Highly Hydroxylated Triterpenes from Salvia kronenburgii

Abstract

The three new triterpenes (1-3) and five known triterpenes and a sterol were isolated from the acetone extract of a Turkish collection of Salvia kronenburgii. The structures of the new triterpenes were established as 1beta,2alpha-dihydroxy-3beta-acetoxy-11-oxours-12-ene (1), 2alpha,20beta-dihydroxy-3beta-acetoxyurs-9(11),12-diene (2), and 1beta,2alpha-dihydroxy-3beta-acetoxyurs-9(11),12-diene (3) on the basis of spectral analyses, including 1D and 2D NMR and mass spectroscopy. It is probable that compounds 2 and 3 are artifacts from dehydration of the corresponding allylic alcohols. 1beta,2alpha,3beta,11alpha-Tetrahydroxyurs-12-ene (5), the most abundant compound in the extract, was found to be highly cytotoxic to renal, non-small cell lung, and breast cancer cell lines.

Bioactive Triterpenes from the Root of Salvia miltiorrhiza Bunge

“…The first additional oxymethine (δ 3.52, dd, J = 11.2, 4.8 Hz) was then assigned as C‐7 as results of the downfield shifts of C‐6 (δ 29.1, CH 2 ) and C‐8 (δ 47.9, C), HMBC correlations of H‐5/C‐7 and H‐26/C‐7, and the spin coupling system of H‐5–H‐6–H‐7 observed in the COSY spectrum (Topcu et al ., ; Lakhal et al ., ). The second additional oxymethine (δ 3.57, dd, J = 11.6, 4.8 Hz) was assigned as C‐16 as evidenced by downfield‐shifted resonances of respective C‐15 (δ 34.0) and C‐17 (δ 40.6) and HMBC correlations of H‐16/C‐14,17,18 and H 3 ‐28/C‐16 (Tamai et al ., ; Topcu et al ., ). Thus, the planar structure of 1 is urs‐12‐ene‐2,3,7,16‐tetraol.…”

“…The first additional oxymethine (δ 3.52, dd, J = 11.2, 4.8 Hz) was then assigned as C-7 as results of the downfield shifts of C-6 (δ 29.1, CH 2 ) and C-8 (δ 47.9, C), HMBC correlations of H-5/C-7 and H-26/C-7, and the spin coupling system of H-5-H-6-H-7 observed in the COSY spectrum (Topcu et al, 2004;Lakhal et al, 2014). The second additional oxymethine (δ 3.57, dd, (Tamai et al, 1989;Topcu et al, 2004). Thus, the planar structure of 1 is urs-12-ene-2,3,7,16-tetraol.…”

Untitled

“…11α-hydroxyurs-12-en-3-one (3) [5][6][7] 11α-methoxyurs-12-ene-1β,3β -diol (4) 8 11α-methoxyurs-12-ene-1β,3β,15α-triol (5) 8 11α-methoxyurs-12-ene-1β,3β,28-triol (6) 3-oxo-11α-hydroxy-17,22-seco-urs-12-en-22,17-lactone (urmiensolide B ) (40) 4 3-oxo-1β,11α,20-trihydroxyursolic acid (41) 28 3-oxo-urs-12-en-28-oic acid , ursonic acid (42) 12,14,24,29 3-oxo-urs-12-ene (43) 6 3-oxo-urs-12-ene-lβ,11α-diol (44) 30 3-oxo-ursolic acid methyl ester (45) 31 3α-acetoxy-urs-12-ene-1β,11α-diol (46) 9,10 3α-hydroxy-13(28)-epoxy-urs-11-ene (47) 5,7 3α-hydroxy-2α-methoxyurs-12-en-28-oic acid (48) Urs-9(11),12-dien-3β-ol (71) 5,7 Urs-9(11),12-dien-3β-yl acetate , α-amiradienyl acetate (72) 17, [39][40][41] Ursol-28-oic acid methyl ester (ursolic acid methyl ester) (73) 1-3, 42, 59 Ursolic acid (74) 1-2, 5-7, 17, 12, 14, 15, 21, 22, 25-27, 31-36, 39, 40-101, 102-109, 110 Uvaol (75) 17, 24, 43-49, 63, 71, 81, 82, 94-96, 111, 112, 110 α-amyrin (76) 2, 6, 3, 17, 24, 29, 32, 52, 60, 66, 68, 69, 72-74, 90, 91, 94-98, 113-116 3α-acetyl-amyrin (77) …”

“…11-oxo-β-amyrin (89) 1-3 11α-hydroxy-β-amyrin (90) [1][2][3]23 1β,11α-dihydroxyolean-18-en-3-one (91) 28 1β,2α,3β,11α-tetrahydroxy-olean-12-ene (92) 9,10 1β,2α-dihydroxy-3β-acetoxy-olean-9(11),12-diene (93) 9,10 1β,3β-dihydroxy-olean-9(11),12-dienyl (94) Friedelin (202) [1][2][3]17 Hopanone (203) 113 Stigmast-4-en-3-one (204) [153][154][155][156] Hydrangenone (205) 157 Isoperadione (206) [153][154][155][156] Peradione (207) [153][154][155][156] Perovskone (208) [153][154][155][156] Salvadiol (209) [153][154][155][156] Salvadione-A (210) [153][154][155][156] Salvadione-B (211) [153][154][155][156] Salvadione C (212) 158 Perovskone B (213) 158 Salvatrione (214) [153]…”

Structure Elucidation of a New Rearranged Abietane Diterpene from a Biologically Active Plant, Salvia eriophora

“…Salvia species are rich sources of abietane diterpenes, and Turkish Salvia species have shown high diversity for this type of compound, some of them having rearranged structures with either open (aethiopinonelike quinonoid abietanes) or closed (microstegiollike) A rings [6]. Our group has investigated over 50 Salvia species [7,8] and isolated more than 200 abietane diterpenes, over 150 of them being new [9][10][11][12], besides a limited number of pimarane [13][14][15] and labdane diterpenes [16]. Phytochemical and pharmacological studies revealed that the diterpenoids are the principal secondary metabolites responsible for most of the biological activities of Salvia species [17].…”