뎁사이드

뎁사이드(영어: depside)는 에스터 결합으로 연결된 2개 이상의 단일 고리 방향족 단위체로 구성된 폴리페놀 화합물의 한 유형이다. 뎁사이드는 지의류에서 가장 흔히 발견되지만, 진달래과, 꿀풀과, 양귀비과, 도금양과를 포함한 관다발식물에서도 분리되었다.^[1]^[2]^[3]^[4]

특정 뎁사이드는 생체외에서 항생제, 항HIV제, 항산화제 및 항증식 활성을 가지고 있다.^[4]^[5]^[6]^[7] 프로스타글란딘 합성 및 류코트라이엔 B₄ 생합성의 저해제로서 일부 뎁사이드는 생체외에서 항염증 활성을 갖는다.^[8]^[9]^[10]^[11]

뎁시데이스는 뎁사이드 결합을 절단하는 반응을 촉매하는 효소 유형이다. 이러한 효소들 중 하나는 탄네이스이다.^[12]

예

지의류인 크립토테시아 루브로신타(Cryptothecia rubrocincta)에서 발견되는 기로포르산은 뎁사이드이다. 클라도니아속의 지의류에서 분리된 메로클로로파에산은 프로스타글란딘 합성의 저해제이다.^[13]

일부 뎁사이드는 항HIV제로 설명된다.^[14]

같이 보기

에스터 결합을 형성하기 위해 살리실산의 자가 축합으로 형성된 살살레이트 homodimer formed from self-condensation of salicylic acid to form ester linkage.

각주

↑ Ono M, Masuoka C, Koto M, Tateishi M, Komatsu H, Kobayashi H, Igoshi K, Ito Y, Okawa M, Nohara T (October 2002). “Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein A, from the fruit of rabbiteye blueberry (Vaccinium ashei)”. 《Chem. Pharm. Bull.》 50 (10): 1416–7. doi:10.1248/cpb.50.1416. PMID 12372879.
↑ Zgórka G, Głowniak K (August 2001). “Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family”. 《J Pharm Biomed Anal》 26 (1): 79–87. doi:10.1016/S0731-7085(01)00354-5. PMID 11451645.
↑ Hillenbrand M, Zapp J, Becker H (April 2004). “Depsides from the petals of Papaver rhoeas”. 《Planta Med.》 70 (4): 380–2. doi:10.1055/s-2004-818956. PMID 15095160.
↑ ^가 ^나 Reynertson KA, Wallace AM, Adachi S, Gil RR, Yang H, Basile MJ, D'Armiento J, Weinstein IB, Kennelly EJ (August 2006). “Bioactive depsides and anthocyanins from jaboticaba (Myrciaria cauliflora)”. 《J. Nat. Prod.》 69 (8): 1228–30. doi:10.1021/np0600999. PMID 16933884.
↑ Kumar KC, Müller K (June 1999). “Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth”. 《J. Nat. Prod.》 62 (6): 821–3. doi:10.1021/np980378z. PMID 10395495.
↑ Neamati N, Hong H, Mazumder A, Wang S, Sunder S, Nicklaus MC, Milne GW, Proksa B, Pommier Y (March 1997). “Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching”. 《J. Med. Chem.》 40 (6): 942–51. doi:10.1021/jm960759e. PMID 9083483.
↑ Nielsen J, Nielsen PH, Frisvad JC (1998). “Fungl depside, guisinol, from a marine derived strain of Emericella unguis”. 《Phytochemistry》 50 (2): 263–265. doi:10.1016/s0031-9422(98)00517-2.
↑ Gerrard JM, Peterson DA (February 1984). “Structure of the active site of prostaglandin synthase from studies of depsides: an alternate view”. 《Prostaglandins Leukot Med》 13 (2): 139–42. doi:10.1016/0262-1746(84)90003-9. PMID 6425861.
↑ Sankawa U, Shibuya M, Ebizuka Y, Noguchi H, Kinoshita T, Iitaka Y, Endo A, Kitahara N (July 1982). “Depside as potent inhibitor of prostaglandin biosynthesis: a new active site model for fatty acid cyclooxygenase”. 《Prostaglandins》 24 (1): 21–34. doi:10.1016/0090-6980(82)90174-5. PMID 6812170.
↑ Kumar KC, Müller K (June 1999). “Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism”. 《J. Nat. Prod.》 62 (6): 817–20. doi:10.1021/np9803777. PMID 10395494.
↑ Kumar KCS, Müller K (April 2000). “Depsides as non-redox inhibitors of leukotriene B₄ biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid”. 《Eur J Med Chem》 35 (4): 405–11. doi:10.1016/S0223-5234(00)00132-X. PMID 10858601.
↑ Haslam E, Stangroom JE (April 1966). “The esterase and depsidase activities of tannase”. 《Biochem. J.》 99 (1): 28–31. doi:10.1042/bj0990028. PMC 1264952. PMID 5965343.
↑ Shibata, Shoji; Chiang, Hsüch-Ching (1965). “The structures of cryptochlorophaeic acid and merochlorophaeic acid”. 《Phytochemistry》 4: 133–139. doi:10.1016/S0031-9422(00)86155-5.
↑ Neamati, Nouri; Hong, Huixiao; Mazumder, Abhijit; Wang, Shaomeng; Sunder, Sanjay; Nicklaus, Marc C.; Milne, George W. A.; Proksa, Bohumil; Pommier, Yves (1997). “Depsides and Depsidones as Inhibitors of HIV-1 Integrase: Discovery of Novel Inhibitors through 3D Database Searching†”. 《Journal of Medicinal Chemistry》 40 (6): 942–951. doi:10.1021/jm960759e. ISSN 0022-2623. PMID 9083483.

[pmid12372879-1] Ono M, Masuoka C, Koto M, Tateishi M, Komatsu H, Kobayashi H, Igoshi K, Ito Y, Okawa M, Nohara T (October 2002). “Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein A, from the fruit of rabbiteye blueberry (Vaccinium ashei)”. 《Chem. Pharm. Bull.》 50 (10): 1416–7. doi:10.1248/cpb.50.1416. PMID 12372879.

[pmid11451645-2] Zgórka G, Głowniak K (August 2001). “Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family”. 《J Pharm Biomed Anal》 26 (1): 79–87. doi:10.1016/S0731-7085(01)00354-5. PMID 11451645.

[pmid15095160-3] Hillenbrand M, Zapp J, Becker H (April 2004). “Depsides from the petals of Papaver rhoeas”. 《Planta Med.》 70 (4): 380–2. doi:10.1055/s-2004-818956. PMID 15095160.

[pmid16933884-4] 가 ^나 Reynertson KA, Wallace AM, Adachi S, Gil RR, Yang H, Basile MJ, D'Armiento J, Weinstein IB, Kennelly EJ (August 2006). “Bioactive depsides and anthocyanins from jaboticaba (Myrciaria cauliflora)”. 《J. Nat. Prod.》 69 (8): 1228–30. doi:10.1021/np0600999. PMID 16933884.

[pmid10395495-5] Kumar KC, Müller K (June 1999). “Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth”. 《J. Nat. Prod.》 62 (6): 821–3. doi:10.1021/np980378z. PMID 10395495.

[pmid9083483-6] Neamati N, Hong H, Mazumder A, Wang S, Sunder S, Nicklaus MC, Milne GW, Proksa B, Pommier Y (March 1997). “Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching”. 《J. Med. Chem.》 40 (6): 942–51. doi:10.1021/jm960759e. PMID 9083483.

[7] Nielsen J, Nielsen PH, Frisvad JC (1998). “Fungl depside, guisinol, from a marine derived strain of Emericella unguis”. 《Phytochemistry》 50 (2): 263–265. doi:10.1016/s0031-9422(98)00517-2.

[pmid6425861-8] Gerrard JM, Peterson DA (February 1984). “Structure of the active site of prostaglandin synthase from studies of depsides: an alternate view”. 《Prostaglandins Leukot Med》 13 (2): 139–42. doi:10.1016/0262-1746(84)90003-9. PMID 6425861.

[pmid6812170-9] Sankawa U, Shibuya M, Ebizuka Y, Noguchi H, Kinoshita T, Iitaka Y, Endo A, Kitahara N (July 1982). “Depside as potent inhibitor of prostaglandin biosynthesis: a new active site model for fatty acid cyclooxygenase”. 《Prostaglandins》 24 (1): 21–34. doi:10.1016/0090-6980(82)90174-5. PMID 6812170.

[pmid10395494-10] Kumar KC, Müller K (June 1999). “Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism”. 《J. Nat. Prod.》 62 (6): 817–20. doi:10.1021/np9803777. PMID 10395494.

[pmid10858601-11] Kumar KCS, Müller K (April 2000). “Depsides as non-redox inhibitors of leukotriene B₄ biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid”. 《Eur J Med Chem》 35 (4): 405–11. doi:10.1016/S0223-5234(00)00132-X. PMID 10858601.

[12] Haslam E, Stangroom JE (April 1966). “The esterase and depsidase activities of tannase”. 《Biochem. J.》 99 (1): 28–31. doi:10.1042/bj0990028. PMC 1264952. PMID 5965343.

[13] Shibata, Shoji; Chiang, Hsüch-Ching (1965). “The structures of cryptochlorophaeic acid and merochlorophaeic acid”. 《Phytochemistry》 4: 133–139. doi:10.1016/S0031-9422(00)86155-5.

[NeamatiHong1997-14] Neamati, Nouri; Hong, Huixiao; Mazumder, Abhijit; Wang, Shaomeng; Sunder, Sanjay; Nicklaus, Marc C.; Milne, George W. A.; Proksa, Bohumil; Pommier, Yves (1997). “Depsides and Depsidones as Inhibitors of HIV-1 Integrase: Discovery of Novel Inhibitors through 3D Database Searching†”. 《Journal of Medicinal Chemistry》 40 (6): 942–951. doi:10.1021/jm960759e. ISSN 0022-2623. PMID 9083483.

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