It has been a long time between drinks. The main reason is that I have been busy and whenever I have any spare time I try to read up on the Zurich reformers, Huldrych Zwingli and Heinrich Bullinger. See my blog if you are interested: www.zurichconnection.blogspot.com.
One professor in Zurich wrote to me: “Du wärst problemlos in der Lage, so etwas zu schreiben”. That is, he thinks I have lots of spare time, especially for writing – it is really the reverse. 2010 was a very busy year. I also have virtually no access to the literature since I am no longer in chemistry and so it is hard to keep tabs on developments.
As far as I can see Anthony R. Carroll of Griffith University, Queensland, Australia, has not yet published his work on idiospermamine B C34H38N6 nor has J. B. Bremner (who was at Wollongong University, Australia) published his structure of the alkaloid isolated from Psychotria malayana. This alkaloid has a MW of 574 and I predict that it is C34H40N6.
However, I was able to access volume 63 of The Alkaloids: Chemistry and Biology. The following is summarized from the review of Yuen-Mun Choo and Teo-Seok Kam of the University of Malaya. Some of the material overlaps with what I have posted earlier but this review is more comprehensive:
Three calycanthine-type alkoaloids, (-)-calycanthine, (-)-isocalycanthine and meso-chimonanthine were isolated from Psychotria forsteriana from New Caledonia. This was the second time the levorotatory isomer of calycanthine was isolated after that isolated from Pausinystalia macroceras (Rubiaceae). It also represents the first isolation of meso-chimonanthine.
(-)-calycanthine and (+)-chimonanthine were also isolated from the skin of the Colombian poison dart frog, Phyllobates terribilis.
The aerial parts of Psychotria glomerulata from Panama afforded glomerulatine A ((8-8a), (8’-8’a)-tetradehydro-(-) calycanthine as the major alkaloid together with some glomerulatine B (8-8a), (8’-8a’)-tetradehydro-N’-demthyl-(-)calycanthine and (8-8a)-didehydro-(-)calycanthine.
Psychotria colorata afforded (8-8a), (8’-8’a)-tetradehydroisocalycanthine 3a (R) 3’a(R) as well as some (-)-calycanthine, isocalycanthine, (+)-chimonanthine, hodgkinsine and qudrigemine C.
(8-8a), (8’-8’a)-tetradehydroisocalycanthine 3a (R) 3’a(R) is identical to dehydrobhesine which together with bhesine ((8-8’a)-dehydroisocalycanthine) was isolated from the bark extract of the Malayan plant Bhesa paniculata.
The leaves of Argostemma yappii (Rubiaceae) from Indonesia gave (+)-isochimonanthine.
The seeds of chimonanthus praecox from Japan gave a new chimonanthine derivative, chimonanthidine (an extra NMe).
From Psychotria oleoides from New Caledonia were isolated three new tryptamine oligomers, qudrigemine C, isopsychotridine A and isopsychotridine B in addition to hodgkinsine and psychotridine.
From Calycodendron milnei from Vanuatu were isolated hodgkinsine and calycosidine.
A new tryptamine tetramer, psycholeine, was isolated from Psychotria oleoides using bioassay-guided fractionation. This is a meso-calycanthine subunit linked at C(7’) and C(7’’) to two N-methylpyrrolidinoindoline units.
A review of P. oleides and P. lyciiflora led to the isolation of new pyrrolidinoindoline alkaloids: Nb-demethly-meso-chimonanthine from P. lyciiflora and quadrigemine I, oleoidine and caledonine from P. oleides.
The review naturally mentions the isolation of idiopsermuline from the seeds of Idiospermum australiense by R.K. Duke et al from the Pharmacy Department of the University of Sydney. However, because my work has not been published there is no knowledge of my isolation of idiospermine.
A review of the Malaysian species, Psychotria rostrata, gave two new tryptamine oligomers: psychotrimine and psychopentamine.
Friday, December 31, 2010
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