Anti-inflammatory Lanostanoids and Lactone Derivatives from Antrodia camphorata

Abstract

Four new lanostanoids, ethyl lucidenate A (1), ethyl lucidenate F (2), 15-O-acetylganolucidate A (3), and 3,11,15,23-tetraoxo-27ξ-lanosta-8,16-dien-26-oic acid (4), and two new lactone derivatives, 5-hydroxy-5-(methoxymethyl)-4-methylfuran-2(5H)-one (5) and 3-(4-methoxy-2-oxo-2H-pyran-6-yl)propanoic acid (6), together with four known compounds, 11α-hydroxy-3,7-dioxolanost-8,24(E)-dien-26- oic acid (7), 3,7,11-trioxo-5α-lanosta-8,24(E)-dien-26-oic acid (8), methyl 3,7,11,12,15,23-hexaoxo-5α-lanost-8-en-26-oate (9), and ethyl 3,7,11,12,15,23-hexaoxo-5α-lanost-8-en-26-oate (10), were characterized from Antrodia camphorata. The structures of these new compounds were determined by analysis of their spectroscopic data, including 1D and 2D NMR experiments. Ten components were evaluated for anti-inflammatory activity by examining their effect on LPS-iNOS-dependent NO production in murine macrophage (RAW 264.7) cells. Among them, compounds 1, 3, 7, 8, 9, and 10 significantly suppressed the NO concentration in LPS-treated RAW 264.7 cells with IC50 values ≤ 10 μM.

Triterpenes as Potentially Cytotoxic Compounds

“…Taking into consideration the structure, triterpenes may be divided into linear ones—mainly derivatives of squalene, tetracyclic and pentacyclic, containing respectively four and five cycles, as well as two- and tricyclic ones [10]. Representatives of those show anti-cancer properties [11,12] as well as anti-inflammatory [13], anti-oxidative [14], anti-viral [15,16], anti-bacterial [17] and anti-fungal ones [18]. A good example could be the betulinic acid and its derivatives which have been investigated for their strong cytotoxic properties [19,20].…”

Synthesis of Chiral Cyclopentenones

“…Selection of synthetic bioactive and natural molecules containing a chiral cyclopentenone functionality, such as prostaglandins and prostanoid derivatives, pentenomycins, lathyranoic acid A, , untenone A, , sesquiterpene from Acorus calamus rhizomes, daphmacromines, kjellmanianone, litseaverticillols, terpestacin, , przewalskin B, azadiradione, minwanenone, jiadifenin, , rupestonic acid, (+)-achalensolide, guaiane, parthenin, didemnenones, , lanostanoid from Antrodia camphorate, hookerolides A–D, 4α-phorbol-12,13-didecanoate, lobocrasol, gochnatiolides A–C, ainsliadimer-B, 4α-4-deoxyphorbol, and guaiane glycosides …”

Antcamphins A–L, Ergostanoids from Antrodia camphorata

“…The fruiting body of A. camphorata has long been used in Taiwan folk medicine for the treatment of food, alcohol, and drug intoxication, diarrhea, abdominal pain, hypertension, skin inflammation, and liver cancer . Previous studies on the chemical constituents of A. camphorata revealed it was rich in ergostane and lanostane triterpenoids, which showed anti-inflammatory, immunomodulatory, hepatoprotective, and antitumor activities. , …”