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Chemical constituents of leaves and stem bark of Plumeria obtusa.
Phytochemistry. 2004 Jul; 65(14):2077-84.P

Abstract

The continued studies on the constituents of the fresh leaves and stem bark of Plumeria obtusa Linn. have led to the isolation and characterization of four new triterpenoids, dammara-12,20(22)Z-dien-3-one (1), dammara-12,20(22)Z-dien-3beta-ol (2), olean-12-en-3beta,27-diol (3), and 27-hydroxyolean-12-en-3-one (4) and 12 known compounds, which included eight triterpenoids; dammara-3beta,20(S),25-triol (5), urs-12-en-3beta-hydroxy-27-Z-feruloyloxy-28-oic acid (6), 3beta-hydroxyolean-12-en-28-oic acid (7), 3beta,27-dihydroxylupan-29-ene (8), 3beta-hydroxylupan-29-en-28-oic acid (9), 3beta-hydroxyursan-12-en-28-oic acid (11), 3beta-hydroxy-27-p-coumaroyloxy-olea-12-en-28-oic acid (12) and urs-12-en-3-one (15); an iridoid 1alpha-plumieride (10); a cardenolide 3alpha,14beta-dihydroxy-17beta-card-20(22)-enolide (13); a fatty acid ester methyl n-octadecanoate (14) and a steroid 3beta-hydroxy-delta5-stigmastane (16). The new constituents were characterized through spectroscopic studies including 1D (1H and 31C NMR) and 2D (COSY-45, NOESY, J-resolved, HMQC and HMBC) NMR and chemical transformations. This is the first report on the isolation of dammarane triterpenoids from P. obtusa. Compounds 5 and 6 are hitherto unreported from P. obtusa. The known compounds were identified by comparison of their spectral data with those reported in the literature.

Authors+Show Affiliations

Siddiqui BS
H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, Pakistan. bina@khi.comsats.net.pk
Ilyas F
No affiliation info available
Rasheed M
No affiliation info available
Begum S
No affiliation info available

MeSH

ApocynaceaeMagnetic Resonance SpectroscopyModels, ChemicalMolecular StructurePlant LeavesPlant StemsTriterpenes

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15279975

Citation

Siddiqui, Bina S., et al. "Chemical Constituents of Leaves and Stem Bark of Plumeria Obtusa." Phytochemistry, vol. 65, no. 14, 2004, pp. 2077-84.
Siddiqui BS, Ilyas F, Rasheed M, et al. Chemical constituents of leaves and stem bark of Plumeria obtusa. Phytochemistry. 2004;65(14):2077-84.
Siddiqui, B. S., Ilyas, F., Rasheed, M., & Begum, S. (2004). Chemical constituents of leaves and stem bark of Plumeria obtusa. Phytochemistry, 65(14), 2077-84.
Siddiqui BS, et al. Chemical Constituents of Leaves and Stem Bark of Plumeria Obtusa. Phytochemistry. 2004;65(14):2077-84. PubMed PMID: 15279975.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chemical constituents of leaves and stem bark of Plumeria obtusa. AU - Siddiqui,Bina S, AU - Ilyas,Firdous, AU - Rasheed,Munawwer, AU - Begum,Sabira, PY - 2003/11/07/received PY - 2004/04/07/revised PY - 2004/7/29/pubmed PY - 2004/12/16/medline PY - 2004/7/29/entrez SP - 2077 EP - 84 JF - Phytochemistry JO - Phytochemistry VL - 65 IS - 14 N2 - The continued studies on the constituents of the fresh leaves and stem bark of Plumeria obtusa Linn. have led to the isolation and characterization of four new triterpenoids, dammara-12,20(22)Z-dien-3-one (1), dammara-12,20(22)Z-dien-3beta-ol (2), olean-12-en-3beta,27-diol (3), and 27-hydroxyolean-12-en-3-one (4) and 12 known compounds, which included eight triterpenoids; dammara-3beta,20(S),25-triol (5), urs-12-en-3beta-hydroxy-27-Z-feruloyloxy-28-oic acid (6), 3beta-hydroxyolean-12-en-28-oic acid (7), 3beta,27-dihydroxylupan-29-ene (8), 3beta-hydroxylupan-29-en-28-oic acid (9), 3beta-hydroxyursan-12-en-28-oic acid (11), 3beta-hydroxy-27-p-coumaroyloxy-olea-12-en-28-oic acid (12) and urs-12-en-3-one (15); an iridoid 1alpha-plumieride (10); a cardenolide 3alpha,14beta-dihydroxy-17beta-card-20(22)-enolide (13); a fatty acid ester methyl n-octadecanoate (14) and a steroid 3beta-hydroxy-delta5-stigmastane (16). The new constituents were characterized through spectroscopic studies including 1D (1H and 31C NMR) and 2D (COSY-45, NOESY, J-resolved, HMQC and HMBC) NMR and chemical transformations. This is the first report on the isolation of dammarane triterpenoids from P. obtusa. Compounds 5 and 6 are hitherto unreported from P. obtusa. The known compounds were identified by comparison of their spectral data with those reported in the literature. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/15279975/Chemical_constituents_of_leaves_and_stem_bark_of_Plumeria_obtusa_ DB - PRIME DP - Unbound Medicine ER -