Sesquiterpenoid Tropolone Glycosides from Liriosma ovata

Abstract

Two new sesquiterpenoid tropolone glycosides, liriosmasides A (1) and B (2), along with two known compounds, secoxyloganin and oplopanpheside C, were isolated from a methanol extract of the roots of Liriosma ovata. The structures of 1 and 2 were elucidated by spectroscopic methods including 1D and 2D NMR and by high-resolution mass spectrometry involving an ultra-high-performance liquid chromatography-quadrupole-orbital ion trap mass spectrometric (UHPLC-Q-Orbitrap MS) method. Compound 1 showed weak inhibitory activity against HIV RNase H.

Isolation, Biosynthesis and Chemical Modifications of Rubterolones A–F: Rare Tropolone Alkaloids from Actinomadura sp. 5‐2

“…The newly isolated rubterolones belong to the rare class of tropolone‐containing natural products, which have only recently received scientific attention . The first bacterial‐derived tropolone alkaloid, rubrolone A ( 7 ) was reported in 1978 from Streptomyces enchinoruber , but it took nearly 40 years until rubrolones B–D were identified and a putative biosynthetic pathway proposed .…”

Troponoid Compounds as Therapeutic Agents and as Targets and Templates for Chemical Synthesis

“…which exerts modest inhibitory activity against HIV RNase H, is an example of such a system and is one that presents particular synthetic challenges (see end of Section 7). 18 Natural products incorporating the -tropolone (26) and -tropolone (27) motifs (Figure 5) are also known. For example, the bis-phenylated strepantibin C (28) was isolated from a mud dauber wasp-associated Streptomyces sp.…”

Eglerisine, a Novel Sesquiterpenoid Tropolone from Dulacia egleri with Antiproliferative Effect against an Acute Myeloid Leukemia Lineage

“…Naturally occurring tropolonoids are relatively rare [11,12], but they have already been described in the genus Dulacia [4,5]. Herein, we report the structural elucidation as well as the antiproliferative effect in a human acute myeloid leukemia cell line of a novel sesquiterpenoid tropolone derivative named eglerisine (1) isolated from the stems of D. egleri.…”

“…The genus Dulacia is taxonomically closely related to the genus Liriosma [1, 2], and Liriosma ovata (syn. Dulacia inopiflora), popularly known as "muirapuama" or "potency wood", and has been used for the treatment of impotence, neuromuscular problems, disorders of the nervous system, rheumatism, cardiac and gastrointestinal asthenia, and for the prevention of baldness [3,4]. There are few reports on the genus Dulacia.…”

“…There are few reports on the genus Dulacia. Previous chemical studies described the isolation of secondary metabolites belonging to different classes, such as sesquiterpenoids, alkaloids, and isoprenoid glycosides from Dulacia guianensis and D. inopiflora [3][4][5][6][7]. The species Dulacia egleri (Rangel) Sleumer, popularly known as "ratʼs wood", is endemic to Brazil and is distributed in the regions North and Midwest.…”