Abstract
The ethanolic extract of Pentas lanceolata (Forssk.) Deflers was investigated from a phytochemical point of view and in particular on the monoterpenoid glucosides content. Iridoid glucosides have a taxonomic relevance, e.g., asperuloside and its derivative are characteristic of the Rubioideae subfamily where this species is comprised. In the light of earliest phylogenetic molecular study which proposed to merge P. lanceolata in the Spermacoceae tribe, a phytochemical approach also becomes necessary for a correct classification of this species. A total of 12 compounds were identified in detail, ten of these are iridoid glucosides: asperuloside, asperulosidic acid, tudoside, E-uenfoside and Z-uenfoside previously identified in this genus; whereas, deacetyl-asperulosidic acid, ixoside, griselinoside, 6β,7β-epoxysplendoside were recognized here for the first time from P. lanceolata. Among the non-iridoidic compounds ursolic acid and d-xylose were identified.
Similar content being viewed by others
References
Bianco A, Guiso M, Iavarone C, Passacantilli P, Trogolo C (1978) New iridoid glucosides from rubiaceae. Gazz Chim Ital 108(1–2):13–16
Bianco A, Caciola P, Guiso M, Iavarone C, Trogolo C (1981) Carbon-13-nuclear magnetic resonance spectroscopy of free iridoid glucosides in D2O solution. Gazz Chim Ital 111:201
Bianco A (1990) The Chemistry of Iridoids, in, Atta-ur-Rahman Ed., Studies in Natural Products Chemistry, Elsevier, Amsterdam, Vol 7 p. 439–497
Breitmaier E, Voelter W (1990) Carbon-13-nmr spectroscopy. VCH, New York
Bremer B, Manen JF (2000) Phylogeny and classification of the subfamily rubioideae (rubiaceae). Plant Syst Evol 225(1–4):43–72
Damtoft S, Jensen SR, Nielsen BJ (1979) Iridoids in Verbena. Taxon 28(5–6):525–528. doi:10.2307/1219790
Endale M, Alao JP, Akala HM, Rono NK, Eyase FL, Derese S, Ndakala A, Mbugua M, Walsh DS, Sunnerhagen P, Erdelyi M, Yenesew A (2012) Antiplasmodial quinones from Pentas longiflora and Pentas lanceolata. Planta Med 78(1):31–35
Gnoatto SCB, Dassonville-Klimpt A, Da Nascimiento S, Galéra P, Boumediene K, Gosmann G, Sonnet P, Moslemi S (2008) Evaluation of ursolic acid isolated from Ilex paraguriensis and derivatives on aromatase inhibition. Eur J Med Chem 43:1865–1877
Inouye H, Fuji K (1964) Monoterpene glycosides. III. Stereochemical relations between monotropeine, asperuloside, and aucubine, and the absolute configuration of the last. Chem Pharm Bull 12(8):901–905
Inouye H, Okigawa M, Shimokawa N (1969) Monoterpene glucosides. VIII. Artifacts formed during extraction of asperuloside and paederoside. Chem Pharm Bull 17(9):1949–1954
Inouye H, Yoshida T, Tobita S, Okigawa M (1970) Monoterpene glucosides. IX. Chemical correlation between asperuloside loganin. Tetrahedron 26(16):3905–3915
Inouye H, Takeda Y, Nishimura H, Kanomi A, Okuda T, Puff C (1988) Studies on monoterpene glucosides and related natural products. part 61. chemotaxonomic studies of rubiaceous plants containing iridoid glycosides. Phytochemistry 27(8):2591–2598
Jensen SR, Nielsen BJ (1982) Iridoid glucosides in fouquieriaceae. Phytochemistry 21(7):1623–1629
Kanchanapoom T, Kasai R, Yamasaki K (2002) Iridoid and phenolic glycosides from Morinda coreia. Phytochemistry 59:551–556
Kigondu EVM, Rukunga GM, Gathirwa JW, Irungu BN, Mwikwabe NM, Amalemba GM, Omar SA, Kirira PG (2001) Antiplasmodial and cytotoxicity activities of some selected plants used by the maasai community Kenya. South African J Bot 77(3):725–729
Nayak BS, Vinutha B, Geetha B, Sudha B (2005) Experimental evaluation of Pentas lanceolata flowers for wound healing activity in rats. Fitoterapia 76(7–8):671–675
Ono M, Oishi K, Abe H, Masuoka C, Okawa M, Ikeda T, Nohara T (2006) New Iridoid Glucosides from the Aerial Parts of Verbena brasiliensis. Chem Pharm Bull 54(10):1421–1424
Pagani F (1984) Constituents of Verbena bonariensis L. (Verbenaceae). Boll Chim Farm 123(10):477–482
Sang S, Cheng X, Zhu N, Wang M, Jhoo J-W, Stark RE, Badmaev V, Ghai G, Rosen R-T, Ho C-T (2001) Iridoid Glycosides from the leaves of Morinda citrifolia. J Nat Prod 64:799–800
Sang S, Wang M, He K, Liu G, Dong Z, Badmaev V, Zheng Q-Y, Ghai G, Rosen RT, Ho C-T (2002) Chemical components in noni fruits and leaves (Morinda citrifolia L.). ACS Symp Series 803:134–150
Schripsema J, Caprini GP, Dagnino D (2006) Revisiono f the structure of citrifolinin A, citrifolinoside, Yopaaoside A, Yopaaoside B, and Morindacin, iridoids from Morinda citrifolia L. and Morinda coreia Ham. Org Lett 8(23):5337–5340
Schripsema J, Caprini GP, van der Heijden R, Bino R, de Vos R, Dagnino D (2007) Iridoids from Pentas lanceolata. J Nat Prod 70(9):1495–1498
Schumann K (1897). In: Engler A, Prantil K (eds) Die Naturlichen Pflantzenfamilien, vol 4. Engelmann, Leipzig, Germany, pp 1–56
Serrilli AM, Ramunno A, Amicucci F, Chicarella V, Santoni S, Ballero M, Serafini M, Bianco A (2008) Iridoidic pattern in endemic sardinian plants: the case of Galium species. Nat Prod Res 22(7):618–622
Sinaphet B, Noiarsa P, Rujirawat S, Otsuka H, Kanchanapoom T (2006) Dolichandroside, a new phenolic triglycoside from Dolichandrone serrulata (DC.) Seem. J Nat Med 60(3):251–254
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(6):1216–1218
Takeda T, Narukawa Y, Hada N (1999) Studies on the constituents of Leonotis nepetaefolia. Chem Pharm Bull 47(2):284–286
Van Puyvelde L, Ntawukiliyayo JD, Portaels F, Hakizamungu E (1994) In vitro inhibition of mycobacteria by Rwandese medicinal plants. Phytother Res 8(2):65–69
Venditti A, Altieri A, Bianco A (2014) Monoterpenoids glycosides content from two mediterranean populations of Crucianella maritima L. Nat Prod Res 28(8):586–588. doi:10.1080/14786419.2014.882920
Verdcourt B (1958) Bull Jard Bot État 28:209–290
Verdcourt B (1976) 1976. In: Polhill RM (ed) Flora of Tropical East Africa. Crown agents for overseas governments and administrations; Whitefriars Press, London, pp 1–213
Vieira IJC, Mathias L, Braz-Filho R, Schripsema J (1999) Iridoids from Borreria verticillata. Org Lett 1(8):1169–1171
Wanyoike GN, Chhabra SC, Lang’at-Thoruwa CC, Omar SA (2004) Brine shrimp toxicity and antiplasmodial activity of five Kenyan medicinal plants. J Ethnopharmacol 90(1):129–133
Wu S, Ma Y, Luo X, Wu D, Liu J (2000) Chemical constituent from Toricellia angulata. Yunnan Zhiwu Yanjiu 22(2):214–218
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Venditti, A., Guarcini, L., Ballero, M. et al. Iridoid glucosides from Pentas lanceolata (Forssk.) Deflers growing on the Island of Sardinia. Plant Syst Evol 301, 685–690 (2015). https://doi.org/10.1007/s00606-014-1106-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00606-014-1106-9