Phytochemical investigations of medicinal plants from Chile and the Fiji Islands.

Persistent Link:
http://hdl.handle.net/10150/187042
Title:
Phytochemical investigations of medicinal plants from Chile and the Fiji Islands.
Author:
He, Kan.
Issue Date:
1995
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
In this dissertation, three different medicinal plants from Chile and the Fiji Islands, Baccharis linearis (R. et P.) Pers, Aristotelia chilensis (Mol.) Stuntz, and Dysoxylum lenticellare Gillespie were chemically studied. Fourteen compounds isolated from Baccharis linearis were identified based on IR, NMR and mass spectroscopic methods. These constituents included three new neo-clerodane type diterpenes, baclinal (1), baclinepoxide (2), and 13-epi-baclinepoxide (3), as well as one new perhydroazulene derivative, baclinic acid (6). The other identified compounds included portulide B (4), jewenol A (5), oleanolic acid (7), stigmasta-7, 22-dien-3 β-ol (8), stigmasta-7, 22-dien-3 β-ol β-D-glucopyranoside (9), maslinic acid (10), lachnophyllum ester (11), nepetin (12), quercetin 3-methyl ether (13) and werneria chromene (14). With the exception of oleanolic acid, lachnophyllum ester, and werneria chromene, all the other compounds are reported for this species for the first time. Oleanolic acid was isolated as the major component with a yield of 0.3% of dry plant material. Werneria chromene and lachnophyllum ester displayed anti-Mycobacterium tuberculosis activity as well as activity in the brine shrimp test (BST). Six alkaloids isolated from Aristotelia chilensis were identified as aristoteline (15), aristotelinone (16), serratoline (17), aristone (18), 2-epi-aristotelone (19), and aristotelone (20). Serratoline was previously isolated from Aristotelia serrata, a species native to New Zealand. This is the first study that reports serratoline as a natural constituent of A. chilensis from Chile. Another alkaloid, 2-epi-aristotelone, was previously obtained as a synthetic product and is reported here for the first time as naturally occurring. Aristoteline was isolated as the major compound (370 mg) with a yield of only 0.04% as based on dry biomass. Aristoteline showed a weak activity in the brine shrimp test. This work also led to the isolation and characterization of three biflavonoids from Dysoxylum lenticellare. Two biflavonoids were identified as isoginkgetin (21) and bilobetin (22), two of the active components in extracts of Ginkgo biloba, which are used to increase blood-flow and as vascular dilating agents. The third compound was elucidated as the novel natural product robustaflavone 4', 7"-dimethyl ether (23).
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Baccharis linearis -- Chile.; Aristotelia chilensis -- Chile.; Dysoxylum lenticellare -- Fiji.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Pharmaceutical Sciences; Graduate College
Degree Grantor:
University of Arizona
Committee Chair:
Timmermann, Barbara N.

Full metadata record

DC FieldValue Language
dc.language.isoenen_US
dc.titlePhytochemical investigations of medicinal plants from Chile and the Fiji Islands.en_US
dc.creatorHe, Kan.en_US
dc.contributor.authorHe, Kan.en_US
dc.date.issued1995en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.description.abstractIn this dissertation, three different medicinal plants from Chile and the Fiji Islands, Baccharis linearis (R. et P.) Pers, Aristotelia chilensis (Mol.) Stuntz, and Dysoxylum lenticellare Gillespie were chemically studied. Fourteen compounds isolated from Baccharis linearis were identified based on IR, NMR and mass spectroscopic methods. These constituents included three new neo-clerodane type diterpenes, baclinal (1), baclinepoxide (2), and 13-epi-baclinepoxide (3), as well as one new perhydroazulene derivative, baclinic acid (6). The other identified compounds included portulide B (4), jewenol A (5), oleanolic acid (7), stigmasta-7, 22-dien-3 β-ol (8), stigmasta-7, 22-dien-3 β-ol β-D-glucopyranoside (9), maslinic acid (10), lachnophyllum ester (11), nepetin (12), quercetin 3-methyl ether (13) and werneria chromene (14). With the exception of oleanolic acid, lachnophyllum ester, and werneria chromene, all the other compounds are reported for this species for the first time. Oleanolic acid was isolated as the major component with a yield of 0.3% of dry plant material. Werneria chromene and lachnophyllum ester displayed anti-Mycobacterium tuberculosis activity as well as activity in the brine shrimp test (BST). Six alkaloids isolated from Aristotelia chilensis were identified as aristoteline (15), aristotelinone (16), serratoline (17), aristone (18), 2-epi-aristotelone (19), and aristotelone (20). Serratoline was previously isolated from Aristotelia serrata, a species native to New Zealand. This is the first study that reports serratoline as a natural constituent of A. chilensis from Chile. Another alkaloid, 2-epi-aristotelone, was previously obtained as a synthetic product and is reported here for the first time as naturally occurring. Aristoteline was isolated as the major compound (370 mg) with a yield of only 0.04% as based on dry biomass. Aristoteline showed a weak activity in the brine shrimp test. This work also led to the isolation and characterization of three biflavonoids from Dysoxylum lenticellare. Two biflavonoids were identified as isoginkgetin (21) and bilobetin (22), two of the active components in extracts of Ginkgo biloba, which are used to increase blood-flow and as vascular dilating agents. The third compound was elucidated as the novel natural product robustaflavone 4', 7"-dimethyl ether (23).en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectBaccharis linearis -- Chile.en_US
dc.subjectAristotelia chilensis -- Chile.en_US
dc.subjectDysoxylum lenticellare -- Fiji.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplinePharmaceutical Sciencesen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.chairTimmermann, Barbara N.en_US
dc.contributor.committeememberHoffmann, Joseph J.en_US
dc.contributor.committeememberMartin, Arnold R.en_US
dc.contributor.committeememberGlass, Richard S.en_US
dc.contributor.committeememberGervay, Jacquelynen_US
dc.identifier.proquest9531067en_US
dc.identifier.oclc700294646en_US
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