Squamocin-O1 and squamocin-O2, new adjacent bis-tetrahydrofuran acetogenins from the seeds of Annona squamosa

被引：29
|
作者：
Araya, H
Sahai, M
Singh, S
Singh, AK
Yoshida, M
Hara, N
Fujimoto, Y [1 ]
机构：
[1] Tokyo Inst Technol, Dept Chem & Mat Sci, Meguro Ku, Tokyo 1528551, Japan
[2] Natl Inst Agroenvironm Sci, Tsukuba, Ibaraki 3058604, Japan
[3] Banaras Hindu Univ, IMS, Dept Med Chem, Varanasi 221005, Uttar Pradesh, India
[4] Natl Canc Ctr, Res Inst, Div Pharmacol, Chuo Ku, Tokyo 1040045, Japan
来源：
PHYTOCHEMISTRY | 2002年 / 61卷 / 08期
关键词：
Annona squamosa; Annonaceae; bis-tetrahydrofuran acetogenin; squamocin;
D O I：
10.1016/S0031-9422(02)00351-5
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：
Two bis-tetrahydrofuran acetogenins, squamocin-O-1 (1) and squamocin-O-2 (2), were isolated from a MeOH extract of seeds of Annona squamosa L. Their structures were determined by spectral means including precursor-ion scanning mass spectral analysis for their aminal derivatives. The configurations at the oxymethine chiral centers were assigned as 12R,15R,16R,19R,20R,23R,24S,28S,36S for 1 and 12S,15R,16R,19R,20R,23R,24S,28S,36S for 2, based on H-1 NMR analysis of their Mosher's ester derivatives and CD data. (C) 2002 Elsevier Science Ltd. All rights reserved.
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收藏
页码：999 / 1004
页数：6
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共 27 条
  • [1] SQUAMOCIN, A NEW CYTO-TOXIC BIS-TETRAHYDROFURAN CONTAINING ACETOGENIN FROM ANNONA-SQUAMOSA
    FUJIMOTO, Y
    EGUCHI, T
    KAKINUMA, K
    IKEKAWA, N
    SAHAI, M
    GUPTA, YK
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1988, 36 (12) : 4802 - 4806
  • [2] Two New Adjacent Bis-Tetrahydrofuran Annonaceous Acetogenins from Seeds of Annona cornifolia
    Rodrigues dos Santos Lima, Luciana Alves
    Santos Pimenta, Lucia Pinheiro
    Diamantino Boaventura, Maria Amelia
    [J]. PLANTA MEDICA, 2009, 75 (01) : 80 - 83
  • [3] New adjacent bis-tetrahydrofuran annonaceous acetogenins from Annona muricata
    Chang, FR
    Liaw, CC
    Lin, CY
    Chou, CJ
    Chiu, HF
    Wu, YC
    [J]. PLANTA MEDICA, 2003, 69 (03) : 241 - 246
  • [4] Purpurediolin and purpurenin, two new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenins from the seeds of Annona purpurea
    Chávez, D
    Mata, R
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (05): : 580 - 584
  • [5] Bulladecin and atemotetrolin, two bis-tetrahydrofuran acetogenins from Annona atemoya seeds
    Duret, P
    Hocquemiller, R
    Cave, A
    [J]. PHYTOCHEMISTRY, 1998, 48 (03) : 499 - 506
  • [6] ANNONACEOUS ACETOGENINS FROM THE SEEDS OF ANNONA-SQUAMOSA - ADJACENT BIS-TETRAHYDROFURANIC ACETOGENINS
    SAHAI, M
    SINGH, S
    SINGH, M
    GUPTA, YK
    AKASHI, S
    YUJI, R
    HIRAYAMA, K
    ASAKI, H
    ARAYA, H
    HARA, N
    EGUCHI, T
    KAKINUMA, K
    FUJIMOTO, Y
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (06) : 1163 - 1174
  • [7] Purpuracenin:: a new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenin from the seeds of Annona purpurea
    Chávez, D
    Mata, R
    [J]. PHYTOCHEMISTRY, 1999, 50 (05) : 823 - 828
  • [8] Spinencin, a new bis-tetrahydrofuran acetogenin from the seeds of Annona spinescens
    Queiroz, EF
    Roblot, F
    Laprevote, O
    Serani, L
    Cave, A
    [J]. JOURNAL OF NATURAL PRODUCTS, 1997, 60 (08): : 760 - 765
  • [9] ANNONACEOUS ACETOGENINS FROM THE SEEDS OF ANNONA-SQUAMOSA - NON-ADJACENT BIS-TETRAHYDROFURANIC ACETOGENINS
    FUJIMOTO, Y
    MURASAKI, C
    SHIMADA, H
    NISHIOKA, S
    KAKINUMA, K
    SINGH, S
    SINGH, M
    GUPTA, YK
    SAHAI, M
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (06) : 1175 - 1184
  • [10] New nonadjacent bis-THF ring acetogenins from the seeds of Annona squamosa
    Yang, Haijun
    Zhang, Ning
    Li, Xiang
    He, Liwei
    Chen, Jianwei
    [J]. FITOTERAPIA, 2009, 80 (03) : 177 - 181
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