Pentacyclic Triterpenoids from the Roots ofRhodomyrtus tomentosa

Abstract

Eight pentacyclic triterpenoids were isolated from the methanol extract of the roots of Rhodomyrtus tomentosa. By application of spectroscopic methods (especially 1D-, 2D-NMR, MS), the structures were established as 23-cis-p-coumaroyloxy-2α,3β-dihydroxyolean-12-en-28-oic acid (1), 23-trans-p-coumaroyloxy-2α,3β-dihydroxyolean-12-en-28-oic acid (2), 3β-O-trans-ferulyl-2α,23-dihydroxyolean-12-en-28-oic acid (3), 3β-O-trans-p-coumaroyl-2α,23-dihydroxyolean-12-en-28-oic acid (4), 3β-O-cis-p-coumaroyl-2α,23-dihydroxyolean-12-en-28-oic acid (5), maslinic acid (6), arjunolic acid (7), and 2α,3β-dihydroxytaraxer-20-en-28-oic acid (8). Among them, compounds 1 and 3 were new oleanane-type triterpenoids, while compounds 2, 4～6 and 8 were isolated from this plant for the first time. This is the first report on the chemical constituents from the roots of R. tomentosa.

Triterpenoid saponins and C21 steroidal glycosides from Gymnema tingens and their glucose uptake activities

“…The other isolated compounds (Fig. 1) were identified as 23- cis-p -coumaroyloxy-2α,3β-dihydroxyolean-12-en-28-oic acid ( 5 ), 39 23- trans-p -coumaroyloxy-2α,3β-dihydroxyolean-12-en-28-oic acid ( 6 ), 40 3β,23-dihydroxy-olean-12-en-28-oic acid 23-caffeate ( 7 ), 41 tomentoid A ( 8 ), 42 stephanoside B ( 10 ), 43 tinctoroside B ( 11 ), 44 by comparison of their NMR spectra with those of the known compounds.…”

Phytochemicals Constituents in Medicinal Plant Syzygium aqueum (Burm.) Alston (Myrtaceae)

“…According to the above data, Compound-1 was verified as 3-O-trans-ferulyl-2a, 23dihydroxyolean-12-en-28-oic acid (C40H56O8), and its spectra data was compared with literature data. [22]. The structure of 3-O-trans-ferulyl-2a, 23dihydroxyolean-12-en-28-oic acid is shown in Table 7.…”

Triterpenoid Glycosides from the Leaves of Lyonia ovalifolia var. hebecarpa and Their Antitumor Activities

“…在 13 C NMR (表 2)谱中显示化合物 1 有 35 个碳信号, 结合其 DEPT 和 HSQC 谱, 可以将 35 个碳信号归属为 6 个甲基(δ C 13.8, C-24; 18.2, C-26; 27.2, C-27; 29.1, C-28; 34.0, C-29; 24.2, C-30); 13 个亚甲基, 其中包含 3 个连氧 亚甲基(δ C 62.4, C-25; 65.1, C-23; 66.9, C-5'); 9 个次甲基, 其中包含 5 个连氧次甲基(δ C 69.9, C-4'; 73.1, C-2'; 74.9, C-3'; 83.7, C-3; 106.6, C-1')和 1 个 sp 2 杂化次甲基(δ C 124.1, C-12); 7 个季碳, 其中包含 6 个 sp 3 杂化季碳(δ C 32.1, C-20; 33.7, C-17; 41.4, C-8; 42.1, C-14; 43.3, C-10; 44.0, C-4)和 1 个 sp 2 杂化季碳(δ C 146.1, C-13). 化合物 1 糖部分的 13 C NMR 数据(δ C 66.9, C-5'; 69.9, C-4'; 73.1, C-2'; 74.9, C-3'; 106.6 C-1')与文献报道的 3α-[(α-L-arabinopyranosyl)-oxy]-24S-[(α-L-arabinopyranosyl)-oxy]-25hydroxy-9,10-seco-cycloartan-1(10)-en-30-oic acid 的阿拉 伯糖部分 13 C NMR 数据基本一致 [11] , 初步证实化合物 1 [19] . 化合物 1 的其它 NOESY 相关信息进一步确定了其相对构型(图 3).…”

“…除了得到阿拉伯糖外, 酸水解化合物 1 还得到苷元 1a, 通过比较 1a 和(3β)-olean-12-ene-3,23-diol [18] 的 NMR 数据相似, 并经 1 H-1 H COSY, HSQC, HMBC 和 NOESY 等 2D NMR 数据分析确定其结构为齐墩果-12-烯-3β,23,25-三醇. 齐墩果烷类三萜化合物的绝对构型均已 确定 [19] , 且没有对映-齐墩果烷类三萜化合物报道, 因 此, 从生源关系角度可以推测其绝对构型为 3S*,4R*, 5R*,8R*,9S*,10S*,14S*,17R*,18R*. 检索 Scifinder Scholar 数据库发现, 该化合物最早 于 1974 年从小果珍珠花 L. ovalifolia var.…”