Abstract
Rubiaceous plants of the genusGenipa grow throughout tropical America, and Genipa americana L. (synonym G. caruto H.B. & K.) (Fig. 1 A) is native to the wet or moist areas of Cuba, Hispaniola, Puerto Rico, the Virgin Islands, and from Guadeloupe of Trinidad; also from southern Mexico to Panama, and from Colombia and Venezuela to Peru, Brazil, Bolivia, Paraguay, and Argentina. The fruit (Fig. 1B, C), which is edible and popular as a source for beverages, has many colloquial names: marmalade box in the former British West Indies, genipa, jagua orcaruto in Puerto Rico and several other Spanish-speaking countries; genipapo, jenipapo or jenipa in parts of Columbia and Brazil; chipara, chibara or guanapay among Colombian Indians; carucarutoto, caruto rebalsero, or guaricha in Venezuela, tapoeripa in Surinam, lana in Guyana; bi, bicito or totumillo in Bolivia; huitoc, vito, vitu or palo Colorado in Peru; maluco in Mexico; crayo, irayol de montana, guaitil or tapaculo in Costa Rica; irayol, tambor or tine-duentes in EL Salvador; and guayatil Colorado or jagua blanca in Panama (Morton 1987; Silva et al. 1977). This tree is strictly tropical and grows well in a humid atmosphere and deep loamy soil. The erect trunk of the tree with spreading branches is over 30 m in height. The leaves, deciduous, especially at the rapid lowering of ambient temperatures, are opposite but mostly clustered at the tip of the branch, oblong, 10–30 cm in length, and have a prominent midrib. The tubular five-petaled flowers are yellowish, and ca. 4 cm in width. The elliptic fruit, ca. 10 cm in length, and bearing a short hollow tube at the apex, contains white flesh, which turns yellow to bluish-purple and finally to jet-black on exposure to the air (Morton 1987). It was reported that the natives bathed their limbs and sometimes the whole body, when tired, in a clear juice obtained from the fruits, which turned everything it touched as black as fine and polished jet (Oviedo 18th century).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Berkowitz WF, Choudhry SC, Hrabie J A (1982) Conversion of asperuloside to optically active prostaglandin intermediates. J Org Chem 47: 824–829
Bonini C, Iavarone C, Trogolo C, Dabio R (1985) One-pot conversion of 6-hydroxy-Δ7-iridoid glucosides into cis-2-oxabicyclo[3,3,0]oct-7-enes and transformation into Corey’s lactone analogue. J Org Chem 50: 958–961
Djerassi C, Gray JD, Kind FA (1960) Naturally occurring oxygen heterocycles IX. Isolation and characterization of genipin. J Org Chem 25: 2174–2177
Djerassi C, Nakano T, James AN, Zalkow LH, Eisenbraun EJ, Shoolery JN (1961) Terpenoids XLVII. The structure of genipin. J Org Chem 26: 1192–1206
Endo T, Taguchi H (1973) The constituents of Gardenia jasminoides, geniposide and genipin gentiobioside. Chem Pharm Bull 21: 2684–2688
Filho LGP, Bobbio PA, Falanghe H (1965) Constituent from Genipa americana (Rubiaceae): mannitol. Monatsh Chem 96: 2017–2018
Fujikawa S, Fukui Y, Koga K, Iwashita T, Komura H, Nomoto K (1987a) Structure of genipocyanin Gj, a spontaneous reaction product between genipin and glycine. Tetrahedron Lett 28: 4699–4700
Fujikawa S, Fukui Y, Koga K, Kumada J (1987b) Brilliant skyblue pigment formation from Gardenia fruits. J Ferment Technol 65: 419–424
Fujikawa S, Nakamura S, Koga K (1988) Genipin, a new type of protein crosslinking reagent from Gardenia fruits. Agric Biol Chem 52: 869–870
Guarnaccia R, Madyastha KM, Tegtmeyer E, Coscia CJ (1972) Geniposidic acid, an iridoid glucoside from Genipa americana. Tetrahedron Lett 5125–5127
Guedes ZBL, Oria HF (1978) Nutritive value of edible fruits from Ceara, Brazil. Rev Bras Farm 59: 91–97
Hatsushima S (1975) Flora of Ryukyus, added and corrected. Okinawan Assoc Biol Education, Naha
Heyne K (1950) De Nuttige Planten Van Indonesië, 3e Druk. N.V. Uitgeverij W. van Hoeve-’s-Gravenhage/Bandung, p 1399
Inouye H, Takeda Y, Saito S, Nishimura H, Sakuragi R (1974) Studies on monoterpene glucosides and related natural products XXV. On the iridoid glucosides of Gardenia jasminoides Ellis forma grandiflora [Lour.] Makino (1). Yakugaku Zasshi 94: 577–586
Inouye H, Takeda Y, Inoue K, Kawamura I, Yatsuzuka M, Touyama R, Ikumoto T, Shingu T, Yokoi T (1983) Structure of blue pseudoazulene-skeleton pigment derived from genipin and amino acids. In: Abstr 26th Symp on the Chemistry of natural products, Kyoto, pp 577–584
Kasahara YS (1986) Medicinal herb index in Indonesia. PT Eisai Indonesia, Jakarta
Kobayashi K, Uesato S, Ueda S, Inouye H (1985) Studies on monoterpene glucosides and related natural products LV. Iridane skeleton formation from acyclic monoterpenes in the biosynthesis of iridoid glucosides in Gardenia jasminoides f. grandiflora cell suspension cultures. Chem Pharm Bull 33: 4228–4234
Linsmaier EM, Skoog F (1965) Organic growth factor requirements of tobacco tissue cultures. Physiol Plant 18: 100–127
Mell CD (1922) Interesting dyestuff plants. Text Color 44: 107–111
Mell CD (1928) Interesting source of natural dyestuffs. Text Color 50: 602–604
Miyagoshi M, Amagaya S, Ogihara Y (1988) Choleretic actions of iridoid compounds. J Pharmacobio- Dyn 11: 186–190
Morton JF (1987) Fruits of warm climates. Media, Incorporated, Greensboro
Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassays in tobacco tissue cultures. Physiol Plant 15: 473–497
Nadal NGM, Rodriguez LV, Hernandes T (1965) Marmalade box genip, Am Perfumer Cosmet 80: 37–38
Naruto M, Ohno K, Naruse N (1978) The synthesis of useful chiral prostanoid intermediates and naturally occurring prostaglandins from aucubin. Chem Lett 1419–1422
Ohwi J (1965) Flora of Japan. In: Meyer FG, Walker EH (eds) Flora of Japan. Smithsonian Institution, Washington, DC, p 825
Okuyama H, Toyama R, Sawada Y (1977) Food coloring agent. J Patent Kokai 77 53932
Oviedo BV (18th century) Cualidades y Riquezas del nuevo Reino de Granada, 18th century manuscript published in 1930 by Cuervo LA. Biblioteca de Historia Nacional, Bogota
Santana MBM, Cabala-Rosand P (1982) Dynamics of nitrogen in a shaded cacao plantation. Plant Soil 67: 271–281
Shimomura H, Sashida Y, Nakata H, Yamamoto A, Kawakubo Y, Kawasaki J (1983) Germination and growth inhibitors in fruits of Gardenia jasminoides. Plant Cell Physiol 24: 123–126
Silva MF, Lisbõa PLB, Lisbõa RCL (1977) Names vulgares de plantas amazönieas. Conselho Nacional de Desenvolvimento científico e Tecnológico, Inst Nac Resquisas Amazonia, Manaus
Takeda Y, Nishimura H, Inouye H (1976) Studies on monoterpene glucosides and related natural products XXXII. Iridoid glucosides of Tarenna kotoensis var. gyokushinka. Chem Pharm Bull 24: 1216–1218
Tallent WH (1964) Two new antibiotic cyclopentanoid monoterpenes of plant origin. Tetrahedron 20: 1781–1787
Trim AR, Hill R (1952) The preparation and properties of aucubin, asperuloside and some related glycosides. Biochem J 50: 310–319
Ueda S (1986) Production of iridoid-type monoterpene glucosides by cell cultures of rubiaceous plants. In: Somers DA, Gengenbach BG, Biesboer DD, Hackett WP, Green CE (eds) Abstr 6th Int Congr Plant cell culture, Univ Minnesota, Minneapolis, p 139
Ueda S, Iwahashi Y (1991a) Habitat climate-dependent Gardenieae iridoid productivity revealed through callus induction. Naturwissenschaften 78: 171–172
Ueda S, Kobayashi K, Muramatsu T, Inouye H (1981) Studies on monoterpene glucosides and related natural products XL. Iridoid glucosides of cultured cells of Gardenia jasminoides f. grandiflora. Planta Med 41: 186–191
Ueda S, Iwahashi Y, Tokuda H (1991b): Production of anti-tumor-promoting iridoid glucosides in Genipa americana and its cell cultures. J Natural Products 54: 1677–1680
Uesato S, Ueda S, Kobayashi K, Miyauchi M, Itoh H, Inouye H (1986) Intermediacy of 8-epiiridodial in the biosynthesis of iridoid glucosides by Gardenia jasminoides cell cultures. Phytochemistry 25: 2309–2314
Umetani Y, Tanaka S, Tabata M (1982) Glucosylation of extrinsic compounds by various plant cell cultures. In: Fujiwara A (ed) Plant tissue culture 1982, Maruzen, Tokyo, pp 383–384
Weinges K, Iatridou H, Stammler H-G, Weiss J (1989) Chiral building blocks for the synthesis of triquinane sesquiterpenes: derivatives of 2-methylbicyclo[3,3,0]octan-3-ol from catalpol. Angew Chem Int Ed Engl 28: 447–448
Yamauchi K, Fujimoto N, Kawano S, Inouye H (1976) The mechanism of purgative action of geniposide, an iridoid glucoside of the fruit ofGardenia, in mice. Planta Med 30: 39–47
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1993 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Ueda, S. (1993). Genipa americana L. (Marmalade Box): In Vitro Production of Iridoid Glucosides. In: Bajaj, Y.P.S. (eds) Medicinal and Aromatic Plants IV. Biotechnology in Agriculture and Forestry, vol 21. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-77004-3_11
Download citation
DOI: https://doi.org/10.1007/978-3-642-77004-3_11
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-77006-7
Online ISBN: 978-3-642-77004-3
eBook Packages: Springer Book Archive