2010
DOI: 10.1021/ol100715x
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Three New Indole Alkaloids from Trigonostemon lii

Abstract: Three unprecedented indole alkaloids, trigonoliimines A-C (1-3) with a unique polycyclic system, were isolated from the leaves of Trigonostemon lii Y. T. Chang. The structures of 1-3 were determined by the spectroscopic, computational, and CD exciton chirality approaches. Trigonoliimine A showed modest anti-HIV-1 activity (EC(50) = 0.95 microg/mL, TI = 7.9).

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Cited by 137 publications
(41 citation statements)
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“…Numerous structurally interesting compounds such as flavonoidal alkaloids (Kanchanapoom et al, 2002), indole alkaloids (Tan et al, 2010;Zhu et al, 2010), phenanthrenes (Kokpol et al, 1990) and an array of daphnane-type diterpenoids (Chen et al, 2010a;Dong et al, 2011a;Jayasuriya et al, 2000Jayasuriya et al, , 2004Li et al, 2011;Lin et al, 2010;Soonthornchareonnon et al, 2005;Zhang et al, 2010a) have been isolated from this genus. Daphnane-type diterpenoids of Trigonostemon have been shown to possess insecticidal (Jayasuriya et al, 2000(Jayasuriya et al, , 2004, acaricidal (Soonthornchareonnon et al, 2005), cytotoxic (Chen et al, 2010b;Dong et al, 2011b;Lin et al, 2010) and antiviral (Zhang et al, 2010b) properties.…”
Section: Introductionmentioning
confidence: 99%
“…Numerous structurally interesting compounds such as flavonoidal alkaloids (Kanchanapoom et al, 2002), indole alkaloids (Tan et al, 2010;Zhu et al, 2010), phenanthrenes (Kokpol et al, 1990) and an array of daphnane-type diterpenoids (Chen et al, 2010a;Dong et al, 2011a;Jayasuriya et al, 2000Jayasuriya et al, , 2004Li et al, 2011;Lin et al, 2010;Soonthornchareonnon et al, 2005;Zhang et al, 2010a) have been isolated from this genus. Daphnane-type diterpenoids of Trigonostemon have been shown to possess insecticidal (Jayasuriya et al, 2000(Jayasuriya et al, , 2004, acaricidal (Soonthornchareonnon et al, 2005), cytotoxic (Chen et al, 2010b;Dong et al, 2011b;Lin et al, 2010) and antiviral (Zhang et al, 2010b) properties.…”
Section: Introductionmentioning
confidence: 99%
“…Following this hypothesis, we investigated the intramolecular asymmetric arylative dearomatization of Nsubstituted indoles via palladium-catalyzed reductive Heck reactions ( Figure 1). 8,9 The new dearomatization strategy provides a facile approach to chiral indolines bearing C2-quaternary stereocenters, 10 which are frequently occurring core structures of bioactive natural products, such as trigonoliimine C, 11 (-)-isatisine A, 12 and hinckdentine A. 13 Herein, we wish to present our findings of highly enantioselective Pd-catalyzed arylative dearomatization of a variety of indole derivatives.…”
mentioning
confidence: 99%
“…To our delight, the desired product 2a was isolated in lower yields but with excellent enantioselectivities when the reactions were performed in CH 3 CN or DCE (1,2-dichloroethane) ( Table 1, entries [3][4]. Gratifyingly, the yield was remarkably improved to 79% in methanol and the excellent enantioselectivity was retained ( [8][9][10][11]. However, the results were significantly improved when HCO 2 Na was used as a hydride source, leading to product 2a in 85% yield and 97% ee value (Table 1, entry 13).…”
mentioning
confidence: 99%
“…was tested by a microtiter syncytium formation infectivity assay. Compound 54 showed modest anti-HIV-1 activity, with an EC 50 value of 0.95 mg/ml and TI of 7.9 [17].…”
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confidence: 99%
“…Highly aromatized tetranorditerpenes, 45 and 46, were isolated from T. chinensis and T. lii. [17]. Carboline alkaloids 48 -53 were isolated from the roots and stems of T. lii, whereas, unprecedented indole alkaloids with a unique fused-hexacyclic ring system (two five-, three six-, and one seven-membered ring), 54 -56, were isolated from the leaves of T. lii.…”
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confidence: 99%