β-carboline alkaloids from Trigonostemon filipes and Trigonostemon lii

Abstract

Six -carboline alkaloids including three new ones, trifilines AC (13) were isolated from Trigonostemon filipes, along with a new -carboline alkaloid, trigonoine C (7) isolated from Trigonostemon lii. Their structures were elucidated by extensive spectroscopic techniques. Trifilines A (1) and B (2) showed weak anti-HIV-1 activity with EC 50 values of 54.61 μg/mL and 9.75 μg/mL, along with TI (Therapeutic index) values of 1.52 and 1.42, respectively. This is the first time to report the chemical constituents of Trigonostemon filipes.

New Compounds from the Roots and Stems of Trigonostemon lii and Their Cytotoxic Activities

“…In the HMBC spectrum, two NH singlet s showed correlations to C(1a), C(4a), C(5a), and C(13a), and C(8a), C(9a), C(12a), and C(13b), respectively, suggesting that two indole units were determined. Careful comparison of its NMR spectra ( Table ) with those of trifiline A revealed that compound 1 was closely related to it, with a MeCH moiety at C/H 58.2 and 20.4/3.79 – 3.81 ( m ) and 1.59 ( d , J = 6.2) in 1 instead of one CH 2 group in the latter. The 1 H, 1 H‐COSY correlations of CH 2 (5) ( δ (H) (3.37 – 3.39 ( m ) and 2.66 – 2.68 ( m ))/H–C(6) ( δ (H) (3.79 – 3.81 (m))/Me–C(6) ( δ (H) (1.59 ( d , J = 6.2)) and the key HMBC correlations of H–C(6) to C(7) ( δ (C) (49.7 ( t ))/C(13) ( δ (C) (56.5 ( d )) and H(5) to C(4a) ( δ (C) (122.4 ( s )), C(13a) ( δ (C) (136.5 ( s )) and C(5a) ( δ (C) (107.2 ( s )) also supported this difference in 1 ( Fig.…”

“…Trigonostemon includes about 50 species, belongs to the family of Euphorbiaceae, most of them are distributed in tropical and subtropical regions of Asia, and ten species being endemic to South China . It has attracted considerable attention as rich source of new diterpenoids , alkaloids , phenanthrenes , and other kinds of compounds , with diverse structures and significant biological activities. In our continuing investigation on the chemical constitutes from Trigonostemon lii Y.T.…”

Recent studies on the chemical constituents of Trigonostemon plants

“…37 In addition to six β-carboline alkaloids, trigonostemonines A-D (142-145), E (148), and F (152) presented in the former review, 3,38 16 additional β-carboline alkaloids (Fig. 40 2.2.2. ), 39 arenarine C (159), 39 harmicacid methyl ester (160), 39 1,2,3,4-tetrahydro-oxo-β-carboline (161), 39 norharmine (162), 39 harmine (163), 39 trigonoine C (164), 40 trigonoines A (165) and B (166).…”

“…β-Carboline alkaloids. ), 39 arenarine C (159), 39 harmicacid methyl ester (160), 39 1,2,3,4-tetrahydro-oxo-β-carboline (161), 39 norharmine (162), 39 harmine (163), 39 trigonoine C (164), 40 trigonoines A (165) and B (166). 37 In addition to six β-carboline alkaloids, trigonostemonines A-D (142-145), E (148), and F (152) presented in the former review, 3,38 16 additional β-carboline alkaloids (Fig.…”

Recent Advances in the Synthesis of β-Carboline Alkaloids

“…Noctiluca milaris [10] Strychnos johnsonii [11] Lycoris longituba [12] Selaginella delicatula [13] Trichosanthes kirilowii Maxim [14] Rauwolfia caffra [15] Didemnum sp [16] MAO Cnemidocarpa stolonifera [20] apoptosis in PC3 human prostate cancer cell line [20] 8: Eudistoma olivaceum [21] 9: Eudistoma olivaceum [22] 10: Lissoclinum fragile [23] 11: Eudistoma olivaceum [24] 12: analogues of natural products 13: soybean [28] Flindersia laevicarpa [29] 14: analogues of natural products 15: Flindersia Caevicarpa [29] 16: Picrasma quassioides [30] 13: anti-neuroin-flammatory activities [28] 14: n.a. 15: vasorelaxant effect [31] binding affinity to imidazoline I2B receptors [32] 16: cytotoxic activity [33] AMP phosphodiesterase inhibitor [34] anti-inflammatory agent [35,36] trigonostemine [37] 17, 18, 19: Trigonostemone filipes [38] 20: Malassezia furfur [39] Paracoccus marine bacteria [40] Dichotomomyces cejpii [41] 21: Hyrtio erectus [42] Alocasia macrorrhiza [43] 17, 18, 19: cytotoxic activity [44] 20: antiproliferative activity [45] anticancer activity [46,47] 21: antiproliferative activity [48,49] antimalarial activity [46] antiphospholipase A2 [50] and antioxidant activity …”