Haplophyllum perforatum

Furoquinoline Alkaloids.—Glycohaplopine (1 R1 = H, R2 = O-glucosyl, R3 = OMe), a new alkaloid isolated from Haplophyllum perforatum, is believed to contain a /3-glycosidic link.6... 

Isolation and Spectroscopic Studies.—The Table (p. 79) records the isolation of new alkaloids and of alkaloids of established constitution obtained from new sources.2-16 The further investigation of Haplophyllum perforatum raises to nineteen the number of quinoline alkaloids found in this species. Another feature of isolation studies this year is the examination of four species of Myrtopsis. 

Choisya ternata Datura stramonium Haplophyllum perforatum... 

Non-hemiterpenoid Quinolines.—New sources of the simple quinolines 4-methoxy-l-methyl-2-quinolone and its 8-methoxy-derivative (folimine) have been reported the former was isolated from Myrtopsis sellingii9 and from Zanthoxylum cuspidatum,16 and folimine was shown to be a constituent of Haplophyllum perforatum.5 The latter species also contains foliosidine (9), previously isolated from H. foliosum. The micro-organism Pseudomonas aertiginosa has been shown to contain 2-(hept-l-enyl)-4-quinolone (12).10 The structure of the alkaloid was established by n.m.r. and mass spectroscopy and by its synthesis from aniline and the j3-keto-ester Me(CH2)4CH=CHC0CH2C02Me. 

Furoquinoline Alkaloids.—The isopentenyloxyfuroquinoline first obtained from Ptelea aptera and recently isolated from Choisya ternata and from Haplophyllum perforatum was believed to be T-isopentenyloxy-y-fagarine (7), although the alternative 8-isopentenyloxy-7-methoxy arrangement was not excluded rigorously. Structure (7) has now been confirmed by the preparation of the alkaloid from haplopine (1 R = H, R = OH, R = OMe) by reaction with l-chIoro-3-methylbut-2-ene. ... 

Yunusov and his collaborators (87) obtained the alkaloid haplamine from Haplophyllum perforatum. Spectroscopic data indicated that haplamine was a methoxyflindersine, and it was assigned structure 143 on the basis of its reaction with base, followed by methylation, to give 4,6-dimethoxy-l-methyI-2-quinolone, although evidence for the structure of this degradation product was not recorded. The constitution of the alkaloid has since been confirmed by synthesis (see Section III,G,2). 

H. perforatum (Volume IX) Helietta parvifolia Dictamnus albus D. caucasicus Helietta longifoliata Helietta parvifolia Dictamnus albus D. caucasicus Plelea trifoliata Ptelea aptera Choisya ternata H. perforatum Dictamnus caucasicus Haplophyllum perforatum H. perforatum H. perforatum... 

Hydroxy-8-methoxydictamnine (haplopine) has now been found in a number of rutaceous plants (Table I). The alkaloid glycoperine, isolated from Haplophyllum perforatum (M.B) Kar and Kir (175), was shown to be the rhamnoside of haplopine by hydrolysis to L-rhamnose and haplopine. 

Haplophyllidine and perforine are two related alkaloids of unusual structure obtained by Yunusov et al. from Haplophyllum perforatum (Volume IX, pp. 252,178, 179). 

Isolation of alkaloids from Haplophyllum perforatum by cation exchange chromatography has been reported. ... 

Many of the specific activities of plant remedies described by Avicenna have been confirmed by modem research conducted at the Institute of Chemistry of Vegetative Substances (ICVS) of the Academy of Sciences of the Republic of Uzbekistan. For example, according to Avicenna, the plant Haplophyllum perforatum has anti-inflammatory and seda-... 

Synonyms Haplophyllum flexuosa Boiss., Haplophyllum perforatum (M. Bieb.) Kar. Kir., Haplophyllum sieversii Fisch.,... 

Akhmedzhanova VI, Bessonova lA, Yunusov SYu (1974) Haplamine -a new alkaloid from Haplophyllum perforatum. Chem Nat Prod 10(1) 121-122... 

Evoxoidine I 4,8-diOMe, T-OCHiCOCHMej Euodia xanthoxyloides [42], Haplophyllum perforatum [44]... 

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