CHEMICAL STUDIES ON MEXICAN HYPTIS SPECIES .3. STRUCTURE AND STEREOCHEMISTRY OF 4 ALPHA-PYRONES FROM HYPTIS-OBLONGIFOLIA

被引：32

作者：

PEREDAMIRANDA, R ^{[1
]}

GARCIA, M ^{[1
]}

DELGADO, G ^{[1
]}

机构：

[1] NATL AUTONOMOUS UNIV MEXICO, INST QUIM, MEXICO CITY 04510, DF, MEXICO

来源：

PHYTOCHEMISTRY | 1990年 / 29卷 / 09期

关键词：

bioassays; Hyptis oblongifolia; Lamiaceae; plant chemistry; structural determination; triterpenes; α-pyrones;

D O I：

10.1016/0031-9422(90)87117-D

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The absolute stereochemistry of 4-deacetoxy-10-epi-olguine, a six-membered α,β-unsaturated C12-lactone isolated from Hyptis oblongifolia, has been established as 6R-[5R,6S-(diacetyloxy)-1R,2S-(epoxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-one. The structural elucidation of three new bioactive α-pyrones, minor constituents of the aerial parts of this species, has been performed. Their structures were elucidated as 6R-[5R,6S-(diacetyloxy)-1R-(hydroxy)-2R-(methoxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-one, 6R-[5R,6S-(diacetyloxy)-1S,2R-(dihydroxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-one and its corresponding diacetylated product, 6R-[1R,2R,5R,6S-(tetracetyloxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-one, based on spectral, chiroptical and chemical evidence. Five known triterpenoids were also identified: ursolic, maslinic, 2α-hydroxyursolic, pomolic and 2α,3α-dihydroxy oleanolic acids. © 1990.

引用

页码：2971 / 2974

页数：4

共 14 条

[1] MOLECULAR AND CRYSTAL-STRUCTURE OF HYPTOLIDE, A NATURALLY-OCCURRING ALPHA,BETA-UNSATURATED DELTA-LACTONE [J].

ACHMAD, S ;

HOYER, T ;

KJAER, A ;

MAKMUR, L ;

NORRESTAM, R .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1987, 41 (08) :599-609

[2]

ALEMANY A, 1979, TETRAHEDRON LETT, P3583

[3] STEREOCHEMICAL STUDIES ON BORONOLIDE, AN ALPHA-PYRONE FROM TETRADENIA-BARBERAE [J].

DAVIESCOLEMAN, MT ;

RIVETT, DEA .

PHYTOCHEMISTRY, 1987, 26 (11) :3047-3050

[4]

DELGADO G, 1986, J CHEM RES-S, P2565

[5] TRITERPENOID ACIDS FROM CUNILA-LYTHRIFOLIA [J].

DELGADO, G ;

HERNANDEZ, J ;

PEREDAMIRANDA, R .

PHYTOCHEMISTRY, 1989, 28 (05) :1483-1485

[6]

DELGADO G, 1985, HETEROCYCLES, V23, P1869

[7]

KJAER A, 1985, ACTA CHEM SCAND B, V39, P745

[8] COMPUTATION OF VICINAL COUPLING-CONSTANTS IN TETRA-ALDITOL AND HEXA-ALDITOL PERACETATES USING MOLECULAR MECHANICS - A RATIONAL APPROACH TO CONFORMATIONAL-ANALYSIS IN SOLUTION [J].

MASAMUNE, S ;

MA, P ;

MOORE, RE ;

FUJIYOSHI, T ;

JAIME, C ;

OSAWA, E .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (03) :261-263

[9] BRINE SHRIMP - A CONVENIENT GENERAL BIOASSAY FOR ACTIVE-PLANT CONSTITUENTS [J].

MEYER, BN ;

FERRIGNI, NR ;

PUTNAM, JE ;

JACOBSEN, LB ;

NICHOLS, DE ;

MCLAUGHLIN, JL .

PLANTA MEDICA, 1982, 45 (01) :31-34

[10] CHEMICAL STUDIES ON MEXICAN HYPTIS SPECIES .2. TRITERPENOIDS AND FLAVONOIDS FROM HYPTIS-ALBIDA [J].

PEREDAMIRANDA, R ;

DELGADO, G .

JOURNAL OF NATURAL PRODUCTS, 1990, 53 (01) :182-185

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