Cassytha alkaloids. II. Alkaloids of Cassytha pubescens R. Br

Abstract

Three aporphine alkaloids isolated from Cassytha pubescens R.Br. have been identified as nantenine, domesticine, and isoboldine, all of which were previously known to occur in Nandino domestics, and a fourth as laurelliptine, an alkaloid of Beilschnziedia elliptica. One other aporphine alkaloid from C. pubescens is new, namely (+)-l-hydroxy-2-methoxy-9,1O.methylenedioxynoraporphine (nordomesticine).A sixth and minor alkaloid from C. pubescens, identified as sinoacutine, the (-)-enantiomer of salutaridine, appears to be the first example of a morphine group alkaloid to be found in the family Lauraceae.Cassytha pubescens R.Br., known as "downy dodder laurel", is a trailing parmitic vine belonging to the family Lauraceae. It occurs widely in southeastern Australia, and an examination has been made of samples collected in South Australia and near Melbourne in Victoria. Earlier investigations of the related species Cassytha jiliformmi L. led to the characterization of two new aporphine alkaloids, ($)-9-hydroxy-3,10-dimethoxy-1,2-methylenedio~poraporphine~~ and (+)-3-methoxy-1,2,9,10-bismethylenedio~ynoraporphine,~ which belong to a small group of aporphines having a C3 oxygen substituent. The name cassythinel suggested for the former base in our earlier paper should be dropped in favour of ~assyfiline,~ since Professor Tomita's publication on this Cassytha Jiliformis base was received for publication before ours. Although several aporphine alkaloids have been isolated from C. pubescens none has a C3 substituent. Sinoacutine ( I )Particular interest is attached to a minor base, C,,H21N0,, which is not an aporphine and has been identified as the (-)-enantiomer (I) of salutaridine, a dienone alkaloid of the morphine group found naturally in Croton salutaris3 and also obtained by synthesis.3 Direct comparison of the infrared spectra of the Cassytha base and its 0-acetate with spectra of an authentic sample of salutaridine and its 0-acetate * P a r t I, Aust. J . Chem., 1966, 19, 297.

Multispecies interactions among a plant parasite, a pollinator and a seed predator affect the reproductive output of an invasive plant, Cytisus scoparius

“…The production of plant toxins as a response to the parasite or produced by the parasite itself could also explain differences in B. villosus damage between infected and uninfected plants. Cassytha pubescens produces alkaloids (Johns et al . 1966) that may be transferred to the host, as has been found for other secondary metabolites (Sareedenchai & Zidorn 2008).…”

Lauraceae alkaloids

“…3), (+)-N-acetyl-nornantenine ( 27), (+)-cassythidine (28) and didehydroocotein (29) 28 were isolated. From the stem, the alkaloids (S)-3-methoxynordomesticine (30), (S)-N-ethoxycarbonyl-3-methoxynordomesticine (31), (S)-N-formyl-3-methoxynordomesticine (32) and (S)-N-methoxycarbonyl-3-methoxynordomesticine (33) were also detected and identied. The alkaloid (S)-3-methoxynordomesticine (30) showed moderate antifungal activity against Fusarium oxysporum f. sp.…”

Assignments of the1H and13C NMR spectra of 1,4‐diazaphenanthrene (benzo[f]quinoxaline) derivatives

“…A 3J (peri) is found in quinoline. 12 Heteronuclear selective population transfer (SPT) spectra13-16 allowed the identification of ' J ( CH) and long-range CH couplings. As expected, 25 (ortho) is only observed for C-2 and C-3 in the present series except, in addition, for C-9 in 9-chloro-DAP.…”