A New Diterpene Acid From Salvia tomentosa

Abstract

A new diterpene acid, 3-/3-hydroxy-8,ll,13(14),15-abietatetraen-18-oic acid, along with dehydroabietic acid, three triterpenes, namely, ursolic, oleanolic and crateagolic acids, and the steroidal glycoside sitosteryl 3-d-glucoside, were isolated from leaves of A. tomentosa Mill. All of the compounds were characterized by chemical and spectral methods.Many diterpenoids are known from species of Salvia (Family Labiatae). For example, the diterpene carnosol was found in 5. officinalis (1, 2) and S. triloba (3). Later ferruginol was obtained from 5. officinalis (4). Both carnasol and ferruginol have the 8,11,13-abietatrien skeleton. Salvin, one of the antibacterial diterpenes from 5. officinalis, is 11,12-dihydroxy-8,11,13( 14)-abietatrien-20-oic acid (5). In addition, naphthaquinones, namely tanshinone I and II and cryptotanshinone, were isolated from S. miltiorrhizza (6, 7). Several diterpene quiñones (8,9) and diterpene alcohols (10,11) were obtained from different Salvia species.We report here the isolation and structure determination of a new diterpene acid and several known compounds including three triterpenes, a diterpene acid, and a steroidal glycoside from Salvia tomentosa collected in the Mediterranean section of Turkey. The new acid is of the abietane-type common for species of Pinus (12, 13), Agathis (14) and Picea (15) as well as Salvia (3-5).Although the flavonoids in S. tomentosa were described previously (16), this is the first report of terpenoids from this species.

Terpenoids, essential oil composition and fatty acids profile, and biological activities of Anatolian Salvia fruticosa Mill.

“…However, this chemical similarity was not observed for the constituents of S. tomentosa, 38 even though it also belongs to the same subsection.…”

“…As a result, the diterpenoids isolated from Anatolian S. fruticosa were found to be very similar to or the same as those previously obtained from S. officinalis, 37 possibly due to their morphological similarity, belonging to the same subsection of the genus Salvia. However, this chemical similarity was not observed for the constituents of S. tomentosa, 38 even though it also belongs to the same subsection.…”

Nepetaefolins A–J, Cytotoxic Chinane and Abietane Diterpenoids from Caryopteris nepetaefolia

“…The CH 2 Cl 2 phase was subjected to CC, MPLC, preparative HPLC, and preparative TLC, affording 10 new diterpenoids, nepetaefolins A−J (1−10, Figure 1), and seven known diterpenoids. The known triptobenzene L (11), 10 3β-hydroxyabieta-8,11,13-trien-18-oic acid (12), 11 angustanoic acid F (13), 12 7α-hydroxycallitrisic acid (14), 13 15,19dihydroxy-18(4→3)abeo-abieta-3,8,11,13-tetraen-18-oic acid lactone (15), 14 jiadifenoic acid K ( 16), 15 and 16-hydroxy-8,9,11,12-tetradehydro-7,8-dihydroabietic acid (17) 16 were identified by comparison of their observed and reported spectroscopic data.…”

Asymmetric Total Synthesis of Antiochic Acid

“…Antiochic acid 1 and its biosynthetically related polycyclic diterpenes represent a vast multitude in the fascinating realm of terpenoids . Furthermore, they have interesting structures and biological activities (Scheme ). , The antiochic acid 1 possessed several synthetic challenging structural features, including multisubstituted tricyclic core, two quaternary chiral centers, and the styrene type side chain. Although several racemic syntheses of abietane diterpenes have been reported, , antiochic acid 1 had not surrendered to any total synthesis yet.…”