Antibacterial activity of labdane diterpenoids from Stemodia foliosa.
As part of a continuing interest in exploring the chemistry of Brazilian medicinal plants, three new labdane diterpenoids, 6alpha-acetoxymanoyl oxide (1), 6alpha-malonyloxymanoyl oxide (2), and 6alpha-malonyloxy-n-butyl ester manoyl oxide (3), together with the known betulinic acid, lupeol, sitosterol, and stigmasterol, were isolated from the aerial parts of Stemodia foliosa. The structures of 1-3 were established on the basis of interpretation of spectroscopic data, including HRESIMS, and 1D and 2D NMR techniques. All compounds were tested against a bacteria panel consisting of Staphylococcus aureus, Bacillus cereus, B. subtilis, B. anthracis, Micrococcus luteus, Mycobacterium smegmatis, and M. phlei. Compound 2 showed moderate activity against these strains, with MIC values in the range 7-20 microg/mL.
da Silva
Lourinalda Luiza Dantas
LL
Departamento de Química, Universidade Federal Rural de Pernambuco, Rua Dom Manoel de Medeiros, S/N 52171-900 Recife, PE, Brazil.
Nascimento
Márcia Silva
MS
Cavalheiro
Alberto José
AJ
Silva
Dulce Helena Siqueira
DH
Castro-Gamboa
Ian
I
Furlan
Maysa
M
Bolzani
Vanderlan da Silva
Vda S
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001408:Bacillus anthracis / Q000187:drug effects; D001409:Bacillus cereus / Q000187:drug effects; D001412:Bacillus subtilis / Q000187:drug effects; D001938:Brazil; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects; D015394:Molecular Structure; D009168:Mycobacterium phlei / Q000187:drug effects; D020102:Mycobacterium smegmatis / Q000187:drug effects; D053978:Pentacyclic Triterpenes; D010946:Plants, Medicinal / Q000737:chemistry*; D028083:Scrophulariaceae / Q000737:chemistry*; D012855:Sitosterols / Q000302:isolation & purification; D013211:Staphylococcus aureus / Q000187:drug effects; D013265:Stigmasterol / Q000302:isolation & purification; D014315:Triterpenes / Q000302:isolation & purification; D000094062:Betulinic Acid; D000094042:Lupanes
D000900:Anti-Bacterial Agents; D004224:Diterpenes; D053978:Pentacyclic Triterpenes; D012855:Sitosterols; D013265:Stigmasterol; D014315:Triterpenes; D000094062:Betulinic Acid; C531881:6alpha-acetoxymanoyl oxide; C531882:6alpha-malonyloxy-n-butyl ester manoyl oxide; C531883:6alpha-malonyloxymanoyl oxide; C025473:gamma-sitosterol; C010480:lupeol; D000094042:Lupanes