Iridoids in Equatorial and Tropical Flora

Abstract

The leaves of Tecoma chrysantha Jacq. a tree of the tropics, contain together with 6-epiaucubin ( 1), a less polar iridoid 2. Chemical and spectroscopical data demonstrated that 2 contains a residue of 1 esterified by 8-hydroxy-2,6-dimethyl-2,6-octadienoic acid ( 3), a rare monoterpenic product.

Iridoids. An Updated Review. Part I.

“…Ajuga reptans (Labiatae) (32-34) 36. AJUGOSIDE (Leonuride) (revision of stereochemistry at C-6) HO C17H26Ol0 390.39 (D20) 94.5 (C-l), 140.5 (C-3), 104.3 (C-4), 40.6 (C-5), 76.4 (C-6), 47.7 (C-7), 90.1 (C-8), 48.4 (C-9), 22.5 (C-10)*, 99.1 (C-V), 73.6 (C-2'), 76.6 (C-3'), 70.5 (C-4'), 77.1 (C-5'), 61.6(C-6'), 174.8 (0=CMe), 22.4 (O=CMef. Ajuga reptans (Labiatae) (32,34) 37. 6-0-/>-HYDROXYBENZOYL-AJUGOL O C22H28On 468.46 (a] -138.8°(MeOH) (200 MHz CDjOD) 5.51 (H-l, d, 2.4), 6.23 (H-3, dd, 6.2, 2.3), 5.02(H-4, m), 2.98(H-5, dd, 9.2, 2.2), 5.02(H-6, m), 2.28 (H-7, dd, 14.2, 6.4), 2.05 (H-7, dd, 14.2, 4.0), 2.61 (H-9, dd, 9.2, 2.4), 1.40(H-10, s), 4.67(H-V, d, 7.8), 4.0-3.2(H-2'-H-6',m), 7.90(H-2*, d, 9), 6.82 (H-3", d, 9); (CDjOD) (C-l), 141.1 (C-3), 104.6 (C-4), 39.4 (C-5), 80.5 (C-6), 47.9 (C-7), 79.1 (C-8), 51.7 (C-9), 26.1 (C-10), 99.4 (C-V), 74.8 (C-2'), 78.0 (C-3'), 71.7 (C-4'), 78.2 (C-5'), 62.9 (C-6'), 168.0 (C=0), 122.5 (C-l"), 132.8 (C-A 116.1 (C-3"), 163-5 (C-4").…”

“…serótina (Scrophulariaceae) ( 51 (C-3), 105.8(C-4), 39.6(C-5), 89.3 (C-6), 126.2(C-7), 149.9 (C-8), 47.1 (C-9), 59.8 (C-10), 97.1 (C-V), 74.7 (C-2'), 74.4 (C-3'), 70.2 (C-4')*, 77.2 (C-5')b, 61.4(C-6'), 168.2 (0=0, 129.9 (C-l"), 130.4 (C-2"), 129.4 (C-3"), 134.7 (C-4"), 102.4 (C-l"), 73.9 (C-2"), 76. (MeOH) (90MHz D20) 5.23 (H-l, d, 5.0), 6.32(H-3, dd, 6.0, 1.5), 5.18 5.22 (H-l, d, 5), 6.38 (H-3, dd, 6, 1.5), 5.17 (H-4, dd, 6, 3.7), 3.2-2.9(H-5), 4.60 (H-6, bs), 5.98 (H-7, bs), 3-2-2.9(H-9), 4.38 (H-10, bs);(D20)94.7(C-l), 139.0(C-3), 103.9(C-4), (MeOH) (90 MHz D20) 5.36(H-1, d, 4.5), 6.34 (H-3, dd, 6.3, 1.7), 5.17 (H-4, dd, 3), 4.58 (H-6, bs), 5.97 (H-7, bs), 4.36 (H-10, bs), 4.76 (H-V, d), 5.20 (H-l", bs);(D20) 96.0 (C-l), 140.5 (C-3), 106.2 (C-4), 40.6 (C-5), 88.0 (C-6), 128.1 (C-7), 148.8 (C-8), 47.1 (C-9), 60.3 (C-10), 99.2 (C-V), 73.6 (C-2'), 77.0 (C-3')1, 70.4 (C-4'), 76.6 (C-5')1, 61.6 (C-6'), 98.7 (C-1"), 68.2 (C-2"), 79.9 (C-3"), 69.9 (C-4"), 71.6 (C-5"), 61.9 (C-6"), 105.2 (C-l"), 74.0 (C-2"), 76.4 (C-3"), 69.9 (C-4"), 65.9 (C-5"). Verbascum sinuatum (Scrophulariaceae) (55) 68.…”

Phytochemical Investigations on Penstemon hirsutus

“…This substance has been isolated for the first time from a species of the genus Penstemon. Acyclic monoterpene moieties linked to iridoids were found in Tecoma chrysantha]&q\i., Bignoniaceae (27) (amareloside), Penstemon nemorosus Trautv., Scrophulariaceae (1) (nemoroside, nemorososide), and linked to secoiridoids in Menyanthes trifoliata L., Menyanthaceae (28,29) (foliamenthin, dihydrofoliamenthin, menthiafolin). Compound 6 (l^-D-glucopyranosyl-8-hydroxy-2,6-dimethyl-2-octaenoate) (26) from Sambucas ebulus L., Caprifoliaceae (Sambucaceae), represents a monoterpene glucoside similar to 4.…”

“…The compounds 4 and 5 are acyclic monoterpene derivatives of interesting structure with a view to the biosynthesis of iridoid glycosides. There are only a few reports of glycosides consisting of an acyclic monoterpene moiety occurring in species which are known to contain iridoids (24)(25)(26) or of acyclic monoterpene units linked to iridoids (1, 27) or secoiridoids (28,29). The isolation procedure and the structure elucidation of all five compounds are presented in this paper.…”

Identification of iridoid and sesquiterpenes from Buddleia parviflora by NMR spectra

“…The spectral data (IR, 1 H NMR and 13 C NMR) for methyl catalpol (1) [3][4][5], catalpol (2) [6], 7-deoxy-8-epiloganic acid (3) [7][8][9][10], aucubin (4) [2,11], dehydrobuddledin A (5) [12], and buddledin C or 3(15),6-caryophylladien-8-one (6) [13] are in agreement with literature values.…”