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1.
Molecules ; 16(6): 4775-85, 2011 Jun 08.
Article in English | MEDLINE | ID: mdl-21654582

ABSTRACT

The essential oil of Alaska cedar heartwood is known to contain compounds which contribute to the remarkable durability of this species. While previous research has identified several compounds, a complete description of this oil has not been undertaken. In this research a profile of the oil is given in which the major components are identified by GC, isolation and spectroscopic techniques. The major components of the steam distilled essential oil were identified as nootkatin, nootkatone, valencene, nootaktene, carvacrol, methyl carvacrol, nootkatol (2), and eremophil-1(10),11-dien-13-ol (3). The last two compounds were isolated for the first time from Alaska cedar in this research. The absolute stereochemistry at C-2 of nootkatol was shown to have the (S) configuration using the Mosher ester method. Assignment of stereochemistry for valencene-13-ol (3) was established by synthesis from valencene (6). Finally, two related sesquiterpenoids were synthesized from nootkatone and valencene. These sesquiterpenoids were nootkatone-1,10-11,12-diepoxide (5) and valencene-13-aldehyde (4), respectively.


Subject(s)
Naphthalenes/chemistry , Oils, Volatile/chemistry , Sesquiterpenes/chemistry , Alaska , Naphthalenes/analysis , Naphthalenes/isolation & purification , Nuclear Magnetic Resonance, Biomolecular , Oils, Volatile/analysis , Oils, Volatile/isolation & purification , Polycyclic Sesquiterpenes , Sesquiterpenes/analysis , Sesquiterpenes/chemical synthesis , Sesquiterpenes/isolation & purification
2.
Nat Prod Commun ; 5(4): 519-22, 2010 Apr.
Article in English | MEDLINE | ID: mdl-20433063

ABSTRACT

Two new p-cymene based diphenols (1-2) were isolated from the heartwood of Calocedrus decurrans. Structures were elucidated by 1D and 2D NMR techniques and HRMS. Libocedroquinone (3) was also isolated as a natural product for the first time. A new system of nomenclature is proposed for description of such oligomeric p-cymene derivatives.


Subject(s)
Cupressaceae/chemistry , Diterpenes/isolation & purification , Phenols/isolation & purification , Diterpenes/chemistry , Mass Spectrometry , Nuclear Magnetic Resonance, Biomolecular , Phenols/chemistry , Terminology as Topic
3.
Phytochemistry ; 67(14): 1547-53, 2006 Jul.
Article in English | MEDLINE | ID: mdl-16808933

ABSTRACT

A phytochemical investigation of the aerial parts of Chrysothamnus viscidiflorus var. viscidiflorus afforded three new [chrysothol (1), 2 and 4] and seven known compounds, including five sesquiterpenes, two cinnamic acid derivatives, two ketoalcohol derivatives and one coumarin glucoside. The structures of two previously reported compounds, 1b and 1c, were revised on the basis of chemical reaction. Structures of the compounds were determined by extensive NMR studies, including DEPT, COSY, NOE, HMQC, HMBC and X-ray analysis. The unpublished X-ray data of the known compounds 6 and 7 are reported. Compounds chrysothol (1), and 8-10 showed anti-cancer activity against human breast cancer cells.


Subject(s)
Asteraceae/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Humans , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular Structure
4.
Phytochemistry ; 67(5): 424-8, 2006 Mar.
Article in English | MEDLINE | ID: mdl-16458943

ABSTRACT

Salvidorol (1), a irregular nor-abietane-type diterpene, was isolated from the aerial parts of Salvia dorrii, in addition to two epimeric abietane diterpenes (2 and 3). This is the first report of a nor-diterpene with an irregular skeleton. The structures were established by high-field NMR techniques ((1)H-(1)H COSY, DEPT, HMQC, HMBC, NOESY and HRMS) and in case of 2 was confirmed by X-ray analysis.


Subject(s)
Abietanes/chemistry , Carbon/chemistry , Salvia/chemistry , Abietanes/classification , Abietanes/isolation & purification , Crystallography, X-Ray , Humans , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular Structure , Plant Components, Aerial/chemistry , Plant Extracts/chemistry
5.
J Nat Prod ; 67(10): 1705-10, 2004 Oct.
Article in English | MEDLINE | ID: mdl-15497944

ABSTRACT

Five new polyol monoterpenes (1-5) and seven new sesquiterpene lactones (6-12), along with five previously identified compounds, were isolated from the aerial parts of Artemisia suksdorfii. The structures of the new compounds were established by high-field NMR techniques (1H, 13C, 1H-1H DEPT, COSY, HMQC, and HMBC) and in case of 6 confirmed by X-ray analysis.


Subject(s)
Artemisia/chemistry , Lactones/isolation & purification , Monoterpenes/isolation & purification , Sesquiterpenes/isolation & purification , Crystallography, X-Ray , Lactones/chemistry , Molecular Conformation , Molecular Structure , Monoterpenes/chemistry , Nuclear Magnetic Resonance, Biomolecular , Oregon , Sesquiterpenes/chemistry
6.
Phytochemistry ; 65(18): 2539-43, 2004 Sep.
Article in English | MEDLINE | ID: mdl-15451313

ABSTRACT

In a study of Pacific Northwest plants of the Asteraceae family, a nor-ent-kaurane diterpene and a known diterpene, both displaying antibacterial activities, were isolated together with scopoletin and sitosterol-3-O-beta-glucopyranoside from the aerial parts of Antennaria geyeri. Anaphalis margaritacea afforded two hydroxylactones. The structures were established by one and two dimensional NMR techniques, IR and CIMS.


Subject(s)
Asteraceae/chemistry , Diterpenes, Kaurane/chemistry , Lactones/chemistry , Diterpenes, Kaurane/isolation & purification , Hydroxylation , Lactones/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Structure
7.
Phytochemistry ; 65(7): 925-8, 2004 Apr.
Article in English | MEDLINE | ID: mdl-15081296

ABSTRACT

A purple pigment neocandenatone (vestitol[6-->9";7O-->7"]obtusaquinone) was isolated from the heartwood of campincerán (Dalbergia congestiflora), an endemic Mexican tree. The isoflavan-cinnamyl phenol quinone methide structure of this compound was elucidated by HRMS, IR, and 1H and 13C NMR spectroscopic analysis, including 2D experiments (COSY, NOESY, HMQC and HSQC).


Subject(s)
Dalbergia/chemistry , Indolequinones/chemistry , Isoflavones/chemistry , Phenols/chemistry , Pigments, Biological/chemistry , Indolequinones/isolation & purification , Isoflavones/isolation & purification , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Phenols/isolation & purification , Pigments, Biological/isolation & purification
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