camellenodiol | 81426-91-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: camellenodiol
• 英文别名: (4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-4a,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-3,4,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-1H-picen-5-one
• CAS: 81426-91-7
• 化学式: C₂₉H₄₆O₃
• 分子量: 442.682
• InChiKey: DNIUVLCJWDCWGK-VHNCRUBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  camellenodiol 在 chromium trioxide-pyridine complex 作用下， 反应 8.0h， 以41%的产率得到camelledionol
  参考文献：
  名称：

  Medicinal Flowers. XV. The Structures of Noroleanane- and Oleanane-Type Triterpene Oligoglycosides with Gastroprotective and Platelet Aggregation Activities from Flower Buds of Camellia japonica

  摘要：

  从山茶花（菊科）花蕾中提取的甲醇提取物对乙醇或吲哚美辛诱导的大鼠胃粘膜病变有很强的抑制作用。通过生物测定指导下的分离，从甲醇提取物中分离出了 28 个油茶烷类三萜低聚糖苷，即山茶甙 A、B 和 C，以及一个齐墩果烷类三萜低聚糖苷，即山茶甙 D，还有 5 个已知化合物。山茶苷的绝对立体结构是根据化学和物理化学证据确定的，其中包括对正三萜苷元（山茶烯二醇和山茶烯醇）结构的修正。除了对乙醇或吲哚美辛引起的大鼠胃黏膜损伤具有胃保护作用外，主要的低聚糖苷类化合物，即山茶甙 A 和山茶甙 B，还显示出血小板聚集活性。

  DOI：

  10.1248/cpb.55.606
• 作为产物：
  描述：

  camelliosides A 在 glycyrrhizinic acid hydrolase 作用下， 以 acetate buffer 为溶剂， 生成 camellenodiol
  参考文献：
  名称：

  New Noroleanane-Type Triterpene Saponins with Gastroprotective Effect and Platelet Aggregation Activity from the Flowers of Camellia japonica: Revised Structures of Camellenodiol and Camelledionol

  摘要：

  The methanolic extract from the flowers of Camellia japonica was found to exhibit potent gastroprotective effect on ethanol-induced gastric mucosal lesions in rats and platelet aggregation activity. Through bioassay-guided separation, three new 28-noroleanane-type triterpene saponins, camelliosides A, B, and C, and an oleanane-type triterpene saponin, camellioside D, were isolated from the methanolic extract. The absolute stereostructures of camelliosides A-D were determined on the basis of physicochemical and chemical evidence, which included the structure revision of the triterpene part, camellenodiol and camelledionol, using X-Ray crystallographic analysis and modified Mosher's method. Camelliosides A and B showed gastroprotective and platelet aggregating effects.

  DOI：

  10.3987/com-01-9284

文献信息

• Anti-Complement Activity of Norlignans and Terpenes from the Stem Bark of<i>Styrax japonica</i>
  作者：Byung-Sun Min、Sei-Ryang Oh、Kyung-Seop Ahn、Jung-Hee Kim、Joongku Lee、Doo-Young Kim、Eun-Hee Kim、Hyeong-Kyu Lee

  DOI：10.1055/s-2004-835853

  日期：2004.12

  A new norlignan, styraxlignolide A (1), and two new terpenes, styraxosides A (2) and B (3), were isolated from the MeOH-soluble fraction of Styrax japonica Sieb. et Zucc. (Styracaceae) stem bark, together with two known compounds, egonol (4) and masutakeside I (5). The new compounds were determined as 5-(3″-hydroxypropyl)-7-methoxy-2-(3′,4′-dimethoxyphenyl)-benzofuran 3″-O-[β-D-xylopyranoside-(1→6)-β-D-glucopyranoside] (1), 3β,7β-dihydroxy-4α,4β,8β,10β,14α-pentamethyl-5α-gon-16-en-2-one 3-O-[β-D-glucopyranoside-(1→2)-β-D-glucopyranoside] (2), and 3β,17β-dihydroxy-28-norolean-12-en-16-one 3-O-[α-L-rhamopyranoside-(1→2)-β-D-glucuronopyranoside] (3) by spectroscopic means including 2D-NMR. The five compounds were tested in vitro for anti-complement activity against the complement system. Compounds 1, 3, 4, and 5 displayed inhibitory activity in the anti-complement assay, with IC50 values of 123, 65, 33, and 166 μM, respectively. Compound 1a and camellenodiol (3a), obtained from acid hydrolysis of 1 and 3, respectively, did not affect the hemolytic activity of human serum against sensitized erythrocytes. This shows that a sugar seems to play a role of enhancing significantly anti-complement activity.

  in糖类似乎在起作用。
• COSMETIC COMPOSITION FOR SKIN REGENERATION
  申请人：Amorepacific Corporation

  公开号：EP3860552A1

  公开（公告）日：2021-08-11
• [EN] COSMETIC COMPOSITION FOR SKIN REGENERATION<br/>[FR] COMPOSITION COSMÉTIQUE POUR RÉGÉNÉRER LA PEAU
  申请人：AMOREPACIFIC CORP

  公开号：WO2020069683A1

  公开（公告）日：2020-04-09

  A cosmetic composition for skin regeneration comprises a compound represented by a specific chemical formula as an active ingredient.
• New Noroleanane-Type Triterpene Saponins with Gastroprotective Effect and Platelet Aggregation Activity from the Flowers of Camellia japonica: Revised Structures of Camellenodiol and Camelledionol
  作者：Masayuki Yoshikawa、Toshio Morikawa、Emi Fujiwara、Teruki Ohgushi、Yasunobu Asao、Hisashi Matsuda

  DOI：10.3987/com-01-9284

  日期：——

  The methanolic extract from the flowers of Camellia japonica was found to exhibit potent gastroprotective effect on ethanol-induced gastric mucosal lesions in rats and platelet aggregation activity. Through bioassay-guided separation, three new 28-noroleanane-type triterpene saponins, camelliosides A, B, and C, and an oleanane-type triterpene saponin, camellioside D, were isolated from the methanolic extract. The absolute stereostructures of camelliosides A-D were determined on the basis of physicochemical and chemical evidence, which included the structure revision of the triterpene part, camellenodiol and camelledionol, using X-Ray crystallographic analysis and modified Mosher's method. Camelliosides A and B showed gastroprotective and platelet aggregating effects.
• Medicinal Flowers. XV. The Structures of Noroleanane- and Oleanane-Type Triterpene Oligoglycosides with Gastroprotective and Platelet Aggregation Activities from Flower Buds of Camellia japonica
  作者：Masayuki Yoshikawa、Toshio Morikawa、Yasunobu Asao、Emi Fujiwara、Seikou Nakamura、Hisashi Matsuda

  DOI：10.1248/cpb.55.606

  日期：——

  The methanolic extract from the flowers buds of Camellia japonica L. (Theaceae) were found to exhibit potent inhibitory activities on ethanol- or indomethacin-induced gastric mucosal lesions in rats. Through bioassay-guided separation, 28-noroleanane-type triterpene oligoglycosides, camelliosides A, B, and C, and an oleanane-type triterpene oligoglycoside, camellioside D, were isolated from the methanolic extract together with five known compounds. The absolute stereostructures of camelliosides were determined on the basis of chemical and physicochemical evidence, which included the structure revision of the nortriterpene aglycons (camellenodiol and camelledionol). The principal oligoglycosides, camelliosides A and B, showed platelet aggregation activity in addition to the gastroprotective effects on ethanol- or indomethacin-induced gastric mucosal lesions in rats.

  从山茶花（菊科）花蕾中提取的甲醇提取物对乙醇或吲哚美辛诱导的大鼠胃粘膜病变有很强的抑制作用。通过生物测定指导下的分离，从甲醇提取物中分离出了 28 个油茶烷类三萜低聚糖苷，即山茶甙 A、B 和 C，以及一个齐墩果烷类三萜低聚糖苷，即山茶甙 D，还有 5 个已知化合物。山茶苷的绝对立体结构是根据化学和物理化学证据确定的，其中包括对正三萜苷元（山茶烯二醇和山茶烯醇）结构的修正。除了对乙醇或吲哚美辛引起的大鼠胃黏膜损伤具有胃保护作用外，主要的低聚糖苷类化合物，即山茶甙 A 和山茶甙 B，还显示出血小板聚集活性。