Scapiformolactones A-I: Germacrane sesquiterpenoids with an unusual Δ3-15,6-lactone moiety from Salvia scapiformis

Phytochemistry

Volumn 96, Issue , 2013, Pages 378-388

  Lai, Yongji ^a   Xue, Yongbo ^a   Zhang, Mengke ^a   Zhang, Jinwen ^b   Tang, Wei ^c   Liu, Junjun ^a   Lei, Liang ^a   Yan, Juming ^d   Luo, Zengwei ^a   Zuo, Jianping ^c   Li, Yan ^d   Yao, Guangmin ^a   Zhang, Yonghui ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^d KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

Chemical transformation; Conformation; Cytotoxicity; Germacrane sesquiterpene; Immunomodulatory activity; Lamiaceae; Quantum mechanical calculation; Salvia scapiformis

Indexed keywords

LAMIACEAE; SALVIA;

ANTINEOPLASTIC AGENT; HERBACEOUS AGENT; IMMUNOLOGIC FACTOR; LACTONE; SESQUITERPENE;

ARTICLE; B LYMPHOCYTE; CHEMICAL STRUCTURE; CHEMICAL TRANSFORMATION; CHEMISTRY; CONFORMATION; CYTOTOXICITY; DRUG EFFECT; DRUG SCREENING; GERMACRANE SESQUITERPENE; HL 60 CELL LINE; HUMAN; IMMUNOLOGY; IMMUNOMODULATORY ACTIVITY; ISOLATION AND PURIFICATION; LAMIACEAE; NUCLEAR MAGNETIC RESONANCE; QUANTUM MECHANICAL CALCULATION; SALVIA; SALVIA SCAPIFORMIS; T LYMPHOCYTE; X RAY CRYSTALLOGRAPHY;

CHEMICAL TRANSFORMATION; CONFORMATION; CYTOTOXICITY; GERMACRANE SESQUITERPENE; IMMUNOMODULATORY ACTIVITY; LAMIACEAE; QUANTUM MECHANICAL CALCULATION; SALVIA SCAPIFORMIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; B-LYMPHOCYTES; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; DRUGS, CHINESE HERBAL; HL-60 CELLS; HUMANS; IMMUNOLOGIC FACTORS; LACTONES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SALVIA; SESQUITERPENES, GERMACRANE; T-LYMPHOCYTES;

EID: 84888362033     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.10.003     Document Type: Article

References (22)

1. M.S. Ali, S.A. Ibrahim, S. Ahmed, and E. Lobkovsky A new germacranolide and a new ceramide from Salvia nubicola (Lamiaceae) Z. Naturforsch. B 62 2007 1333 1338
2. Z.-X. Fang, and C.-L. Liao Medicinal Flora of Enshi, Hubei vol. 2 2006 Hubei Science and Technology Press Wuhan pp. 292-293
3. B.M. Fraga Natural sesquiterpenoids Nat. Prod. Rep. 29 2012 1334 1366
4. T. Fujiwara, and M. Hayashi Efficient synthesis of rare sugar d-allal via reversal of diastereoselection in the reduction of protected 1,5-anhydrohex-1-en-3-uloses: protecting group dependence of the stereoselection J. Org. Chem. 73 2008 9161 9163
5. A.G. González, T.A. Grillo, A.G. Ravelo, J.G. Luis, M.L. Rodriguez, J. Calle, and A. Rivera Study of Salvia palaefolia: absolute configuration of glechomafuran J. Nat. Prod. 52 1989 1307 1310 (Pubitemid 20101784)
6. M. Grande, I.S. Bellido, P. Torres, and F. Piera 9-Hydroxynerolidol esters and bicyclic sesquiterpenoids from Dittrichia viscosa J. Nat. Prod. 55 1992 1074 1079
7. X.-W. Li, and C.H. Ian Lamiaceae Z.Y. Wu, P.H. Raven, D.Y. Hong, Flora of China vol. 17 1994 Science Press and Missouri Botanical Garden Press Beijing, China, and St. Louis, United States 50 299
8. Y. Li, Y.-Q. Wu, X. Du, and Y.-P. Shi Germacrane sesquiterpene esters from Salvia roborowskii Planta Med. 69 2003 782 784 (Pubitemid 37215035)
9. Y. Liu, C. Li, J.-G. Shi, and Y.-P. Shi Two new sesquiterpenes from Salvia roborowskii MAXIM Helv. Chim. Acta 92 2009 335 338
10. A.V. Marenich, C.J. Cramer, and D.G. Truhlar Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions J. Phys. Chem. B 113 2009 6378 6396
11. OMEGA, version 2.4.6, 2012. OpenEye Scientific Software Inc., Santa Fe, NM, USA, < www.eyesopen.com >.
12. Z.-H. Pan, Y.-Y. Wang, M.-M. Li, G. Xu, L.-Y. Peng, J. He, Y. Zhao, Y. Li, and Q.-S. Zhao Terpenoids from Salvia trijuga J. Nat. Prod. 73 2010 1146 1150
13. A. Rustaiyan, M. Goudarzi, H. Sigari, and Z. Habibi 6β- Tigloyloxyglechomafuran a new furanosesquiterpene from Salvia glutinosa J. Sci. Islamic Repub. Iran 3 1992 42 44
14. M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S. Su, T.L. Windus, M. Dupuis, and J.A.J. Montgomery General atomic and molecular electronic structure system J. Comput. Chem. 14 1993 1347 1363
15. F. Sorm Sesquiterpenes with ten-membered carbon rings. A Review J. Agric. Food Chem. 19 1971 1081 1087
16. P. Ugliengo, G. Appendino, G. Chiari, and D. Viterbo Conformational study of shiromodiol and related epoxygermacranes: X-ray, molecular mechanics and NMR analyses J. Mol. Struct. 222 1990 437 452
17. Y. Wang, Z. Li, H. Zhang, Y. Sha, Y. Pei, and H. Hua New germacrane sesquiterpenes from Salvia chinensis Chem. Pharm. Bull. 56 2008 843 846 (Pubitemid 351872255)
18. Y.-B. Wu, Z.-Y. Ni, Q.-W. Shi, M. Dong, H. Kiyota, Y.-C. Gu, and B. Cong Constituents from Salvia species and their biological activities Chem. Rev. 112 2012 5967 6026
19. G. Xu, L.-Y. Peng, X.-L. Li, Y. Zhao, L. Tu, Q.-S. Zhao, H.-D. Sun, Y. Lu, L. Mao, and Q.-T. Zheng New sesquiterpenoids from Salvia castanea DIELS f. tomentosa Helv. Chim. Acta 88 2005 2370 2374 (Pubitemid 41232858)
20. G. Xu, L.-Y. Peng, A.-J. Hou, J. Yang, Q.-B. Han, H.-X. Xu, and Q.-S. Zhao Isolation, structural elucidation, and chemical transformation of interconvertible 8,12-hemiketal germacranolide sesquiterpenoids from Salvia castanea Diels f. tomentosa Stib Tetrahedron 64 2008 9490 9494
21. G.-M. Yao, Y. Ding, J.-P. Zuo, H.-B. Wang, Y.-B. Wang, B.-Y. Ding, P. Chiu, and G.-W. Qin Dihydrochalcones from the leaves of Pieris japonica J. Nat. Prod. 68 2005 392 396 (Pubitemid 40545477)
22. H. Yoshioka, T.J. Mabry, and H.E. Miller Isabelin, a new germacranolide dilactone from Ambrosia psilostachya DC Chem. Commun. 1968 1679 1681