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USES OF VOACA NGA SPECIES N.G.BISSET PharmacognosyResearch Laboratories, Department of Pharmacy, Chelsea College, Universityof London, Manresa Road, London SW36LX Received4-II-198 5 Dateo fPublicatio n 16-VIII-1985 INTRODUCTION None of the species of the genus has attained any widespread application and evenV. afriLa, the one with the greatest distribution range and the one to which most of the uses described apply, has rather tainted localu e..A few ofti e medicinalapplication s appear to reflect theactivxt.e so fth ealkaloid spre - luntoriEnte (cf. Phytochemistry,Sectio n 3).Th efollowin g paragraphsgiv e aSoutline ox the uses which have been reported in the literature and as annotations on specimenskep ti nth eherbari a listedo np .00 . 1. THE PLANTS 1.1. V.AFRICANA (ANGUSTIFOLIA ?,LUTESCENS, PUBERULA) West Africa: The latex is said to be a rubber adul^t^dU i^put into acariou s tooth (Dalziel, 1937).Th e plant xs reported tob euse dm treatin g scabies (Janot and Goutarel, 1955).Senegal :Th e^amnk a (or Serere^) eat the fruit; theytrea t woundswit hth elatex .Th eplan tx sals oco n^ *obea pan a cea - the leafy branches are put into baths morning and ev«J^d a ^. prepared from them is given to people affected ^r^^S^ss. tierx of the leaves isdrun k as a tonic and against fatigue due^ obr«h^n Inth eCasamanc ea decoctio n ofth eroot stake nthre etime sdad y« . ecomme ed for women to counteract the effects of premature and rapid birth it » a 19 giveninternall y for hernial pain (Kerharo and Adam, ^' ^^hoca; Theleave shav esevera luses :A decoctio ni sapplie da sa wash •aganistduur t , it is put into baths against generalized oedema; it xs, utxhzea a fnction in a drink in the treatment of leprosy; a lotion is ^^^^ (possibly in children; and the juice is placed in the nostrlis oca^.^ Zernal v0 through confusion with other Apocynaceae- *«"* ™""£ °ossibly used -—^(Bouquetand^^ l for adulterating rubber (F. R. Irvine 1584,1931 ) • ™. (F R Irvine 773, boiled with water, and the liquor isdrun k to cure gonorrnc> K • • 1927;/ . K.Odamttin 4, 1933). Nigeria:i ti ssai dtha t to specie is propJ ^ for diseases of babies (Oliver, 1968). In the southern pa^^ ^ ml) bark fibre, together with other fibres is made into ia y The ^ does s and arrows are made from the branches (A. t. ™ ™ ' ^mch 146j i90l); not coagulate and is used for adulterating good rubber^ ^ ophthalmia. S. cohc n0r it is also known as a remedy against \^ ^'o4767 1972).Congo : Thome:Here ,theplanti ssai dt obemedianal(^««toia« ^ ^ and ^ The speciesi suse di n the treatment ofsores ,boils ,absc e , > 1%9). bies.A decoc t isdrun k for heart conditions and Wenorr g ^./JQ/IO; cf. Zaire: A paste of the roots is put on the head to K ^ *Annotation s on herbarium sheets are referred to bycoHecto* )an d number (both yearo fcollection . - j]7 Agric. Univ. WageningenPapers 85-3 (1985) Staner and Boutique, 1937).Th e white and sticky latex is used to catch birds (W. Robijns1927, 1926) . The wood is utilized for construction purposes (H. Lemaire 299, 1913;Leontovitch 148, no date) and also for making targets (A. Dewulf888,1935) . Thebar ki suse d againstintestina lworm sbu ti sa dangerous remedy (A. Corbisier-Baland1177, 1931).Goo dfibre ca n be obtained from the bark (L. Verdick 46,1899 )an d cords for birds are made from it (Homble 1309, 1913).A n infusion of the twigsi sapplie d in bronchitis (deGiorgi 5, 1912)an d theirjuic e is used in treating ophthalmia and in soothing colic (de Giorgi 438 and 499, 1913).Th e leaves are employed against blenorrhagia (de Giorgi 326, 1912). Tanzania: The roots are said to be toxic (H. Koritschoner 1326,1935) . The grated roots are mixed with copra and used to get rid of scabies and for healingwounds .Th elate xi sboile dwit htha t ofFicus species to prepare abird ­ lime (Braun, 1927).A decoction of the roots is drunk against dysmenorrhoea and also asa treatmen t for heart spasms(angin a pectoris?)(Haerdi , 1964).Th e roots (without the outer bark) after drying, powdering, and sieving, are mixed withporridg ean dtake nfo r kidneytrouble san dabnormall y frequent menstrua­ tion in women and urination inme n (Hedberg etal., 1982) .A decoctio n of the stem bark is used against heart spasms (angina pectoris?) (Haerdi, 1964).Th e plant suppliespole sfo r buildingpurpose s(C. K.Ruffo 218, 1969 )bu t isconsid ­ ered to be inferior (Braun, 1927). The fruit and seeds are extracted with cold water for 7day s and the extract taken against internal sores (Hedberg et al., 1982). Angola: Latex from the fruit is used for treating rheumatism and also for feeding babies (J. TexeiraGerez 7654,1883) . Zambia: Wood is burnt to obtain the salt it contains (W. D. Holmes1010, 1952) . Mozambique: Bark is usedfo rmakin grope s(/ .Gomes Pedro 4510, 1953). 1.2. V.BRACTEATA Gabon: The bark is said to be used to become 'high' (F. J. Breteler 6673, 1970). Congo:Th e pulp of the fruit is used topically as a friction in treating rheumatism (Bouquet, 1969).Zaire :Th e latex (Staner and Boutique, 1937) or juiceo fth efruit s (S. deGiorgi 1497, 19.13)i suse dagains t rheumatism. 1.3. V.CHALOTIANA Congo:Th e species is involved in a complicated treatment for hernia (Bou­ quet, 1969). 1.4 V. FOETIDA Indonesia: The latex is applied externally against various skin diseases. On Madura the leaves warmed over a fire are laid on chonic leg sores. In South 118 Agnc. Univ. WageningenPapers 85-3 (1985) Sumatra the leaves are moistened with coconut oil and used externally against head- and stomach-ache, while thewoo d isuse d for making sheaths for knives and otherweapon s (vande n Burg, 1885;Heyne , 1950). 1.5 V.GLOBOSA Philippines: The pounded roots are reported to be used for stupefying eels (Brown, 1921).O n Biliran Island a decoction of the leaves isuse d for cleaning alipunga, akin d ofeczem a (PNH (M. D.Sulit) 21647,1954). 1.6. V.GRANDIFOLIA( PAPUANA) Indonesia: In Central Java the young leaves are mashed and ^jn the stomach against illnessfro m worms and diarrhoeaf^enberg ^u^man 13121,1984) . Papua-New Guinea:Th e plant is said to be taken as a medicine for malaria (M.Fallen et al. 344,1977). 1.7. V.HAVILANDII Sarawak:Bird sea t thefrui t (Hewitt475, 1906). 1.8. V.AFF.MEGACARPA Philippines: Chicle is obtained from ^l^W^^™* drunk forinterna lpain ,an dth eroot sar eboile dan dth eextrac tar u abdominal rigidity (von ReisAltschul , 1973). 1.9. K.SP. CentralAfrica nRepublic : Tocomba t fatigue inth e ^^^ffi giesmi xpowde r from the stem bark with alittl ewate r tomak e pla theywar mbefor e applyingt oth emuscle s(Motte , ivo^- 1.10. V.THOUARSII (OBTUSA) SierraLeone :Th elate x issai d to bever y danger°™J°^^J^ s when isuse d asa cure for toothache (Pyne 25,no•oate ^ • ^ ^ .g thought the grain is ripening the fruits are scattered on <fV , Coast: The to frighten away wild hogs (G. ProctorCooper 431, 1929). ^ ^ Agric.Univ. WageningenPapers 85-3 (1985) local inhabitants do not distinguish this plant from V. africana (q.v.) and its medicinal usesar e the same(Bouque t and Debray, 1974).Mali :Decoction s of theleave san d rootsar edrun k oruse di nbath s tocomba t fatique and weakness and for thetreatmen t ofwound san d against inflammation (Adjanohoun etal. 1980). SouthernNigeria :Th especie si s saidt ob ea prophylacti cagains t diseases of babies (Oliver, 1960).Zaire :Th e fruits (R. E. Delhaye 219, 1957) and latex (Smeyers 152, 1951)ar e used for catching birds. Uganda: The wood has been used for making tool handles {A. G. Bagshawe 82, 1904).Tanzania :Late x from thefrui t servesa sa n insecticide (G. Watkins140 (FH 2413), 1948);boile d with that from other plants it yields a bird-lime. The thickened latex is used tofix the blades of knives in their handles and for repairing baskets. Hunting nets are made from the bast and sheaths for knives from the wood. It is said that insectswil lno tattac k thesof t wood(Braun , 1927).Mozambique :A glu ei s made from the plant (H. Junod365, 1893). Southern Africa (Natal): Here also the milkyjuic efro m theplan t servesa sa bird-lim e(/ . Thode4297, 1916). 2. REFERENCES ADJANOHOUN, E. J., L. AKE ASSI, J. J. FLORET, S. GUINKO, M. KOUMARE, A. M. R. AHYI, and J. RAYNAL, Medicine traditionnelle etpharmacopee. Contribution aux etudes ethnobotaniques et floristiques au Mali, Agence de Cooperation Culturelle et Technique, Paris, 1980, pp. 30, 121, 129, 136. BOUQUET, A, Feticheurs et medicines traditionnelles du Congo (Brazzaville), Mem. O.R.S.T.O.M. no. 36, p. 67(1969) . BOUQUET, A. and M. DEBRAY, Plantes medicinales de la Cote dTvoire, Trav. Docum. O.R.S.T.O.M. no. 32,pp . 38-39(1974) . BRAUN, K., Arch. Pharm. 265,45-61 (1927). BURG, C. L. VAN DEN, De geneesheer in Nederlandsch-Indie, Ernst, Batavia, 1885, vol. 3, Materia medica,p .409 . DALZIEL, J. M., The usefulplants of West TropicalAfrica, Crown Agents for the Colonies, London, 1937, p. 383. GUERRERO, L. M., Medicinal uses of Philippine plants, in: BROWN, W. H. (ed.), Minor products of Philippineforests, Department of Agriculture and Natural Resources, Bull. no. 22, vol. 3, p. 81(1921) . HAERDI, F., Die Eingeborenen-Heilpflanzen des Ulanga-Distriktes Tanganyikas (Ostafrika), Acta Tropica Suppl.8 ,pp . 129-133(1964) .
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    Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Varicose Veins Chemical Activity Count (+)-ALLOMATRINE 1 (+)-ALPHA-VINIFERIN 1 (+)-CATECHIN 7 (+)-EUDESMA-4(14),7(11)-DIENE-3-ONE 1 (+)-GALLOCATECHIN 2 (+)-HERNANDEZINE 1 (+)-ISOCORYDINE 1 (+)-PRAERUPTORUM-A 1 (+)-PSEUDOEPHEDRINE 1 (+)-SYRINGARESINOL 1 (-)-16,17-DIHYDROXY-16BETA-KAURAN-19-OIC 1 (-)-ACETOXYCOLLININ 1 (-)-ALPHA-BISABOLOL 2 (-)-ARGEMONINE 1 (-)-BETONICINE 1 (-)-BISPARTHENOLIDINE 1 (-)-BORNYL-CAFFEATE 2 (-)-BORNYL-FERULATE 2 (-)-BORNYL-P-COUMARATE 2 (-)-DICENTRINE 1 (-)-EPIAFZELECHIN 1 (-)-EPICATECHIN 3 (-)-EPICATECHIN-3-O-GALLATE 1 (-)-EPIGALLOCATECHIN 1 (-)-EPIGALLOCATECHIN-3-O-GALLATE 2 (-)-EPIGALLOCATECHIN-GALLATE 3 (-)-HYDROXYJASMONIC-ACID 1 Chemical Activity Count (-)-N-(1'-DEOXY-1'-D-FRUCTOPYRANOSYL)-S-ALLYL-L-CYSTEINE-SULFOXIDE 1 (1'S)-1'-ACETOXYCHAVICOL-ACETATE 2 (15:1)-CARDANOL 1 (2R)-(12Z,15Z)-2-HYDROXY-4-OXOHENEICOSA-12,15-DIEN-1-YL-ACETATE 1 (7R,10R)-CAROTA-1,4-DIENALDEHYDE 1 (E)-4-(3',4'-DIMETHOXYPHENYL)-BUT-3-EN-OL 2 1,2,6-TRI-O-GALLOYL-BETA-D-GLUCOSE 1 1,7-BIS(3,4-DIHYDROXYPHENYL)HEPTA-4E,6E-DIEN-3-ONE 1 1,7-BIS(4-HYDROXY-3-METHOXYPHENYL)-1,6-HEPTADIEN-3,5-DIONE 1 1,7-BIS-(4-HYDROXYPHENYL)-1,4,6-HEPTATRIEN-3-ONE 1 1,8-CINEOLE 3 1-(METHYLSULFINYL)-PROPYL-METHYL-DISULFIDE 1 1-O-(2,3,4-TRIHYDROXY-3-METHYL)-BUTYL-6-O-FERULOYL-BETA-D-GLUCOPYRANOSIDE 1 10-ACETOXY-8-HYDROXY-9-ISOBUTYLOXY-6-METHOXYTHYMOL 2 10-DEHYDROGINGERDIONE 1 10-GINGERDIONE 1 11-HYDROXY-DELTA-8-THC 1 11-HYDROXY-DELTA-9-THC 1 12,118-BINARINGIN 1 12-ACETYLDEHYDROLUCICULINE
  • Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline Or Sarpagine Unit: a Review

    Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline Or Sarpagine Unit: a Review

    molecules Review Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review Md Toufiqur Rahman, Veera V. N. Phani Babu Tiruveedhula and James M. Cook * Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer Street, Milwaukee, WI 53201, USA; [email protected] (M.T.R.); [email protected] (V.V.N.P.B.T.) * Correspondence: [email protected]; Tel.: +1-414-229-5856; Fax: +1-414-229-5530 Academic Editor: Michael Wink Received: 29 September 2016; Accepted: 4 November 2016; Published: 14 November 2016 Abstract: Bisindole natural products consist of two monomeric indole alkaloid units as their obligate constituents. Bisindoles are more potent with respect to their biological activity than their corresponding monomeric units. In addition, the synthesis of bisindoles are far more challenging than the synthesis of monomeric indole alkaloids. Herein is reviewed the enantiospecific total and partial synthesis of bisindole alkaloids isolated primarily from the Alstonia genus of the Apocynaceae family. The monomeric units belong to the sarpagine, ajmaline, macroline, vobasine, and pleiocarpamine series. An up-to-date discussion of their isolation, characterization, biological activity as well as approaches to their partial and total synthesis by means of both synthetic and biosynthetic strategies are presented. Keywords: Alstonia genus; Apocynaceae family; sarpagine; macroline; ajmaline; bisindole alkaloids; biomimetic synthesis; partial and total synthesis; enantiospecific and regiospecific synthesis of alkaloids; bioactive indole alkaloids 1. Introduction Indole alkaloids are of extraordinary significance due to their structural diversity, medicinal properties and are an essential part of the drug discovery process (see the Merck Index for details) [1].