Structural and bioactive studies of terpenes and cyclopeptides from the Genus Rubia

Abstract

Genus Rubia fell into about 70 species distributed widely around the world, a total of 36 species and 2 varieties were reported from China. The extracts and phytochemicals of Rubia plants had drawn considerable attention due to their potent bioactivities. As the two major ingredients from these plants, pentacyclic triterpenes and cyclopeptides were becoming a hot topic over the past twenty years for their remarkable anticancer, antioxidant and other effects. This paper compiled all 65 terpenes and 44 cyclopeptides with their distributions, physiological activities and melting points (or optical rotations) as reported in 85 references; besides, structure-activity relationships of these derivatives were briefly discussed. The information involved in this paper was expected to be meaningful for the further studies of the Genus Rubia.

Natural cyclopeptide RA-V inhibits the NF-κB signaling pathway by targeting TAK1

“…The roots and rhizomes of the Rubia plants, including Rubia cordifolia , were recorded as a traditional Chinese medicine in Chinese Pharmacopeia and have been widely used for the treatment of menoxenia, rheumatism, contusions, and tuberculosis. Rubiaceae-type cyclopeptides (RAs), quinones, and triterpenes have been isolated from the Rubia plants 3 – 6 . Among them, RA-VII, a Rubiaceae-type cyclopeptide, was reported to have undergone phase I clinical trials at the NCI as an anticancer drug in Japan in 1990s 3 .…”

“…Among them, RA-VII, a Rubiaceae-type cyclopeptide, was reported to have undergone phase I clinical trials at the NCI as an anticancer drug in Japan in 1990s 3 . To date, 56 RAs have been isolated from higher plants 6 – 10 , and these compounds have attracted considerable attention over the past three decades because of their unique bicyclic structures and amazing antitumour activities in vitro and in vivo, particularly RA-VII and RA-V (Fig. 1a ).…”

Synthesis and biological evaluation of T-OA analogues as the cytotoxic agents

“…3-Carbonylolean-12-en-28-oic acid-(3,5,6-trimethylpyrazin-2-yl)methyl amine (8) 1,806.68, 1,636.08, 1,457.64, 1,399.09, 1,088.14, 1,047.84, 1,020 1,650.04, 1,521.92, 1,453.66, 1,414.60, 1,387.74, 1,364.02, 1,328.34, 1,206.29, 1,178.78, 1,129 …”

“…In the present study, a series of novel T-OA analogues were designed and synthesized via amino condensation reaction, inspired by the potent bioactivities of ligustrazine amide derivatives and potent advantages of pentacyclic triterpenes on antitumor effects [6][7][8][9]; refer to the structural features of T-OA, OA, glycyrrhetinic acid (GA), ursolic acid (UA), betulinic acid (BA), and TMP served as starting materials. Firstly, pentacyclic triterpenes evolved into 3-keto or/and 3-acetyl derivatives; then, a mixture of these derivatives and TMP-NH 2 (3, 5, 6-trimethylpyrazine-2-methanamine) could provide a series of novel T-OA analogues under special conditions.…”

The Contractive Effect of Rubia tinctorum L. Extract on the Isolated Aorta Smooth Muscle and Its Protective Effect Against the Damage Caused by Hyperglycemic Solution in Rat

“…The anthraquinones of Rubiaceae have biological activities such as antimicrobial, hypotensive, analgesic, antimalarial, antioxidant, antileukemic, and mutagenic effects (2). Studies in Rubia plants have led to the separation of biological components, including 148 anthraquinones and naphthoquinones, 65 terpenes, and 44 cyclopeptides, some of them have strong anticancer and antioxidant activities (3). On the other hand, some compounds of madder such as lucidin have shown mutagenic effects in bacterial and mammalian systems (5).…”