Transannular cyclization of (4S,5S)-germacrone-4,5-epoxide into guaiane and secoguaiane-type sesquiterpenes

Natural Product Communications

Volumn 7, Issue 4, 2012, Pages 441-446

  Kuroyanagi, Masanori ^a   Shirota, Osamu ^a   Sekita, Setsuko ^a   Nakane, Takahisa ^b  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

(4S,5S) Germacrone 4,5 epoxid; Germacrane; Guaiane; Secoguaiane; Sesquiterpene; Transannular cyclization

Indexed keywords

CARBON; CURCUMA AROMATICA EXTRACT; EPOXIDE; GERMACRONE; GERMACRONE 4,5 EPOXIE; OXYGEN; PLANT EXTRACT; SESQUITERPENE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CONFORMATION; CURCUMA; CURCUMA AROMATICA; CYCLIZATION; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; HEAT TREATMENT; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOCHEMISTRY;

CURCUMA AROMATICA;

EID: 84860712518     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1200700406     Document Type: Article

References (17)

1. Adio AM. (2009) Germacrenes A-E and related compounds: thermal, photochemical and acid induced transannular cyclization. Tetrahedron, 65, 1533-1552.
2. 2,5]undAcenes. European Journal of Organic Chemistry, 3434-3441.
3. Hikino H, Konno C, Nagashima T, Kohama T, Takemoto T. (1977) Stereoselective epoxidation of germacradienes by enzymes and selective transannular cyclization of germacradienes and their epoxides. Chemical & Pharmaceutical Bulletin. 25, 6-18.
4. Justica J, Álvalez de Cienfuegos L, Estévez RE, Paradas M, Lasanta AM, Oller JL, Rosales A, Cuerva JM, Oltra JE. (2008) Ti-catalyzed transannular cyclization of epoxygermacrolides. Synthesis of antifungal (+)-tuberiferine and (+)-dehydrobrachylaenolide. Tetrahedron, 64, 11938-11943.
5. Shiobara Y, Asakawa Y, Kodama M, Yasuda K, Takemoto T. (1985) Curcumenone, curcumanolide A and curcumanolide B, three sesquiterpenoids from Curcuma zedoaria. Phytochemistry, 24, 2629-2633.
6. Matsuda H, Morikawa T, Toguchida I, Ninomiya K, Yoshikawa M. (2001) Medicinal foodstuffs. XXVIII. Inhibitors of nitric oxide production and new sesquiterpenes, zedoagrofuran, 4-epicurcumenol, neocurcumenol, gajystsulactones A and B, and zedoarolides A and B, from Zedoariae Rhizoma. Chemical & Pharmaceutical Bulletin, 49, 1558-1566. (Pubitemid 33126583)
7. Kuroyanag M, Ueno A, Ujiie K, Sato S. (1987) Structures of sesquiterpenes from Curcuma aromatica Salisb. Chemical & Pharmaceutical Bulletin, 35, 53-59. (Pubitemid 17021374)
8. Kuroyanagi M, Ueno A, Koyama K, Natori S. (1990) Structures of sesquiterpenes of Curcuma aromatica Salisb. II. Studies on minor sesquiterpenes. Chemical & Pharmaceutical Bulletin, 38, 55-58. (Pubitemid 20138363)
9. Ohshiro M, Kuroyanagi M, Ueno A. (1990) Structures of sesquiterpenes from Curcuma longa. Phytochemistry, 29, 2201-2205.
10. Sakui N, Kuroyanagi M, Ishitobi Y, Sato M, Ueno A. (1991) Biotransformation of sesquiterpenes by cultured cells of Curcuma zedoaria. Phytochemistry, 31, 143-147.
11. Sakamoto S, Tsuchiya N, Kuroyanagi M, Ueno A. (1994) Biotransformation of germacrone by suspension cultured cells. Phytochemistry, 35, 1215-1219. (Pubitemid 2065907)
12. Piet DP, Schrijvers R, Franssen MCR, deGroot A. (1995)) Biotransformation of germacrane epoxides by Chichorium intybus. Tetrahedron, 51, 6303-6314.
13. Asakawa Y, Takahashi H, Toyota M. (1991) Biotransformation of germacrane-type sesquiterpenoids by Aspergillus niger. Phytochemistry, 30, 3993-3997.
14. Endo J, Itokawa H, Iitaka Y. (1978) Studies on the essential oil of Asarum caulescens. 21st Symposium on the Chemistry of Natural Products, symposium paper, 401-408.
15. Yoshihara M, Yang C, Zheng C, Shibuya H, Hamamoto Y, Tanaka N, Kitagawa I. (1986) Chemical conversion of (4S,5S)-(+)-germacrone 4,5-epoxide, a plausible biogenetic intermediate found in the essential oil of Zedoariae Rhizoma from Yakushima, Japan. Chemical & Pharmaceutical Bulletin, 34, 434-437. (Pubitemid 16129672)
16. Hikino H, Sakurai Y, Takemoto T. (1968) Structure of procurcumenol. Chemical & Pharmaceutical Bulletin, 16, 1605-1607.
17. Fruchier A, Rascol JP, Andary C, Privat G. (1981) A tropone derivative from Orobanche rapum-genistae. Phytochemistry, 20, 777-779.