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Five new prenylated p-hydroxybenzoic acid derivatives with antimicrobial and molluscicidal activity from Piper aduncum leaves.
Planta Med. 1993 Dec; 59(6):546-51.PM

Abstract

Five new prenylated benzoic acid derivatives, methyl 3-(3,7-dimethyl-2,6-octadienyl)-4-methoxybenzoate (1), 1-(1-methylethyl)-4-methyl-3-cyclohexenyl 3,5-bis(3-methyl-2-butenyl)-4-hydroxybenzoate (2), 1-(1-methylethyl)-4-methyl-3-cyclohexenyl 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoate (3), methyl 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoate (4), and 4-hydroxy-3-(3-methyl-2-butenyl)-5-(3-methyl-2-butenyl)-benzoic acid (5) were isolated from the dried leaves of Piper aduncum L. (Piperaceae). Together with the new metabolites, four known prenylated benzoic acid derivatives, 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoic acid (6), 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoic acid (nervogenic acid, 7), methyl 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoate (8), and methyl 4-hydroxy-3-(3-methyl-2-butenyl)-benzoate (9) as well as, dillapiol (10), myristicin, and the three sesquiterpenes humulene, caryophyllene epoxide, and humulene epoxide were isolated. Compounds 7, 8, and 9 are reported as natural products for the first time. The structures of the isolates were elucidated by spectroscopic methods, mainly 1D-and 2D-NMR spectroscopy. Isolates 4-7, 9, and 10 were molluscicidal while 2, 5-7, and 9 displayed significant antibacterial activities.

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Authors+Show Affiliations

Orjala J
Department of Pharmacy, Swiss Federal Institute of Technology (ETH), Zurich.
Erdelmeier CA
No affiliation info available
Wright AD
No affiliation info available
Rali T
No affiliation info available
Sticher O
No affiliation info available

MeSH

Anti-Infective AgentsHydroxybenzoatesMagnetic Resonance SpectroscopyMolluscacidesPlants, MedicinalProtein Prenylation

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

8302955

Citation

Orjala, J, et al. "Five New Prenylated P-hydroxybenzoic Acid Derivatives With Antimicrobial and Molluscicidal Activity From Piper Aduncum Leaves." Planta Medica, vol. 59, no. 6, 1993, pp. 546-51.
Orjala J, Erdelmeier CA, Wright AD, et al. Five new prenylated p-hydroxybenzoic acid derivatives with antimicrobial and molluscicidal activity from Piper aduncum leaves. Planta Med. 1993;59(6):546-51.
Orjala, J., Erdelmeier, C. A., Wright, A. D., Rali, T., & Sticher, O. (1993). Five new prenylated p-hydroxybenzoic acid derivatives with antimicrobial and molluscicidal activity from Piper aduncum leaves. Planta Medica, 59(6), 546-51.
Orjala J, et al. Five New Prenylated P-hydroxybenzoic Acid Derivatives With Antimicrobial and Molluscicidal Activity From Piper Aduncum Leaves. Planta Med. 1993;59(6):546-51. PubMed PMID: 8302955.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Five new prenylated p-hydroxybenzoic acid derivatives with antimicrobial and molluscicidal activity from Piper aduncum leaves. AU - Orjala,J, AU - Erdelmeier,C A, AU - Wright,A D, AU - Rali,T, AU - Sticher,O, PY - 1993/12/1/pubmed PY - 1993/12/1/medline PY - 1993/12/1/entrez SP - 546 EP - 51 JF - Planta medica JO - Planta Med VL - 59 IS - 6 N2 - Five new prenylated benzoic acid derivatives, methyl 3-(3,7-dimethyl-2,6-octadienyl)-4-methoxybenzoate (1), 1-(1-methylethyl)-4-methyl-3-cyclohexenyl 3,5-bis(3-methyl-2-butenyl)-4-hydroxybenzoate (2), 1-(1-methylethyl)-4-methyl-3-cyclohexenyl 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoate (3), methyl 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoate (4), and 4-hydroxy-3-(3-methyl-2-butenyl)-5-(3-methyl-2-butenyl)-benzoic acid (5) were isolated from the dried leaves of Piper aduncum L. (Piperaceae). Together with the new metabolites, four known prenylated benzoic acid derivatives, 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoic acid (6), 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoic acid (nervogenic acid, 7), methyl 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoate (8), and methyl 4-hydroxy-3-(3-methyl-2-butenyl)-benzoate (9) as well as, dillapiol (10), myristicin, and the three sesquiterpenes humulene, caryophyllene epoxide, and humulene epoxide were isolated. Compounds 7, 8, and 9 are reported as natural products for the first time. The structures of the isolates were elucidated by spectroscopic methods, mainly 1D-and 2D-NMR spectroscopy. Isolates 4-7, 9, and 10 were molluscicidal while 2, 5-7, and 9 displayed significant antibacterial activities. SN - 0032-0943 UR - https://www.unboundmedicine.com/medline/citation/8302955/Five_new_prenylated_p_hydroxybenzoic_acid_derivatives_with_antimicrobial_and_molluscicidal_activity_from_Piper_aduncum_leaves_ L2 - http://www.thieme-connect.com/DOI/DOI?10.1055/s-2006-959758 DB - PRIME DP - Unbound Medicine ER -