Antitumor plants. 8. Lychnopholic acid, a novel trioxygenated caryophyllene derivative from Lychnophora affinis Gardn

Abstract

3), ZHC2H, 116.4 (1)°, and (assuming a symmetrical HC2H groups), C3-, 1.081 (1) A and zCiC3H, 120.5 (2)°,22 The F1C2H plane is displaced from the SC2Ci angle bisector plane by an angle of 7.2°b ringing these hydrogens closer to the S atom. The dipole moment of 3 is 1.36 (2) D.The mechanism proposed in eq 2 to account for the scrambling of 13C and deuterium labeling in 3 is consistent with the long, and presumably weakened, C2-S bond in 3.23•24 Aliene episulfide has a gas-phase lifetime varying from ~3 min (room temperature) to ~20 min (dry ice temperature) at ~0.05 Torr and may be revolatilized after condensation at -196 °C. Efforts are currently underway to define more precisely the equilibrium of eq 1 by experimental as well as theoretical methods and to synthesize cyclopropanethiones by nonpyrolytic routes.26

Antimicrobial Activity of Constituents Isolated fromLychnophora salicifolia (Asteraceae)

“…The organic layer was evaporated and the residue (8 g) was chromatographed on a silica gel 60 (Vetec) column eluted with a hexane-AcOEt gradient into several fractions, giving lupeol (1.2 g), lychnopholic acid acetate (2.3 g) and lychnopholic acid (1.3 g), respectively. The spectral data of all compounds were identical to those previously reported (Raffauf et al, 1978;Bolhmann et al, 1980).…”

“…The occurrence of caryophyllene derivatives, including lychnopholic acid (1) and acetyl lychnopholic acid (2), has been previously reported in the genus Lychnophoru (Raffauf et al, 1978;Bohlmann et al, 1980), whereas we have isolated these compounds from aerial parts of L. salicifolia. The stereochemistry of 1 and 2 shown in Fig.…”

“…Some of these plants, including L. salicifolia, L. ericoides and L. pinaster, are known popularly as 'arnica'. Phytochemical studies with this genus have demonstrated the presence of triterpenes, lactones, caryophyllene derivatives, sesquiterpene lactones and flavonoids (Raffauf et al, 1978;Bohlmann et al, 1980Bohlmann et al, , 1981Bohlmann et al, , 1983Lopes et al, 1991;Costa et al, 1992). Pharmacological reports have shown that these plants possess antinociceptive, antiinflammatory and antitumoral activities (Bastos et al, 1987;Costa et al, 1992;Saude et al, 1994).…”

Cytosporolides A−C, Antimicrobial Meroterpenoids with a Unique Peroxylactone Skeleton from Cytospora sp.

“…; − and Sch 725432, 601253, 601254, and 725434 from Chrysosporium pilosum . Some unique caryophyllenes have also been isolated from the plants, such as guajadial and psidials A−C from the leaves of Psidium guajava L , and lychnopholic acid from Lychnophora affinis Gardn . On the other hand, natural peroxylactones are very rare; only three examples have been reported to date, with two isolated from the brown seaweed Taonia atomaria and plakinidone from the caribbean sponge Plakortis angulospiculatus , respectively.…”

Caryophyllenes from a Fungal Culture of Chrysosporium pilosum

“…Caryophyllene and its related analogues have been widely isolated from plants, such as black pepper ( Piper nigrum L.), cinnamon ( Cinnamomum spp. ), oregano ( Origanum vulgare L.), clary sage oil ( Salvia sclarea L.), Lychnophora affinis Gardn., Inula spiraefolia , and Pulicaria sp. − Caryophyllenes have also been discovered from various fungal species, such as Pestalotiopsis sp., Wallemia sebi , Poronia punctata , , Naematoloma fasciculare , and Hypoxylon terricola . Due to their advantageous taste and odor, some caryophyllene analogues have been used as flavors, food additives, and fragrances and in perfumery and cosmetics. − Certain caryophyllene derivatives have been reported to display antimicrobial activity and cytotoxic activity or immunosuppressive activity .…”