Ardisiatetrons A and B: tetronic acid derivatives and triterpenes from the leaves of Ardisia quinquegona and their biological activity.
Anti-Leishmania activity
Ardisia quinquegona
Primulaceae
Tetronic acid
Triterpene
Journal
Journal of natural medicines
ISSN: 1861-0293
Titre abrégé: J Nat Med
Pays: Japan
ID NLM: 101518405
Informations de publication
Date de publication:
Jun 2021
Jun 2021
Historique:
received:
24
02
2021
accepted:
31
03
2021
pubmed:
28
4
2021
medline:
10
6
2021
entrez:
27
4
2021
Statut:
ppublish
Résumé
From the leaves of Ardisia quinquegona, two alkylated tetronic acid derivatives, named ardisiatetrons A and B (1, 2), and four triterpenoids (3-6) were isolated together with one known compound (7) by a combination of various kinds of chromatography. The structure of new methyl migrated triterpene (3) was confirmed by X-ray crystallographic analysis. Compounds 2, 3, and 7 showed moderate anti-Leishmania activity and cytotoxicity towards A549 cells.
Identifiants
pubmed: 33905079
doi: 10.1007/s11418-021-01513-1
pii: 10.1007/s11418-021-01513-1
doi:
Substances chimiques
Antiprotozoal Agents
0
Furans
0
Phytochemicals
0
Triterpenes
0
tetronic acid
N2B9NB89C0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
643-654Références
Hatusima S (1975) Flora of the Ryukyus. Added and corrected. The Biological Society of Okinawa, Naha, p 375
Zhong X-N, Otsuka H, Ide T, Hirata E, Takushi A, Takeda Y (1997) Three flavonol glycosides from leaves of Myrsine sequinii. Phytochemistry 46:943–946
doi: 10.1016/S0031-9422(97)00366-X
Zhong X-N, Ide T, Otsuka H, Hirata E, Takeda Y (1998) (+)-Isolarisiresinol 3a-O-sulpahte from leaves of Myrsine seguinii. Phytochemistry 49:1777–1778
doi: 10.1016/S0031-9422(98)00256-8
Zhong X-N, Otsuka H, Ide T, Hirata E, Takushi A, Takeda Y (1998) Hydroquinone glycoside from leaves of Myrsine seguinii. Phytochemistry 49:2149–2153
doi: 10.1016/S0031-9422(98)00384-7
Zhong X-N, Otsuka H, Ide T, Hirata E, Takeda Y (1999) Hydroquinone diglycosides acyl esters from the leaves of Myrsine seguinii. Phytochemistry 52:923–927
doi: 10.1016/S0031-9422(99)00334-9
Otsuka H, Zhong X-N, Hirata ST, Takeda Y (2001) Myrsinosionosides A–E: megastigmane glycosides from the leaves of Myrsine seguinii. Chem Pharm Bull 49:1093–1097
doi: 10.1248/cpb.49.1093
Matsunami K, Otsuka H, Takeda Y (2011) Myriseguinosides A–E, five new glycosides from the fruits of Myrssine seguinii. Chem Pharm Bull 59:1274–1280
doi: 10.1248/cpb.59.1274
Asaumi S, Kawakami S, Sugimoto S, Matsunami K, Otsuka H, Shinzato T (2018) Alkylated benzoquinones: ardisiaquinones A–H from the leaves of Ardisia quinquegona and their anti-Leishmania acrivity. Chem Pharm Bull 66:757–763
doi: 10.1248/cpb.c18-00281
Asaumi S, Kawakami S, Sugimoto S, Matsunami K, Otsuka H, Shinzato T (2019) Alkylated benzoquinones: quinquequinones A–H from the leaves of Ardisia quinquegona and their anti-Leishmania activity. Chem Pharm Bull 67:79
doi: 10.1248/cpb.c19-e6701
Dar AA, Dangroo NA, Raina A, Qayum A, Singh S, Kumar A, Sangwan PL (2016) Biologically active xanthones from Codonopsis ovata. Phytochemistry 132:102–108
doi: 10.1016/j.phytochem.2016.10.002
Ibraheim ZZ (2002) Triterpenes from Rubia cordiflora. Bull Pharm Sci Assuit Univ 25:155–164
Bourguet-Kondracki M-L, Guyot M (1999) A new sesquiterpene tetronic acid derivatives from the marine sponge, Smenospongia sp. Tetrahedron Lett 40:3149–3150
doi: 10.1016/S0040-4039(99)00384-6
Parsons IC, Gray AI, Waterman PG (1993) New triterpenes and flavonoids from the leaves of Bosistoa brassii. J Nat Prod 56:46–53
doi: 10.1021/np50091a007
Januário AH, Vieira PC, Fernandes da Silva MFDG, Fernandes JB, de Brito Silva JJ, Conserva LM (2009) Alcaloides β-indolopiridoquinzolínicos de Esenbeckia grandiflora Mart. (Rutaceae). Quim Nova 32:2034–2038
doi: 10.1590/S0100-40422009000800010
Sheldrick GM (1996) SADABS. University of Göttingen, Göttingen
Sheldrick GM (2014) SHELXT-integrated space-group and crystal structure determination. Acta Crystallogr A 71:3–8
doi: 10.1107/S2053273314026370
Sheldrick GM (2015) Crystal structure refinement with SHELXL. Acta Crystallogr C 71:3–8
doi: 10.1107/S2053229614024218
Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Method 65:55–63
doi: 10.1016/0022-1759(83)90303-4