Ficus septica

Aida, M., Hano, Y., and Nomura, T., Constituents of the Moraceae plants. 26. Eicusins A and B, two new cyclic-monoterpene-substituted isoflavones from Ficus septica Barm. E., Heterocycles, 41, 2761, 1995. 

Tylophora asthmatica, Cynanchum vincetoxkum, Pergularia pallida, Vincetoxicum officinale (Asclepiadaceae), Ficus septica (Moraceae)... 

Tylophora crebriflora S. T. Blake (T. floribunda Benth.) occurs in North Queensland. Extraction of the plant material with hot methanol afforded the crude mixture of alkaloids which was purified by chromatography on cellulose powder using propanol-2 N acetic acid as the eluent. Further purification by repeated chromatography yielded tylophorine (Bf 0.5 in butan-l-ol-acetic acid 97 3) and tylocrebrine (R 0.2 in the same solvent system) (mp 218°-220° [a] D — 45° + 2° (c 0.1, CHCI3). (+ )-Tylocrebrine isolated from Ficus septica Forst. f. was found (4) to have mp 220°-222° and [a] f + 20.5° + 2° (c 0.8, CHCI3). 

The joint occurrence of tylophorine and tylocrebrine with the seco-phenanthroindolizidine alkaloid septicine (XXI) in Ficus septica (4) lends support to the biogenetic scheme outlined above. It is also of interest that septicine is transformed to a mixture of tylophorine and tylocrebrine on UV-irradiation. It is quite possible that the amorphous base (mp 125°-130°), of Chopra et al. 10) is in fact septicine. 

The structure of (+)-ficuseptine-A (15), Fig, (5), a new phenanthroindolizidine N-oxide isolated from leaf extracts of Ficus septica, was elucidated by means of comprehensive spectroscopic methods [3]. The relative stereochemistry was deduced from NOE correlations, while the (13aS) absolute configuration was inferred from a positive optical rotation at the sodium D line and a positive Cotton effect at 265 nm, a well-established correlation in this alkaloid series. Seven known alkaloids were also isolated in this investigation, including (+)-... 

The structure proposed for septicine (20), the dehydroindolizidine constituent of Ficus septica, has recently been confirmed by two independent syntheses. The first synthesis proceeded from veratraldehyde, which was condensed with homoveratric acid to give the unsaturated acid (21) this was then converted into the primary chloride (22) by standard methods. Alkylation of L-prolinol with this chloride gave the amino-alcohol (23), which was converted into its O-methanesulphonate ester. Reaction of this ester with sodium hydride in anhydrous... 

In addition to benzylisoquinolines, the family Lauraceae furnishes phenanthro-quinolizidine alkaloids such as the previously mentioned cryptopleurine (31) [77], a highly cytotoxic and vesicant substance first isolated from Cryptocarya pleurosperma [78]. These alkaloids are closely related structurally to the phenanthroindolizidines, a group of bases found in the families Asclepidaceae and Moraceae that are likewise vesicant. An example is tylocrebrine (56), which is elaborated by a Queensland plant from each family, Tylophora crebriflora [79] and Ficus septica [80], respectively. In the latter it occurs along with the seco analogue septicine (57), its presumed biosynthetic precursor. Apart from phenanthroindolizidines, certain Ficus spp. produce some simple pyrrolidine bases such as ficine (58) that are noteworthy because of their flavonoid substituents [81],... 

Ficus septica Forst. f. ( ) had been shown to elaborate i-tylophorine and d-tylocrebrine as well as a third alkaloid, septicine, C24H29O4N (mp 136°), which was regarded as 6,7-bis(3,4-dimethoxyphenyl)-6,7-dihydroindolizidine (93). More recently F. pantoniana has yielded a new type of alkaloid, ficine, C20H19O4N (mp 235°), and isoficine (mp 167°). Most of the evidence for the structure of these alkaloids (XXXVIII and XXXIX, respectively) was obtained by spectral studies. However, an equilibrium mixture of the two results when ficine is heated with 70% hydrochloric acid. Furthermore, alkali treatment or pyrolysis in vacuo of ficine generate chrysin (XL) (94). This is the first reported example of an alkaloid containing a flavonoid nucleus. 

Oku, H., Inafuku, M., Ishikawa, T., Takamine, T. et al. (2015) Molecular cloning and biochemical characterization of isoprene synthases from the tropical trees Ficus virgata. Ficus septica, and Casuarina equisetifolia. J. Plant Res., 128, 849-861. 

Jistulosa Reinw. ex Blume collected in Singapore, and from the leaves of a Japanese specimen of Ficus septica. 

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