Top

Published in:

01-01-2017 | Note

Chodatiionosides A and B: two new megastigmane glycosides from Chorisia chodatii leaves

Authors: Mamdouh Nabil Samy, John Refaat Fahim, Sachiko Sugimoto, Hideaki Otsuka, Katsuyoshi Matsunami, Mohamed Salah Kamel

Published in: Journal of Natural Medicines | Issue 1/2017

Abstract

Phytochemical investigation of Chorisia chodatii Hassl. leaves led to the isolation of an unusual rearranged megastigmane glycoside; chodatiionoside A (1) and another new megastigmane glycoside; chodatiionoside B (2), together with three known megastigmane glycosides (3–5) and one known flavonoid glycoside (6). Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments (¹H, ¹³C, DEPT, COSY, HSQC and HMBC) in combination with HR-ESI–MS, CD and modified Mosher’s method. As a result, chodatiionoside A has been elucidated as a first example of an unusual rearranged form of megastigmane.

Huxley A (1992) Dictionary of gardening: the new royal horticultural society. Macmillan, London.

Ravenna P (1998) On the identity, validity and actual placement in Ceiba of several Chorisia species (Bombacaceae) and description of two new South American species. Oniro 3:42–51

Bailey LH (1976) Hortus third: a concise dictionary of plants cultivated in the United States and Canada. Staff of the L.H Bailey Hortorium, Cornell University, Ithaca

Adjanohoun EJ (1988) Contribution aux etudes ethnobotaniques et floristiques en Republique Populaire du Congo. ACCT, Paris

Refaat J, Samy MN, Desoukey SY, Ramadan MA, Sugimoto S, Matsunami K, Kamel MS (2015) Chemical constituents from Chorisia chodatii flowers and their biological activities. Med Chem Res 24:2939–2949CrossRef

Matsuda N, Isawa K, Kikuchi M (1997) Megastigmane glycosides from Lonicera gracilipes var. glandulosa. Phytochemistry 45:777–779CrossRef

Otsuka H, Hirata E, Shinzato T, Takeda Y (2003) Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium. Phytochemistry 62:763–768CrossRefPubMed

Kai H, Baba M, Okuyama T (2007) Two new megastigmanes from the leaves of Cucumis sativus. Chem Pharm Bull 55:133–136CrossRefPubMed

Joshi KR, Devkota HP, Yahara S (2013) Chemical analysis of flowers of Bombax ceiba from Nepal. Nat Prod Commun 8:583–584

10.

Matsunami K, Nagashima J, Sugimoto S, Otsuka H, Takeda Y, Lhieochaiphant D, Lhieochaiphant S (2010) Megastigmane glucosides and an unusual monoterpene from the leaves of Cananga odorata var. odorata, and absolute structures of megastigmane glucosides isolated from C. odorata var. odorata and Breynia officinalis. J Nat Med 64:460–467CrossRefPubMed

11.

Darwish AGG, Samy MN, Sugimoto S, Otsuka H, Abdel-Salam H, Matsunami K (2016) Effects of hepatoprotective compounds from the leaves of Lumnitzera racemosa on acetaminophen-induced liver damage in vitro. Chem Pharm Bull 64:360–365CrossRefPubMed

12.

Samy MN, Khalil HE, Sugimoto S, Matsunami K, Otsuka H, Kamel MS (2015) Amphipaniculosides A–D, triterpenoid glycosides, and amphipaniculoside E, an aliphatic alcohol glycoside from the leaves of Amphilophium paniculatum. Phytochemistry 115:261–268CrossRefPubMed

13.

Samy MN, Sugimoto S, Matsunami K, Otsuka H, Kamel MS (2014) One new flavonoid xyloside and one new natural triterpene rhamnoside from the leaves of Syzygium grande. Phytochem Lett 10:86–90CrossRef

Title: Chodatiionosides A and B: two new megastigmane glycosides from Chorisia chodatii leaves
Authors: Mamdouh Nabil Samy
John Refaat Fahim
Sachiko Sugimoto
Hideaki Otsuka
Katsuyoshi Matsunami
Mohamed Salah Kamel
Publication date: 01-01-2017
Publisher: Springer Japan
Published in: Journal of Natural Medicines / Issue 1/2017
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-016-1052-7

At a glance: The ONWARDS insulin icodec trials

Springer Medicine

Chodatiionosides A and B: two new megastigmane glycosides from Chorisia chodatii leaves

Abstract

At a glance: The ONWARDS insulin icodec trials

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 1/2017

Marine spongean polybrominated diphenyl ethers, selective growth inhibitors against the cancer cells adapted to glucose starvation, inhibits mitochondrial complex II

Screening of promising chemotherapeutic candidates from plants against human adult T-cell leukemia/lymphoma (V): coumarins and alkaloids from Boenninghausenia japonica and Ruta graveolens

Ephedra Herb extract activates/desensitizes transient receptor potential vanilloid 1 and reduces capsaicin-induced pain

Three new ent-kaurane diterpenes from the herbs of Wedelia prostrata

5′-AMP-activated protein kinase plays an essential role in geniposide-regulated glucose-stimulated insulin secretion in rat pancreatic INS-1 β cells

Aged garlic extract suppresses platelet aggregation by changing the functional property of platelets