Abstract
Four new triterpenoids, 3β,12β,16β,21β,22-pentahydroxyhopane (1), 12β,16β,21β,22-tetrahydroxyhopan-3-one (2), 3-oxo-olean-12-ene-28,30-dioic acid (3), and 3β-hydroxyoleana-11,13(18)-diene-28,30-dioic acid 30-methyl ester (4); 21 new triterpenoid saponins, glinusopposides A–U (5–25); and 12 known compounds (26–37) were isolated from the whole plants of Glinus oppositifolius. The structures of the new compounds were elucidated based on the analysis of one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and mass spectrometry (MS) data. All compounds from the plants were measured for antifungal activities against Microsporum gypseum and Trichophyton rubrum. Glinusopposide B (6), glinusopposide Q (21), glinusopposide T (24), and glinusopposide U (25) showed strong inhibitory activities against M. gypseum (MIC50 7.1, 6.7, 6.8, and 11.1 μM, respectively) and T. rubrum (MIC50 14.3, 13.4, 11.9, and 13.0 μM, respectively). For those active compounds with an oleanane skeleton, glycosylation (21–26) or oxidation (3) of 3-OH was helpful in increasing the activity; replacement of the 30-methyl group (29) by a carboxymethyl group (26) enhanced the activity; the presence of 11,13(18) double bonds (20) decreased the activity.
Highlights
Dermatophytosis is one of the most common skin diseases in animals and humans, which is mainly caused by Epidermophyton, Microsporum and Trichophyton [1,2]
Compound 1 had the molecular formula C30 H52 O5 based on 13 C-nuclear magnetic resonance (NMR) data (Table 1) and the positive ion at m/z 515.3718 [M + Na]+ in the high resolution electrospray ionization mass spectroscopy (HRESIMS)
The full NMR assignments and connections were determined by 1 H-detected heteronuclear single quantum coherence (HSQC), H-detected heteronuclear multiple bond correlation (HMBC), and 1 H-1 H correlation spectroscopy (COSY) analyses
Summary
Dermatophytosis is one of the most common skin diseases in animals and humans, which is mainly caused by Epidermophyton, Microsporum and Trichophyton [1,2]. (Syn: Mollugo spergula L. and Mollugo oppositifolia L; family: Molluginaceae) is a small herb widely distributed in tropical Asia, tropical Africa, and Australia [3]. It has been used for treating skin and various infectious diseases in Bangladesh, China, India, Mali and Myanmar [4,5,6]. It is used to treat leprosy, leukoderma, heart, and skin diseases in the traditional medicine of Myanmar [5]. Molecules 2019, 24, 2206 is used to treat leprosy, leukoderma, heart, and skin diseases in the traditional medicine of Myanmar [5]. We isolated 25 new reported the anti-fungal activities of G. oppositifolius.
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