全 文 ：黄果西番莲中的一个新内酯类成分
吕 青1 , 谭 睿2 , 张永利1 , 程永现1
?
(1 中国科学院昆明植物研究所植物化学与西部植物资源持续利用国家重点实验室 , 云南 昆明 650204;
2 西南交通大学生物工程学院 , 四川 成都 610031)
摘要 : 从黄果西番莲 ( Passiflora edulis Sims) 压榨果汁中分离得到一个新的内酯类成分 , 波谱技术鉴定其
结构为西番莲内酯。该化合物未显示对 DPPH 自由基的清除活性。
关键词 : 黄果西番莲 ; 西番莲内酯 ; DPPH
中图分类号 : Q 946 文献标识码 : A 文章编号 : 0253 - 2700 (2007) 03 - 375 - 02
A New Lactone from Passiflora edulis (Passifloraceae )
LU Qing
1
, TAN Rui
2
, ZHANG Yong-Li
1
, CHENG Yong-Xian
1 *
( 1 State Key Laboratory of Phytochemistry and Plant Resources in West China , Kunming Instituteof Botany,
The Chinese Academy of Sciences, Kunming 650204 , China;
2 College of Bioengineering, Southwest J iaotong University, Chengdu 610031 , China)
Abstract: A new unsaturated hexalactone named passiflactone (1 ) has been isolated from the petroleum ether extract of
crude juiceof Passiflora edulis Sims . The structure was identified on the basis of extensive NMR and MS techniques . No
antioxidative effect was observed for compound1 against DPPH scavenging assay .
Key words: Passiflora edulis; Passiflactone; DPPH assay
The Passiflora is the largest genus in the family
Passifloraceae, which includes about 500 species, dis-
tributing over temperate and tropical zones of the
world . The plants of this genus are shrubs and herbs,
someof them are grown in the tropics for their edible
fruits, many others are grown outdoors in the warmer
part of the world for their exotic flowers . Passiflora
edulis Sims, known as passion fruit, is themost widely
grown plantof thegenus Passiflora, its leaves are used
in the treatment of sedative, diuretic, tonic, hyperten-
sion, skin diseases, anthelmintic, anti-diarrheal ,
menopausal symptoms, colic of infants and dysentery
(Dhawan et al . 2004; Jamir et al . 1999) , while, the
fruits are used as digestive stimulant and gastric carci-
noma, in addition, fruits of Passiflora edulis is well
known for its unique flavor as popular juice . To date,
much investigations has been done on this plant . The
structure types covered glycosides, phenols, alkaloids,
carotenoids, L-scorbic acid, ahocyanins, γ-lctones, fa-
vor components, volatileoil constituents, carbohydrates,
minerals, enzyme cytoplasmic pyruvate kinase, ccloar-
tane triterpenes (Dhawan et al . 2004 ) . Pharmacologi-
cal effects involved non specific CNS depressant effects
of the aqueous extracts, mild anti-fungal activity
against Microsporumgypseum, Chrysosporiumtropicum
and Trichophyton terrestre ( Dhawan et al . 2004 ) .
During our phytochemical investigation on Passiflora
edulis cultured in southwest China, a new compound,
passiflactone, was readily isolated by liquild-liquild
partition followingby re-crystallization . Herein, were-
ported its isolation and structure elucidation .
Passiflactone (1) was purified fromthe petroleum
ether extract of the crude juice of Passiflora edulis as
colorless needles . The UV maximum absorption at 310
云 南 植 物 研 究 2007 , 29 (3) : 375～376
Acta Botanica Yunnanica

? ?Corresponding author . Tel?Fax . + 86 - 871 - 5223048 , E-mail : yxcheng@mail .kib. ac. cn
Recieved date: 2006 - 09 - 26 , Accepted date: 2006 - 10 - 15
作者简介 : 吕青 ( 1972 - ) 女 , 学士 , 主要从事天然产物的提取、分离与纯化工作。
nmindicated the presenceof conjugated ketone group .
The high-resolution EIMS implied a molecular formula
of C8 H8 O4 [M + Na] + at m?z 191 .0325 (calcd . for
C8 H8 O4 Na 191 .0320 ) . The 1 H NMR displayed three
singlets atδ5 .90 , 2 .62 and 2 .23 , respectively . Two
methyls, one methine and five quarternary carbons
were demonstrated in the
13
C NMR and DEPT spectra,
thereinto, the signal resonated atδ205 .2 was assigned
as ketone due to its chemical shift, the signals atδ
161 .2 , 169 .0 and 181 .0 were oxygen atom bearing
carbons . Due to the scarcity of proton-proton spin sys-
tem, the assembly of backbone was completely per-
formed via HMBC interactions . Theobservationof HM-
BC correlations of H - 8 with C - 7 and C - 4 , H - 5
withC - 3 , C - 4 , C - 6 , C - 7 and C - 9 , H - 9 with C
- 5 and C - 6 indicated the partial structure of C - 3 to
C - 9 . Taking the chemical shifts of C - 2 , C - 3 , C - 6
and thedegrees of unsaturation into account, the rema-
iningmoiety shouldbe alactonefunctional group andC
- 2 linked with C - 6 via oxygen atom . Thus, the
structure of compound 1 was assigned as 4-acetyl-3-
hydroxy-6-methyl-pyran-2-one .
Passiflora species are very popular, not only be-
causeof their fruits, but also because the tea of their
leaves has been largely used in America and European
countries as a folk medicine . The phytochemical inves-
tigations of leaves extracts from P . alata and P . edulis
has been extensively studied over the past decades,
however, passiflactoneas anew natural occurring prod-
uct was the first isolation in the genus of Passiflora,
which will add new facet for the structure profileof this
plant . Considering the presence of ketone-enol func-
tional group, antioxidant efficiency of 1 was evaluated
against DPPH scavenging assay, only slight effect was
observed even at a concentration of 300μg?mL .
Experimental
General Experimental Procedures Melting point was
determined on a XRC-1 micro-melting point apparatus and was
uncorrected . UV spectrum was recorded on a Shimadzu UV-
2401PC spectrophotometer . 1 H ( 400 MHz ) and 13 C NMR
(100 .6 MHz) spectra were recorded at 300 K on aBrucker AM-
400 spectrometer in CDCl3 with TMS as an internal reference .
HMBC spectrum were measured with a Bruker DRX-500 spec-
trometer . EI-MS, including high resolution EI-MS was carried
out on a VG Auto Spec-3000 spectrometer .
Plant Material The fruits of Passiflora edulis Sims were
collected at Jiangcheng County of Yunnan Province, China, in
September 2004 . The specieswas presented byMrs . J iaWangat
the Xishuangbanna Green Ecological Food Corporation Limited,
who was responsible for collection of cultured P . edulis around
foregoing reagion .
Extraction and Purification The fresh fruits of P . edulis
(1. 25 kg) were coldly squeezed to afford the crude juice ( 450
g) . Thecrude juicewas diluted with water andfollowed byparti-
tion against petroleum ether , EtOAC and n-BuOH, respectively .
Removal of part solvent from petroleum ether extracts under re-
duced pressure and placement at ambient temperature yielded
colorless needles, which was recrystalized to afford 1 ( 80 .0
mg) .
4-acetyl-3-hydroxy-6-methyl-pyran-2-one ( 1 ) : colorless
needle; mp: 105 - 107℃ ; UVλmax (CHCl3 ) nm: 310 ( logε
4 .08) , 212 ( logε3 .57 ) ; 1 H NMR (400 MHz, CDCl3 ) : 5 . 90
(1H , s, H - 5) , 2 . 62 (3H, s, H - 8) , 2 .23 (3H , s, H - 9 ) ;
13 C NMR (100 MHz, CDCl3 ) : 205 .2 (s, C - 7) , 181 .0 (s, C
- 3) , 169 .0 (s, C - 6) , 161.2 (s, C - 2) , 101 .4 ( d, C - 5) ,
99 .8 (s, C - 4) , 30 .1 ( q, C - 8) , 20 .7 ( q, C - 9) ; EIMS m?
z: 168 ( 100) [M] + , 153 (85 ) [M-Me] + , 125 ( 40 ) [M-
Ac] + , 85 ( 72 ) . HREIMS m?z: 191 .0325 ( calcd . for
C8 H8 O4 Na191 .0320) .
Acknowledgment: We would like to thank Mrs . J . Wang and
L . Li at the Xishuangbanna Green Ecological Food Corporation
Limitedfor kind provision of P . edulis juice . Mrs Y . Wu and
H . L . Liang, Mr . Y . N . Heat theAnalysis Center of our insti-
tute are also acknowledged for recording UV , Mass and NMR
spectra .
References:
Dhaw ?an K , Dhawan S, Sharma A , 2004 . Passiflora: a review update
[ J ] . J Ethnopharmacol , 94 (1 ) : 1—23
J ami ?r TT , Sharma HK , Dolui AK , 1999 . Folklore medicinal plants of
Nagaland, India [ J ] . Fitoterapia, 70 (4 ) : 395—401
673 云 南 植 物 研 究 29 卷