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Hydrolyzable tannins of tamaricaceous plants. III. Hellinoyl- and macrocyclic-type ellagitannins from Tamarix nilotica.
J Nat Prod. 2010 May 28; 73(5):870-9.JN

Abstract

Three new hellinoyl-type ellagitannins, nilotinins M4 (7), D7 (8), and D8 (9), and a new macrocyclic-type, nilotinin D9 (10), together with eight known tannins, hirtellins B (2), C (11), and F (12), isohirtellin C (13), tamarixinin A (3), tellimagrandins I and II, and 1,2,6-tri-O-galloyl-beta-d-glucose (14), were isolated from an aqueous acetone extract of Tamarix nilotica dried leaves. Nilotinin M4 (7) is a monomeric tannin possessing a hellinoyl moiety. The structure of 8 demonstrated replacement of one of the HHDP groups at the glucose core O-4/O-6 in ordinary dimeric tannins with a galloyl moiety at O-6. This is a new structural feature among the tamaricaceous ellagitannins. On the basis of the results, reported spectroscopic assignments for 2, 3, and the macrocyclic tannins 11-13 were revised. Unusual shifts in the NMR spectra of these macrocyclic tannins are also discussed in relation to their conformations. Several tannins isolated from T. nilotica were assessed for possible cytotoxic activity against four human tumor cell lines, and nilotinin D8 (9) and hirtellin A (1) showed high cytotoxic effects.

Authors+Show Affiliations

Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Tsushima, Okayama 700-8530, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20405847

Citation

Orabi, Mohamed A A., et al. "Hydrolyzable Tannins of Tamaricaceous Plants. III. Hellinoyl- and Macrocyclic-type Ellagitannins From Tamarix Nilotica." Journal of Natural Products, vol. 73, no. 5, 2010, pp. 870-9.
Orabi MA, Taniguchi S, Yoshimura M, et al. Hydrolyzable tannins of tamaricaceous plants. III. Hellinoyl- and macrocyclic-type ellagitannins from Tamarix nilotica. J Nat Prod. 2010;73(5):870-9.
Orabi, M. A., Taniguchi, S., Yoshimura, M., Yoshida, T., Kishino, K., Sakagami, H., & Hatano, T. (2010). Hydrolyzable tannins of tamaricaceous plants. III. Hellinoyl- and macrocyclic-type ellagitannins from Tamarix nilotica. Journal of Natural Products, 73(5), 870-9. https://doi.org/10.1021/np900829g
Orabi MA, et al. Hydrolyzable Tannins of Tamaricaceous Plants. III. Hellinoyl- and Macrocyclic-type Ellagitannins From Tamarix Nilotica. J Nat Prod. 2010 May 28;73(5):870-9. PubMed PMID: 20405847.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Hydrolyzable tannins of tamaricaceous plants. III. Hellinoyl- and macrocyclic-type ellagitannins from Tamarix nilotica. AU - Orabi,Mohamed A A, AU - Taniguchi,Shoko, AU - Yoshimura,Morio, AU - Yoshida,Takashi, AU - Kishino,Kaori, AU - Sakagami,Hiroshi, AU - Hatano,Tsutomu, PY - 2010/4/22/entrez PY - 2010/4/22/pubmed PY - 2010/6/26/medline SP - 870 EP - 9 JF - Journal of natural products JO - J Nat Prod VL - 73 IS - 5 N2 - Three new hellinoyl-type ellagitannins, nilotinins M4 (7), D7 (8), and D8 (9), and a new macrocyclic-type, nilotinin D9 (10), together with eight known tannins, hirtellins B (2), C (11), and F (12), isohirtellin C (13), tamarixinin A (3), tellimagrandins I and II, and 1,2,6-tri-O-galloyl-beta-d-glucose (14), were isolated from an aqueous acetone extract of Tamarix nilotica dried leaves. Nilotinin M4 (7) is a monomeric tannin possessing a hellinoyl moiety. The structure of 8 demonstrated replacement of one of the HHDP groups at the glucose core O-4/O-6 in ordinary dimeric tannins with a galloyl moiety at O-6. This is a new structural feature among the tamaricaceous ellagitannins. On the basis of the results, reported spectroscopic assignments for 2, 3, and the macrocyclic tannins 11-13 were revised. Unusual shifts in the NMR spectra of these macrocyclic tannins are also discussed in relation to their conformations. Several tannins isolated from T. nilotica were assessed for possible cytotoxic activity against four human tumor cell lines, and nilotinin D8 (9) and hirtellin A (1) showed high cytotoxic effects. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/20405847/Hydrolyzable_tannins_of_tamaricaceous_plants__III__Hellinoyl__and_macrocyclic_type_ellagitannins_from_Tamarix_nilotica_ L2 - https://doi.org/10.1021/np900829g DB - PRIME DP - Unbound Medicine ER -