Sesquiterpenoids from the Root Tubers of Lindera aggregata

Abstract

Six new sesquiterpenoids, linderanlide A–F (1–5 and 12), and nine previously reported sesquiterpenoids (6–11 and 13–15) have been isolated from the root tubers of Lindera aggregata. The new structures have been elucidated by extensive spectroscopic interpretation, including UV, IR, NMR, HR‐ESI‐MS, and CD spectra. The structures of compounds 1, 2, 6, 7, and 9 were further confirmed by single-crystal X‐ray diffraction analysis. The absolute configurations of compounds 3–5 were determined by CD spectral analysis.

Lindera aggregate - Lauraceae - sesquiterpenoids - absolute configuration

References

• 1 Cheng X L, Ma S C, Wei F, Wang G L, Xiao X Y, Lin R C. A new sesquiterpene isolated from Lindera aggregata (SIMS) KOSTERM.  Chem Pharm Bull. 2007;  55 1390-1392
• 2 Gan L S, Zheng Y L, Mo J X, Liu X, Li X H, Zhou C X. Sesquiterpene lactones from the root tubers of Lindera aggregata.  J Nat Prod. 2009;  72 1497-1501
• 3 Lin C T, Chu F H, Chang S T, Chueh P J, Su Y C, Wu K T, Wang S Y. Secoaggregatalactone-A from Lindera aggregata induces apoptosis in human hepatoma Hep G2 cells.  Planta Med. 2007;  73 1548-1553
• 4 Li W X, Lei M, Fei D Q, Gao K. Eremophilane-type sesquiterpenoids derivatives from Ligularia hodgsonii.  Planta Med. 2009;  75 635-640
• 5 Wang H X, Liu C M, Liu Q, Gao K. Three types of sesquiterpenes from rhizomes of Atractylodes lancea.  Phytochemistry. 2008;  69 2088-2094
• 6 Liu C M, Fei D Q, Wu Q H, Gao K. Bisabolane sesquiterpenes from the roots of Ligularia cymbulifera.  J Nat Prod. 2006;  69 695-699
• 7 Fei D Q, Li S G, Liu C M, Wu G, Gao K. Eremophilane-type sesquiterpene derivatives from the roots of Ligularia lapathifolia.  J Nat Prod. 2007;  70 241-245
• 8 Wu S L, Li W S. Terpenoids from Neolitsea buisanensis.  Phytochemistry. 1991;  30 4160-4162
• 9 Li W S. Sesquiterpene lactones from the root of Neolitsea acutotrinervia.  J Nat Prod. 1992;  55 1614-1619
• 10 Tori K, Ueyama M, Horibe I, Tamura Y, Takeda K. Carbon-13 NMR spectra of some furanosesquiterpenes, major components of Lindera strychnifolia.  Tetrahedron Lett. 1975;  16 4583-4586
• 11 Takeda K, Horibe I, Teraoka M, Minato H. Absolute configuration of linderalactone and linderane.  Chem Commun. 1968;  637
• 12 Gao K, Li X. Analysis of the configuration and conformation of germacrane type sesquiterpenoids.  Chin J Magn Reson. 2004;  21 249-261
• 13 Yuan T, Yang S P, Zhang C R, Zhang S, Yue J M. Two limonoids, khayalenoids A and B with an unprecedented 8-oxa-tricyclo[4.3.2.0^{2, 7}]undecane motif, from Khaya senegalensis.  Org Lett. 2009;  11 617-620
• 14 Li W S, Duh C Y. Sesquiterpene lactones from Neolitsea villosa.  Phytochemistry. 1993;  32 1503-1507
• 15 Nagashima F, Kishi K, Hamada Y, Takaoka S, Asakawa Y. ent-Verticillane-type diterpenoids from the Japanese liverwort Jackiella javanica.  Phytochemistry. 2005;  66 1662-1670
• 16 Takeda K, Horibe I, Minato H. Components of the root of Lindera strychnifolia Vill. Part XIV. Sesquiterpene lactones from the root of Lindera strychnifolia Vill.  J Chem Soc C. 1968;  569-572
• 17 Choi J Y, Choi E H, Jung H W, Oh J S, Lee W H, Lee J G, Son J K, Kim Y, Lee S H. Melanogenesis inhibitory compounds from Saussureae Radix.  Arch Pharm Res. 2008;  31 294-299