PhenolicUltraviolet irradiationViola ibukiana
ISSN
0253-2964
Publisher
Wiley
DOI
http://dx.doi.org/10.5012/bkcs.2005.26.3.451
Type
Article
Appears in Collections:
1. Journal Articles > Journal Articles
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