Structure of kerlinic acid from Salviakeerlii. Chemical correlation with melisodoric acid

Abstract

The structure of kerlinic acid, a neo-clerodane diterpenoid isolated from Salviakeerlii (Labiatae), was deduced from spectral data and chemical correlation with melisodoric acid.

Clerodane Diterpenes from the Marine Sponge Raspailia bouryesnaultae Collected in South Brazil

“…One quaternary methyl group at δ H 0.87/δ C 21.3, one tertiary methyl group at δ H 0.91/δ C 15.6, and another methyl group at δ H 1.88/δ C 15.6 were located, as in raspailol, at C-9, C-8, and C-4, and corresponded to C-20, C-17, and C-18. Comparison of spectroscopic data of compound 3 with those of previously reported clerodane diterpenes showed similar structural features to kerlinic acid, a substance isolated from the plant species Salvia keerlii [12]. Both compounds have the same molecular formula and substituents, but compound 3 is characterized by the cis ring fusion at the decalin moiety.…”

Constituents from Salvia Species and Their Biological Activities

“…Compounds 148 , 149 , and 151 – 153 , isolated from S. texana , have a keto group at C-12 and three double bonds between C-7 and C-8, C-9 and C-11, and C-13 and C-14. Among them, 149 and 151 have a keto group at C-6, and 153 has a hydroxy group at C-7. , 156 – 160 , obtained from four Salvia species, bear the same structural features: a keto group at C-12 and four double bonds between C-5 and C-6, C-7 and C-8, C-9 and C-11, and C-13 and C-14. ,,− …”

“…436 and 434 were neoclerodane diterpenes that possess an γ-hydroxy-α,β-unsaturated γ-lactone moiety . Kerlinic acid ( 424 ) was isolated from S. keerlii with a carboxy group at C-5 . Thymonin ( 425 ) and 7β-hydroxythymonin ( 428 ) were two diterpenes that were isolated from S. thymoides , and 426 was an acetyl derivative of 425 ; allylic oxidation of 425 gave the α,β-unsaturated aldehyde 427 , and 429 and 430 were acetyl derivatives of 428 …”

“…26,57,65,67,68,73,74,82,90,104−110 They have the same C ring: two keto groups at C-11 and C-14 and two double bonds between C-8 and C-9, C-12, and C-13. Recently, a new natural abietane diterpenoid 7-oxoroyleanone-12-methyl ether (183) and six known diterpenoids 7αacetoxyroyleanone-12-methyl ether, cryptojaponol (102), inuroyleanol (103), horminone (162), 7-acetylhorminone (163), and royleanone (166) were isolated from the root of S. barrelieri Ettling. Among the diterpenoids, the new diterpenoid 183 showed the highest superoxide anion scavenging activity whereas 103 showed both the highest 1,1-diphenyl-2picrylhydrazyl (DPPH) scavenging activity and inhibition of lipid peroxidation in the β-carotene−linoleic acid system.…”

“…20 Kerlinic acid (424) was isolated from S. keerlii with a carboxy group at C-5. 102 Thymonin (425) and 7β-hydroxythymonin (428) were two diterpenes that were isolated from S. thymoides, and 426 was an acetyl derivative of 425; allylic oxidation of 425 gave the α,β-unsaturated aldehyde 427, and 429 and 430 were acetyl derivatives of 428. 177 431−433 were examples from three Salvia species: S. regal, 125 S. melissodora, 178 and S. lasiantha.…”