€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF NATURAL PRODUCTS***** Lin LZ Cordell GA Ni CZ Clardy J New humantenine-type alkaloids from Gelsemium elegans. In: J Nat Prod (1989 May-Jun) 52(3):588-94 ISSN: 0163-3864 The alkaloid extract of the whole plant of Gelsemium elegans has afforded four new alkaloids: N-desmethoxyrankinidine [1], 11- hydroxrankinidine [3], 11-hydroxyhuman-humantenine [4] and humantenirine [6]. The structures of 5 was established through X-ray crystallographic analysis, and the structures of the other three new alkaloids were deduced by spectral analysis (1H, 13C, APT, 2D-COSY and 2D-HETCOR). €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Schun Y Cordell GA Cytotoxic steroids of Gelsemium sempervirens. In: J Nat Prod (1987 Mar-Apr) 50(2):195-8 ISSN: 0163-3864 A new pregnane derivative, 12 beta-hydroxy-5 alpha-pregn-16-ene-3,20- dione, along with the known derivative 12 beta-hydroxy-pregna-4,16- diene-3,20-dione have been isolated from a MeOH extract of the stem of Gelsemium sempervirens and found to be the principal cytotoxic entities. The 13C-nmr spectra of both compounds were assigned by comparison with other pregnane analogs thereby allowing confirmation of the stereochemistry at C-5 in compound. Heteronuclear 2D correlation and selective INEPT experiments indicated the need to revise a number of 13C-nmr assignments of pregn-4,16-dien-3,20-dione. Nine indole alkaloids, gelsemine, gelsevirine, 21-oxogelsemine, gelsedine, 14 beta-hydroxygelsedine, gelsenicine, humantenidine, humantenirine, and koumidine were found to be inactive in the KB and P-388 cytotoxicity test systems. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Schun Y Cordell GA Rankinidine, a new indole alkaloid from Gelsemium rankinii. In: J Nat Prod (1986 Sep-Oct) 49(5):806-8 ISSN: 0163-3864 A new oxindole alkaloid, rankinidine (1), has been isolated from the MeOH extract of the stem of Gelsemium rankinii. Its structure was elucidated by comparison with an analog, humantenirine (3), which also occurred in this plant. Registry Numbers: 106466-66-4 (rankinidine) 82375-29-9 (humantenine) 82375-30-2 (humantenirine) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Schun Y Cordell GA 14 beta-Hydroxygelsedine, a new oxindole alkaloid from Gelsemium sempervirens. In: J Nat Prod (1985 Sep-Oct) 48(5):788-91 ISSN: 0163-3864 An extract of the stem of Gelsemium sempervirens has afforded a new oxindole alkaloid, 14 beta-hydroxygelsedine, whose structure and stereochemistry were deduced by spectral methods, principally high resolution 1H nmr, 2-D COSY, and decoupling experiments. Registry Numbers: 96681-54-8 (14-hydroxygelsedine) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****YAKUGAKU ZASSHI. JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN***** Sakai S [Chemical studies of indole alkaloids] In: Yakugaku Zasshi (1995 May) 115(5):351-69 ISSN: 0031-6903 (Published in Japanese) Up to now, more than two thousands indole alkaloids having structural variety have been found from the three families of Gentianales: Loganiaceae, Apocynaceae, and Rubiaceae plants. These compounds generally possess characteristic biological activities and many of them are utilized for the medicinal purpose and for the lead- compounds to develop new synthetic drugs. The author of this review has been investigated the alkaloidal constituents of the above mentioned plants native to Japan and overseas countries. Especially, a cooperative work with Thai researchers concerning the plants in Thailand was developed. On the basis of biogenetic consideration of the structures of monoterpenoid indole alkaloids, chemical bond cleavage between the C3-N4 linkage in the C/D ring of indole alkaloids was discovered. It was speculated that, either in biogenesis, the flexibility of the ring-opening compounds having ten membered ring enabled the construction of indole alkaloids having highly strained polycyclic structures. Along with this conception, the syntheses of structurally complex indole alkaloids utilizing a biomimetic procedure have been investigated. In this review, recent results on the chemical synthesis of many skeletally varied Gelsemium alkaloids (Loganiaceae plant) are mainly described. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****YAO HSUEH HSUEH PAO [ACTA PHARMACEUTICA SINICA]***** Luo SR Li T Yang JS [Determination of gelsemium alkaloids by RP-HPLC] In: Yao Hsueh Hsueh Pao (1993) 28(9):695-8 ISSN: 0513-4870 (Published in Chinese) Gelsemium elegans Benth is a kind of traditional Chinese medicine, eight alkaloids have been isolated from this herb. In recent years, an HPLC method for the separation and determination of five of these alkaloids, ie. gelsemium A (G), koumine (F), kumantenidine (D), kumantenine (B) and kumantenmine (A) is described, dichroine being used as the internal standard. In this report a RP column of C18 and the mobile phase methanol--water--n-butylamine (78:22:0.1 V/V) were employed. The flow rate was 1.0 ml/min, the column temperature was 25 degrees C and the detection wavelength was 256 nm. The calibration curves showed good linearity over the range of 0.02-0.12 microgram, r = 0.9835-0.9977 and the recoveries were 95.01-99.70% for the five alkaloids. The method is simple, sensitive and reproducible and can be used for the quality control of Gelsemium preparations for clinical evaluation. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€